Structure of 39736-29-3
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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. : | 39736-29-3 |
Formula : | C7H10N2O2S2 |
M.W : | 218.30 |
SMILES Code : | O=C(C1=C(N)N=C(SC)S1)OCC |
MDL No. : | MFCD01830310 |
InChI Key : | WAFDSQXKSGGKCD-UHFFFAOYSA-N |
Pubchem ID : | 384908 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 5 |
Fraction Csp3 | 0.43 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 54.33 |
TPSA ? Topological Polar Surface Area: Calculated from |
118.75 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.27 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.55 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.63 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.46 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.09 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.8 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.82 |
Solubility | 0.33 mg/ml ; 0.00151 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.69 |
Solubility | 0.00445 mg/ml ; 0.0000204 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.92 |
Solubility | 2.61 mg/ml ; 0.012 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) |
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) |
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 |
-5.82 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) |
2.67 |
* 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 |
---|---|---|
99% | With diisopropylamine In N,N-dimethyl-formamide at 100℃; for 5 h; | The synthesis of ethyl 4-amino-2-(methylthio)thiazole-5-carboxylate Ethyl 2-mercaptoacetate (50 g, 0.416 mol) was dissolved in 500 ml of dimethylformamide and added with dimethyl N-thienodithioimino carbonate (67 g, 0.416 mol) and diisopropylamine (112 ml, 0.624 mol). After heating at 100° C. for 5 hours, the mixture was extracted with 500 ml of saturated ammonium chloride and 500 ml of ethylacetate, dried with sodium sulfate, filtered and concentrated under vacuum. After washing the solid with n-hexane, the title compound (90 g, 99percent) was obtained. 1H-NMR (400 MHz, CDCl3); δ 5.84 (brs, 2H), 4.26 (q, J=7.2 Hz, 2H), 2.63 (s, 3H), 1.32 (t, J=7.2 Hz, 3H); LC-MS 219 (MH+) |
89% | With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; | Ethyl 2-mercaptoacetate (5 g, 42 mmol, 1.0 eq) was dissolved in DMF (50 mL) and added with N-thienodi-thioimino carbonate (6.1 g, 42 mmol, 1.0 eq) and DIPEA (16.3 g, 126 mmol, 3.0 eq). After heating at 100 °C for 5 h, the mixture was diluted with saturated aqueous ammonium chloride (100 mL) and extracted with EtOAc (100 mLx2). The combined organic layer was washed with brine, dried, concentrated. The solid was washed with n-hexane and dried under vacuum to give the title compound (8 g, yield: 89percent) as a yellow solid. ESI-MS (M+H)+: 219.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Stage #1: for 1 h; Reflux Stage #2: With triethylamine In ethanol for 4 h; Reflux |
The ethyl bromoacetate (1.96 g, 11.76 mmol) was added to a stirred solution of potassium methyl cyanimidodithiocarbonate 1 (2.0 g, 11.76 mmol) in EtOH (50 mL). The mixture was heated to reflux for 1 h. After cooling, Et3N (2.38 g, 23.52 mmol) was added and the mixture was heated to reflux for 4 h. The ethanol was evaporated and the residue was triturated with water (20 mL) followed by filtering. The solid was dried and then recrystallized from acetone to give compound 2 (2.4 g, 93percent). Light yellow solid; mp 101-103 °C; 1H NMR (400 MHz, CDCl3) δ (ppm): 5.80 (brs, 2H), 4.26 (q, 2H, J = 7.2 Hz), 2.63 (s, 3H), 1.32 (t, 3H, J = 7.2 Hz); HRMS (ESI) Calcd. for C7H11N2O2S2 [M+H]+: 219.0256; Found: 219.0248. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
155 mg | at 20℃; for 0.333333 h; Green chemistry | General procedure: To asolution of acyclic 1,3-dicarbonyl compounds 12 (1.0 mmol) in EtOH (3.0 mL) was added NBS (178 mg, 1 mmol). Thereaction mixture was stirred for 10 min (30 min for 12b and 12e) at roomtemperature. Afterwards 7 (1 mmol)was added and the reaction mixture was stirred for another 20 min at roomtemperature. After that, the solvent was evaporated under reducedpressure, and the residue was purified viaa short silica gel column to afford the desired product 11. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
138 mg | at 20℃; for 0.333333 h; Green chemistry | General procedure: To asolution of acyclic 1,3-dicarbonyl compounds 12 (1.0 mmol) in EtOH (3.0 mL) was added NBS (178 mg, 1 mmol). Thereaction mixture was stirred for 10 min (30 min for 12b and 12e) at roomtemperature. Afterwards 7 (1 mmol)was added and the reaction mixture was stirred for another 20 min at roomtemperature. After that, the solvent was evaporated under reducedpressure, and the residue was purified viaa short silica gel column to afford the desired product 11. |
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