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CAS No. : | 22888-70-6 | MDL No. : | MFCD00872186 |
Formula : | C25H22O10 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SEBFKMXJBCUCAI-HKTJVKLFSA-N |
M.W : | 482.44 | Pubchem ID : | 31553 |
Synonyms : |
Silibinin A;Silybin;Silymarine I;Silybine;Silibinin;Flavobin;Silymarin I;NSC 651520;Silibinin
|
Num. heavy atoms : | 35 |
Num. arom. heavy atoms : | 18 |
Fraction Csp3 : | 0.24 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 10.0 |
Num. H-bond donors : | 5.0 |
Molar Refractivity : | 120.55 |
TPSA : | 155.14 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -7.89 cm/s |
Log Po/w (iLOGP) : | 2.4 |
Log Po/w (XLOGP3) : | 1.9 |
Log Po/w (WLOGP) : | 1.71 |
Log Po/w (MLOGP) : | -0.4 |
Log Po/w (SILICOS-IT) : | 1.92 |
Consensus Log Po/w : | 1.51 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.14 |
Solubility : | 0.0346 mg/ml ; 0.0000717 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.78 |
Solubility : | 0.00799 mg/ml ; 0.0000166 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.5 |
Solubility : | 0.0153 mg/ml ; 0.0000316 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 4.92 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With pyridine; iodine; magnesium chloride; at 100℃; for 1h; | A solution of Silybin (100 mg, 0.2 mmol) and iodine (50 mg, 0.2 mmol) in pyridine (4.0 mL) was added anhydrous metal chloride (0.4 mmol), and the reaction mixture was stirred at 100 C for 1 h, then the solvent was removed under reduced pressure. Sodium dithionite (150 mg), distilled water (25.0 mL) and H3PO4 (85%, 2.0 mL) were added to the mixture and stirred at room temperature for 3 h, then filtered and washed with water. The filter residue was extracted with EtOAc (3 × 50 mL), then dried with anhydrous Na2SO4. The solvent was evaporated under reduced pressure and the residue was purified by silica gel flash chromatography using petroleum ether/actone (3/2, v/v) as eluent to give pure product DHS. 1H NMR (400 MHz, DMSO-d6) delta 12.43 (s, 1H, 5-OH), 10.87 (s, 1H, 7-OH), 9.62 (s, 1H, 3-OH), 9.21 (s, 1H, 20-OH), 7.88-7.69 (m, 2H, 13-H and15-H), 7.14 (d, J = 8.7 Hz, 1H, 16-H), 7.05 (d, J = 1.8 Hz, 1H, 18-H), 6.90 (dd, J = 8.1, 1.8 Hz, 1H, 22-H), 6.82 (d, J = 8.1 Hz, 1H, 21-H), 6.47 (d, J = 2.0 Hz, 1H, H-8), 6.20 (d, J = 2.0 Hz, 1H, H-6), 5.03 (t, J = 5.3 Hz, 1H, 23-OH), 4.97 (d, J = 8.0 Hz, 1H, 11-H), 4.37-4.19 (m, 1H, 10-H), 3.80 (s, 3H, 19-OCH3), 3.57 (d, J = 13.1 Hz, 1H, 23-H); 13C NMR (100 MHz, DMSO-d6) delta 176.47, 164.58, 161.16, 156.70, 148.12, 147.54, 146.20, 145.50, 143.85, 136.80, 127.69, 124.22, 121.74, 121.05, 117.33, 116.68, 115.79, 112.16, 103.55, 98.75, 94.06, 78.98, 76.36, 60.56, 56.17. HRESIMS m/z 481.11414 [M+H]+ (calcd for C25H21O10, 481.11347); 503.09655, [M+Na]+ (calcd for C25H20NaO10, 503.09542). Consistent with the reported literatures. |
49% | With sodium hydrogencarbonate; In methanol; for 16h;Reflux; | General procedure: Silybin (2.5 g, 5.183 mmol) and NaHCO3 (1.74 g, 20.798 mmol) were dissolved in MeOH (100 mL) and the mixture was heated under re?ux for 16 h. The mixture was then left to cool to room temperature and poured into ice-cold water containing HCl (400 mL, 5% v/v). The precipitate formed was ?ltered off, washed with H2O, dissolved in a mixture of EtOAc/acetone (1:1), and evaporated to give 2.17 g of dry residue. The solid was crystallized from MeOH (1000 mg, 40% yield). The mother liquor was ?ltered through a silica gel pad (CHCl3/acetone/HCOOH 90:10:1-70:30:1) to obtain, after concentration, another portion of the product, which after recrystallization from MeOH yielded pure 2 (270 mg, 11%). Thus, the total yield of 2 was 51%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11.9 g (94%) | 1:1 Silybin/soy phosphatidylcholine complex A suspension of 4.82 g silybin (0.010 moles) in 150 ml acetone was treated at room temperature with stirring with 9.2 g (0.012 moles) of "Lipoid S 100" (average molecular weight 770). The reaction mixture became clear after about 3 hours and was concentrated in vacuo to a volume of 30 ml. After being diluted with 300 ml n-hexane the complex was precipitated and was collected by filtration after one night and dried in vacuo at 40 C. The yield was 11.9 g (94%) of product in the form of a yellowish white powder. E1% =172.8 at 288 nm (CH3 OH). Analysis: (MW=1252) calc. % N=1.12; P=2.48; found % N=1.15; P=2.55. | |
1:2 Silybin/soy phosphatidylcholine complex A suspension of 4.82 g silybin (0.010 moles) in 75 ml dioxane was treated with stirring, with a solution containing 15.4 g (0.020 moles) of "Lipoid S 100". The reaction mixture became clear after 4 hours and was freeze-dried, giving 20 g of pale yellow complex. E1% =160 at 288 nm (CH3 OH). Analysis: (MW=2022) calc. % N=1.38; P=3.07; found % N=1.35; P=3.11. | ||
