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[ CAS No. 218600-44-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
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There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

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Chemical Structure| 218600-44-3
Chemical Structure| 218600-44-3
Structure of 218600-44-3 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 218600-44-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 218600-44-3 ]

SDS Specification
Alternatived Products of [ 218600-44-3 ]

Product Details of [ 218600-44-3 ]

CAS No. :218600-44-3 MDL No. :MFCD07772296
Formula : C31H41NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 491.66 Pubchem ID :-
Synonyms :
CDDO;RTA 401
Chemical Name :(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydropicene-4a(2H)-carboxylic acid

Calculated chemistry of [ 218600-44-3 ]

Physicochemical Properties

Num. heavy atoms : 36
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.74
Num. rotatable bonds : 1
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 139.97
TPSA : 95.23 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.14
Log Po/w (XLOGP3) : 6.39
Log Po/w (WLOGP) : 6.29
Log Po/w (MLOGP) : 3.98
Log Po/w (SILICOS-IT) : 5.77
Consensus Log Po/w : 5.11

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -6.85
Solubility : 0.0000698 mg/ml ; 0.000000142 mol/l
Class : Poorly soluble
Log S (Ali) : -8.18
Solubility : 0.00000323 mg/ml ; 0.0000000066 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -6.5
Solubility : 0.000154 mg/ml ; 0.000000313 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 5.92

Safety of [ 218600-44-3 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P264-P270-P301+P310-P321-P330-P405-P501 UN#:2811
Hazard Statements:H301 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 218600-44-3 ]

* 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.

  • Downstream synthetic route of [ 218600-44-3 ]

[ 218600-44-3 ] Synthesis Path-Downstream   1~87

  • 1
  • [ 218600-53-4 ]
  • [ 218600-44-3 ]
YieldReaction ConditionsOperation in experiment
71% With lithium iodide; In N,N-dimethyl-formamide; Compound 10 was prepared by formylation of OA (Compound 9) (Simonsen and Ross, 1957) with ethyl formate in the presence of sodium methoxide in THE (Clinton et al., 1961). Compound 7 was obtained by introduction of a double bond at C-1 of Compound 10 with phenylselenenyl chloride in ethyl acetate and sequential addition of 30% hydrogen peroxide (Sharpless et al., 1973). Compound II was synthesized from Compound 10 by addition of hydroxylamine in aqueous ethanol; cleavage of Compound 11 with sodium methoxide gave Compound 12 (Johnson and Shelberg, 1945). Compound 14 was prepared from Compound 13 (Picard et al., 1939) by alkali hydrolysis followed by Jones oxidation. Compound 15 was prepared by formylation of Compound 14 with ethyl formate in the presence of sodium methoxide in benzene. Compound 16 was synthesized from Compound 15 by addition of hydroxylamine. Nitrile 17 was obtained by cleavage of isoxazole 16 with sodium methoxide (yield, 100%), followed by introduction of a double bond at C-1 with PhSeCl-H2O2 (yield, 40%). CDDO (6) was prepared in 71% yield by halogenolysis of 17 with lithium iodide in DMF (Dean, P. D. G., 1965).
70.3% With lithium iodide; In N,N-dimethyl-formamide; at 153℃; for 12.0h;Inert atmosphere; Dissolve 2 g of CDDO-Me in 80 ml of anhydrous DMF, add 12 g of anhydrous lithium iodide, protect with nitrogen and heat to reflux (153 C) for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature, the reaction solution was diluted with 200 ml of ethyl acetate, 200 ml of 5%Dilute hydrochloric acid, partition, aqueous layer was washed with ethyl acetate (120ml × 2), the organic layers were combined and washed with saturated sodium chloride(200ml), dried over anhydrous sodium sulfate, suction filtered and dried. residue was purified by column chromatography (PE / EA = 3: 1) to give 1.37g of white powder. Yield 70.3%.
Reference： [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 2711 - 2714
[2]Patent: US9278913,2016,B2 .Location in patent: Page/Page column 13-14
[3]Patent: CN106632576,2017,A .Location in patent: Paragraph 0064; 0065; 0066; 0067; 0068; 0069
[4]Journal of Medicinal Chemistry,2000,vol. 43,p. 4233 - 4246
[5]Journal of Medicinal Chemistry,2016,vol. 59,p. 2396 - 2409
  • 2
  • [ 106-95-6 ]
  • [ 218600-44-3 ]
  • (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid allyl ester [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 3
  • [ 218600-44-3 ]
  • [ 443104-14-1 ]
YieldReaction ConditionsOperation in experiment
100% With oxalyl dichloride; In dichloromethane; Dinitrile 1 was synthesized from CDDO by the method as shown in Scheme 1. Oxalyl chloride gave acyl chloride 19 in quantitative yield. Amide 3 was prepared in 91% yield from 19 with ammonia gas in benzene. Dehydration of 3 with thionyl chloride gave 1 in 89% yield (Drefahl and Huneck, 1958). Ester 5 was synthesized in 83% yield from CDDO by a nucleophilic substitution method using an alkyl halide and DBU in toluene (reflux) (Ono et al., 1978) (Method A) Amides including imidazolides were synthesized in good yield by condensation reactions (Method B, scheme 1) between acyl chloride 19 and the corresponding amines and imidazoles. Tetra-O-acetyl-beta-D-glucopyranoside 2 was prepared in 75% yield from tetra-O-acetyl-alpha-D-glucopyranoside bromide (Lemieux, 1963) and CDDO using a phase-transfer catalyst (Bliard et al., 1994) (Scheme 2) (Method C). Because in the 1H-NMR spectrum (300 MHz, CDCl3) of 2 the anomeric proton was observed at delta5.70 ppm (1H, d, J=7.8 Hz) the proton was assigned the beta-configuration.
