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Chemical Structure| 71216-20-1 Chemical Structure| 71216-20-1

Structure of 71216-20-1

Chemical Structure| 71216-20-1

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Product Details of [ 71216-20-1 ]

CAS No. :71216-20-1
Formula : C7H4BrNS2
M.W : 246.15
SMILES Code : SC1=NC2=CC(Br)=CC=C2S1
MDL No. :MFCD08460052
InChI Key :OKHQGCOLOHTELL-UHFFFAOYSA-N
Pubchem ID :4408260

Safety of [ 71216-20-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 71216-20-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 9
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 54.57
TPSA ?

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

79.93 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.45
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

3.11
Log Po/w (WLOGP)?

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

3.35
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.

2.53
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

4.1
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.11

Water Solubility

Log S (ESOL):?

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

-3.93
Solubility 0.0289 mg/ml ; 0.000117 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.

-4.46
Solubility 0.00859 mg/ml ; 0.0000349 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

-3.94
Solubility 0.0284 mg/ml ; 0.000115 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

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

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

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

Yes
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.

-5.59 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

1.0 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)

2.12

Application In Synthesis of [ 71216-20-1 ]

* 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.

  • Upstream synthesis route of [ 71216-20-1 ]

[ 71216-20-1 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 768-11-6 ]
  • [ 71216-20-1 ]
YieldReaction ConditionsOperation in experiment
81% at 130℃; for 12 h; Inert atmosphere General procedure: To a solution of benzothiazoles or benzoxazoles (1, 1 mmol) in DMSO (3 mL), was added KOH (280 mg, 5 equiv) and 1,3-propanedithiol (207 μL, 2 mmol). The reaction mixture was heated under argon at 130 °C for 12 h. After cooling to room temperature, water (10 mL) was added. The pH of the reaction mixture was adjusted to 3–4 using 5percent HCl. The resulting mixture was extracted with ethyl acetate (15 mL ×2). The organic layer was washed with water and brine, dried over anhydrous MgSO4 and concentrated using rotary evaporator. The crude product was purified by silica gel column chromatography using ethyl acetate/n-hexane as eluent to afford the corresponding heteroaryl thiols 3.
45.7% With 1.3-propanedithiol; potassium carbonate In dimethyl sulfoxide at 130℃; for 12 h; Inert atmosphere; Sealed tube 5-bromobenzothiazole 214.08 mg (1.0 mmol), 1,3-propanedithiol 325 μL (3.0 mmol), potassium carbonate552mg (4.0mmol) and 2mL DMSO, placed in a reaction tube equipped with a magnetic stirrer, sealed with nitrogen, heated and stirred,The reaction was carried out in an oil bath at 120 ° C for 12 hours. After the reaction is completed, the reaction solution is transferred to a separatory funnel by washing with water, and an appropriate amount is added. Dilute hydrochloric acid, adjust the pH of the aqueous phase to 1-3, and extract the organic phase with dichloromethane, and transfer the upper organic phase with anhydrous magnesium sulfate. dry. Steam distillation under reduced pressure and separation by column chromatographyThe pink solid product was 112.4 mg, yield 45.7percent.
References: [1] Beilstein Journal of Organic Chemistry, 2019, p. 279 - 284.
[2] Patent: CN108530374, 2018, A, . Location in patent: Paragraph 0032; 0033.
  • 2
  • [ 2924-09-6 ]
  • [ 140-89-6 ]
  • [ 71216-20-1 ]
YieldReaction ConditionsOperation in experiment
95% at 140℃; for 2 h; Step A: 5-Bromobenzothiazole-2-thiol; To a solution of 5-bromo-2-fluorobenzenamine (200 mg, 1.28 mmol) in N-methyl-2- pyrrolidine (1.5 mL) was added potassium o-ethyl carbonodithioate (410 mg, 2.56 mmol). The mixture was heated at 140 0C for 2 h. The reaction mixture was poured into a large amount of water, acidified with concentrated hydrochloric acid, and filtered to give 5-bromo- benzothiazole-2-thiol 300 mg (95 percent).
References: [1] Patent: WO2007/110364, 2007, A1, . Location in patent: Page/Page column 57.
  • 3
  • [ 3638-73-1 ]
  • [ 140-89-6 ]
  • [ 71216-20-1 ]
References: [1] Patent: WO2013/42137, 2013, A1, . Location in patent: Page/Page column 33; 34.
  • 4
  • [ 3460-18-2 ]
  • [ 71216-20-1 ]
References: [1] Patent: US5451594, 1995, A, .
 

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