Structure of 43156-48-5
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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. : | 43156-48-5 |
Formula : | C12H12N2S |
M.W : | 216.30 |
SMILES Code : | NC1=C(N)C=C(SC2=CC=CC=C2)C=C1 |
MDL No. : | MFCD01073766 |
InChI Key : | YLEPPBFOGUYOEI-UHFFFAOYSA-N |
Pubchem ID : | 3016417 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 65.82 |
TPSA ? Topological Polar Surface Area: Calculated from |
77.34 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.85 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.72 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.02 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.95 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.15 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.54 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.35 |
Solubility | 0.0956 mg/ml ; 0.000442 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.0 |
Solubility | 0.0217 mg/ml ; 0.0001 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.31 |
Solubility | 0.0105 mg/ml ; 0.0000485 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 |
-5.69 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 |
1.0 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) |
2.06 |
* 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 |
---|---|---|
21.2 g | With platinum on activated charcoal; hydrogen; In ethanol; at 70 - 90℃; under 7500.75 - 15001.5 Torr; for 8.0h; | A 500ml four-necked flask equipped with a thermometer and a stirring device, was added in a weight ratio of 2-nitro-phenylsulfanyl aniline ethanol 4 times, 36.9g of 2-nitro-phenylsulfanyl aniline, weight ratio of 2-nitro-phenylsulfanyl aniline 0.1 times platinum on carbon, turned stirred and heated to 70-90 hydrogen atmosphere, to a pressure 1.0-2.0MPa, hydrogenation reaction of 8 hours, platinum on carbon catalyst was filtered off, The ethanol was evaporated to give 4-phenylthio-o-phenylenediamine 21.2g, was used directly in the next reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In N-methyl-acetamide; water; potassium carbonate; acetic acid; | EXAMPLE 40 5-Phenylmercapto-benzimidazole-2-methyl-carbaminate 20.9 g Of S-methyl-thiourea were reacted as described in Example 1 in 27 ml of water with 13.5 ml of chloroformic acid methyl ester, 45.7 ml of 25percent sodium hydroxide solution, 27 ml of glacial acetic acid, 100 ml of water and 29 g of 3,4-diaminodiphenyl-thioether. After recrystallization from a mixture of glacial acetic acid and methanol, 14 g of 4-phenylmercapto-benzimidazole-2-methyl-carbaminate melting at 233°C were obtained. For preparing the 3,4-diamino-diphenyl-thioether used as starting material, 22 g of thiophenol were heated for 6 hours under reflux in 100 ml of dimethylformamide with 5-chloro-2-nitroaniline in the presence of 30g of anhydrous potassium carbonate. The whole was allowed to cool, 100 ml of water were added and the crude product was filtered off with suction. After recrystallization from isopropanol, 38 g of 3-amino-4-nitro-diphenyl-thioether melting at 112°C were obtained. 38 g Of the 3-amino-4-nitro-diphenyl-thioether so obtained were added to a solution prepared by dissolving 180 g of crystal-water containing stannous chloride in 200 ml of glacial acetic acid and saturation with gaseous hydrochloric acid at room temperature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With stannous chloride; sodium; potassium hydrogencarbonate; In hydrogenchloride; chloroform; | [This material may also be obtained by reaction of 2-acetamido-4-chloro-1-nitrobenzene with sodium phenylmercaptide essentially as described above for the free amine.] 3.5 G. of <strong>[43156-47-4]2-amino-4-phenylthio-1-nitrobenzene</strong> in 8 ml. conc. hydrochloric acid is treated with a solution of 16 g. of stannous chloride in 8 ml. conc. hydrochloric acid. The mixture is heated for 1 hour on a steam bath, cooled and treated with potassium bicarbonate and chloroform. The mixture is filtered and the chloroform layer evaporated. The residue is triturated with hot cyclohexane yielding 1,2-diamino-4-phenylthiobenzene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; water; acetone; | <strong>[43156-47-4]2-amino-4-phenylthio-1-nitrobenzene</strong> is treated with 2 g. iron powder and 1 g. ferrous sulfate in a refluxing mixture of 160 ml. methanol and 40 ml. water for six hours. The mixture is filtered and concentrated. The residue is extracted with benzene and 1,2-diamino-4-phenylthiobenzene isolated as a gum. 1.6 G. 1,2-diamino-4-phenylthiobenzene is dissolved in 30 ml. acetone and treated with 4 g. methoxycarbonyl isothiocyanate at room temperature overnight. The mixture is concentrated under vacuum and the residue triturated with ether. Recrystallization from methanol-chloroform yields pure 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-phenylthiobenzene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86.8% | With hydrogenchloride; In toluene; at 20 - 55℃; for 2h; | 355.0 g of methyl cyanamidoformate which was cryopreserved in the step 1 was added to a solution of 545.5 g of the intermediate 4 in toluene in the step 5 at room temperature.Raise the temperature to 45-55 C, and add 67.65 g of concentrated hydrochloric acid (36.5%) under stirring. After the addition is completed, stir at 55-60 C for 2 hours.After completion of the reaction, the temperature was lowered to 10-15 C, filtered, and the filter cake was washed with 202.5 g of methanol.The moisture product was dried under hot air at 70 C for 6 hours to obtain 124.5 g of dry product, the purity was 99.7%, and the total yield of the product was 86.8%. |
A400978 [1019453-85-0]
2-((2,4-Dimethylphenyl)thio)aniline
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