Structure of 30616-38-7
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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. : | 30616-38-7 |
Formula : | C13H10N2OS |
M.W : | 242.30 |
SMILES Code : | OC1=CC=C(N)C=C1C2=NC3=CC=CC=C3S2 |
MDL No. : | MFCD00197455 |
InChI Key : | UBRCBHVOYDSGKZ-UHFFFAOYSA-N |
Pubchem ID : | 738658 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 17 |
Num. arom. heavy atoms | 15 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 71.48 |
TPSA ? Topological Polar Surface Area: Calculated from |
87.38 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.12 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.22 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.26 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.06 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.44 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.82 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.96 |
Solubility | 0.0267 mg/ml ; 0.00011 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.73 |
Solubility | 0.00454 mg/ml ; 0.0000187 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.56 |
Solubility | 0.00669 mg/ml ; 0.0000276 mol/l |
Class? Solubility class: Log S scale |
Moderately 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) |
Yes |
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) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.49 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 |
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) |
2.46 |
* 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 |
---|---|---|
23% | With pyridine; at 0 - 20℃; for 8h; | Benzoyl chloride (0.25 mL, 1.5 mM) was added into a solution of compound 4 (520 mg, 1.5 mM)in pyridine (10 mL) at 0 oC. The mixture was stirred at rt for 7 h after stirred for another 1 h under ice bath. The solvent was removed under reduced pressure. The obtained grey solid was purified by silica gel column chromatography using PE DCM (1/2) as the eluent.The obtained white solid was recrystallized with glacial acetic acid to furnish compound BTHPB (120 mg, 0.35 mmol) in 23% yield as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With polyphopshoric acid; at 180 - 200℃; for 4h; | A mixture of 2-aminophenol (0.436g, 4 mmol) and 5-aminosalicylic acid (0.612g, 4 mmol) was stirred in 15 mL PPA at 200 oC for 4 h. Then the reaction mixture was cooled down, and poured into 400 mL cold water to give a yellow precipitate. After filtered, the yellow precipitate was washed by 10% Na2CO3. The obtained crude product was separated by silica gel column chromatography (silica gel, CH2Cl2 as eluent) to get compound 2 (yellow solid, yield 0.702 g, 77%). TLC (CH2Cl2): Rf ? 0.1; m.p.: 188.2~190.0 oC(Lit. 190~190.5 oC [S1]). FT-IR spectrum(KBr pellet, cm-1):3410, 3325, 3051, 2361, 1635, 1597, 1496, 1438,1311, 1275, 1252, 1194, 995, 912, 830, 793, 756, 724, 696, 640; 1H NMR (DMSO-d6, 600 MHz) (ppm): 11.90(s, 1H), 7.97 (d, 1H, J = 7.8 Hz), 7.88 (d, 1H, J = 7.8 Hz), 7.49 (t, 1H, J = 7.8Hz), 7.39 (t, 1H, J = 7.8 Hz), 7.01 (d, 1H, J = 3.0 Hz), 6.95 (d, 1H, J = 8.4Hz), 6.80 (dd, 1H, J1 = 8.4 Hz , J2 = 2.4 Hz); 13CNMR (150 MHz, CDCl3) delta 169.78, 154.96, 151.26, 144.87, 137.30,129.79, 128.32, 125.34, 125.25, 123.38, 120.98, 115.45. |
53% | With polyphosphoric acid; at 170℃; for 5h; | In a general way, the precursors were obtained byreaction of an equimolar amount of 5-aminosalicylicacid (3) (4.0 g, 26.12 mmol) and 2-aminophenol (4)(2.8 g, 26.12 mmol) or 2-aminothiophenol (5) (2.76 mL,26.12 mmol) in polyphosphoric acid (PPA) (60 mL) at170 C for 5 h. The reaction was followed by TLC usingdichloromethane as the eluent. The reaction mixture waspoured onto crushed ice and neutralized with NaHCO3(20%). The precipitate was filtered and dried at 60 oC.The obtained compounds were purified by columnchromatography eluted with dichloromethane. |
49% | With polyphosphoric acid; at 180℃; for 3h; | Compound 2 (2-aminothiophenol, 2 g, 16 mmol), compound 3 (4-amino salicylic acid, 2.45 g, 16 mmol) and polyphosphoric acid (35 mL) were added into a 100 mL round-bottom flask. The mixture was heated to 180 oC and stirred for 3 h, which was turned from colorless to atrovirens. The mixture was poured into a beaker with 30 g ice immediately, and pH was adjustedby NaOH. Compound 4 (1.9 g, 7.84 mmol) was obtained by filtration in 49% yield as green solid. |
