Structure of 383135-47-5
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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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Search for reports by entering the product batch number.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 383135-47-5 |
Formula : | C10H12O4S |
M.W : | 228.27 |
SMILES Code : | CCS(=O)(=O)C1=CC=C(CC(O)=O)C=C1 |
MDL No. : | MFCD02664818 |
InChI Key : | FJOLLUNLZJLQMN-UHFFFAOYSA-N |
Pubchem ID : | 4329829 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.3 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 55.89 |
TPSA ? Topological Polar Surface Area: Calculated from |
79.82 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.21 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.69 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.19 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.47 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.24 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.56 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.35 |
Solubility | 1.02 mg/ml ; 0.00445 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.98 |
Solubility | 0.238 mg/ml ; 0.00104 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.9 |
Solubility | 0.287 mg/ml ; 0.00126 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 |
-6.49 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 |
0.56 |
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) |
1.91 |
* 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 |
---|---|---|
61% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; | General procedure: Iodine(18.80 g, 74.1 mmol) was added to 1-(2,5-dichlorophenyl)ethanone (10.67 ml,74.1 mmol) and thiourea (11.27 g, 148.0mmol). Thereaction mixture was stirred and heatedto 100 °C overnight. After cooling to room temperature, the reaction mixture was triturated with diethylether (about 50 mL) to remove any unreacted iodine and1-(2,5-dichlorophenyl)ethanone. Thesolid residue was put in cold distilled water (100 mL) and treated withammonium solution to pH 9-10. The precipitated thiazole was collected togive 4-(2,5-dichlorophenyl)-1,3-thiazol-2-amine (11.2 g, 62percentyield) as a yellow solid. MS(ES+) m/z 245.0, 247.0 (MH+).A solution of[4-(ethylsulfonyl)phenyl]acetic acid (0.239 g, 1.1 mmol), 4-(2,5-dichlorophenyl)-1,3-thiazol-2-amine(0.245 g, 1.0 mmol), EDC (0.230 g, 1.2 mmol) and HOBt (0.184 g, 1.2 mmol) in dichloromethane(DCM) (10 mL) was stirred at room temperature overnight. The mixture was pouredinto water, and extracted with DCM. The organic phase was washed with water andbrine, dried over anhydrous sodium sulfate, filtered and concentrated under reducedpressure to give the crude product. The crude was purified by mass directedautopreparation (MDAP) to afford N-[4-(2,5-dichlorophenyl)-1,3-thiazol-2-yl]-2-[4-(ethylsulfonyl)phenyl]acetamide(6a) (177 mg, 37percent yield) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; | ) Iodine(3.330 g, 13.1mmol) was added to 1-phenyl-1-butanone (1.947 g, 13.1 mmol) and thiourea (2.000 g, 26.3 mmol). The reactionmixture was stirred and heatedto 100 C overnight. After cooling to room temperature, the reaction mixture was triturated with diethylether (about 50 mL) to remove any unreacted iodine and 1-phenyl-1-butanone. Thesolid residue was put in cold distilled water (100 mL) and treated with ammoniasolution to pH 9-10. The precipitation was collectedto afford 5-ethyl-4-phenyl-1,3-thiazol-2-amine (2.650 g, 13.0 mmol, 99% yield) as a yellowsolid. It was directly used in the next step without further purification. MS(ES+) m/z 205.1 (MH+). A solution of 5-ethyl-4-phenyl-1,3-thiazol-2-amine (89 mg, 0.4 mmol),[4-(ethylsulfonyl)phenyl]acetic acid (100 mg, 0.4 mmol), EDC (101 mg, 0.5 mmol)and HOBt (81 mg, 0.5 mmol) in dichloromethane (DCM) (5 mL) was stirred at RT overnight. Solvent was removed under reduced pressure and the residuewas purified by MDAP to afford N-(5-ethyl-4-phenyl-1,3-thiazol-2-yl)-2-[4-(ethylsulfonyl)phenyl]acetamide(7b) (76 mg, 40% yield) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 12h; | Step-iii:2-(4-(ethylsulfonyl)phenylV To a 50 mL round bottom flask, were added <strong>[17583-10-7]2-amino-5,6-dihydrobenzo[d]thiazol-7(4H)-one</strong> (0.05 g, 0.297 mmol), 2-(4-(ethylsulfonyl)phenyl)acetic acid (0.067 g, 0.297 mmol) and dichloromethane (10 mL). To the same flask, EDCI.HC1 (0.0623 g, 0.327 mmol) and HOBt (0.044 g, 0.327 mmol) were added. The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was quenched with aqueous sodium bicarbonate. The reaction mixture was extracted with dichloromethane. The organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to get crude product. The crude product was purified by flash chromatography using 3 percent methanol in dichloromethane to get the title compound [10 mg, 9 percent]. *H NMR (300 MHz, CDCls): delta 9.46 (s, 1H), 7.92 (d, 2H), 7.54 (d, 2H), 3.94 (s, 2H), 3.18 (q, 2H), 2.89 (t, 2H), 2.61 (t, 2H), 2.19-2.15 (m, 2H), 1.32 (t, 3H); LC-MS: 379.1 [M+H]+. |
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