1:0.3 Silybin/soy phosphatidylcholine complex A solution containing 2.41 g (0.005 moles) of silybin and 100 ml dioxane was treated at 60 C. with 0.770 g (0.001 moles) of "Lipoid S 100" for an hour. The reaction mixture was evaporated to dryness in vacuo and the residue was dissolved in 100 ml chloroform. |
Among the preferred AhR ligands, mention may be made of: Flavonoids a. Catechin b. Apigenin Epigallocatechin 3-gallate d. Quercetin e. Silibinin f. Resveratrol g. Yangonin h. Indole-3-carbinol i. Tryptamine ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfur trioxide trimethylamine complex; In N,N-dimethyl-formamide; acetonitrile; at 100℃;Microwave irradiation; | Chemical Synthesis of Diversified Library of Sulfated Molecules. The polyphenolic precursors of the sulfated molecules were either commercially available as <strong>[22888-70-6]silibinin</strong> (1), chlorogenic acid (3), and pentagalloyl glucopyranoside (5) or were chemically synthesized as reported earlier for polyphenolic 1,2,3,4-tetrahydroisoquinoline (THIQ) derivatives (7-14) (see Figure 1). 10,11 Briefly, synthesis of polyphenolic THIQ derivatives was achieved in quantitative yields using Horner-Wadsworth-Emmons and Pictet-Spengler reactions followed by EDCI-mediated amidation and BBr3-assisted deprotection10. Sulfated <strong>[22888-70-6]silibinin</strong> (SS, 2), and sulfated chlorogenic acid (SCA, 4) were synthesized by the microwave-assisted synthesis developed earlier.11 Briefly, the polyphenolic precursors (1, 3, and 5) and trimethylamine-sulfur trioxide (5 equivalents/-OH group) were mixed in equivolume mixture of DMF and CH3CN (3 mL) in microwave tube. The reaction tube was sealed and microwaved (CEM-discover microwave synthesizer) for 0.5-2 h at 100 C. Sulfated THIQ derivatives were synthesized in an equivolume mixture of DMF and CH3CN (3 mL) containing the trimethylamine-sulfur trioxide complex (6 equivalents/-OH group) which was heated for 5 h at 80 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With potassium carbonate; In acetone; for 3h;Inert atmosphere; Reflux; | To a 150 mL three-neck round-bottom flask, silybin A (122 mg, 0.253 mmol) and K2CO3 (293 mg, 2.03 mmol) were dissolved in acetone (80 mL, 0.003 M). After stirring for 10 min, CH3I (244 muL,3.95 mmol) was added dropwise. The reaction mixture was heated at reflux under N2 for 3 h and monitored by HPLC. After cooling to rt, the reaction was quenched by the addition of 2% aqueous HCl (pH 1.5) and diluted with H2O (125 mL). The mixture was extractedwith EtOAc (2 x 80 mL). The organic phases were combinedand dried over Na2SO4, filtered, and then the solvent was removed under reduced pressure. The compounds were purified as described in Section 2.2. Yield: 51 mg, 41%; white solid; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12% | With boron trifluoride diethyl etherate; In diethyl ether; at 80℃; for 48h; | BF3OEt2 (2.7 mL,21.9 mmol, 50% solution in OEt2) was added to a stirred solution of 1a (2.7 g, 5.6 mmol, >99% optical purity) in EtOAc(30 mL) and the mixture was kept at 80 C for 48 h. The reaction mixture was quenched by the addition of an ice-cold solution of saturated NaHCO3 (100 mL), and after stirring for10 min both phases were separated. The aqueous phase was extracted with EtOAc (3 × 50 mL), the combined organic layers were dried (Na2SO4) and evaporated. The crude mixture was purified by column chromatography (CHCl3/acetone/HCO2H95:5:1, twice), yielding 12 (0.32 g; 12%, >96% purity) and a mixture of 2a and 13. After evaporation of the solvent, the residue containing compounds 2a and 13 (1 g) was then dissolved in a mixture of MTBE/n-butanol (30 mL, 9:1, v/v),Novozym 435 (0.3 g, ?10000 U/g, 30% w/w) was added and the mixture was shaken at 45 C and 650 rpm for 72 h to give a13/2a ratio of ca. 2:3 (HPLC). After enzyme removal by filtration,the solution was evaporated, and the crude mixture was purified by column chromatography (CHCl3/acetone/HCO2H90:10:1) to remove 1a. Subsequent preparative HPLC separation(A Chromolith SemiPrep RP-18e monolithic column,100 × 10 mm, Merck) of the mixture of 2a and 13 was carried out with an isocratic mobile phase CH3OH/H2O 50:50, a flowrate of 5 mL/min at 25 C, and UV detection at 285 nm; tr (2a)= 6.6 min, tr (13) = 7.8 min.) yielding 2a (20 mg, 0.7% yield,>98% purity) and 13 (7 mg, 0.3% yield, >96% purity). [alpha]D22+69.7 (c 0.11, acetone); ECD spectrum, see Supporting InformationFile 1, Figure S4; 1H and 13C NMR data, see Table 7;HRMS (ESI-TOF) m/z: [M + Na]+ calcd for C27H24O11Na,547.1211; found, 547.1209. