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

ID: ALA3108837

PubChem CID: 53255440

Max Phase: Preclinical

Molecular Formula: C18H15Cl2N3O4S

Molecular Weight: 440.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(NS(=O)(=O)c2ccc(C(=O)NCc3ccc(Cl)c(Cl)c3)cc2)no1

Standard InChI:  InChI=1S/C18H15Cl2N3O4S/c1-11-8-17(22-27-11)23-28(25,26)14-5-3-13(4-6-14)18(24)21-10-12-2-7-15(19)16(20)9-12/h2-9H,10H2,1H3,(H,21,24)(H,22,23)

Standard InChI Key:  NZTINPKUMFFOJT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    4.8429   -6.1890    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1328   -6.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4239   -6.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7184   -6.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0070   -6.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0077   -5.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7174   -4.9611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4221   -5.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2942   -4.9541    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2932   -6.6062    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5525   -6.5990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2603   -6.1907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3889   -4.9593    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.7995   -5.6658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2061   -4.9570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9630   -6.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6739   -6.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6739   -5.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9630   -4.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2603   -5.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3858   -4.1361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0691   -2.8412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2526   -2.9270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0878   -3.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7972   -4.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4015   -3.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2042   -3.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5522   -7.4162    0.0000 O   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
 11 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3108837

   N-[(3,4-dichlorophenyl)methyl]-4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]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: 440.31

Molecular Weight (Monoisotopic): 439.0160

AlogP: 4.02

#Rotatable Bonds: 6

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: 5.74

CX Basic pKa: 0.39

CX LogP: 3.63

CX LogD: 2.75

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.60

Np Likeness Score: -2.17

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