With oxalyl dichloride; In dichloromethane; at 0 - 25℃; for 12.0h; A mixture of CDDO(6.1 mmol) and oxalyl chloride (5 mL) in anhydrous CH2Cl2 (50 mL)was stirred at room temperature overnight. The solvent wasremoved in vacuo, and the residue was coevaporated with anhydrousCH2Cl2 three times, and then used for the next reactionwithout further purification.
With oxalyl dichloride; In dichloromethane; at 18 - 22℃; for 16.0h;Inert atmosphere; To a magnetically-stirred solution of compound 6 (Honda et ah, 2000b) (2.00 g, 4.07 mmol) in CH2Cl2 (15 mL) under a nitrogen atmosphere was added dropwise over 30 min a solution of oxalyl chloride (1.04 g, 8.19 mmol) in CH2Cl2 (4 mL). Gas evolution was observed after each drop, but no exotherm was noted. After stirring the yellow reaction solution for 16 h at -18-22 C, a sample (~3 drops) of the solution was quenched in a CH2C12/CH3OH (95/5) solution (-1-2 mL) and warmed just to reflux. TLC <n="101"/>(silica gel, CH2CVMeOH (1/1): showed a major product spot (Rf 0.8) corresponding to a spot from authentic RTA-402 methyl ester. Only a trace of compound 6 was present just off the baseline. The reaction solution was concentrated by rotary evaporation, and the residue dried under vacuum to give light tan solids (2.2 g) identified as the acid chloride of compound 6 from the 1H NMR spectrum. To a magnetically-stirred solution of this acid chloride of compound 6 (0.3Og, 0.59 mmol) in anhydrous THF (7.5 mL) at room temperature was added dropwise a solution of ethanolamine (0.08 g, 1.31 mmol) in CH2Cl2 (~20 mL). After stirring at room temperature for 30 min, the reaction mixture was quenched in 5% HCl (~20 mL). The CH2Cl2 layer was washed with water (~20 mL) and dried (MgSO4). The filtrate was concentrated to a resin which generated a crystalline foam upon drying under high vacuum. The foam obtained was purified by column chromatography (silica gel, 100% EtOAc) to give 402-40 (0.12 g, 38% yield) as an off-white solid: 1H NMR (400 MHz, CDCl3) delta 8.15 (s, 1H), 6.54 (br, 1H), 6.05 (s, 1H), 3.71 (m, 2H), 3.47 (m, 2H), 3.21 (br, 1H), 3.08 (m, 1H), 2.92 (br d, 1H, J = 13.2 Hz), 1.99 (m, 2H), 1.20-2.02 (m, 13H), 1.50 (s, 3H), 1.37 (s, 3H), 1.26 (s, 3H), 1.17 (s, 3H), 1.03 (s, 3H), 0.99 (s, 3H), 0.90 (s, 3H); m/z 535.35 (M+l).
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
[2]Journal of Medicinal Chemistry,2004,vol. 47,p. 4923 - 4932
[3]Patent: US2004/2463,2004,A1 .Location in patent: Page/Page column 9
[4]European Journal of Medicinal Chemistry,2018,vol. 149,p. 269 - 280
[5]Patent: WO2009/146216,2009,A2 .Location in patent: Page/Page column 86; 99-100
  • 4
  • [ 218600-44-3 ]
  • [ 572-09-8 ]
  • (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid (2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With potassium carbonate;Aliquat 336; In dichloromethane; water; Dinitrile 1 was synthesized from CDDO by the method as shown in Scheme 1. Oxalyl chloride gave acyl chloride 19 in quantitative yield. Amide 3 was prepared in 91% yield from 19 with ammonia gas in benzene. Dehydration of 3 with thionyl chloride gave 1 in 89% yield (Drefahl and Huneck, 1958). Ester 5 was synthesized in 83% yield from CDDO by a nucleophilic substitution method using an alkyl halide and DBU in toluene (reflux) (Ono et al., 1978) (Method A) Amides including imidazolides were synthesized in good yield by condensation reactions (Method B, scheme 1) between acyl chloride 19 and the corresponding amines and imidazoles. Tetra-O-acetyl-beta-D-glucopyranoside 2 was prepared in 75% yield from tetra-O-acetyl-alpha-D-glucopyranoside bromide (Lemieux, 1963) and CDDO using a phase-transfer catalyst (Bliard et al., 1994) (Scheme 2) (Method C). Because in the 1H-NMR spectrum (300 MHz, CDCl3) of 2 the anomeric proton was observed at delta5.70 ppm (1H, d, J=7.8 Hz) the proton was assigned the beta-configuration.
