Structure of 93-85-6
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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. : | 93-85-6 |
Formula : | C8H6N2O2S |
M.W : | 194.21 |
SMILES Code : | C1=C(C(O)=O)C=CC2=C1SC(=N2)N |
MDL No. : | MFCD00054180 |
InChI Key : | ZEAKWWWXCZMODH-UHFFFAOYSA-N |
Pubchem ID : | 66740 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 50.98 |
TPSA ? Topological Polar Surface Area: Calculated from |
104.45 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 |
1.48 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.58 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.85 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.76 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.37 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.42 |
Solubility | 0.734 mg/ml ; 0.00378 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.28 |
Solubility | 0.102 mg/ml ; 0.000524 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.99 |
Solubility | 2.0 mg/ml ; 0.0103 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 |
-6.43 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 |
0.56 |
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) |
1.92 |
* 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 |
---|---|---|
59% | at 100℃; for 6 h; | (2) 2-amino-benzo[d]thiazole-6-carboxylic and:; 13.0g (0.07mol) 4-amino-3-thiocyano-benzonitrile was weighed, dissolved in 120ml water, stirred uniformly, added with 60ml concentrated hydrochloric acid, reacted under refluxing and stirring at about 100°C for 6h. After the reaction, the reaction mixture was stood, filtered to obtain a precipitated solid, and dried out to obtain a light yellow solid product 8.5g (59.0percent). mp 280-282°C. 1H-NMR (ppm, d6-DMSO) δ: 7.45(d, J=8.40 Hz,1H), 7.67(dd,J1= 8.40Hz, J2=1.68Hz, 1H), 8.22 (d,J=1.68 Hz,1H),8.51(br-s, 2H,NH2). |
59% | at 100℃; for 6 h; | (2) 2-amino-benzo[d]thiazole-6-carboxylic acid 13.0 g (0.07 mol) 4-amino-3-thiocyano-benzonitrile was weighed, dissolved in 120 ml water, stirred uniformly, added with 60 ml concentrated hydrochloric acid, reacted under refluxing and stirring at about 100° C. for 6 h. After the reaction, the reaction mixture was stood, filtered to obtain a precipitated solid, and dried out to obtain a light yellow solid product 8.5 g (59.0percent). mp 280-282° C. 1H-NMR (ppm, d6-DMSO) δ: 7.45 (d, J=8.40 Hz, 1H), 7.67 (dd, J1=8.40 Hz, J2=1.68 Hz, 1H), 8.22 (d, J=1.68 Hz, 1H), 8.51 (br-s, 2H, NH2). |
59% | With hydrogenchloride In water at 100℃; for 6 h; | Weigh 13.0 g (0.07 mol) of 4-amino-3-thiocyano-benzonitrile,Dissolve in 120ml water, stir evenly, add 60ml concentrated hydrochloric acid,The reaction was stirred under reflux at about 100 ° C for 6 h. After the reaction was completed, it was allowed to stand.The solid was separated by filtration and dried to give 8.5 g (59.0percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With bromine In methanol at -10 - -5℃; for 2 h; | Synthesis of 2-aminobenzothiazole-6-carbolic Acid(2)NaSCN (65 g, 0.8 mol) was added to a suspension of commercially available 4-amino-benzoic acid (1, 100 g, 0.73 mol) in MeOH followed by the addition of Br2 (38 ml, 0.73 mol) in portions. The above solution was allowed to cool to -10° C. and stirred for 2 h while keeping the inner temperature below -5° C. The precipitate was then filtered and suspended in 350 ml of 1 M HCl. The suspension was heated to reflux for 30 min. After immediate filtration, 150 ml concd HCl was added to the hot filtrate to give 70 g (yield 42percent) of 2-amino-benzothiazole-6-carboxylic acid (2) (as a white solid), which was dried and used without further purification. |
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