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30%; 10% | General procedure: BF3·OEt2 (2 mL,15.926 mmol, 50% solution in OEt2) was added to a stirred solution of 1a (2 g, 4.146 mmol, >99% optical purity) in DMF(15 mL) and further stirred for 1 h at 50 C. The reaction was quenched by the addition of an ice-cold solution of saturated NaHCO3 (100 mL), extracted with EtOAc (3 × 50 mL), the combined organic layers were dried (Na2SO4) and evaporated.The residue was dissolved in MeOH (10 mL) and a few drops of water were added. After several hours, the crystals formed were filtered off (ca. 1.1 g, virtually pure trans-isomer) and the mother liquor was evaporated (0.84 g, ca. 30% of cis-isomer,according to HPLC). The evaporated residue was then dissolved in a mixture of acetone/vinyl acetate (100 mL, 9:1, v/v),Novozym 435 (0.84 g, ?10000 U/g, 100% w/w) was added, and the mixture was shaken at 45 C and 650 rpm for 48 h. After enzyme removal by filtration, the solution was evaporated and the crude mixture was purified by column chromatography(CHCl3/acetone/HCO2H 95:5:1, twice) yielding 2a (0.6 g, 30%yield, >98% optical purity) and 12 (0.2 g, 10% yield, >97%optical purity). 1H and 13C NMR data see Table 5. HRMS(ESI-TOF) m/z: [M - H]- calcd for C27H23O11, 523.1246;found, 523.1245. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | With Novozym 435; In acetonitrile; at 45℃; for 72h;Molecular sieve; Enzymatic reaction; | General procedure: Silybin (1a or 1b, 0.621 mmol, 2.7 eq.) and divinyldodecanedioate (0.230 mmol, 1 eq.) were dissolved in anhydrous acetonitrile (9 mL). Novozym 435 (150 mg) and 4 A molecular sieves (50 mg) were added to the solution. The reaction mixture was incubated at 45 C, 500 rpm. After 72 h, the reaction was stopped by filtering off the enzyme and the solvent was evaporated under reduced pressure. The crude product was purified by gel filtration using Sephadex LH 20 column,140 × 1.8 cm (eluent MeOH/H2O 4:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7% | With potassium carbonate; In acetone; for 4h;Reflux; Inert atmosphere; | General procedure: K2CO3 (5.8 mmol, 7 eq.) and p-xylylene dibromide (0.42 mmol, 0.5 eq.) or m-xylylene dibromide(0.42 mmol, 0.5 eq.) were added to the solution of silybin (1 or 1a or 1b, 400 mg, 0.83 mmol, 1 eq.) in dry acetone (20 mL). The mixture was stirred and refluxed for 4 h under nitrogen. The reaction was quenched by the addition of conc. HCl (1 mL), diluted with water (50 mL) and extracted with ethyl acetate (2 × 30 mL). The organic layer was dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (linear gradient from chloroform/acetone 85:15 to acetone 100%) and the title compound was isolated as a white amorphous solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With Novozym 435; In acetonitrile; at 45℃; for 72h;Molecular sieve; Enzymatic reaction; | 12-Vinyl dodecanedioate-23-O-silybin B (2b, 0.278 mmol, 1 eq.) and silybin A (1a, 0.556 mmol,2 eq.) were dissolved in anhydrous acetonitrile (9 mL). Novozym 435 (100 mg) and 4 A molecular sieves (100 mg) were added to the solution. The reaction mixture was incubated at 45 C, 500 rpm. After 72 h, the reaction was stopped by filtering off the enzyme and the solvent was evaporated underreduced pressure. The crude product was purified by gel filtration using Sephadex LH 20 column140 × 1.8 cm (eluent MeOH/H2O 4:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; water; at 20 - 50℃; | In a 50 mL beaker, SIL (0.25 g, 5.18 × 10-4 mmol) was dissolved in 5 mL of methanol. 5 mL of aqueous beta-CD (0.59 g, 5.18 × 10-4 mmol) was prepared in another 50 mL beaker separately. Asolution of SIL was added slowly to the solution of beta-CD at room temperature and sonicated in an Ultra-sonicator for 30 minutes to get a homogenous solution. Then the solution was warmed to 50 C for 10-15 minutes and kept at room temperature for two days. The solid precipitated was analyzed with spectroscopic techniques. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71.1% | With potassium carbonate; In acetone; for 4h;Inert atmosphere; Reflux; | K2CO3 (4.20 g; 30.4 mmol) and benzyl bromide (1.0 mL; 8.42 mmol) were added to the solution of silybin A or B (1a or 1b, 2.10 g; 4.36 mmol; for 1a 100% d.e.; for 1b 91.2% d.e.) in dry acetone (120 mL). The mixture was stirred at reflux for 4 h under nitrogen and monitored by TLC (CHCl3/acetone/HCO2H 9:2:0.1). The reaction was quenched by addition of conc. HCl (4 mL) and after short stirring the reaction mixture was diluted with water (200 mL) and extracted with EtOAc (3 * 100 mL). The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography (CHCl3/acetone from 9:1 to 9:2) to afford the following compounds, respectively: (2R,3R)-7-(Benzyloxy)-3,5-dihydroxy-2-((2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)chroman-4-one (7-O-benzyl silybin A, 5a). White amorphous solid (yield 71.1%, 1.77 g, 3.10 mmol). MS-ESI m/z: [M+Na]+ Calcd. for C32H28O10Na 595.2; found 595.