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
[2]Patent: US2004/2463,2004,A1 .Location in patent: Page/Page column 9-11
  • 5
  • [ 218600-44-3 ]
  • benzyl halide [ No CAS ]
  • (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid benzyl ester [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 6
  • [ 218600-44-3 ]
  • cyclopropylmethyl halide [ No CAS ]
  • (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid cyclopropylmethyl ester [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 7
  • [ 218600-44-3 ]
  • ethyl halide [ No CAS ]
  • (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid ethyl ester [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 8
  • [ 218600-44-3 ]
  • n-butyl halide [ No CAS ]
  • (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid butyl ester [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 9
  • [ 218600-44-3 ]
  • n-octyl halide [ No CAS ]
  • (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid octyl ester [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 10
  • [ 16096-97-2 ]
  • [ 218600-44-3 ]
  • (4aS,6aR,6bS,8aS,12aS,14aR,14bS)-11-Cyano-12-((2R,3R)-2,3-dihydroxy-4-mercapto-butylsulfanyl)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-14-oxo-1,3,4,5,6,6a,6b,7,8,8a,9,12,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2215 - 2219
  • 11
  • [ 218600-44-3 ]
  • [ 359860-27-8 ]
  • 11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2<i>H</i>-picene-4a-carboxylic acid {2-[2-(2-{2-[5-(2-oxo-hexahydro-thieno[3,4-<i>d</i>]imidazol-6-yl)-pentanoylamino]-ethoxy}-ethoxy)-ethoxy]-ethyl}-amide [ No CAS ]
Reference： [1]Molecular Pharmacology,2006,vol. 69,p. 1182 - 1193
  • 12
  • [ 218600-44-3 ]
  • [ 774183-03-8 ]
Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4923 - 4932
  • 13
  • [ 218600-44-3 ]
  • [ 774183-02-7 ]
Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4923 - 4932
  • 14
  • [ 218600-44-3 ]
  • [ 774182-97-7 ]
Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4923 - 4932
  • 15
  • [ 218600-44-3 ]
  • [ 774183-04-9 ]
Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4923 - 4932
  • 16
  • [ 218600-44-3 ]
  • [ 774183-05-0 ]
Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4923 - 4932
  • 17
  • [ 218600-44-3 ]
  • N-(6-aminohexyl)-2-cyano-3,12-dioxooleana-1,9(11)-dien-28-amide formate [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4923 - 4932
  • 18
  • [ 218600-44-3 ]
  • N-(6-aminohexyl)-2-cyano-3,12-dioxooleana-1,9(11)-dien-28-amide trifluoroacetate [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4923 - 4932
  • 19
  • [ 218600-44-3 ]
  • N-[3-(6-aminohexyl)aminocarbonyl]propyl-2-cyano-3,12-dioxooleana-1,9(11)-dien-28-amide formate [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4923 - 4932
  • 20
  • [ 218600-44-3 ]
  • N-[3-(6-aminohexyl)aminocarbonyl]propyl-2-cyano-3,12-dioxooleana-1,9(11)-dien-28-amide trifluoroacetate [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4923 - 4932
  • 21
  • [ 218600-44-3 ]
  • 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-onitrile [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 22
  • [ 218600-44-3 ]
  • [ 443103-21-7 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 23
  • [ 218600-44-3 ]
  • (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid methylamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 24
  • [ 218600-44-3 ]
  • (4aR,6aS,6bR,8aS,12bR,14bS)-8a-(Imidazole-1-carbonyl)-4,4,6a,6b,11,11,14b-heptamethyl-3,13-dioxo-3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-picene-2-carbonitrile [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 25
  • [ 218600-44-3 ]
  • (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid dimethylamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 26
  • [ 218600-44-3 ]
  • (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid hydrazide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 27
  • [ 218600-44-3 ]
  • (4aR,6aS,6bR,8aS,12aS,12bR,14bS)-4,4,6a,6b,11,11,14b-Heptamethyl-3,13-dioxo-8a-(pyrazole-1-carbonyl)-3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-picene-2-carbonitrile [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 28
  • [ 218600-44-3 ]
  • (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid propylamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 29
  • [ 218600-44-3 ]
  • (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid phenylamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 30
  • [ 218600-44-3 ]
  • (4aR,6aS,6bR,8aS,12aS,12bR,14bS)-4,4,6a,6b,11,11,14b-Heptamethyl-3,13-dioxo-8a-(pyrrolidine-1-carbonyl)-3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-picene-2-carbonitrile [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 31
  • [ 218600-44-3 ]
  • CDDO-NFM [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 32
  • [ 218600-44-3 ]
  • (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid benzylamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 33
  • [ 218600-44-3 ]
