Structure of 96-72-0
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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. : | 96-72-0 |
Formula : | C6H5ClN2O4S |
M.W : | 236.63 |
SMILES Code : | NS(=O)(=O)C1=C(Cl)C=CC(=C1)[N+]([O-])=O |
MDL No. : | MFCD00035780 |
InChI Key : | ZAJALNCZCSSGJC-UHFFFAOYSA-N |
Pubchem ID : | 66784 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H317 |
Precautionary Statements: | P261-P280 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 5.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 51.27 |
TPSA ? Topological Polar Surface Area: Calculated from |
114.36 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.09 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.94 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.98 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.12 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-1.41 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.29 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.08 |
Solubility | 1.95 mg/ml ; 0.00823 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.93 |
Solubility | 0.279 mg/ml ; 0.00118 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.97 |
Solubility | 2.55 mg/ml ; 0.0108 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) |
No |
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 |
-7.08 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) |
2.25 |
* 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 |
---|---|---|
With bis(triphenylphosphine)palladium(II) dichloride; potassium carbonate; triphenylphosphine; In propan-1-ol; water; at 100℃; for 3h;Inert atmosphere; | 2-Chloro-5-nitrobenzenesulfonamide (674 mg, 2.85 mmol) and i-cyclopropyl-4-(4,4,5,5-tetramethyl-i,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.00 g, 4.27 mmol) were dissolved in npropanol (34 ml) and bis(triphenylphosphine)palladium(l I) dichioride (CAS 13965-03-2)(100 mg, 142 pmol) and triphenylphosphine (37.3 mg, 142 pmol) were added. Thereaction was purged with argon for 5 minutes and aq. potassium carbonate (5.7 ml, 1.0 M,5.7 mmol) was added. The reaction was heated at 100°C for 3h. Afterwards the mixturewas filtered over Celite and the solvent was removed under reduced pressure. Ethyl acetate and water were added. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over Whatmanfilter and the solvent was removed under reduced pressure.The crude was used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2-Chloro-5-nitrobenzenesulfonamide (674 mg, 2.85 mmol) and 1 -cyclopropyl-4-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 /-/-pyrazole (1 .00 g, 4.27 mmol) were dissolved in n- propanol (34 ml) and bis(triphenylphosphine)palladium(ll) dichloride (CAS 13965-03-2) (100 mg, 142 muetaetaomicronIota) and triphenylphosphine (37.3 mg, 142 muetaetaomicronIota) were added. The reaction was purged with argon for 5 minutes and aq. potassium carbonate (5.7 ml, 1.0 M, 5.7 mmol) was added. The reaction was heated at 100°C for 3h. Afterwards the mixture was filtered over Celite and the solvent was removed under reduced pressure. Ethyl acetate and water were added. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over Whatmanfilter and the solvent was removed under reduced pressure. The crude was used in the next step without further purification. (0458) 2-(1 -Cyclopropyl-1 /-/-pyrazol-4-yl)-5-nitrobenzenesulfonamide (1.17 g, 3.79 mmol) and 1 ,1 -dimethoxy-/V,/V-dimethylmethanamine (1 .0 ml, 7.6 mmol) were dissolved in DMF (25 ml) and the reaction was stirred at room temperature until completion of the reaction. The solvent was removed under reduced pressure and the crude was used without further purification in the next step. (0459) 2-(1 -Cyclopropyl-1 /-/-pyrazol-4-yl)-/V-[(dimethylamino)methylidene]-5- nitrobenzenesulfonamide (1.84 g, 5.06 mmol) was dissolved in THF (30 ml) and the flask was flushed with nitrogen. Palladium on charcoal (10percent loading, 53.9 g, 506 muetaetaomicronIota) was added and the flask was evacuated and subsequently flushed with hydrogen (1 bar). Stirring was continued at room temperature until completion of the reaction. The reaction mixture was filtered over Celite and the solvent was removed under reduced pressure. The crude was used without further purification in the next step (1.3 g, 53percent purity, 75percent yield over 3 steps). (0460) LC-MS (Method A): Rt = 0.70 min; MS (ESIpos): m/z = 334 [M+H]+ |
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