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | Silybin A (50 mg,0.104 mmol, 1.0 eq, purity>95%, were dissolved in THF(20 mL)and PPh3(164 mg,0.624 mmol, 6 equiv) and p-nitrobenzoic acid (52mg, 0.312 mmol, 3 equiv) were added. To this mixture a solution of DIAD (122.5 muL, 0.624 mmol, 6 equiv) in 15 mL of THF were added dropwise (over 1 h) at room temperature. After the addition the mixture was stirred at room temperature overnight. 15 mLof 2M sodium hydroxide were added and the mixture was stirred for 1.5 h at room temperature. The mixture was acidified to pH>4 with 2M HCl and extracted with dichloromethane (3× 20 mL). The combined organic phases were washed with brine, dried over sodium sulfate and the solvent was removed. The residue was purified by column chromatography (CH2Cl2/MeOH 30:1 25:1 20:1) to give title compound 2a(16 mg, 0.035 mmol, 33%) as a yellow solid.HPLCpurity: 98.7%, tR= 17.09 min(GM2).ESI-MS: 465.15 [M+H]+. 1H NMR(400 MHz, acetone-d6)delta 12.97 (s, 1H, 5-OH), 7.62 (dd, J= 9.0, 2.0 Hz, 1H, 15-H), 7.61 (d, J= 2.0 Hz, 1H, 13-H), 7.17(d, J= 2.0 Hz, 1H, 18-H), 7.10 (d, J= 9.0 Hz, 1H, 16-H), 7.01 (dd, J= 8.2, 1.9 Hz, 1H, 22-H), 6.91 (d, J= 8.0 Hz, 1H, 21-H), 6.69 (s, 1H, 3-H), 6.59 (d, J= 1.5 Hz, 1H, 8-H), 6.26 (d, J= 1.5 Hz, 1H, 6-H), 5.06 (d, J= 8.0 Hz, 1H, 11-H), 4.28 (ddd, J= 8.2, 3.9, 2.8 Hz, 1H, 10-H), 3.89 (s, 3H, 19-OCH3), 3.80 (dd, J= 12.5, 2.5 Hz, 1H, 23a-H), 3.55 (dd, J= 12.4, 3.9 Hz, 1H, 23b-H).1HNMR (400 MHz, CD3OD) delta 7.56 (d, J = 2.0 Hz, 1 H, 13-H), 7.53 (dd, J = 8.3, 2.3 Hz, 1 H, 15-H), 7.13 (d, J= 8.8 Hz, 1H, 16-H), 7.05 (d, J= 1.8 Hz, 1H, 18-H), 6.94 (dd, J= 8.3, 2.0 Hz, 1H, 22-H), 6.86 (d, J= 8.0 Hz, 1H, 21-H), 6.63 (s, 1H, 3-H), 6.46 (d, J= 2.0 Hz, 1H, 8-H), 6.21 (d, J= 1.8 Hz, 1H, 6-H), 4.98 (d, J= 8.0 Hz, 1H, 11-H), 4.18 (ddd, J= 8.0, 4.4, 2.4 Hz, 1H, 10-H), 3.89 (s, 3H, 19-OCH3), 3.75 (dd, J= 12.3, 2.3 Hz, 1H, 23a-H), 3.51 (dd, J= 12.3, 4.3 Hz, 1H, 23b-H). 13C NMR(101 MHz, acetone-d6) delta 182.17 (4-CO), 164.22 (2-C), 163.51 (7-C), 162.46 (5-C), 157.92 (9-C), 147.69 (19-C), 147.32 (20-C), 147.26 (12a-C), 144.47 (16a-C), 127.85 (17-C), 124.12 (14-C), 120.85 (22-CH), 119.98 (15-CH), 117.44 (16-CH), 115.05 (21-CH), 114.94 (13-CH), 111.13 (18-CH), 104.49 (3-CH), 103.97 (4a-C), 98.93 (6-CH), 93.97 (8-CH), 79.21 (10-CH), 76.42 (11-CH), 60.80 (23-CH2O), 55.51 (19-OCH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With sodium hydroxide; In ethanol; water; at 55℃; for 0.5h; | The 1mmol (0.075g) glycine and 1mmol (0.04g) NaOH dissolved in 1mL distilled water, placed in 100mL Erlenmeyer flasks, document.write(""); (2) The 1mmol (0.482g) was dissolved in 50mL silibin in ethanol was slowly added dropwise to an Erlenmeyer flask, MgSO4Dehydration, solution pH = 8.5,55 water bath, stirring 0.5h, document.write(""); (3) thin track, stop the reaction mixture was suction filtered, recrystallized from ethanol and dried under vacuum. Synthesized product as a pale yellow solid, yield 63%, m.p. 222 ~ 224 , |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With sodium hydroxide; In ethanol; water; at 60℃; for 0.333333h; | The 1mmol (0.089g) alanine and 1mmol (0.04g) NaOH dissolved in 1mL of distilled water, placed in 100mL conical flask and stir until dissolved, document.write(""); (2) Weigh 1mmol (0.482g) was dissolved <strong>[22888-70-6]silibinin</strong> containing 50mL of anhydrous ethanol was slowly added dropwise conical flask, 60 stirring, the reaction was gradually appear yellow solid at room temperature after 20min reflux color Burn turns brown, document.write(""); (3) a thin layer of tracking, MgSO 4Dehydration, the solution pH = 8.5,55 water bath and stirred for 0.5h, TLC tracking, stop the reaction mixture was suction filtered, recrystallized from ethanol and dried under vacuum synthesized product is a yellow-brown solid in 42% yield, m.p. 228 ~ 229 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With sodium hydroxide; In ethanol; water; at 20℃; for 0.333333h; | Weigh 1mmol (0.149g) lysine and 1mmol (0.04g) NaOH dissolved in 1mL distilled water, placed in 100mL Erlenmeyer flasks, 65 deg.] C water bath, magnetically stirred and