  • (4aR,6aS,6bR,8aS,12aS,12bR,14bS)-4,4,6a,6b,11,11,14b-Heptamethyl-3,13-dioxo-8a-(piperidine-1-carbonyl)-3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-picene-2-carbonitrile [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 34
  • [ 218600-44-3 ]
  • (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid dipropylamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 35
  • [ 218600-44-3 ]
  • (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid hexylamide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 36
  • [ 218600-44-3 ]
  • (4aR,6aS,6bR,8aS,12aS,12bR,14bS)-8a-([1,4']Bipiperidinyl-1'-carbonyl)-4,4,6a,6b,11,11,14b-heptamethyl-3,13-dioxo-3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-picene-2-carbonitrile [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 37
  • [ 218600-44-3 ]
  • (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl ester [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1027 - 1030
  • 38
  • [ 65023-19-0 ]
  • [ 218600-44-3 ]
Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4233 - 4246
[2]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 2711 - 2714
[3]Journal of Medicinal Chemistry,2016,vol. 59,p. 2396 - 2409
  • 39
  • [ 65023-20-3 ]
  • [ 218600-44-3 ]
Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4233 - 4246
[2]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 2711 - 2714
[3]Patent: US9278913,2016,B2
[4]Journal of Medicinal Chemistry,2016,vol. 59,p. 2396 - 2409
  • 40
  • [ 218600-50-1 ]
  • [ 218600-44-3 ]
Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4233 - 4246
[2]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 2711 - 2714
[3]Patent: US9278913,2016,B2
[4]Journal of Medicinal Chemistry,2016,vol. 59,p. 2396 - 2409
  • 41
  • [ 218600-52-3 ]
  • [ 218600-44-3 ]
Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4233 - 4246
[2]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 2711 - 2714
[3]Patent: US9278913,2016,B2
  • 42
  • [ 305818-39-7 ]
  • [ 218600-44-3 ]
Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4233 - 4246
  • 43
  • [ 305818-40-0 ]
  • [ 218600-44-3 ]
Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4233 - 4246
  • 44
  • [ 218600-51-2 ]
  • [ 218600-44-3 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 2711 - 2714
[2]Patent: US9278913,2016,B2
  • 45
  • methyl 2-cyano-3,12-dioxoolean-9(11)-en-28-oate [ No CAS ]
  • [ 218600-44-3 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 2711 - 2714
[2]Patent: US9278913,2016,B2
[3]Journal of Medicinal Chemistry,2016,vol. 59,p. 2396 - 2409
  • 46
  • [ 80841-78-7 ]
  • [ 218600-44-3 ]
  • C36H45NO7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene;Heating / reflux; Dinitrile 1 was synthesized from CDDO by the method as shown in Scheme 1. Oxalyl chloride gave acyl chloride 19 in quantitative yield. Amide 3 was prepared in 91% yield from 19 with ammonia gas in benzene. Dehydration of 3 with thionyl chloride gave 1 in 89% yield (Drefahl and Huneck, 1958). Ester 5 was synthesized in 83% yield from CDDO by a nucleophilic substitution method using an alkyl halide and DBU in toluene (reflux) (Ono et al., 1978) (Method A) Amides including imidazolides were synthesized in good yield by condensation reactions (Method B, scheme 1) between acyl chloride 19 and the corresponding amines and imidazoles. Tetra-O-acetyl-beta-D-glucopyranoside 2 was prepared in 75% yield from tetra-O-acetyl-alpha-D-glucopyranoside bromide (Lemieux, 1963) and CDDO using a phase-transfer catalyst (Bliard et al., 1994) (Scheme 2) (Method C). Because in the 1H-NMR spectrum (300 MHz, CDCl3) of 2 the anomeric proton was observed at delta5.70 ppm (1H, d, J=7.8 Hz) the proton was assigned the beta-configuration.
Reference： [1]Patent: US2004/2463,2004,A1 .Location in patent: Page/Page column 9
  • 47
  • [ 218600-44-3 ]
  • [ 1192122-92-1 ]
YieldReaction ConditionsOperation in experiment
90% With diphenyl phosphoryl azide; triethylamine; at 0 - 20℃; Scheme 1: Reagents and conditions pertaining to Scheme 1 : (a) DPPA, Et3N, 0 C to rt, 6 h, 90%; (b) 80 C, 2 h; (c) 12 N HCl (aq), 99%.Amine 402-14 was synthesized from acid 1 (Honda et ah, 2000b) in 3 steps (Scheme 1). Acid 1 (Honda et ah, 2000b) was treated with DPPAZEt3N to give the corresponding azide 402-11 in 90% yield. The Curtius rearrangement of compound 2 gave isocyanate 3, which was treated with concentrated HCl to give amine 402-14 in quantitative yield.; Compound 2: Et3N (8.44 niL, 60.7 mmol) and DPPA (2.50 g, 9.08 mmol) were added successively to a solution of compound 1 (1.49 g, 3.03 mmol) in toluene (30 mL) at 0 C. After stirring at room temperature for 6 h, the solvent was removed by evaporation to give an oil which was purified by column chromatography (silica gel, 0 to 10% EtOAc in CH2Cl2) to give azide 2 (1.41 g, 90%) as a white foam solid: 1H NMR (400 MHz, CDCl3) delta 8.03 (s, 1H), 5.98 (s, 1H), 2.98 (m, 1H), 2.93 (d, 1H, J = 4.8 Hz), 1.66-1.96 (m, 8H), 1.49 (s, 3H), 1.46-1.62 (m, 3H), 1.36 (s, 3H), 1.26 (s, 3H), 1.18-1.34 (m, 4H), 1.18 (s, 3H), 1.01 (s, 3H), 1.00 (s, 3H), 0.91 (s, 3H); m/z 517.3 (M+l), 489.3 (M-N2+ 1).
