3,4-dichloro-N-(4-(N-(5-methylisoxazol-3-yl)sulfamoyl)phenyl)benzamide

ID: ALA3108853

PubChem CID: 1010711

Max Phase: Preclinical

Molecular Formula: C17H13Cl2N3O4S

Molecular Weight: 426.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(NS(=O)(=O)c2ccc(NC(=O)c3ccc(Cl)c(Cl)c3)cc2)no1

Standard InChI:  InChI=1S/C17H13Cl2N3O4S/c1-10-8-16(21-26-10)22-27(24,25)13-5-3-12(4-6-13)20-17(23)11-2-7-14(18)15(19)9-11/h2-9H,1H3,(H,20,23)(H,21,22)

Standard InChI Key:  DRRCQQFLVIBMJI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    8.8677   -4.8520    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.2782   -5.5585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6849   -4.8497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3217   -6.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6115   -6.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0312   -6.4917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7391   -6.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4417   -6.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1526   -6.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1526   -5.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4417   -4.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7391   -5.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8646   -4.0288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5479   -2.7339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7314   -2.8197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5666   -3.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2760   -4.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8803   -3.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6829   -3.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3209   -5.2645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9021   -6.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925   -6.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1938   -7.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9108   -7.7238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6176   -7.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9126   -8.5426    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4887   -7.7220    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  5  1  0
  6  4  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 12  2  0
  1 13  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 14 18  1  0
 18 19  1  0
 13 16  1  0
 10  1  1  0
  4 20  2  0
  5 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25  5  1  0
 24 26  1  0
 23 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3108853

   3,4-dichloro-N-(4-{[(5-methyl-3-isoxazolyl)amino]sulfonyl}phenyl)benzamide

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: 426.28

Molecular Weight (Monoisotopic): 425.0004

AlogP: 4.34

#Rotatable Bonds: 5

Polar Surface Area: 101.30

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.88

CX Basic pKa: 0.38

CX LogP: 3.92

CX LogD: 3.06

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.63

Np Likeness Score: -2.36

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