dissolved, document.write(""); (2) The 1mmol (0.482g) was dissolved in 50mL silibinin ethanol was slowly added dropwise to the mixture, the gradual emergence of yellow precipitate the reaction at room temperature 20min, MgSO4Dehydration, solution pH = 8.5,55 water bath, stirring 0.5h, document.write(""); (3) thin track, stop the reaction mixture was suction filtered, recrystallized from ethanol and dried under vacuum, the synthesized product as a pale yellow solid, yield 55%, m.p. 243 ~ 245 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21.5% | With potassium carbonate; In acetone; at 45℃; for 48h; | Dissolve 2.41 g (5 mmol) of <strong>[22888-70-6]silibinin</strong> in 110 ml of acetone, add 8.5 ml (100 mmol) of 1,2-dibromoethane and 0.345 g (2.5 mmol) of potassium carbonate at 45 (: stirred reaction 2 d, TLC monitoring. After the reaction was stopped, spin acetone, 100 ml of water was added, extracted with EA, respectively, washed with water and saturated sodium chloride layer EA, the organic layer was separated, the organic layer Drying over anhydrous sodium sulphate, filtration and concentration of the filtrate The silica gel column was separated to give 0.63 g of a yellow solid in a yield of 21.5% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | General procedure: To a solution or suspension of the respective acid (0.315 mmol,1.05 eq) in 5 mL of dichloromethane, 2 muL of dimethylformamideand 28.4 muL of oxalylchloride (0.33 mmol, 1.1 eq) were added. Theresulting mixture was stirred at room temperature for 1 h and wasadded to a solution of 146mg of <strong>[22888-70-6]silibinin</strong> (0.3 mmol, 1 eq) and 192 muL of triethylamine (1.35 mmol, 4.5 eq) in 10 mL tetrahydrofuran.The reaction mixture was stirred at room temperature for2-16 h. The reaction was quenched with 30 mL of water andextracted with ethyl acetate (3 x 30 mL). The combined organicphases were washed with 10 mL of 1M HCl-solution and 20 mL ofbrine, dried over sodium sulfate and the solvent was removed in vacuo. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75%; 19% | With pyridine; aluminum (III) chloride; iodine; at 110℃; for 1h; | A solution of Silybin (100 mg, 0.2 mmol) and iodine (50 mg, 0.2 mmol) in pyridine (4.0 mL) was added anhydrous metal chloride (0.4 mmol), and the reaction mixture was stirred at 100 C for 1 h, then the solvent was removed under reduced pressure. Sodium dithionite (150 mg), distilled water (25.0 mL) and H3PO4 (85%, 2.0 mL) were added to the mixture and stirred at room temperature for 3 h, then filtered and washed with water. The filter residue was extracted with EtOAc (3 × 50 mL), then dried with anhydrous Na2SO4. The solvent was evaporated under reduced pressure and the residue was purified by silica gel flash chromatography using petroleum ether/actone (3/2, v/v) as eluent to give pure product DHS. 1H NMR (400 MHz, DMSO-d6) delta 12.43 (s, 1H, 5-OH), 10.87 (s, 1H, 7-OH), 9.62 (s, 1H, 3-OH), 9.21 (s, 1H, 20-OH), 7.88-7.69 (m, 2H, 13-H and15-H), 7.14 (d, J = 8.7 Hz, 1H, 16-H), 7.05 (d, J = 1.8 Hz, 1H, 18-H), 6.90 (dd, J = 8.1, 1.8 Hz, 1H, 22-H), 6.82 (d, J = 8.1 Hz, 1H, 21-H), 6.47 (d, J = 2.0 Hz, 1H, H-8), 6.20 (d, J = 2.0 Hz, 1H, H-6), 5.03 (t, J = 5.3 Hz, 1H, 23-OH), 4.97 (d, J = 8.0 Hz, 1H, 11-H), 4.37-4.19 (m, 1H, 10-H), 3.80 (s, 3H, 19-OCH3), 3.57 (d, J = 13.1 Hz, 1H, 23-H); 13C NMR (100 MHz, DMSO-d6) delta 176.47, 164.58, 161.16, 156.70, 148.12, 147.54, 146.20, 145.50, 143.85, 136.80, 127.69, 124.22, 121.74, 121.05, 117.33, 116.68, 115.79, 112.16, 103.55, 98.75, 94.06, 78.98, 76.36, 60.56, 56.17. HRESIMS m/z 481.11414 [M+H]+ (calcd for C25H21O10, 481.11347); 503.09655, [M+Na]+ (calcd for C25H20NaO10, 503.09542). Consistent with the reported literatures. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With pyridine; aluminum (III) chloride; iodine; at 110℃; for 2h; | A solution of Silybin (100 mg, 0.2 mmol) and iodine (50 mg, 0.2 mmol) in pyridine (4.0 mL) was added anhydrous aluminum trichloride (0.6 mmol), and the reaction mixture was stirred at 110 C for 2 h, then the solvent was removed under reduced pressure. Sodium dithionite (150 mg), distilled water (25.0 mL) and H3PO4 (85%, 2.0 mL) were added to the mixture and stirred at room temperature for 3 h, then filtered and washed with water. The filter residue was extracted with EtOAc (3 × 50 mL), then dried with anhydrous Na2SO4. The solvent was evaporated under reduced pressure and the residue was purified by silica gel flash chromatography using petroleum ether/actone (10:8, v/v) as eluent to give pure product DHDMS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | Silybin (1), palmitic