Structure of 55305-43-6
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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. : | 55305-43-6 |
Formula : | C14H12N2O2S |
M.W : | 272.32 |
SMILES Code : | O=S(C1=CC=C(C)C=C1)(N(C#N)C2=CC=CC=C2)=O |
MDL No. : | MFCD00159358 |
InChI Key : | CIIFNSIDKZSDBR-UHFFFAOYSA-N |
Pubchem ID : | 4465625 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 19 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.07 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 73.17 |
TPSA ? Topological Polar Surface Area: Calculated from |
69.55 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.38 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.04 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.75 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.8 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.43 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.48 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.71 |
Solubility | 0.0527 mg/ml ; 0.000194 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.17 |
Solubility | 0.0186 mg/ml ; 0.0000682 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.65 |
Solubility | 0.00611 mg/ml ; 0.0000224 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) |
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) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.8 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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.54 |
* 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 |
---|---|---|
General procedure: In an Erlenmeyer flask, the aniline (10.0 mmol) was dissolved in an aqueous solution of H4BF4 (50%, 5.0 mL,40.0 mmol) and a saturated solution of sodium nitrite (760 mg, 11.0 mmol) was added dropwise at 0 C. The excess oxidant was removed by the addition of urea. Then, the precipitated diazonium salt was filtered off and dissolved in a small amount of acetone. Diethyl ether was added to the clear solution, causing the precipitation of the arenediazonium tetrafluoroborate, which was filtered off and washed with diethyl ether (3×10.0 mL). The arenediazonium tetrafluoroborate was dried in vacuo (10-3 mbar) for 10 minutes and was then directly used without further purification. (II) General synthesis of N-cyano-N-phenyl-p-methylbenzenesulfonamide(NCTS): (see reference 2) Dry 250 ml Schlenk flask was a solution of phenylurea (10.9 g, 8 mmol) in pyridine (54 mL). The flask was stirred in room temperature water bath. p-Toluenesulfonylchloride (52.8 g, 27.7 mmol) was added potion wise over 5 minutes. The reaction mixture was stirred for another additional 20 minutes and poured into to ice-cooled water (400 mL) with mechanical stirring. Precipitate formed during mechanical stirring was filtered and then washed with water. The crude product was treated with 50 ml of ethanol and precipitated from the same solvent. The precipitate was purified with column chromatography using heptane:EtOAc (15:1) as eluent to yield N-cyano-N-phenyl-p-methylbenzenesulfonamide as colorless solid (16.5 g, 76%). (III) General synthesis of aryl nitriles from the corresponding arenediazonium salts. To a solution of arenediazonium tetrafluoroborate (0.5 mmol) in EtOH (3.0 mL) was added NCTS (272 mg, 1.0 mmol), Pd(OAc)2 (16.8 mg, 0.075 mmol), Ag2CO3 (68.7mg, 0.25 mmol). The mixture was stirred at 58 for 15 h under air atmosphere. Then the reaction mixture was cooled to room temperature and filtered through a pad of celite (1.0 g) and rinsed with CH2Cl2 (10.0 mL). The resulting organic solution was concentrated under reduced pressure and further purified by flash chromatography (SiO2, petroleum ether/EtOAc gradient), yielding the corresponding aryl nitriles. |
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