Structure of 2810-04-0
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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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CAS No. : | 2810-04-0 |
Formula : | C7H8O2S |
M.W : | 156.20 |
SMILES Code : | O=C(C1=CC=CS1)OCC |
MDL No. : | MFCD00005436 |
InChI Key : | JZGZKRJVTIRPOK-UHFFFAOYSA-N |
Pubchem ID : | 76052 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 5 |
Fraction Csp3 | 0.29 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 40.41 |
TPSA ? Topological Polar Surface Area: Calculated from |
54.54 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.25 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.33 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.92 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.25 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.66 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.08 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.45 |
Solubility | 0.556 mg/ml ; 0.00356 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.11 |
Solubility | 0.12 mg/ml ; 0.000768 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.13 |
Solubility | 1.15 mg/ml ; 0.00736 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) |
Yes |
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 |
-5.6 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) |
2.1 |
* 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 |
---|---|---|
78% | With sodium hydride; In 1,4-dioxane; for 2h;Reflux; | General procedure: A methyl ketone (1 eq.) was added to dry 1,4-dioxane and NaH (60 % oil suspension, 5eq.) was added in portions to the mixture in an ice-bath. The resulting mixture was stirred atroom temperature for 1 h. The required ester (5 eq.) was added to the mixture and refluxed for1 h. After cooling, 10 % HCl solution was added to the reaction mixture and extracted withCH2Cl2 (3×20 mL). The crude product was dried over MgSO4. Recrystallization or columnchromatography gave the product, which was dried in vacuo (25 C, 0.5 mbar), affordingspectroscopically pure product.12 More details of the syntheses of the individual products andtheir spectral data are given in the Supplementary material to this paper. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.54 g (93%) | With sodium; In ethanol; | EXAMPLE 40 3-(2-Thenoyl)-<strong>[5654-97-7]7-azaoxindole</strong>-1-N-t-butylcarboxamide 3-(2-Thenoyl)-<strong>[5654-97-7]7-azaoxindole</strong> was first prepared according to the procedure of Example 1B, using <strong>[5654-97-7]7-azaoxindole</strong> (1.5 g, 11.2 mmol), sodium (1.3 g, 56.5 mmol), ethanol (25 mL), and ethyl-thiophene-2-carboxylate (3 mL, 22.3 mmol). Yield: 2.54 g (93%). The title compound was prepared from 3-(2-thenoyl)-<strong>[5654-97-7]7-azaoxindole</strong> according to the procedure of Example 1C, using 3-(2-thenoyl)-<strong>[5654-97-7]7-azaoxindole</strong> (500 mg, 2.0 mmol), t-butyl isocyanate (0.35 mL, 3.0 mmol), triethylamine (0.6 mL, 4.4 mmol) and DMSO (10 mL). The crude product was purified by flash chromatography on silica gel using 9:1 chloroform/methanol and recrystallized from methanol/chlorform. Yield: 70 mg (25%). 1 H NMR (DMSO-d6): delta9.34 (s, 1H), 8.81 (d, J=3.5 Hz, 1H), 8.54 (d, J=8.0 Hz, 1H), 7.91-7.87 (m, 2H), 7.25-7.18 (m, 2H), 1.41 (s, 9H). MS m/e (relative percent) 343 (35), 244 (81), 160 (100), 111 (9). IR (KBr disc) 1718, 1654, 1629, 1607, 1554, 1534, 1497, 1433 cm-1. Analysis calc'd for C17 H17 N3 O3 S: C 59.46, H 4.99, N 12.24; found: C 59.24, H 4.77, N 12.14. M.p.>250 C. |
2.54 g (93%) | With sodium; In ethanol; | Example 40 3-(2-Thenoyl)-<strong>[5654-97-7]7-azaoxindole</strong>-1-N-t-butylcarboxamide 3-(2-Thenoyl)-<strong>[5654-97-7]7-azaoxindole</strong> was first prepared according to the procedure of Example 1B, using <strong>[5654-97-7]7-azaoxindole</strong> (1.5 g, 11.2 mmol), sodium (1.3 g, 56.5 mmol), ethanol (25 mL), and ethyl-thiophene-2-carboxylate (3 mL, 22.3 mmol). Yield: 2.54 g (93%). The title compound was prepared from 3-(2-thenoyl)-<strong>[5654-97-7]7-azaoxindole</strong> according to the procedure of Example 1C, using 3-(2-thenoyl)-<strong>[5654-97-7]7-azaoxindole</strong> (500 mg, 2.0 mmol), t-butyl isocyanate (0.35 mL, 3.0 mmol), triethylamine (0.6 mL, 4.4 mmol) and DMSO (10 mL). The crude product was purified by flash chromatography on silica gel using 9:1 chloroform/methanol and recrystallized from methanol/chlorform. Yield: 70 mg (25%). 1H NMR (DMSO-d6): delta 9.34 (s, 1 H), 8.81 (d, J = 3.5 Hz, 1 H), 8.54 (d, J = 8.0 Hz, 1 H), 7.91-7.87 (m, 2 H), 7.25-7.18 (m, 2 H), 1.41 (s, 9 H). MS m/e (relative percent) 343 (35), 244 (81), 160 (100), 111 (9). IR (KBr disc) 1718, 1654, 1629, 1607, 1554, 1534, 1497, 1433 cmmin1. Analysis calc'd for C17H17N3O3S: C 59.46, H 4.99, N 12.24; found: C 59.24, H 4.77, N 12.14. M.p. > 250C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
607 mg (79%) | In ethanol; | B. 5,6-Dichloro-3-(2-thenoyl)-4-azaoxindole Pellets of sodium metal (0.29 g, 12.6 mmol) were added to dry ethanol (10 mL) in a dry round-bottomed flask. When dissolution of the sodium was complete, solid <strong>[136888-26-1]5,6-dichloro-4-azaoxindole</strong> (500 mg, 2.46 mmol) was added followed by ethyl 2-thiophenecarboxylate (0.67 mL. 5.0 mmol). The mixture was heated at reflux for one day under nitrogen. The mixture was cooled, poured into ice/water and acidified to pH 3 with 6N HCl solution. The title compoundcompound was collected by filtration and dried in vacuo to afford 607 mg (79%). |