Structure of 59937-01-8
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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. : | 59937-01-8 |
Formula : | C12H11NO2S |
M.W : | 233.29 |
SMILES Code : | O=C(C1=CSC(C2=CC=CC=C2)=N1)OCC |
MDL No. : | MFCD06205115 |
InChI Key : | UKKGDCGESAFSJY-UHFFFAOYSA-N |
Pubchem ID : | 10036966 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 11 |
Fraction Csp3 | 0.17 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 63.64 |
TPSA ? Topological Polar Surface Area: Calculated from |
67.43 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.88 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.17 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.99 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.91 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.86 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.96 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.53 |
Solubility | 0.0691 mg/ml ; 0.000296 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.26 |
Solubility | 0.0129 mg/ml ; 0.0000554 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.3 |
Solubility | 0.0117 mg/ml ; 0.0000501 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 |
-5.47 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 |
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) |
2.82 |
* 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 |
---|---|---|
98% | With water; sodium hydroxide; In methanol; at 20℃; for 1.03h; | A solution of ethyl 2-phenylthiazole-4-carboxylate (Example 4B, 3.046 g, 13.06 mmol) in methanol (20 mL) was treated with a solution of NaOH (1.044 g, 26.1 mmol) in water (10 mL) added dropwise over 2 min and the resulting solution was stirred at room temperature for 1 h. The methanol was then evaporated under reduced pressure and the residual paste was diluted with a mixture of water (30 mL) and ethyl acetate (200 mL). The pH was adjusted to ~3 with concentrated hydrochloric acid, the organic phase was separated and the aqueous phase was re-extracted with ethyl acetate (2 x 150 mL). The combined organic extract was washed with brine (3 x 35 mL) and dried over anhydrous magnesium sulfate. After concentration of the solvent under reduced pressure, the solid residue obtained was dried in vacuo for 18 h to yield 2.629 g (98%) of the title compound as a white crystalline solid. LC (Method A): 1.842 min. HRMS(ESI) Anal.Calcd for C10H8NO2S [M+H]+ m/z 206.027; found 206.0266. 1H NMR (CDCL3, 400 MHz) delta ppm: 8.30 (s, 1H), 7.94 - 8.05 (m, 2H), 7.4 - 7.55 (m, 3H). |
94.9% | With sodium hydroxide; In methanol; at 20℃; for 4h; | General procedure: Sodium hydroxide (2N) was added to a solution of intermediate 2a-i (1 equiv.) in methanol at ambient temperature. The reaction mixture was stirred for 4h and the methanol was removed by rotary evaporation. The resultant mixture was adjusted to pH=5-6 with 1N HCl solution. The precipitated white solid was collected by filtration and dried to give the carboxylic acid intermediate (1a-i). |
80% | With lithium hydroxide monohydrate; In tetrahydrofuran; methanol; water; at 20℃; for 4h; | General procedure: To a solution of the obtained ethyl ester intermediate (1 equiv) in 2:3:1 THF/MeOH/H2O (18 ml) was added LiOH·H2O (1.5 equiv). After stirring at room temperature for 4 h, the volatiles were removed under reduced pressure. The residue was acidified with 1N hydrochloric acid solution, and then filtered and the filter cake was washed with 5 mL of water, dried in vacuum to afford a white powder. Recrystallization from 75% EtOH gave the desired compounds 1-8. |
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