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Chemical Structure| 24072-75-1 Chemical Structure| 24072-75-1

Structure of 24072-75-1

Chemical Structure| 24072-75-1

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Product Details of [ 24072-75-1 ]

CAS No. :24072-75-1
Formula : C7H4Cl2N2S
M.W : 219.09
SMILES Code : NC1=NC2=CC(Cl)=C(Cl)C=C2S1
MDL No. :MFCD00053558
InChI Key :GHKHTBMTSUEBJD-UHFFFAOYSA-N
Pubchem ID :32206

Safety of [ 24072-75-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H317-H319
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 24072-75-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 9
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 54.04
TPSA ?

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

67.15 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.97
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

3.29
Log Po/w (WLOGP)?

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

3.19
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.

2.44
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

3.69
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.91

Water Solubility

Log S (ESOL):?

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

-3.83
Solubility 0.0327 mg/ml ; 0.000149 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.

-4.38
Solubility 0.00923 mg/ml ; 0.0000421 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

-3.85
Solubility 0.0309 mg/ml ; 0.000141 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

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

No
Log Kp (skin permeation)?

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

-5.3 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

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)

2.21

Application In Synthesis of [ 24072-75-1 ]

* 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 [ 24072-75-1 ]

[ 24072-75-1 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 333-20-0 ]
  • [ 95-76-1 ]
  • [ 24072-75-1 ]
YieldReaction ConditionsOperation in experiment
19% at 0 - 15℃; for 16 h; j00320j To a mixture of 3,4-dichloroaniline (10 g, 62 mmol) and potassium thiocyanate (48 g, 0.49 mol) in acetic acid (160 mL) at 0 °C was added slowly with constant stirring a solution of liquidbromine (31 g, 0.19 mol) in acetic acid (160 mL). The temperature was maintained at 0 °C throughout the addition. The solution was stirred for 2 hours at 0°C and 14 hours at 15 °C, then diluted with water (100 mL), adjusted to pH 78 with ammonium hydroxide and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine (3 x 300 mL) and concentrated in vacuo. The residue was purified by prep-HPLC [Instmment: GX-B; Column: GEMNI 250 x 50 mm, particle size: 10 .im; Mobile phase: 25-50percent acetonitrile in H20 (add 0.1percent TFA, v/v)j to give compound B- 24 (2.6 g, 19percent yield) as a white solid. LCMS (J): tR=0.694 mi (ES) m/z (M+H)219.0. ‘H-NMR (CD3OD, 400 MHz): 7.89 (s, 1H), 7.55 (s, 1H).
References: [1] Patent: WO2017/69980, 2017, A1, . Location in patent: Paragraph 00319; 00320.
[2] Bioorganic Chemistry, 2016, vol. 67, p. 130 - 138.
  • 2
  • [ 19250-09-0 ]
  • [ 24072-75-1 ]
  • [ 25150-27-0 ]
References: [1] Patent: WO2016/42172, 2016, A1, . Location in patent: Page/Page column 78; 79.
  • 3
  • [ 1147550-11-5 ]
  • [ 95-76-1 ]
  • [ 24072-75-1 ]
  • [ 25150-27-0 ]
References: [1] Heterocyclic Communications, 2002, vol. 8, # 3, p. 275 - 280.
  • 4
  • [ 19250-09-0 ]
  • [ 24072-75-1 ]
References: [1] Medicinal Chemistry Research, 2013, vol. 22, # 9, p. 4211 - 4222.
  • 5
  • [ 95-76-1 ]
  • [ 24072-75-1 ]
References: [1] Medicinal Chemistry Research, 2013, vol. 22, # 9, p. 4211 - 4222.
  • 6
  • [ 33240-95-8 ]
  • [ 24072-75-1 ]
References: [1] Medicinal Chemistry Research, 2013, vol. 22, # 9, p. 4211 - 4222.
  • 7
  • [ 333-20-0 ]
  • [ 95-76-1 ]
  • [ 24072-75-1 ]
  • [ 25150-27-0 ]
References: [1] Journal of Heterocyclic Chemistry, 1971, vol. 8, p. 309 - 310.
  • 8
  • [ 95-76-1 ]
  • [ 24072-75-1 ]
References: [1] European Journal of Medicinal Chemistry, 2010, vol. 45, # 9, p. 4293 - 4299.
[2] Archiv der Pharmazie, 2010, vol. 343, # 11-12, p. 692 - 699.
  • 9
  • [ 1147550-11-5 ]
  • [ 95-76-1 ]
  • [ 24072-75-1 ]
References: [1] Journal of Enzyme Inhibition and Medicinal Chemistry, 2011, vol. 26, # 4, p. 527 - 534.
 

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