Structure of 139481-28-0
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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. : | 139481-28-0 |
Formula : | C22H17N3O4 |
M.W : | 387.39 |
SMILES Code : | O=C(OC)C1=CC=CC([N+]([O-])=O)=C1NCC2=CC=C(C3=CC=CC=C3C#N)C=C2 |
MDL No. : | MFCD09029084 |
InChI Key : | ZIRAEAZVSCADHC-UHFFFAOYSA-N |
Pubchem ID : | 15654651 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 29 |
Num. arom. heavy atoms | 18 |
Fraction Csp3 | 0.09 |
Num. rotatable bonds | 7 |
Num. H-bond acceptors | 5.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 110.49 |
TPSA ? Topological Polar Surface Area: Calculated from |
107.94 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.87 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.98 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.19 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.58 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.49 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.42 |
Log S (ESOL):? ESOL: Topological method implemented from |
-5.38 |
Solubility | 0.00163 mg/ml ; 0.0000042 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-6.99 |
Solubility | 0.00004 mg/ml ; 0.000000103 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-7.36 |
Solubility | 0.0000168 mg/ml ; 0.0000000434 mol/l |
Class? Solubility class: Log S scale |
Poorly 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 |
No |
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) |
No |
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) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.13 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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
3.09 |
* 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 |
---|---|---|
2-Tert-butoxy carbonylamino-3-nitro benzoic acid methyl ester (400 gm) was dissolved in toluene (2000 ml) and then added potassium carbonate (400 gm) at room temperature. 4-(2-cyanophenyl)benzyl bromide (400 gm) and Tetra-n-butylammonium bromide were added to the reaction mass. Gradually temperature raised to 80 to 85C. The reaction mass maintained for 12 hours at 80 to 85C. The reaction mass was cooled to room temperature and filtered on hiflo-bed. Collected the filtrate and concentrated to remove toluene. To the residue was added methanol (800 ml) and cooled to room temperature. The reaction mass was stirred for 4 hours at room temperature and filtered. Methanol (2900 ml) was added to the wet compound obtained and then added concentrated hydrochloric acid (725 ml) at room temperature. The reaction mass was heated to reflux and maintained for 3 hours at reflux. The reaction mass was further cooled to room temperature and filtered. Methanol (2900 ml) was added to the wet compound obtained and stirred for 45 minutes at room temperature. The separated solid was filtered and dried at 45 to 50C for 6 hours to obtain 450 gm of 2-(2'-cyanobiphenyl- 4-yl-methylamino)-3-nitro benzoic acid methyl ester. |
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