Structure of 6963-62-8
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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. : | 6963-62-8 |
Formula : | C12H12N2O2 |
M.W : | 216.24 |
SMILES Code : | CCOC(=O)C1=NNC=C1C1=CC=CC=C1 |
MDL No. : | MFCD01927509 |
InChI Key : | BQUUXGPEWAUSLS-UHFFFAOYSA-N |
Pubchem ID : | 244544 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 11 |
Fraction Csp3 | 0.17 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 60.11 |
TPSA ? Topological Polar Surface Area: Calculated from |
54.98 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.87 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.39 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.25 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.61 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.74 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.17 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.93 |
Solubility | 0.253 mg/ml ; 0.00117 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.19 |
Solubility | 0.141 mg/ml ; 0.000652 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.24 |
Solubility | 0.0124 mg/ml ; 0.0000574 mol/l |
Class? Solubility class: Log S scale |
Moderately 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 |
-5.92 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) |
2.3 |
* 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 |
---|---|---|
35% | With ethanol; sodium ethanolate; for 1.0h; | General procedure: To a stirred solution of arylidenemalonate 4 (0.5 mmol) and a -diazo- b -ketosulfone 2 (143 mg, 0.6 mmol, 1.2 equiv) in dry EtOH(5 mL) was added Cs2CO3 (245 mg, 0.75 mmol, 1.5 equiv) at 0C andthe resulting mixture was stirred until the reaction was complete(monitored by TLC). Then the reaction mixture was concentrated invacuo and the crude residue was directly subjected to silica gel column chromatography (pet ether/ethyl acetate: 8/2) to affordpure pyrazole carboxylate 5. |
18% | With ethanol; sodium ethanolate; for 5.0h; | General procedure: To a stirred solution of arylidenemalonate 4 (0.5 mmol) and a -diazo- b -ketosulfone 2 (143 mg, 0.6 mmol, 1.2 equiv) in dry EtOH(5 mL) was added Cs2CO3 (245 mg, 0.75 mmol, 1.5 equiv) at 0C andthe resulting mixture was stirred until the reaction was complete(monitored by TLC). Then the reaction mixture was concentrated invacuo and the crude residue was directly subjected to silica gel column chromatography (pet ether/ethyl acetate: 8/2) to affordpure pyrazole carboxylate 5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With ethanol; caesium carbonate; for 4.0h; | General procedure: To a stirred solution of arylidenemalonate 4 (0.5 mmol) and a -diazo- b -ketosulfone 2 (143 mg, 0.6 mmol, 1.2 equiv) in dry EtOH(5 mL) was added Cs2CO3 (245 mg, 0.75 mmol, 1.5 equiv) at 0C andthe resulting mixture was stirred until the reaction was complete(monitored by TLC). Then the reaction mixture was concentrated invacuo and the crude residue was directly subjected to silica gel column chromatography (pet ether/ethyl acetate: 8/2) to affordpure pyrazole carboxylate 5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With ethanol; sodium ethanolate; for 1.5h; | General procedure: To a stirred solution of 7 (0.5mmol, 1 equiv) and alpha-diazo-beta-ketosulfone 2 (143mg, 0.6mmol, 1.2 equiv) in dry EtOH (5mL) was added NaOEt (51mg, 0.75mmol, 1.5 equiv) at 0C and the resulting mixture was stirred at the same temperature until the reaction was complete (monitored by TLC). Then the reaction mixture was concentrated in vacuo and the crude residue was directly subjected to silica gel column chromatography (pet ether/ethyl acetate: 8/2) to afford pure 3, 5 or 8. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With ethanol; caesium carbonate; at 80.0℃; for 0.25h;Microwave irradiation; | General procedure: In a 10mL microwave glass vial containing EtOH (1mL), was added pyrazoline 6 (0.1mmol) followed by Cs2CO3 (16.5mg, 0.05mmol, 0.5 equiv) and the resulting mixture was subjected to microwave irradiation for 10-15minat 80C until the completion of reaction (monitored by TLC). After removal of EtOH in vacuo, the residue was treated with water (10mL) and the aqueous layer was extracted with EtOAc (2×10mL). The combined organic layer was dried over anhydrous Na2SO4, filtered and the filtrate was then concentrated in vacuo. The residue was recrystallized from EtOAc/hexane (1:1) to obtain pure 5 in quantitative yields. |
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