Structure of 3034-47-7
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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. : | 3034-47-7 |
Formula : | C3HClN2O2S |
M.W : | 164.57 |
SMILES Code : | ClC1=NC=C(S1)[N+](=O)[O-] |
MDL No. : | MFCD09743979 |
InChI Key : | USOMXSLAPRWFCV-UHFFFAOYSA-N |
Pubchem ID : | 12542663 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 5 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 35.95 |
TPSA ? Topological Polar Surface Area: Calculated from |
86.95 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.19 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.14 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.7 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.88 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.98 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.03 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.55 |
Solubility | 0.46 mg/ml ; 0.00279 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.6 |
Solubility | 0.0415 mg/ml ; 0.000252 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.28 |
Solubility | 8.6 mg/ml ; 0.0522 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) |
No |
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 |
-5.78 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 |
2.0 |
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 |
2.0 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) |
2.98 |
* 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 |
---|---|---|
In DMF (N,N-dimethyl-formamide); at 100℃; for 3.0h; | (2R, 4S) -4-Amino-2-ethyl-6-trifluoromethyl-3, 4-dihydro-2H- quinoline-1-carboxylic acid ethyl ester (200 mg) and 2-chloro-5-nitro- thiazole (416 mg) are dissolved in N, N-dimethylformamide (1 ml), and the mixture is stirred at 100°C for 3 hours. The reaction solution is cooled to room temperature, and thereto are added an aqueous citric acid solution and ethyl acetate. The organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by column chromatography (silica gel; hexane : ethyl acetate = 4: 1No.1 : 1) to give (2R, 4S)-2-ethyl-4-(5-nitorthiazol-2- yl) amino-6-trifluoromethyl-3, 4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (148 mg). MS (m/z): 445 [M+H] + |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In sodium hydroxide; acetone; | EXAMPLE 34 [4-(5-Nitrothiazol-2-yl)-oxy]-nitrostyrene 4Hydroxynitrostyrene (3.3 g.) and anhydrous potassium carbonate (2.76 g.) were stirred at room temperature in dry acetone (30 ml.) for 3 hours. To the reaction mixture was added <strong>[3034-47-7]2-chloro-5-nitrothiazole</strong> (3.3 g.) and the stirring continued at room temperature for 3 hours. After keeping the reaction mixture overnight at room temperature, it was diluted with water (150 ml.). The product was filtered off and was suspended in 1percent NaOH sol. (30 ml.) followed by 3percent CH3 COOH (50 ml.). The crude product was crystallized from benzene-hexane; m.p. 152°-4° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium ethanolate; In ethanol; dimethyl sulfoxide; | EXAMPLE 33 beta-Methyl-[4-(5-nitrothiazol-2-yl)-oxy]-nitrostyrene beta-Methyl-4-hydroxynitrostyrene (5.37 g.) prepared according to the process of the invention and sodium ethoxide (2.04 g.) were stirred in ethanol (20 ml.) at room temperature for 1 hour. The solvent was removed at 40°-45° C under reduced pressure and the residue was suspended in solvent ether and filtered to get the sodium salt of beta-methyl-4-hydroxynitrostyrene (5.2 g.) 2-Chloro-5-nitrothiazole (4.28 g) and the sodium salt of beta-methyl-4-hydroxynitrostyrene (5.2 g. were mixed in DMSO (Dimethysulfoxide) (10 ml.) under cooling. The mixture was warmed at 50°-55° C for 2 hours. The reaction mixture was diluted with cold water and the separated product was suspended in ethanol. The crude product was crystallized from benzene-hexane: m.p. 102°-3° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.3% | With potassium carbonate; In acetonitrile; at 30 - 80℃; for 1.0h; | General procedure: To a suspension of 7-chloro-4-(piperazin-1-yl)quinoline (1mmol) and potassium carbonate (1.5mmol) in acetonitrile was added the corresponding alkyl halide (1mmol) at 30°C. The reaction mixture was then heated to 80°C for 1h (monitored by TLC and LCMS for completion) and cooled to 30°C. The mixture was then filtered through celite bed, and acetonitrile was evaporated in vacuo. The resultant residue was diluted with water and dichloromethane, and the layers separated. The aqueous layer was re-extracted with dichloromethane (2×5mL). The combined organic extract was washed with brine, dried over sodium sulphate and evaporated in vacuo. |
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