2-(3,4-dichlorophenyl)-N-(4-(N-methyl-N-(5-methylisoxazol-3-yl)sulfamoyl)phenyl)acetamide

ID: ALA3108839

PubChem CID: 53255438

Max Phase: Preclinical

Molecular Formula: C19H17Cl2N3O4S

Molecular Weight: 454.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(N(C)S(=O)(=O)c2ccc(NC(=O)Cc3ccc(Cl)c(Cl)c3)cc2)no1

Standard InChI:  InChI=1S/C19H17Cl2N3O4S/c1-12-9-18(23-28-12)24(2)29(26,27)15-6-4-14(5-7-15)22-19(25)11-13-3-8-16(20)17(21)10-13/h3-10H,11H2,1-2H3,(H,22,25)

Standard InChI Key:  SWWKJJXNISLZFP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.5239   -6.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8137   -6.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1049   -6.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3994   -6.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6879   -6.1012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6887   -5.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3983   -4.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1031   -5.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9752   -4.8633    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9742   -6.5154    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.2335   -6.5082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9413   -6.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0699   -4.8685    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.4805   -5.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8871   -4.8662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6440   -6.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3549   -6.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3549   -5.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6440   -4.8767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9413   -5.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0668   -4.0453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7501   -2.7504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9336   -2.8362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7688   -3.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4782   -4.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0825   -3.4954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8852   -3.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5232   -5.2810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3570   -3.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  3  8  2  0
  6  9  1  0
  5 10  1  0
  2  3  1  0
 11  1  1  0
 11 12  1  0
 14 13  2  0
 13 15  2  0
 12 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 12 20  2  0
 13 21  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 22 26  1  0
 26 27  1  0
 21 24  1  0
 18 13  1  0
  1 28  2  0
 21 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3108839

   2-(3,4-dichlorophenyl)-N-[4-[methyl-(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]acetamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 454.34

Molecular Weight (Monoisotopic): 453.0317

AlogP: 4.30

#Rotatable Bonds: 6

Polar Surface Area: 92.51

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.12

CX Basic pKa: 0.26

CX LogP: 4.12

CX LogD: 4.12

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.60

Np Likeness Score: -2.06

References

1. Brimacombe KR, Walsh MJ, Liu L, Vásquez-Valdivieso MG, Morgan HP, McNae I, Fothergill-Gilmore LA, Michels PA, Auld DS, Simeonov A, Walkinshaw MD, Shen M, Boxer MB..  (2014)  Identification of ML251, a Potent Inhibitor of T. brucei and T. cruzi Phosphofructokinase.,  5  (1): [PMID:24900769] [10.1021/ml400259d]

2. Miana GE, Ribone SR, Vera DMA, Sánchez-Moreno M, Mazzieri MR, Quevedo MA..  (2019)  Design, synthesis and molecular docking studies of novel N-arylsulfonyl-benzimidazoles with anti Trypanosoma cruzi activity.,  165  [PMID:30641409] [10.1016/j.ejmech.2019.01.013]

Source

Source(1):

• Scientific Literature