Structure of 54381-08-7
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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. : | 54381-08-7 |
Formula : | C12H10N2O3 |
M.W : | 230.22 |
SMILES Code : | OC1=CC=C(NC2=CC=CC=C2[N+]([O-])=O)C=C1 |
MDL No. : | MFCD00239470 |
InChI Key : | HSDSBIUUVWRHTM-UHFFFAOYSA-N |
Pubchem ID : | 3846708 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 17 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 66.83 |
TPSA ? Topological Polar Surface Area: Calculated from |
78.08 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.78 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.3 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.04 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.6 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.02 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.95 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.67 |
Solubility | 0.0491 mg/ml ; 0.000213 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.62 |
Solubility | 0.00558 mg/ml ; 0.0000242 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.78 |
Solubility | 0.0383 mg/ml ; 0.000166 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) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
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 |
-5.36 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 |
3.0 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) |
2.59 |
* 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 |
---|---|---|
82.2% | Procedure: A, B, C and D placed in a 2 liter 3 neck flask equipped with a stirrer and a reflux condenser. The reaction is heated by means of a heating mantle, with stirring, to reflux (about 115 C) for 23 hours. The reaction is allowed to cool to room temperature and the resulting mixture filtered. Solid that is obtained is a salt residue and is discarded. The filtrate is evaporated of solvent on a rotary evaporator. The resulting solid is recrystallized from aqueous ethanol (50/50). Weight of pure product obtained = 189 g. m.p. = 144-145.5 C., % yield = 82.2%. | |
75% | Procedure: A, B, C and D are mixed in a small autoclave and heated to 170-180 C for 28 hours. The reaction mixture was then cooled and filtered. The filtrate was evaporated of solvent on a rotovac and the resulting solid was recrystallized from a mixture of ethanol and water (50/50). 33.3 grams (75% yield) of a red brown crystalline material was obtained having a melting point in a range of 140-141 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride;palladium-carbon; In methanol; dimethyl sulfoxide; ethyl acetate; | Preparation 14 2-Butyl-3-(4-hydroxyphenyl)benzimidazole A mixture of (8.0 g, 51 mmol, 1.0 eq) 1-chloro-2-nitrobenzene and (5.54 g, 51 mmol, 1.0 eq) 4-aminophenol in 40 ml of dry dimethylsulfoxide was heated to reflux for 18 hours. The reaction mixture was cooled, poured into 400 ml of 0.1N HCl and 400 ml ethyl acetate, stirred, and filtered through celite. The filtrate layers were separated, and the aqueous layer was extracted with ethyl acetate. The ethyl acetate extracts were combined, washed twice with H2O, once with brine, dried over MgSO4, and concentrated to give 8 g of a dark oil. Silica gel chromatography eluding with 20% ethyl acetate/hexane gave 1.63 g, 14%, of a red solid. A mixture of (1.6 g, 6.89 mmol, 1.0 eq) <strong>[54381-08-7]4-N-(2-nitrophenyl)amino phenol</strong> and 800 mg of 10% Pd/C in 100 ml ethyl acetate was placed on a Parr hydrogenation apparatus and shaken under 50 psi H2 for 3 hours. The mixture was filtered through celite, concentrated in vacuo , and chromatographed on a silica gel column eluding with 50% ethyl acetate/hexane to give 1.3 g, 94%, of an orange-yellow solid. A mixture of (600 mg, 3.00 mmol, 1.0 eq) 4-N-(2-aminophenyl)amino phenol and 10 ml valeric anhydride was heated to reflux for 18 hours. The mixture was taken up in 50 ml of methanol, basified with 2N NaOH to pH 10, and stirred 1 hour at room temperature. The reaction mixture was then neutralized and extracted twice with ethyl acetate. The ethyl acetate extracts were combined, washed twice with H2O, once with brine, dried over MgSO4 and concentrated to give 1 g of an oil. Silica gel chromatography eluding with 21/2% CH3OH-CH2Cl2 gave 124 mg, 16%, solid. M.P.: 192-194C. |