90% With diphenyl phosphoryl azide; triethylamine; In toluene; at 20℃; for 6.0h; Et3N (8.44 mL, 60.7 mmol) and DPPA (2.50 g, 9.08 mmol) were added successively to a solution of compound 6 (1.49 g, 3.03 mmol) in toluene (30 mL) at 0 C. After stirring at room temperature for 6 h, the solvent was removed by evaporation to give an oil, which was purified by column chromatography (silica gel, 0 to 10% EtOAc in CH2Cl2) to give azide 402-11 (1.41 g, 90%) as a white foam solid: 1H NMR (400 MHz, CDCl3) delta 8.03 (s, 1H), 5.98 (s, 1H), 2.98 (m, 1H), 2.93 (d, 1H, J = 4.8 Hz), 1.66-1.96 (m, 8H), 1.49 (s, 3H), 1.46-1.62 (m, 3H), 1.36 (s, 3H), 1.26 (s, 3H), 1.18-1.34 (m, 4H), 1.18 (s, 3H), 1.01 (s, 3H), 1.00 (s, 3H), 0.91 (s, 3H); m/z 517.3 (M+l), 489.3 (M-N2+l).
Reference： [1]Patent: WO2009/129546,2009,A1 .Location in patent: Page/Page column 107; 116
[2]Patent: WO2009/146216,2009,A2 .Location in patent: Page/Page column 85; 98
  • 48
  • [ 218600-44-3 ]
  • [ 1191917-53-9 ]
YieldReaction ConditionsOperation in experiment
94% With diethylamino-sulfur trifluoride; In chloroform; at 20℃; for 6.5h; A mixture of compound 6 (Honda et al, 2000b) (252 mg, 0.51 mmol) and (diethylamino)sulfur trifluoride (0.12 mL, 0.9 mmol, 1.8 equiv) in chloroform (7.0 mL) was stirred at ambient temperature for 6.5 h. The reaction was diluted with chloroform (20 mL) and quenched with water (20 mL). The mixture was partitioned, and the CH2Cl2 layer was washed with brine (20 mL) and dried (MgSO4). The filtrate was concentrated and the residue purified by preparative TLC using hexanes/ethyl acetate (65/35), to give 402-55 (239 mg, 94% yield) as a pale yellow solid: 1H NMR (400 MHz, CDCl3) delta 8.03 (s, 1H), 5.99 (s, 1H), 3.00 (br, 1H), 2.95 (m, 1H), 2.01 (m, 2H), 1.22-1.83 (m, yyH), 1.50 (s, 3H), 1.39 (s, 3H), 1.26 (s, 3H), 1.18 (s, 3H), 1.03 (s, 3H), 1.01 (s, 3H), 0.93 (s, 3H); m/z 535.43 (M+I+CH3CN).
Reference： [1]Patent: WO2009/146216,2009,A2 .Location in patent: Page/Page column 87; 100
  • 49
  • [ 218600-44-3 ]
  • [ 443104-14-1 ]
  • [ 1224947-97-0 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2275 - 2278
  • 50
  • [ 1309236-68-7 ]
  • [ 1309943-46-1 ]
  • [ 218600-44-3 ]
Reference： [1]Chemical Communications,2011,vol. 47,p. 9495 - 9497
  • 51
  • [ 1309236-68-7 ]
  • [ 218600-44-3 ]
Reference： [1]Chemical Communications,2011,vol. 47,p. 9495 - 9497
  • 52
  • [ 147506-92-1 ]
  • [ 218600-44-3 ]
  • [ 1309943-46-1 ]
  • [ 1707-75-1 ]
Reference： [1]Chemical Communications,2011,vol. 47,p. 9495 - 9497
  • 53
  • [ 218600-44-3 ]
  • [ 1309943-46-1 ]
Reference： [1]Chemical Communications,2011,vol. 47,p. 9495 - 9497
  • 54
  • [ 218600-44-3 ]
  • N-[(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-octadecahydropicen-4a-yl]-2,2-difluoropropanamide [ No CAS ]
Reference： [1]Patent: WO2013/163344,2013,A1
[2]Patent: WO2013/163344,2013,A1
  • 55
  • [ 218600-44-3 ]
  • [ 1192122-92-1 ]
  • [ 1192122-95-4 ]
YieldReaction ConditionsOperation in experiment
With diphenyl phosphoryl azide; triethylamine; In toluene; at 0 - 20℃; Compound 1: To a solution of toluene (400 mL), RTA 401 (which can be prepared according to the methods taught, for example, by Honda, et al, 1998; Honda et al, 2000b; Honda et al, 2002; Yates et al, 2007; and U.S. Patents 6,326,507 and 6,974,801, which are incorporated herein by reference) (20.0 g, 40.6 mmol) and Et3N (17.0 mL, 122.0 mmol) were added into a reactor and cooled to 0 C with stirring. Diphenyl phosphoryl azide (DPPA) (13.2 mL, 61.0 mmol) was added with stirring at 0 C over 5 min and the mixture was continually stirred at room temperature overnight (HPLC-MS check shows no RTA 401 left). The reaction mixture was directly loaded on a silica gel column and purified by column chromatography (silica gel, 0% to 5% EtOAc in CH2Cl2) to give compound 1 (19.7 g, ~94%, partially converted into compound 2) as a white foam.
