Structure of 402-46-0
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 402-46-0 |
Formula : | C6H6FNO2S |
M.W : | 175.18 |
SMILES Code : | NS(=O)(=O)C1=CC=C(F)C=C1 |
MDL No. : | MFCD00025384 |
InChI Key : | LFLSATHZMYYIAQ-UHFFFAOYSA-N |
Pubchem ID : | 120231 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P301+P312+P330-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 37.39 |
TPSA ? Topological Polar Surface Area: Calculated from |
68.54 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.01 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.71 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.97 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.73 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.41 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.97 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.71 |
Solubility | 3.41 mg/ml ; 0.0195 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.73 |
Solubility | 3.28 mg/ml ; 0.0187 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.24 |
Solubility | 1.01 mg/ml ; 0.00577 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) |
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 |
-6.86 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 |
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) |
1.8 |
* 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 |
---|---|---|
41% | With caesium carbonate; In dimethyl sulfoxide; at 168℃;Inert atmosphere; | A round bottom flask was charged with 4-fluorobenzenesulfonamide (945 mg, 5.4 mmol), L-proline-t-butyl ester HCl (1.24 g, 6 mmol), and cesium carbonate (4.2 g, 12 mmol) and suspended in 10 ml anhydrous DMSO. The mixture was placed in a preheated oil bath and equipped with a condenser, and heated under nitrogen at 168 oC overnight. HPLC analysis of the mixture indicated complete conversion of the benzenesulfonamide starting material. The mixture was transferred to an Erlenmeyer flask, the reaction pot was diluted with 2 ml of concentrated HCl, and added to the mixture in the Erlenmeyer flask and allowed to stir. The aqueous was then extracted with ethyl acetate (3 x 50 ml), and the combined extracts were washed with water (3 x 15 ml). The volatiles were then removed under vacuum, and 1.24 g of crude material was obtained. The desired intermediate was isolated using MPLC, utilizing a 0 to 60% gradient of acetone in DCM, affording 0.56 g (41%):1H NMR (300 MHz, DMSO-d6)d ppm 7.58 (d, J= 9.0 Hz, 2H), 6.98 (s, 2H), 6.54 (d, J= 9.0 Hz, 2H), 4.28 (d, J= 8.4 Hz, 1H), 2.35-2.22 (m, 2H), 2.04-1.96 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In dimethyl sulfoxide; at 168℃;Inert atmosphere; | A round bottom flaskwas charged with 4-fluorobenzenesulfonamide (945 mg, 5.4 mmol), L-proline-t-butyl ester HCl(1.24 g, 6 mmol), and cesium carbonate (4.2 g, 12 mmol) and suspended in 10 mL anhydrousDMSO. The mixture was placed in a preheated oil bath and equipped with a condenser, and10 heated under nitrogen at 168 C overnight. HPLC analysis of the mixture indicated completeconversion of the benzenesulfonamide starting material. The mixture was transferred to anErlenmeyer flask, the reaction pot was diluted with 2 mL of concentrated HCl, and added to themixture in the Erlenmeyer flask and allowed to stir. The aqueous was then extracted with ethylacetate (3 x 50 mL ), and the combined extracts were washed with water (3 x 15 mL ). The15 volatiles were then removed under vacuum, and 1.24 g of crude material was obtained. Thedesired intermediate was isolated using MPLC, utilizing a 0 to 60% gradient of acetone in DCM,affording 35 (0.56 g, 41 %): 1H NMR (300 MHz, DMSO-d6) 8 ppm 7.58 (d, J= 9.0 Hz, 2H), 6.98(s, 2H), 6.54 (d, J= 9.0 Hz, 2H), 4.28 (d, J= 8.4 Hz, 1H), 2.35-2.22 (m, 2H), 2.04-1.96 (m, 2H). |
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