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Chemical Structure| 120-75-2 Chemical Structure| 120-75-2
Chemical Structure| 120-75-2

2-Methylbenzothiazole

CAS No.: 120-75-2

4.5 *For Research Use Only !

Cat. No.: A228257 Purity: 98%

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Product Details of [ 120-75-2 ]

CAS No. :120-75-2
Formula : C8H7NS
M.W : 149.21
SMILES Code : CC1=NC2=C(S1)C=CC=C2
MDL No. :MFCD00005794
InChI Key :DXYYSGDWQCSKKO-UHFFFAOYSA-N
Pubchem ID :8446

Safety of [ 120-75-2 ]

GHS Pictogram:

Calculated chemistry of [ 120-75-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 9
Fraction Csp3 0.12
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 44.59
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

41.13 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.11
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

3.0
Log Po/w (WLOGP)?

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

2.6
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.

1.84
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

3.65
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.64

Water Solubility

Log S (ESOL):?

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

-3.32
Solubility 0.0712 mg/ml ; 0.000477 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.

-3.53
Solubility 0.0442 mg/ml ; 0.000296 mol/l
Class?

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

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

-3.34
Solubility 0.0687 mg/ml ; 0.00046 mol/l
Class?

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

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

Yes
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

No
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

No
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

No
Log Kp (skin permeation)?

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

-5.08 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

1.0
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

0.0 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)

1.91

Application In Synthesis [ 120-75-2 ]

* 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.

  • Downstream synthetic route of [ 120-75-2 ]

[ 120-75-2 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 120-75-2 ]
  • [ 34270-90-1 ]
  • [ 111529-03-4 ]
  • 2
  • [ 120-75-2 ]
  • [ 21512-16-3 ]
  • 5-(2-benzothiazol-2-yl-vinyl)-thiophene-2-carbonitrile [ No CAS ]
  • 4
  • [ 6668-24-2 ]
  • [ 1141-88-4 ]
  • [ 120-75-2 ]
  • [ 124530-83-2 ]
  • [ 93-55-0 ]
  • 5
  • [ 120-75-2 ]
  • [ 599-91-7 ]
  • [ 60126-38-7 ]
  • 6
  • [ 120-75-2 ]
  • [ 7044-92-0 ]
  • C26H20N2S2 [ No CAS ]
  • 7
  • [ 120-75-2 ]
  • [ 68-12-2 ]
  • [ 4263-52-9 ]
  • 3-(2-sulfoethyl)-{3-[3-(2-sulfoethyl)-3H-benzothiazol-2-ylidene]propenyl}benzothiazol-3-ium [ No CAS ]
  • 8
  • [ 19591-17-4 ]
  • [ 120-75-2 ]
YieldReaction ConditionsOperation in experiment
84% General procedure: To an oven-dried Schlenk tube were added Na2S•9H2O (or K2S, 3.0mmol), o-haloanilide (1.0 mmol), and MCM-41-NHC-CuI (228 mg, 0.1 mmol). The tube was sealed and then evacuated and backfilled withargon, and DMF (2 mL) was injected with a syringe. The mixture washeated to 80 C with stirring for 12 h (140 C and 24 h for o-bromoanilide).Upon cooling to ambient temperature, the mixture was centrifugatedto separate the copper catalyst. The catalyst recovered waswashed with deionized water (3 × 2 mL) and acetone (3 × 2 mL) anddried in vacuo at 80 C for 1 h, and used in the next run. Then conc. HCl(0.8 mL) was added into the resultant solution. After stirring for 10 h atambient temperature, 10 mL saturated aq. NaHCO3 was added into thesolution and the resulting mixture was then extracted with EtOAc forthree times. After being washed with water and brine, the organic layerwas dried over anhydrous MgSO4 and concentrated under the reducedpressure. The residue was then purified via column chromatography onsilica gel (hexane/ethyl acetate) to furnish the expected product 2.
  • 9
  • [ 120-75-2 ]
  • [ 110677-45-7 ]
  • [ 1338711-70-8 ]
YieldReaction ConditionsOperation in experiment
75% Under nitrogen, to a solution of 0.16 ml (1.2 mmol) of 2-methylbenzothiazole in 10 ml of anhydrous THF at -78 C was added dropwise, 0.56 ml (1.4 mmol) of 2.5 M n-BuLi in hexane. The mixture was stirred at -78 C for 30 min, then 0.27 g (1.0 mmol) of <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> in 5 ml of anhydrous THF was added dropwise. The reaction was stirred at -78 C for 1 h, then allowed to warm to ambient temperature and stirred overnight. Next, 0.20 ml of acetic acid was added, and the mixture was diluted with 50 ml of CH2Cl2. The solution was dried over MgSO4, filtered, and concentrated in vacuo. A yellow power was obtained by recyrstallized from ethanol. (0.38 g, yield: 75%). m.p. 176.5-178 C. 1H NMR (300 MHz, CDCl3) δppm 7.88-7.94 (d, 2H), 7.70-7.72 (d, 1H), 7.52-7.59 (d, 1H), 7.50-7.51 (d, 2H), 7.40-7.43 (m, 2H), 7.27-7.30 (m, 6H), 7.26 (m, 2H), 5.44-5.46 (m, 1H), 3.55-3.57 (m, 2H), 2.84-2.85 (s, 1H). MS(M+) 420.1356. Anal. Calc. for C27H20N2OS: C, 77.12%; H, 4.79%; N, 6.66%. Found: C, 77.20%; H, 4.84%; N, 6.72%.
  • 10
  • [ 120-75-2 ]
  • [ 41042-12-0 ]
  • C19H18N2O2S [ No CAS ]
  • 11
  • [ 120-75-2 ]
  • [ 1202-25-1 ]
  • [ 17822-23-0 ]
  • 12
  • [ 120-75-2 ]
  • [ 41042-12-0 ]
  • [ 109-77-3 ]
  • C22H18N4OS [ No CAS ]
  • 13
  • [ 120-75-2 ]
  • [ 42906-19-4 ]
  • (E)-4-(2-(benzo[d]thiazol-2-yl)vinyl)-N,N-di-p-tolylaniline [ No CAS ]
 

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