Reference： [1]Patent: WO2013/163344,2013,A1 .Location in patent: Page/Page column 69; 70
  • 56
  • [ 218600-44-3 ]
  • [ 1192122-95-4 ]
YieldReaction ConditionsOperation in experiment
Compound 2: Compound 1 (19.7 g, -38.1 mmol) and benzene (250 mL) were added into a reactor and heated to 80 C with stirring for 2 h (HPLC-MS check shows no compound 1 left). The reaction mixture was concentrated at reduced pressure to afford crude compound 2 as a solid residue, which was used for the next step without purification.
Reference： [1]Patent: WO2013/163344,2013,A1 .Location in patent: Page/Page column 69; 70
[2]Patent: WO2009/129546,2009,A1
  • 57
  • [ 218600-44-3 ]
  • [ 1192123-13-9 ]
Reference： [1]Patent: WO2013/163344,2013,A1
[2]Patent: WO2013/163344,2013,A1
[3]Patent: WO2009/129546,2009,A1
  • 58
  • [ 218600-44-3 ]
  • C31H41NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With dihydrogen peroxide; In methanol; water; acetonitrile; at 20℃; for 30.0h; Compound TX63160: At room temperature RTA 401 (101 mg, 0.20 mmol) was dissolved in acetonitrile (1.4 mL) and MeOH (0.7 mL), to which H202 solution (30% in water, 0.1 mL, 1 mmol) was added. The mixture was stirred for 30 h at room temperature. The reaction mixture was concentrated, and the crude product was partitioned between EtOAc and water. The organic phase was separated and washed with water, then dried over Na2SO4 and concentrated to give the desired product TX63160 (94 mg, 90%) as a white solid. ?H NMR (400 MHz, CDC13) oe 6.08 (s, 1H), 4.34 (s, 1H), 3.06-3.04 (m, 1H), 3.02 (s, 1H), 2.00-1.90 (m, 3H), 1.78-1.47 (m, 8H), 1.39-1.21 (m, 4H), 1.30 (s, 3H), 1.27 (s, 3H), 1.19 (s, 3H), 1.12 (s, 3H), 1.09 (s, 3H), 1.01 (s, 3H), 0.91 (s, 3H); m/z = 508.3 (M+1).
Reference： [1]Patent: WO2013/188818,2013,A1 .Location in patent: Page/Page column 44; 57
  • 59
  • [ 508-02-1 ]
  • [ 218600-44-3 ]
Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 2396 - 2409
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 2396 - 2409
[3]Patent: CN106632576,2017,A
  • 60
  • [ 25493-69-0 ]
  • [ 218600-44-3 ]
Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 2396 - 2409
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 2396 - 2409
  • 61
  • [ 25493-94-1 ]
  • [ 218600-44-3 ]
Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 2396 - 2409
  • 62
  • [ 4339-72-4 ]
  • [ 218600-44-3 ]
Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 2396 - 2409
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 2396 - 2409
  • 63
  • [ 79-03-8 ]
  • [ 16106-20-0 ]
  • [ 218600-44-3 ]
  • 1-isosorbide mononitrate 2-cyano-3-propionyloxy-12-oxoolean-2(3),9(11)-diene-28-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% CDDO (100 mg, 0.2 mmol) was dissolved in 2.5 ml of dry DMF, and isosorbide mononitrate(57.3 mg, 0.3 mmol), K2CO3 (41 mg, 0.3 mmol) was stirred overnight at room temperature and compound V was added the next morning (27.8 mg, 0.3 mmol). For 6 h, the reaction solution was diluted with an appropriate amount of dichloromethane (50 mL), saturated sodium bicarbonate solution And saturated brine each washing 3 times. The organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated to a white solid which was rapidly passed Silica gel column chromatography gave white solid I3 (35 mg, 35%).
Reference： [1]Patent: CN107118250,2017,A .Location in patent: Paragraph 0071; 0072; 0073; 0074
  • 64
  • [ 16106-20-0 ]
  • [ 75-36-5 ]
  • [ 218600-44-3 ]
  • 1-isosorbide mononitrate 2-cyano-3-acetoxy-12-oxoolean-2(3),9(11)-diene-28-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% CDDO (100 mg, 0.2 mmol) was dissolved in 2.5 ml of dry DMF and isosorbide dinitrate was added(57.3 mg, 0.3 mmol), K2CO3 (41 mg, 0.3 mmol) was stirred overnight at room temperature and compound V was added the next morning(23.6 mg, 0.3 mmol). After 6 hours, the reaction solution was diluted with an appropriate amount of dichloromethane (50 mL), saturated sodium bicarbonate solutionAnd saturated with saline 3 times. The organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated to a rapidly passing white solidSilica gel column chromatography gave white solid I2 (35 mg, 35%).
