Structure of 41959-35-7
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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. : | 41959-35-7 |
Formula : | C8H9N3O2 |
M.W : | 179.18 |
SMILES Code : | [N+](=O)([O-])C2=CC=C1NCCNC1=C2 |
MDL No. : | MFCD03788188 |
InChI Key : | ZVDCYZVYRXZJQF-UHFFFAOYSA-N |
Pubchem ID : | 10197942 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 57.63 |
TPSA ? Topological Polar Surface Area: Calculated from |
69.88 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.03 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.49 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.29 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.01 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.7 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.42 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.17 |
Solubility | 1.23 mg/ml ; 0.00684 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.56 |
Solubility | 0.488 mg/ml ; 0.00272 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.43 |
Solubility | 0.664 mg/ml ; 0.00371 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 |
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) |
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 |
-6.34 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 |
1.0 |
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) |
2.36 |
* 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 |
---|---|---|
57% | With dmap; triethylamine; In dichloromethane; at 20℃; for 2.0h; | A mixture of 1 ,2,3,4-tetrahydro-6-nitro- quinoxaline (22.324 mmol), di-tert-butyl dicarbonate (22.324 mmol), triethylamine (44.648 mmol) and 4-dimethylaminopyridine (4.465 mmol) in DCM (40 ml) was stirred at room temperature for 2 hours. The reaction mixture was poured onto water and extracted with DCM. The organic layer was decanted, dried over MgSO4, filtered and evaporated to dryness. The residue (7.7g) was purified by HPLC (9Og SiO2 15/40 mum - eluent: DCM 100 to DCM/MeOH 99/1 ). The pure fractions were collected and evaporated to dryness, yielding 3.55g (57%) of intermediate 33. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61.43% | With dmap; triethylamine; In dichloromethane; at 0 - 20℃; | To a stirred solution of 789 <strong>[41959-35-7]6-nitro-1,2,3,4-tetrahydroquinoxaline</strong> (0.5 g, 2.79 mmol, 1.0 eq) in 743 DCM (20 mL) was added 155 triethylamine (1.17 mL, 8.37 mmol, 3.0 eq) and 790 DMAP (68 mg, 0.558 mmol, 0.2 eq) at rt. The resulting mixture was allowed to cool to 0 C. followed by addition of 482 di-tert-butyl dicarbonate (1.41 mL, 6.139 mmol, 2.2 eq), the reaction mixture was stirred at RT for overnight. The progress of reaction was monitored by LCMS. The reaction mixture was diluted with DCM (50 mL), and washed with water (2×50 mL) dried over Na2SO4, filtered and concentrated and purified by combi flash [silica gel 100-200 mesh; elution 0-35% 19 EtOAc in 20 Hexane] to afford the desired compound 791 di-tert-butyl 6-nitro-2,3-dihydroquinoxaline-1,4-dicarboxylate (0.65 g, 61.43%) as yellow viscous. (0776) LCMS: (M+1)+380.4. |
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