anhydride, CeCl37H2O and all chemicals were purchased from Sigma Aldrich(Saint-Quentin Fallavier, France). The reaction was monitored by thin-layer chromatography (TLC) onF254 silica gel (Merck Millipore Fontenay sous Bois, Paris, France) and the spots were visualized with aUV light.In a 50 mL flask equipped with magnetic stirring, palmitic anhydride (0.40 mmol),and CeCl37H2O (0.10 mmol) were added with 20 mL of THF. The mixture was kept under vigorousstirring for 30 min. Then, a solution of 1 (0.40 mmol) in 20 mL of THF was added dropwise and thereaction was stirred for 24 h at room temperature. After completion, the solvent was evaporatedunder reduced pressure and the crude product was solubilized in the minimum volume of CH2Cl2and purified by column chromatography on silica gel (Grade 633, 200-425 mesh). Elution withCH2Cl2/ethanol (97/3) afforded 2 (Rf: 0.34) as a white amorphous solid with 66% of yield and 25% ofunreacted 1 (Rf: 0.25) after elution with CH2Cl2/ethanol (80/20). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With potassium carbonate; In acetonitrile; at 80℃; for 15h; | 7.5g Me2SO4 (6 equivalents),13.9 g of K2CO3 (10 equivalents) and 60 mL of acetonitrile were placed in a reaction flask and stirred.4.8 g of silybin (1 equivalent) was dissolved in 80 mL of acetonitrile and dropped into the reaction flask.The reaction temperature was controlled at 80 C.The reaction was stopped after 15 hours of reaction.The reaction mixture was evaporated to give a solvent.To give the product as a white solid material was recrystallized from ethanol-pentamethyl <strong>[22888-70-6]silibinin</strong> 4.4g.Yield 81.0% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With pyridine; hydroxylamine hydrochloride; at 70℃; | Step A: will contain (2R,3R)-3,5,7-trihydroxy-2-{(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl -2,3-dihydrobenzo[b][1,4]dioxan-6-yl}chroman-4-one (500 mg, 1.04 mmol),A mixture of hydroxylamine hydrochloride (94 mg, 1.35 mmol) and pyridine (5 mL) was stirred at 70 C overnight. After the reaction,The product is purified by column chromatography (200-300 mesh silica gel,Dichloromethane: methanol = 1:100 to 1:40 elution),(2R,3S)-3,5,7-trihydroxy-2-{(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-2,3 -Dihydrobenzo[b][1,4]dioxan-6-yl}chroman-4-one oxime (46) (481 mg). The yield was 93.0%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Silybin (5 g, 10.4 mmol), 37% aqueous formaldehyde solution (5.7 g, 62.4 mmol), and N-methylpiperazine (6.24 g, 62.4 mmol) were placed in 50 mL of methanol and stirred at room temperature. TLC (dichloro Methane: methanol = 5: 1) The reaction was followed. The reaction was complete in 20 hours, and the reaction was terminated. A solid precipitated during the reaction. After filtration, the solid was slurried with 100 mL of ethanol for 2 h, and filtered under reduced pressure. After drying the solid, 1.4 g of (I-5) was obtained (yield 19.1%).The obtained (I-5) was dissolved in a methanol-hydrochloric acid solution (50 mL), and concentrated and dried to obtain (I-5) hydrochloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Silybin (5 g, 10.4 mmol), 37% aqueous formaldehyde solution (5.7 g, 62.4 mmol), and L-prolinol (6.30 g, 62.4 mmol) were placed in 50 mL of methanol, stirred at room temperature, and TLC (dichloromethane) : Methanol = 5: 1) The reaction was followed. The reaction was completed in 20 hours, and the reaction was terminated. A solid precipitated during the reaction. After filtration, the solid was slurried with 100 mL of ethanol for 2 h, and filtered under reduced pressure. After drying the solid, 2.2 g of (I-6) was obtained (yield: 30%). The obtained (I-6) was dissolved in a methanol-hydrochloric acid solution (50 mL), stirred and concentrated to dryness to obtain (I-6) hydrochloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.95 g | Silybin (5.0 g, 10.4 mmol), 37% aqueous formaldehyde solution (0.48 g, 5.2 mmol), and piperidine (0.44 g, 5.2 mmol) were placed in 50 mL of methanol and stirred at room temperature. The reaction was followed by TLC (dichloromethane: methanol = 10: 1). The reaction was complete within 24 hours, and the reaction was terminated. Spin dry under reduced pressure to obtain 5.7 g of crude product, add 100 ml of ethyl acetate to beat for 2 h, filter under reduced pressure, and then isolate by silica gel column chromatography (CH2Cl2-CH3OH = 10: 1-8: 1) to obtain 0.9 g (I-1) Rate 30%). The obtained (I-1) was dissolved in a methanol-hydrochloric acid solution (100 ml), stirred for 0.5 h, and concentrated and dried to obtain 0.95 g of (I-1) hydrochloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.9 g | Silybin (5.0 g, 10.4 mmol), 37% aqueous formaldehyde solution (3.38 g, 41.7 mmol), and piperidine (3.55 g, 41.7 mmol) were placed in 25 mL of methanol, and stirred at room temperature. TLC (dichloromethane: methanol) = 10: 1) The reaction was followed, the reaction was complete in 24 hours, and the reaction was terminated. The crude product was spin-dried under reduced pressure to obtain 6.5 g of crude product, and 100 ml of ethanol was slurried for 2 h, and then filtered under reduced pressure. The solid was dried to obtain (I-2) 3.7 g (yield 52.9%). The obtained (I-2) was dissolved in a methanol-hydrochloric acid solution (100 ml), stirred for 0.5 h, and concentrated and dried to obtain 3.9 g of (I-2) hydrochloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.12 g | Silybin (5.0 g, 10.4 mmol), 37% aqueous formaldehyde solution (3.38 g, 41.7 mmol), and piperidine (3.55 g, 41.7 mmol) were placed in 25 mL of methanol, and stirred at room temperature. TLC (dichloromethane: methanol) = 10: 1) The reaction was followed, the reaction was complete in 24 hours, and the reaction was terminated. The crude product was spin-dried under reduced pressure to obtain 6.5 g of crude product, and 100 ml of ethanol was slurried for 2 h, and then filtered under reduced pressure. The solid was dried to obtain (I-2) 3.7 g (yield 52.9%). The obtained (I-2) was dissolved in a methanol-hydrochloric acid solution (100 ml), stirred for 0.5 h, and concentrated and dried to obtain 3.9 g of (I-2) hydrochloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6.2 g | Silybin (10 g, 20.8 mmol), 37% aqueous formaldehyde solution (11.5 g, 124.8 mmol), and diethylamine (9.23 g, 124.8 mmol) were placed in 100 mL of methanol and stirred at room temperature. TLC (dichloromethane: methanol) = 10: 1) The reaction was followed. The reaction was complete after 30 hours, and the reaction was terminated. 18 g of crude product was spin-dried under reduced pressure. 100 mL of ethanol was slurried for 2 h and filtered under reduced pressure. The solid was dried to obtain 6.0 g (I-4) (yield: 38.5%). The obtained (I-4) was dissolved in a methanol-hydrochloric acid solution (100 mL), stirred for 0.5 h, and concentrated and dried to obtain 6.2 g of (I-4) hydrochloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With potassium carbonate; In acetone; at 60℃; | Dissolve 964mg (2mmol) of silybin in 20ml acetone,Add 776 mg (4 mmol) of N-bromoethylmorpholine and 276 mg (2 mmol) of potassium carbonate, and stir overnight at 60C to stop the reaction.After acetone was distilled off under reduced pressure, 30ml of water was added and extracted with ethyl acetate (3X30ml). The ethyl acetate extract was washed with water and saturated sodium chloride, respectively.After drying with anhydrous sodium sulfate, filtering, and vacuum distillation to remove ethyl acetate, the product was separated on a silica gel column.Obtained 795 mg of white solid with a yield of 67%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11.2% | With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 12h; Inert atmosphere; | General procedure for the synthesis of compounds3a-i General procedure: To a solution of silibinin (241.2 mg, 0.50 mmol, 1.0 eq) inDMF (3.6 mL, 15.0 vol) was added K2CO3 (69.2 mg,0.50 mmol, 1.0 eq) and carbamyl chloride 1a-i(0.53 mmol, 1.05 eq). The mixture was stirred at 25°Cunder N2 atmosphere for 12 h. After completion of thereaction (monitored by TLC), the reaction mixture dilutedwith water (4.0 mL) and the resulting precipitate wascollected, washed with water. The solid was purified bycolumn chromatography (CH2Cl2/MeOH=15:1) to givethe title compound 3a-i. |
11.2% | With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 12h; Inert atmosphere; | General procedure for the synthesis of compounds3a-i General procedure: To a solution of silibinin (241.2 mg, 0.50 mmol, 1.0 eq) inDMF (3.6 mL, 15.0 vol) was added K2CO3 (69.2 mg,0.50 mmol, 1.0 eq) and carbamyl chloride 1a-i(0.53 mmol, 1.05 eq). The mixture was stirred at 25°Cunder N2 atmosphere for 12 h. After completion of thereaction (monitored by TLC), the reaction mixture dilutedwith water (4.0 mL) and the resulting precipitate wascollected, washed with water. The solid was purified bycolumn chromatography (CH2Cl2/MeOH=15:1) to givethe title compound 3a-i. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39.7% | With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 25℃; for 15h; Inert atmosphere; | General procedure for the synthesis of compounds2a-i General procedure: To a solution of silibinin (241.2 mg, 0.50 mmol, 1.0 eq) inTHF (3.6 mL, 15.0 vol) was added DIPEA (129.2 mg, 1.0 mmol, 2.0 eq), 4-DMAP (12.2 mg, 0.10 mmol, 0.2 eq)and carbamyl chloride 1a-i (0.53 mmol, 1.05 eq). Themixture was stirred at 25 °C under N2 atmosphere for15 h. After completion of the reaction, the reaction mixturediluted with water (20 mL) and extracted with ethylacetate (20 mL) twice. The combined organic layer waswashed with brine (20 mL), dried over Na2SO4 and filtered.The filtrate was concentrated to give the crudeproduct. The residue was purified by column chromatography(CH2Cl2/MeOH = 15:1) to give the title compound 2a-i. |
