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

ID: ALA3108841

PubChem CID: 53255404

Max Phase: Preclinical

Molecular Formula: C19H17Cl2N3O4S

Molecular Weight: 454.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(NS(=O)(=O)Cc2ccc(NC(=O)Cc3ccc(Cl)c(Cl)c3)cc2)no1

Standard InChI:  InChI=1S/C19H17Cl2N3O4S/c1-12-8-18(23-28-12)24-29(26,27)11-13-2-5-15(6-3-13)22-19(25)10-14-4-7-16(20)17(21)9-14/h2-9H,10-11H2,1H3,(H,22,25)(H,23,24)

Standard InChI Key:  AHSRQPISLJBYRW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   12.7648   -8.8490    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.1736   -9.5566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3564   -9.5568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3430   -8.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0560   -8.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4737   -8.4381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4401   -9.2593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9591   -8.5982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1836   -8.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1839   -9.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9618   -9.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2139  -10.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5120   -9.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8019  -10.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0930   -9.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875  -10.0754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6761   -9.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6768   -8.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3865   -8.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0912   -8.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9633   -8.4292    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9623  -10.0813    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.2216  -10.0741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9294   -9.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6321  -10.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3430   -9.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6321   -8.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9294   -8.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5113   -8.8469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  5  1  0
  1  6  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  7 11  1  0
 11 12  1  0
  6  9  1  0
  5  1  1  0
 13 14  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  2  0
 18 21  1  0
 17 22  1  0
 14 15  1  0
 23 13  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26  4  1  0
  4 27  2  0
 27 28  1  0
 24 28  2  0
 13 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3108841

   2-(3,4-dichlorophenyl)-N-[4-[(5-methyl-1,2-oxazol-3-yl)sulfamoylmethyl]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: 454.33

Molecular Weight (Monoisotopic): 453.0317

AlogP: 4.41

#Rotatable Bonds: 7

Polar Surface Area: 101.30

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.53

CX Basic pKa: 0.42

CX LogP: 3.66

CX LogD: 3.00

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.55

Np Likeness Score: -2.21

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