Structure of 56278-50-3
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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. : | 56278-50-3 |
Formula : | C9H6N2S |
M.W : | 174.22 |
SMILES Code : | N#CCC1=NC2=CC=CC=C2S1 |
MDL No. : | MFCD00051633 |
InChI Key : | ZMZSYUSDGRJZNT-UHFFFAOYSA-N |
Pubchem ID : | 342465 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302+H312+H332-H315-H319-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.11 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 49.14 |
TPSA ? Topological Polar Surface Area: Calculated from |
64.92 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.78 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.29 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.36 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.15 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.41 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.2 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.85 |
Solubility | 0.245 mg/ml ; 0.00141 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.29 |
Solubility | 0.0892 mg/ml ; 0.000512 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.46 |
Solubility | 0.0608 mg/ml ; 0.000349 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 |
-5.74 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) |
2.14 |
* 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 |
---|---|---|
88% | at 99.84℃; for 0.15h;Microwave irradiation; | General procedure: Reactions were performed in a focused microwave reactor (CEM Discover TM), with power of 105W and a temperature of 373K. The solid products were isolated by crystallization of the reaction mixture from ethanol and washed with a mixture of hexane/ethanol (7:3) to give the corresponding compounds. The solid products obtained were purified by flash column chromatography using ethyl acetate-ether (3:7) or dichloromethane as an eluent to obtain pure compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With morpholine; sulfur; at 85.0℃; for 4.0h; | To a solution of 2-(benzo[djthiazol-2-yl)acetonitrile (300 mg, 1.72 mmol) in ethanol (10 mL) was added <strong>[1245648-32-1]tert-butyl 4-oxo-2-(trifluoromethyl)piperidine-1-carboxylate</strong> (460 mg, 1.72 mmol), elemental sulfur (55 mg, 1.72 mmol) and morpholine (150 mg, 1.72 mmol) at room temperature and the resulting reaction mixture was heated to reflux at 85 °C for 4 h and monitored by TLC. The reaction mixture was dried under vacuum pressure and the crude compound was purified by trituration with methanol to afford the mixture of the title compounds as an off white solid (700 mg, yield 89percent). LCMS: [M+Hj = 456.0; R = 3.50 mm, [M+Hj = 455.9; R = 3.59 mm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52.07% | With piperidine; In ethanol; at 80℃; | General procedure: 4.1.3.1. Procedure A. To a warm solution of the corresponding 2-(benzo[d]thiazol-2-yl)acetonitrile (1 mmol) in absolute ethanol(8 mL) was added the corresponding aldehyde (1 mmol) and catalytic amount of piperidine (0.2 mmol). The reaction mixture was then stirred and heated to 80 C for 0.5-1 h, (as monitored byTLC and LCMS for completion), the precipitate formed was collected by suction and recrystallised from ethanol to give the desired product in good yield as mentioned below. 4.1.3.23. (E)-4-(5-(2-(Benzo[d]thiazol-2-yl)-2-cyanovinyl)thiophen-2-yl)benzoic acid (21) The compound was synthesized according to the above general procedure A using 2-(benzo[d]thiazol-2-yl)acetonitrile (0.25 g, 1.44 mmol), 4-(5-formyl thiophen-2-yl) benzoic acid (0.33 g, 1.44 mmol), piperidine (0.025 g, 0.29 mmol) to afford 21 (0.29 g, 52.07%) as brown coloured solid. M.p: 289-291 C. 1H NMR (DMSO-d6): deltaH 13.01 (s, 1H), 8.34 (s, 1H), 8.20 (t, J = 7.2 Hz, 1H), 8.16 (t, J = 8.0 Hz, 1H), 8.11-7.87 (m, 4H), 7.67 (m, 2H), 7.28 (d, J = 8.0 Hz, 2H). 13C NMR (DMSO-d6): deltac 170.1, 161.7, 152.4, 143.9, 141.5, 139.8, 138.4, 135.1, 131.0, 130.9, 128.4, 127.9, 126.8(2C), 125.1, 124.9(2C), 123.7, 120.4, 117.4, 113.2. ESI-MS m/z 387.51 (M-H)+. Anal Calcd for C21H12N2O2S2; C, 64.93; H, 3.11; N, 7.21; Found: C, 64.86; H, 3.12; N, 7.23. |
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