Structure of 120-75-2
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 120-75-2 |
Formula : | C8H7NS |
M.W : | 149.21 |
SMILES Code : | CC1=NC2=C(S1)C=CC=C2 |
MDL No. : | MFCD00005794 |
InChI Key : | DXYYSGDWQCSKKO-UHFFFAOYSA-N |
Pubchem ID : | 8446 |
GHS Pictogram: |
![]() |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 44.59 |
TPSA ? Topological Polar Surface Area: Calculated from |
41.13 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.11 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.0 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.6 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.84 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.65 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.64 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.32 |
Solubility | 0.0712 mg/ml ; 0.000477 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.53 |
Solubility | 0.0442 mg/ml ; 0.000296 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.34 |
Solubility | 0.0687 mg/ml ; 0.00046 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 |
-5.08 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) |
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 |
---|---|---|
84% | General procedure: To an oven-dried Schlenk tube were added Na2S•9H2O (or K2S, 3.0mmol), o-haloanilide (1.0 mmol), and MCM-41-NHC-CuI (228 mg, 0.1 mmol). The tube was sealed and then evacuated and backfilled withargon, and DMF (2 mL) was injected with a syringe. The mixture washeated to 80 C with stirring for 12 h (140 C and 24 h for o-bromoanilide).Upon cooling to ambient temperature, the mixture was centrifugatedto separate the copper catalyst. The catalyst recovered waswashed with deionized water (3 × 2 mL) and acetone (3 × 2 mL) anddried in vacuo at 80 C for 1 h, and used in the next run. Then conc. HCl(0.8 mL) was added into the resultant solution. After stirring for 10 h atambient temperature, 10 mL saturated aq. NaHCO3 was added into thesolution and the resulting mixture was then extracted with EtOAc forthree times. After being washed with water and brine, the organic layerwas dried over anhydrous MgSO4 and concentrated under the reducedpressure. The residue was then purified via column chromatography onsilica gel (hexane/ethyl acetate) to furnish the expected product 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Under nitrogen, to a solution of 0.16 ml (1.2 mmol) of 2-methylbenzothiazole in 10 ml of anhydrous THF at -78 C was added dropwise, 0.56 ml (1.4 mmol) of 2.5 M n-BuLi in hexane. The mixture was stirred at -78 C for 30 min, then 0.27 g (1.0 mmol) of <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> in 5 ml of anhydrous THF was added dropwise. The reaction was stirred at -78 C for 1 h, then allowed to warm to ambient temperature and stirred overnight. Next, 0.20 ml of acetic acid was added, and the mixture was diluted with 50 ml of CH2Cl2. The solution was dried over MgSO4, filtered, and concentrated in vacuo. A yellow power was obtained by recyrstallized from ethanol. (0.38 g, yield: 75%). m.p. 176.5-178 C. 1H NMR (300 MHz, CDCl3) δppm 7.88-7.94 (d, 2H), 7.70-7.72 (d, 1H), 7.52-7.59 (d, 1H), 7.50-7.51 (d, 2H), 7.40-7.43 (m, 2H), 7.27-7.30 (m, 6H), 7.26 (m, 2H), 5.44-5.46 (m, 1H), 3.55-3.57 (m, 2H), 2.84-2.85 (s, 1H). MS(M+) 420.1356. Anal. Calc. for C27H20N2OS: C, 77.12%; H, 4.79%; N, 6.66%. Found: C, 77.20%; H, 4.84%; N, 6.72%. |