39.7% | With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 25℃; for 15h; Inert atmosphere; | General procedure for the synthesis of compounds2a-i General procedure: To a solution of silibinin (241.2 mg, 0.50 mmol, 1.0 eq) inTHF (3.6 mL, 15.0 vol) was added DIPEA (129.2 mg, 1.0 mmol, 2.0 eq), 4-DMAP (12.2 mg, 0.10 mmol, 0.2 eq)and carbamyl chloride 1a-i (0.53 mmol, 1.05 eq). Themixture was stirred at 25 °C under N2 atmosphere for15 h. After completion of the reaction, the reaction mixturediluted with water (20 mL) and extracted with ethylacetate (20 mL) twice. The combined organic layer waswashed with brine (20 mL), dried over Na2SO4 and filtered.The filtrate was concentrated to give the crudeproduct. The residue was purified by column chromatography(CH2Cl2/MeOH = 15:1) to give the title compound 2a-i. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13.1% | With potassium carbonate; In N,N-dimethyl-formamide; at 25℃; for 12h;Inert atmosphere; | General procedure: To a solution of silibinin (241.2 mg, 0.50 mmol, 1.0 eq) inDMF (3.6 mL, 15.0 vol) was added K2CO3 (69.2 mg,0.50 mmol, 1.0 eq) and carbamyl chloride 1a-i(0.53 mmol, 1.05 eq). The mixture was stirred at 25Cunder N2 atmosphere for 12 h. After completion of thereaction (monitored by TLC), the reaction mixture dilutedwith water (4.0 mL) and the resulting precipitate wascollected, washed with water. The solid was purified bycolumn chromatography (CH2Cl2/MeOH=15:1) to givethe title compound 3a-i. |
13.1% | With potassium carbonate; In N,N-dimethyl-formamide; at 25℃; for 12h;Inert atmosphere; | General procedure: To a solution of silibinin (241.2 mg, 0.50 mmol, 1.0 eq) inDMF (3.6 mL, 15.0 vol) was added K2CO3 (69.2 mg,0.50 mmol, 1.0 eq) and carbamyl chloride 1a-i(0.53 mmol, 1.05 eq). The mixture was stirred at 25Cunder N2 atmosphere for 12 h. After completion of thereaction (monitored by TLC), the reaction mixture dilutedwith water (4.0 mL) and the resulting precipitate wascollected, washed with water. The solid was purified bycolumn chromatography (CH2Cl2/MeOH=15:1) to givethe title compound 3a-i. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30.2% | With dmap; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 25℃; for 15h;Inert atmosphere; | General procedure: To a solution of silibinin (241.2 mg, 0.50 mmol, 1.0 eq) inTHF (3.6 mL, 15.0 vol) was added DIPEA (129.2 mg, 1.0 mmol, 2.0 eq), 4-DMAP (12.2 mg, 0.10 mmol, 0.2 eq)and carbamyl chloride 1a-i (0.53 mmol, 1.05 eq). Themixture was stirred at 25 C under N2 atmosphere for15 h. After completion of the reaction, the reaction mixturediluted with water (20 mL) and extracted with ethylacetate (20 mL) twice. The combined organic layer waswashed with brine (20 mL), dried over Na2SO4 and filtered.The filtrate was concentrated to give the crudeproduct. The residue was purified by column chromatography(CH2Cl2/MeOH = 15:1) to give the title compound 2a-i. |
30.2% | With dmap; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 25℃; for 15h;Inert atmosphere; | General procedure: To a solution of silibinin (241.2 mg, 0.50 mmol, 1.0 eq) inTHF (3.6 mL, 15.0 vol) was added DIPEA (129.2 mg, 1.0 mmol, 2.0 eq), 4-DMAP (12.2 mg, 0.10 mmol, 0.2 eq)and carbamyl chloride 1a-i (0.53 mmol, 1.05 eq). Themixture was stirred at 25 C under N2 atmosphere for15 h. After completion of the reaction, the reaction mixturediluted with water (20 mL) and extracted with ethylacetate (20 mL) twice. The combined organic layer waswashed with brine (20 mL), dried over Na2SO4 and filtered.The filtrate was concentrated to give the crudeproduct. The residue was purified by column chromatography(CH2Cl2/MeOH = 15:1) to give the title compound 2a-i. |
Tags: 22888-70-6 synthesis path| 22888-70-6 SDS| 22888-70-6 COA| 22888-70-6 purity| 22888-70-6 application| 22888-70-6 NMR| 22888-70-6 COA| 22888-70-6 structure
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H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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