Reference： [1]Patent: CN107118250,2017,A .Location in patent: Paragraph 0067; 0068; 0069; 0070
  • 65
  • [ 1724-17-0 ]
  • [ 218600-44-3 ]
Reference： [1]Patent: CN106632576,2017,A
  • 66
  • [ 69660-90-8 ]
  • [ 218600-44-3 ]
Reference： [1]Patent: CN106632576,2017,A
  • 67
  • [ 218600-44-3 ]
  • O2-(2,4-dinitro-5-{4-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]piperazin-1-yl}phenyl)-1-{N-methyl-2-[2-(S)-(tert-butoxycarbonylamino)proionyl-1-oxo]ethylamino}diazen-ium-1,2-diolate [ No CAS ]
Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 149,p. 269 - 280
  • 68
  • [ 218600-44-3 ]
  • O2-(2,4-dinitro-5-{4-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]piperazin-1-yl}phenyl)-1-{N-methyl-2-[2-(S)-(tert-butoxycarbonylamino)-3-phenylpropionyl-1-oxo]ethylamino}diazen-1-ium-1,2-diolate [ No CAS ]
Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 149,p. 269 - 280
  • 69
  • [ 218600-44-3 ]
  • O2-(2,4-dinitro-5-{4-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]piperazin-1-yl}phenyl)-1-{N-methyl-2-[2-(S)-(tert-butoxycarbonylamino)proionyl-1-oxo]ethylamino}diazen-1-ium-1,2-diolate [ No CAS ]
Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 149,p. 269 - 280
  • 70
  • [ 218600-44-3 ]
  • O2-(2,4-dinitro-5-{4-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]piperazin-1-yl}phenyl)-1-{N-methyl-2-[2-(S)-(tert-butoxycarbonylamino)-3-phenylpropionyl-1-oxo]ethylamino}diazen-1-ium-1,2-diolate [ No CAS ]
Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 149,p. 269 - 280
  • 71
  • [ 218600-44-3 ]
  • 1-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]piperazin [ No CAS ]
Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 149,p. 269 - 280
  • 72
  • [ 218600-44-3 ]
  • O2-(2,4-dinitro-5-{4-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]piperazin-1-yl}phenyl)-1-(piperidine-1-yl)diazen-1-ium-1,2-diolate [ No CAS ]
Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 149,p. 269 - 280
  • 73
  • [ 218600-44-3 ]
  • O2-(2,4-dinitro-5-{4-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]piperazin-1-yl}phenyl)-1-(N-methylethanolamino)diazen-1-ium-1,2-diolate [ No CAS ]
Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 149,p. 269 - 280
  • 74
  • [ 218600-44-3 ]
  • O2-(2,4-dinitro-5-{4-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]piperazin-1-yl}phenyl)-1-(morpholine-1-yl)diazen-1-ium-1,2-diolate [ No CAS ]
Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 149,p. 269 - 280
  • 75
  • [ 218600-44-3 ]
  • O2-(2,4-dinitro-5-{4-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]piperazin-1-yl}phenyl)-1-(N,N-diethylamino)diazen-1-ium-1,2-diolate [ No CAS ]
Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 149,p. 269 - 280
  • 76
  • [ 218600-44-3 ]
  • O2-(2,4-dinitro-5-{4-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]piperazin-1-yl}phenyl)-1-(4-methylpiperazine-1-yl)diazen-1-ium-1,2-diolate [ No CAS ]
Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 149,p. 269 - 280
  • 77
  • [ 218600-44-3 ]
  • O2-(2,4-dinitro-5-{4-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]piperazin-1-yl}phenyl)-1-(pyrrolidine-1-yl)diazen-1-ium-1,2-diolate [ No CAS ]
Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 149,p. 269 - 280
  • 78
  • O<SUP>2</SUP>-(2,4-dinitro-5-(2-bromoethylamino)phenyl)-1-(piperidine-1-yl)diazen-1-ium-1,2-diolate [ No CAS ]
  • [ 218600-44-3 ]
