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Chemical Structure| 30616-38-7

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Product Details of [ 30616-38-7 ]

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

Safety of [ 30616-38-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 30616-38-7 ] Show Less

Physicochemical Properties

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
Ertl P. et al. 2000 J. Med. Chem.

87.38 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.12
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

3.22
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

3.26
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.06
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

3.44
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.82

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.96
Solubility 0.0267 mg/ml ; 0.00011 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-4.73
Solubility 0.00454 mg/ml ; 0.0000187 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-4.56
Solubility 0.00669 mg/ml ; 0.0000276 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble

Pharmacokinetics

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)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

Yes
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

Yes
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.49 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

2.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.46

Application In Synthesis of [ 30616-38-7 ]

* 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.

  • Downstream synthetic route of [ 30616-38-7 ]

[ 30616-38-7 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 30616-38-7 ]
  • [ 108-24-7 ]
  • 1-acetoxy-4-acetylamino-2-benzothiazol-2-yl-benzene [ No CAS ]
  • 2
  • [ 30616-38-7 ]
  • [ 100-52-7 ]
  • [ 60928-37-2 ]
  • 3
  • [ 30616-38-7 ]
  • [ 98-88-4 ]
  • [ 2533-14-4 ]
YieldReaction ConditionsOperation 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.
  • 4
  • [ 30616-38-7 ]
  • [ 75-36-5 ]
  • [ 2842-13-9 ]
  • 5
  • [ 89-57-6 ]
  • [ 137-07-5 ]
  • [ 30616-38-7 ]
YieldReaction ConditionsOperation 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.

  • 6
  • [ 1493-13-6 ]
  • [ 162374-59-6 ]
  • [ 30616-38-7 ]
  • 2-(2-Hydroxy-5-trifluoromethylsulfonamidophenyl)benzothiazole [ No CAS ]
  • 2-(5-Amino-2-trifluoromethylsulfoxyphenyl)benzothiazole [ No CAS ]
  • 7
  • [ 162374-59-6 ]
  • [ 30616-38-7 ]
  • 2-(2-Hydroxy-5-trifluoromethylsulfonamidophenyl)benzothiazole [ No CAS ]
  • 2-(5-Amino-2-trifluoromethylsulfoxyphenyl)benzothiazole [ No CAS ]
  • 9
  • 2-<5-nitro-2-oxy-phenyl>-benzthiazole [ No CAS ]
  • [ 30616-38-7 ]
  • 10
  • [ 100-34-5 ]
  • 2-<2-oxy-phenyl>-benzthiazole [ No CAS ]
  • [ 30616-38-7 ]
  • 11
  • [ 30616-38-7 ]
  • [ 24801-88-5 ]
  • 2-[5'-N-(3-triethoxysilyl)propylureylene-2'-hydroxyphenyl]benzothiazole [ No CAS ]
  • 16
  • [ 121-90-4 ]
  • potassium-salt of/the/ benzohydroxamic acid [ No CAS ]
  • [ 30616-38-7 ]
  • 17
  • [ 30616-38-7 ]
  • [ 87-13-8 ]
  • diethyl 2-[[(3-benzothiazol-2-yl)-4-hydroxyphenylamino]methylene]acrylate [ No CAS ]
  • 18
  • [ 30616-38-7 ]
  • [ 94-05-3 ]
  • [ 1175535-56-4 ]
  • 19
  • [ 30616-38-7 ]
  • [ 65-85-0 ]
  • [ 2533-14-4 ]
  • 20
  • [ 15155-41-6 ]
  • [ 30616-38-7 ]
  • [ 1255709-97-7 ]
  • 21
  • [ 108-30-5 ]
  • [ 30616-38-7 ]
  • [ 1312023-89-4 ]
  • 22
  • [ 30616-38-7 ]
  • [ 108-24-7 ]
  • [ 2842-13-9 ]
  • 23
  • [ 108-77-0 ]
  • [ 30616-38-7 ]
  • [ 1149804-18-1 ]
YieldReaction ConditionsOperation 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.
  • 24
  • [ 16331-52-5 ]
  • [ 30616-38-7 ]
  • [ 1370656-04-4 ]
  • 25
  • [ 30616-38-7 ]
  • [ 25784-91-2 ]
  • [ 391218-47-6 ]
  • 26
  • [ 30616-38-7 ]
  • [ 6959-47-3 ]
  • C25H20N4OS [ No CAS ]
  • 27
  • [ 30616-38-7 ]
  • [ 25776-12-9 ]
  • [ 64-19-7 ]
  • C13H10N2OS*C24H16BF4(1-)*H(1+) [ No CAS ]
  • 28
  • [ 30616-38-7 ]
  • [ 1149804-20-5 ]
  • 29
  • [ 30616-38-7 ]
  • [ 1149804-33-0 ]
  • 30
  • [ 30616-38-7 ]
  • [ 1149804-22-7 ]
  • 31
  • [ 30616-38-7 ]
  • [ 1149804-18-1 ]
  • [ 1149804-25-0 ]
YieldReaction ConditionsOperation 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).
  • 32
  • [ 30616-38-7 ]
  • [ 1149804-25-0 ]
  • 2,4,6-tri[2-(5’-aminyl-2’-hydroxphenyl)benzothiazole]-1,3,5-triazine [ No CAS ]
  • 33
  • [ 30616-38-7 ]
  • [ 1149804-25-0 ]
  • 34
  • [ 30616-38-7 ]
  • 2,4,6-tri[2-(5’-aminyl-2’-hydroxphenyl)benzothiazole]-1,3,5-triazine [ No CAS ]
  • 35
  • [ 108-31-6 ]
  • [ 30616-38-7 ]
  • 1-(3-(benzo[d]thiazol-2-yl)-4-hydroxyphenyl)-1H-pyrrole-2,5-dione [ No CAS ]
YieldReaction ConditionsOperation 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%).
 

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