Structure of 16582-59-5
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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. : | 16582-59-5 |
Formula : | C7H4Cl2N2S |
M.W : | 219.09 |
SMILES Code : | ClC1=CC(Cl)=C2N=C(N)SC2=C1 |
MDL No. : | MFCD01123002 |
InChI Key : | UZGRZSHGRZYCQV-UHFFFAOYSA-N |
Pubchem ID : | 112722 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 54.04 |
TPSA ? Topological Polar Surface Area: Calculated from |
67.15 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.92 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.35 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.19 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.44 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.69 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.92 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.86 |
Solubility | 0.03 mg/ml ; 0.000137 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.44 |
Solubility | 0.008 mg/ml ; 0.0000365 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.85 |
Solubility | 0.0309 mg/ml ; 0.000141 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) |
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 |
-5.26 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) |
2.2 |
* 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 |
---|---|---|
Listed below are some typical examples of said 2-aminobenzothiazole compounds: ... 2-amino-6-iodobenzothiazole 2-amino-6-cyanobenzothiazole 2-amino-6-thiocyanobenzothiazole 2-amino-6-methylbenzothiazole 2-amino-4,6-dichlorobenzothiazole 2-amino-4,6-dibromobenzothiazole 2-amino-5,6-dichlorobenzothiazole 2-amino-5,6-dibromobenzothiazole ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine; In acetic acid; | 2-Amino-4,6-dichlorobenzothiazole 197 g (1.23 mol) of bromine were slowly added dropwise, while cooling with ice, to a solution of 200 g (1.23 mol) of 2,4-dichloroaniline and 200 g (2.46 mol) of sodium thiocyanate in 1.5 1 of glacial acetic acid. Stirring was carried out for 16 hours at about 20 C., after which the solid was separated off and washed with 10% strength sodium hydroxide solution and water. Yield: 205 g. 1 H-NMR (270 MHz; in d6 -dimethyl sulfoxide): delta [ppm]=7.39 (d,1H), 7.80 (d,1H), 8.00 (s,2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tert.-butylnitrite; In 1,2-dichloro-ethane; | 4,6-Dichloro-2-(methylthio)benzothiazole 43.7 g (0.47 mol) of dimethyl disulfide and 154.5 g (1.5 mol) of tert-butyl nitrite were added to a solution of 34 g (0.16 mol) of <strong>[16582-59-5]2-amino-4,6-dichlorobenzothiazole</strong> in 1 liter of 1,2-dichloroethane. Stirring was carried out for 16 hours, followed by washing with water and 10% strength sodium hydroxide solution, drying over magnesium sulfate and evaporating down. Yield: 34 g; mp.: 108 to 110 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tert.-butylnitrite; sodium bromide;copper(I) bromide; In acetonitrile; | 2-Bromo-4,6-dichlorobenzothiazole 35 g (0.24 mol) of copper(I) bromide and 126 g (1.23 mol) of sodium bromide were added to a solution of 27 g (0.12 mol) of <strong>[16582-59-5]2-amino-4,6-dichlorobenzothiazole</strong> in 0.5 1 of acetonitrile, and 16.5 g (0.16 mol) of tert-butyl nitrite were then added dropwise. Stirring was carried out for 16 hours, after which the reaction mixture was acidified with 10% strength hydrochloric acid. The product was then extracted with methyl tert-butyl ether. The organic phase was washed with water, dried over magnesium sulfate and finally evaporated down. Purification of the crude product was carried out by means of column chromatography over silica gel (eluent: 1:1 cyclohexane/ethyl acetate). Yield: 9.1 g. 1 H-NMR (250 MHz; in d6 -dimethyl sulfoxide): delta [ppm]=7.78 (d,1H), 8.24 (d,1H). |
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