  • O2-(2,4-dinitro-5-{2-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]-oxoethylamino}phenyl)-1-(piperidine-1-yl)diazen-1-ium-1,2-diolate [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With potassium carbonate; In acetone; at 45℃; for 4.0h; General procedure: The solution of 3a(1.0 mmol) and CDDO (1.0 mmol) in acetone (10 mL) was addedK2CO3 (1.5 mmol). The mixturewas then heated to 45 C and stirredfor 4 h. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by flash chromatography (PE/EA 3:7, v/v) to afford the compound 4. Synthesis of 5 were in the similar method.4.1.1.2.1. Compound 4.O2-(2,4-Dinitro-5-{2-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]-oxo-ethyl-amino}phenyl)1-(piperidine-1-yl)diazen-1-ium-1,2-diolate. The title compound was obtained in 68% yield as a yellowish solid: mp: 170e172 C; 1H NMR (300MHz, CDCl3, 25C,TMS): d 9.08 (s, 1H, Ar-H), 8.73 (t, J 5.1 Hz, 1H, NH-Ar), 8.05 (s, 1H,C1-H), 6.82 (s, 1H, Ar-H), 5.96 (s, 1H, C11-H), 4.47e4.44 (m, 2H,OCH2), 3.73e3.68 (m, 2H, OCH2), 3.61 (t, J 5.6 Hz, 4H, 2 NCH2),3.07e2.97 (m, 1H, C13-H), 2.90e2.85 (m, 1H, C18-H), 1.46 (s, 3H,CH3), 1.28e1.24 (m, 8H, CH3, 3 CH2), 1.20 (s, 3H, CH3), 1.16 (s, 3H,CH3), 1.00 (s, 3H, CH3), 0.97 (s, 3H, CH3), 0.90 (s, 3H, CH3) ppm; 13CNMR (75MHz, CDCl3, 25 C, TMS): d 198.0,196.2, 177.2,168.0,165.2,155.0, 148.0, 127.3, 126.6, 125.8, 123.5, 114.0, 113.9, 97.9, 61.1, 51.3,49.0, 47.1, 46.8, 45.1, 44.5, 42.0, 41.8, 41.5, 35.1, 33.8, 32.6, 31.1, 30.1,29.3, 29.0, 28.8, 27.5, 26.4, 26.1, 23.9, 23.8, 22.7, 22.5, 22.1, 21.0, 21.0,17.6; ESI-MS: 866 [M Na]; HRMS: m/z: Calcd. for C44H57N7O10[M Na] 866.4167, found 866.4050, ppm error 5.0.
Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 149,p. 269 - 280
  • 79
  • O<SUP>2</SUP>-(2,4-dinitro-5-(2-bromoethylamino)phenyl)-1-(N-methylethanolamino)diazen-1-ium-1,2-diolate [ No CAS ]
  • [ 218600-44-3 ]
  • O2-(2,4-dinitro-5-{2-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]-oxoethylamino}phenyl)-1-(N-methylethanolamino)diazen-1-ium-1,2-diolate [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With potassium carbonate; In acetone; at 45℃; for 4.0h; General procedure: The solution of 3a(1.0 mmol) and CDDO (1.0 mmol) in acetone (10 mL) was addedK2CO3 (1.5 mmol). The mixturewas then heated to 45 C and stirredfor 4 h. The reaction mixture was filtered, and the filtrate wasconcentrated under reduced pressure. The resulting residue waspurified by flash chromatography (PE/EA 3:7, v/v) to afford thecompound 4. Synthesis of 5 were in the similar method.
Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 149,p. 269 - 280
  • 80
  • [ 218600-44-3 ]
  • [ 1192123-16-2 ]
Reference： [1]Patent: WO2009/129546,2009,A1
  • 81
  • [ 218600-44-3 ]
  • [ 1192123-30-0 ]
Reference： [1]Patent: WO2009/129546,2009,A1
  • 82
  • [ 218600-44-3 ]
  • [ 1192123-18-4 ]
Reference： [1]Patent: WO2009/129546,2009,A1
  • 83
  • [ 218600-44-3 ]
  • [ 1192123-65-1 ]
Reference： [1]Patent: WO2009/129546,2009,A1
  • 84
  • [ 218600-44-3 ]
  • [ 1192123-46-8 ]
Reference： [1]Patent: WO2009/129546,2009,A1
  • 85
  • [ 218600-44-3 ]
  • [ 1192123-21-9 ]
Reference： [1]Patent: WO2009/129546,2009,A1
  • 86
  • [ 218600-44-3 ]
  • [ 1192123-78-6 ]
Reference： [1]Patent: WO2009/129546,2009,A1
  • 87
  • [ 67015-15-0 ]
  • [ 443104-14-1 ]
  • C35H49N3O5 [ No CAS ]
  • [ 218600-44-3 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; trimethylamine In dichloromethane at 20℃; Inert atmosphere; Compound 41: The stock solution of compound 35 and Et3N in CH2C12 [12.5 mL,containing compound 35 (2.29 mmol) and trimethylamine (9.19 mmol)j was treated with 3- methoxypropionamidoxime hydrochloride (516 mg, 3.33 mmol) and additional triethylamine (0.46 mL, 3.3 mmol). The mixture stirred overnight at room temperature. The resultant mixturewas diluted with EtOAc; washed with water, sat. aq. NaHCO3 and brine. The organic extract was dried with Na2SO4; filtered and concentrated. The residue was purified by column chromatography (silica gel, eluting with 0 to 10% MeOH in CH2C12) to give a mixture of compound 41 and compound 34 (1.22 g, 2.5:1 - 41:34) as a solid that was used without further purification.
Reference： [1]Current Patent Assignee: REATA PHARMACEUTICALS, INC. - WO2021/16191, 2021, A1 Location in patent: Page/Page column 58; 70; 98

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