at 160℃; for 8h; | General procedure: HBZ and HBT were synthesized according to the procedure reported by Hein et al. [30]. HBZ was prepared by heating equimolar ratio of 1,2-phenylenediamine (1.08g, 0.01mol) and 5-amino-2-hydroxybenzoic acid (1.37g, 0.01mol) at 160C for 8h in 3.5mL polyphosphoric acid. After the completion of the reaction (as indicated by the TLC analysis of small aliquot) the reaction mixture was quenched in ice and neutralized using 10% Na2CO3 solution. Excess base was removed by washing with ice-cold water. The precipitate was dried overnight and recrystallized in methanol to obtain 4-amino-2-(1H-benzimidazol-2-yl)phenol (HBZ). Similarly, 4-amino-2-(benzothiazol-2-yl)phenol (HBT) was synthesized by using 2-aminothiophenol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With sodium hydrogencarbonate; In butanone; at 20℃; for 24h; | Example 5 Preparation of 2-(2-Benzothiazolyl)-5-[[4,6-dichloro-s-triazin-2-yl] amino]-phenol This example illustrates the preparation of the following fluorescent compound of the present invention: Approximately 2.43 g (0.01 mol) of (hydroxy-5-aminophenyl)-benzthiazol, 1.84 g (0.01 mol) of 1,3,5-trichlorotriazine, and 0.85 g (0.01 mol) of sodium bicarbonate were stirred for 24 h at room temperature in 2-Butanone. The resulting precipitate was filtered by suction, washed with 2-Butanone and water, and then dried at 85 C. Analysis of the precipitate showed a yield of 2.5 g (64%) of grey fine needles of 2-(2-Benzothiazolyl)-5-[4,6-dichloro-s-triazin-2-yl]amino]-phenol having about a 99% purity. Differential Thermal Analysis (DTA) demonstrated an endothermic peak of 252 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69.8% | With sodium hydrogencarbonate; In butanone; at 50 - 60℃; for 2h; | Example 12 Preparation of 1,3-bis[[3-(2-Benzothiazolyl)-4-phenyl]-amino]-5-chloro-triazine This example illustrates the preparation of the following fluorescent compound of the present invention: About 3.9 g (0.01 mol) of 2-(2-Benzothiazolyl)-5-[4,6-dichloro-s-triazin-2-yl]amino]-phenol, 2.42 g (0.01 mol) of (hydroxy-5-aminophenyl)-benzthiazole, and 0.8 g of sodium bicarbonate were added to 50 ml 2-butanone to produce a suspension. The suspension was stirred while heated to between 50 - 60 C. The suspension became bright beige. After two hours the mixture was cooled to room temperature and filtered by suction. The product was stirred in 100 ml water at room temperature for 15 min, filtered again by suction, and then dried at 85 C resulting in a grey fine powder with yellow fluorescence. Analysis of the resulting precipitate showed a yield of 5.96 g (69.8 %) of a yellow-beige colored fine powder of 1,3-bis[[3-(2-Benzothiazolyl)-4-phenyl]-amino]-5-chloro-triazine. The compound demonstrated an maximum emission value at 565 nm (yellow-green), a DTA peak of 302 C, an intensity of fluorescence of 68 (1 % draw down, [cd/m2]), and CIE color coordinates of 0.494 and 0.500 (X and Y, respectively). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With acetic acid; for 4h;Reflux; | A mixture of 2 (0.484 g, 2 mmol) and maleic anhydride (0.245 g, 2.5 mmol) in glacial acetic acid (20 mL) was heated under reflux for 4 h. The reaction mixture was left to cool, and poured into 100 mL cold water to give a yellow precipitate. The yellow solid obtained by filtered and washed with sodium carbonate solution. After drying, it was purified by silica gel chromatography using CH2Cl2 as the eluent to give compound 1 as a yellow solid (0.52 g, 81%); TLC (CH2Cl2):Rf ? 0.45; m.p.: 232.5~234.8 oC; FT-IR spectrum (KBrpellet, cm-1): 3092, 2361, 1720, 1596, 1506, 1439, 1412, 1319, 1274,1219, 1185, 1156, 1006, 959, 871, 832, 754, 721, 692; 1H NMR (DMSO-d6, 600 MHz) d(ppm): 11.75(s, 1H), 8.22 (d, 1H, J = 2.4 Hz), 8.16(d, 1H, J = 7.8 Hz), 8.06 (d, 1H, J = 8.4 Hz), 7.56(t, 1H, J = 8.4 Hz), 7.47(t,1H, J = 7.2 Hz), 7.36 (dd, 1H, J1 = 6.6Hz , J2 = 2.4 Hz). 13C NMR (150MHz, CDCl3) delta 173.50, 166.98, 158.90, 154.77, 138.16, 138.03, 134.32, 130.38, 129.83, 128.51, 126.83, 125.62, 125.39, 122.41, 120.69. ESI-MS: calcd for [M+H] + 323.0485, Found 323.0478. |
81% | With acetic acid; for 4h;Reflux; | A method for preparing a fluorescent probe for rapidly detecting biothiols according to the present embodiment,Dissolve 2 mmol of <strong>[30616-38-7]2-(2-hydroxy-5-aminophenyl)benzothiazole</strong> and 2 mmol of maleic anhydride in 20 ml of glacial acetic acid,Heat reflux reaction for 4h,cool down,filter,Column chromatographic purification is rapid detection of bio-thiol fluorescent probes.(yellow solid, 0.52 g, 81%). |