Structure of 1136-86-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 1136-86-3 |
Formula : | C11H14O4 |
M.W : | 210.23 |
SMILES Code : | CC(C1=CC(OC)=C(OC)C(OC)=C1)=O |
MDL No. : | MFCD00008738 |
InChI Key : | VUGQIIQFXCXZJU-UHFFFAOYSA-N |
Pubchem ID : | 14345 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.36 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 56.11 |
TPSA ? Topological Polar Surface Area: Calculated from |
44.76 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.36 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.61 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.91 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.84 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.25 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.79 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.19 |
Solubility | 1.36 mg/ml ; 0.00646 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.16 |
Solubility | 1.45 mg/ml ; 0.00689 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.12 |
Solubility | 0.158 mg/ml ; 0.000753 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.44 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.79 |
* 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 |
---|---|---|
63% | With zirconium(IV) chloride; methoxybenzene; In dichloromethane; at 40℃; for 48h;Sealed tube; | 128 mg (0.5 mmol)3 ', 4', 5''-trimethoxyacetophenone, 117 mg zirconium chloride(ZrCl4) (0.5 mmol)218 yL anisole (2 mmol) and 3 mL of CH2C12 were added to 10 mL of the reaction tube, sealed,40 C for 48 h. After the reaction was stopped, the mixture was extracted with ethyl acetate, washed with saturated brine,Dried over anhydrous sodium sulfate, filtered, the filtrate was distilled under reduced pressure, purified by silica gel column chromatography,The product acetosyringone (3 ', 5'-dimethoxy-4'-hydroxyacetophenone) was about 62 mg in a yield of 63% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With sodium hydroxide; In ethanol; water; at 27℃; for 4.0h; | Example 3(E)-3-(6-(trifluoromethyl) imidazo [2,1- b] tmazol-5-yl)-l-(3,4,5-trimethoxyphenyl) prop- 2-en-l-one (7f)To a stirred solution of trimethoxy acetophenone (210 mg, 1.0 mmol) and a 6- (trifluoromethyl) imidazo [2,1-b] thiazole-5-carbaldehyde (220 mg, 1.0 mmol) in ethanol (20ml) 10% aqueous solution of NaOH was added (5ml). The reaction mixture was stirred at room temperature 27C for 4 h and the reaction was monitored by TLC using ethyl acetate-hexane (3:7) as a solvent system. The solvent was evaporated under vacuum then the residue was dissolved in ethylacetate / water. The organic layer was washed with brine and evaporated. This was further purified by column chromatography using ethyl acetate: hexane (2:8) as a solvent system to obtain the pure product (7f) as yellow solid (329 mg, 80% yield). Mp: 177-180 C lH NMR (CDC13, 300 MHz), delta 3.94-3.96 (b, 9H), 7.17 (d, 1H, J = 15.86 Hz), 7.21 - 7.22 (b, 2H), 7.33 (d, 1H ,J= 5.86 Hz), 7.83 (d, 1H, J= 4.53 Hz ), 7.90 (d, 1H J= 15.86 Hz), ESI-MS:413.38 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In ethanol; at 20℃; for 24h; | General procedure: The relevant N-methyl intermediate (3a-c, 2 mmol), acetophenonederivate (2 mmol) and potassium hydroxide (6 mmol) wasdissolved in ethanol (20 mL) and stirred for 24 h. Then the reactionmixture was filtered and washed with water and cold ethanol. Thecrude product was purified by recrystallization from ethanol anddichloromethane to give pure chalcone (4a-q) with yields of34.2-93.1%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In ethanol; at 20℃; for 24h; | General procedure: The relevant N-methyl intermediate (3a-c, 2 mmol), acetophenonederivate (2 mmol) and potassium hydroxide (6 mmol) wasdissolved in ethanol (20 mL) and stirred for 24 h. Then the reactionmixture was filtered and washed with water and cold ethanol. Thecrude product was purified by recrystallization from ethanol anddichloromethane to give pure chalcone (4a-q) with yields of34.2-93.1%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | General procedure: NaOH (2.0mmol) was added to a solution of 3,4,5-trimethoxyacetophenone (1.2mmol) in methanol. After the mixture was stirred for 15min, substituted benzaldehyde (1.0mmol) was added. The reaction mixture was stirred for 10h and filtered to give the title compounds. | |
71% | With potassium hydroxide; In methanol; water; at 0 - 20℃; | An aqueous solution of 50% KOH (20mL) was added dropwise to a stirred solution of 3′,4′,5′-trimethoxyacetophenone (1, 2.1g, 10.0mmol) and <strong>[31680-08-7]4-methoxy-3-nitrobenzaldehyde</strong> (2, 1.8g, 10.0mmol) in methanol (35mL) at 0C. The resulting mixture was stirred at the same temperature for overnight and monitored by TLC. After completion of reaction, the mixture was poured into water and adjusted to pH=2 with 2N HCl. The precipitated solid was filtered, washed with water and dried to offer the crude product which was purified by chromatography on silica gel eluted with petroleum ether/ethyl acetate (V:V=4:1, 3:1, 2:1) to give the desired compound as a yellow solid (yield: 2.65g, 71.0%). 1H NMR (300MHz, CDCl3) δ 8.17 (d, J=2.0Hz, 1H), 7.80-7.73 (m, 2H), 7.43 (d, J=15.6Hz, 1H), 7.28 (s, 2H), 7.15 (d, J=8.8Hz, 1H), 4.02 (s, 3H), 3.95 (d, J=4.6Hz, 9H). 13C NMR (100MHz, CDCl3) δ 188.42, 154.12, 153.22, 142.80, 141.62, 139.96, 134.50, 133.13, 127.64, 124.71, 121.95, 113.88, 106.17, 60.99, 56.79, 56.47. IR (KBr): 3451, 3065, 2996, 2952, 1653, 1577, 1530, 1457, 1414, 1353, 1276, 1161, 1128, 1002, 771cm-1. Elemental analysis calcd (%) for C19H19NO7: C, 61.12; H, 5.13; N, 3.75; found: C, 61.23; H, 5.24; N, 3.51. HR-MS (m/z) (ESI): calcd for C19H19NO7 [M+H+]: 374.12398; found: 374.11838. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With iodine; In dimethyl sulfoxide; at 110℃; | General procedure: I2 (362.25 mg, 1.43 mmol, 1.1 eq) was added to a mixture of 2j(272.77 mg, 1.3 mmol, 1 eq) and DMSO (3 mL). The solution wasstirred at 110C, then 1a1u (1 eq) in 3 mL DMSO was addeddropwise to the mixture during 1 h. After the complete disappearanceof the starting material, a sodium thiosulfate solution(0.2 g Na2S2O3 in 12 mL water) was added dropwise to the reactionsystem. Filtration and drying, the residue was purified by silica gelchromatography to yield the desired products 4a-4u. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With sodium hydroxide; In dimethyl sulfoxide; at 20℃; | General procedure: To a solution of 3,3-bis(methylsulfanyl)methylenemalononitrile 1 (1.70 g, 10 mmol) in 20 mL of DMSO, keton 2a - j (10 mmol) and powdered sodium hydroxide (0.8 20 mmol) were added, and the mixture was magnetically stirred for 4 - 5 h at room temperature. After addition of 300 mL of water to the mixture, the solution was stirred for 12 h at room temperature. The formed precipitate was collected by filtra- tion and washed several times with water. After drying under air, the formed product was recrystallized using methanol or ethanol to obtain the pure products. |