Structure of 14719-83-6
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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. : | 14719-83-6 |
Formula : | C8H6ClNO4 |
M.W : | 215.59 |
SMILES Code : | C1=C(C=CC(=C1[N+](=O)[O-])Cl)C(OC)=O |
MDL No. : | MFCD00016989 |
InChI Key : | XRTKWPWDSUNLHS-UHFFFAOYSA-N |
Pubchem ID : | 735797 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 51.55 |
TPSA ? Topological Polar Surface Area: Calculated from |
72.12 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.7 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.31 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.03 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.43 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.22 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.54 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.75 |
Solubility | 0.382 mg/ml ; 0.00177 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.46 |
Solubility | 0.0743 mg/ml ; 0.000345 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.48 |
Solubility | 0.717 mg/ml ; 0.00333 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 |
-5.98 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 |
2.0 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) |
1.86 |
* 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 |
---|---|---|
In N,N-dimethyl-formamide; at 70℃; for 8h; | General procedure: To a solution of methyl-4-chloro-3-nitrobenzoate (8.6g, 0.04mol) in DMSO (60mL) was added 0.08mol 4-methylaniline (or benzylamine in DMF). The reaction was heated to 70C and stirred for 8h. The reaction was cooled to 22C and poured into water (1000mL). a precipitate formed, which was collected by filtration and washed with cold water to afford the product (9.4g, 82%) as an orange solid. 3-nitro-4-phenylaminobenzoic acid methyl ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step j. Methyl 3-nitro-4-chlorobenzoate (COMPOUND XIII) (see above for synthesis of 4-chloro-anti-CG) (1 equivalent) is treated with sodium methoxide (1.1 equivalent) in methanol with heating to produce the methyl 3-nitro-4-methoxybenzoate (COMPOUND XIV) which is purified by column chromatography and/or crystallization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With potassium carbonate; In N,N-dimethyl-formamide; at 20.0℃; for 16.0h; | To a solution of methyl 4-chloro-3-nitrobenzoate (4.53 g, 0.021 mol) and methyl 3- mercaptopropionate (2.78 g, 0.023 mol) in DMF (15 mL) was added anhydrous potassium carbonate (0.023 mol, 3.17g). After stirring at ambient temperature for 16 h, the reaction was quenched with ice water. The precipitated product was filtered, washed well with water and dried under vacuum to give the title compound as a bright yellow solid (6.11 g,97%) which was used without further purification: LC/MS (ES) m/z 300 (M+H)+ |
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