2-(3,4-dichlorophenyl)-N-(4-(N-phenylsulfamoyl)phenyl)acetamide

ID: ALA3108857

PubChem CID: 22829926

Max Phase: Preclinical

Molecular Formula: C20H16Cl2N2O3S

Molecular Weight: 435.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cc1ccc(Cl)c(Cl)c1)Nc1ccc(S(=O)(=O)Nc2ccccc2)cc1

Standard InChI:  InChI=1S/C20H16Cl2N2O3S/c21-18-11-6-14(12-19(18)22)13-20(25)23-15-7-9-17(10-8-15)28(26,27)24-16-4-2-1-3-5-16/h1-12,24H,13H2,(H,23,25)

Standard InChI Key:  FEDMRGHSJHSXOK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    8.6861   -4.8850    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.0934   -4.1765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2762   -4.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4299   -6.5268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1401   -6.1147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8496   -6.5247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5575   -6.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2601   -6.5268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9710   -6.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9710   -5.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2601   -4.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5575   -5.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1393   -5.2975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7213   -6.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7249   -5.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0171   -4.8979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3093   -5.3081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3138   -6.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0221   -6.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6096   -6.5417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6034   -4.9015    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.3945   -5.2923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1015   -4.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8049   -5.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5114   -4.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5104   -4.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7969   -3.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0934   -4.0696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  5  4  1  0
  6  5  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
 10  1  1  0
  5 13  2  0
  4 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 18 20  1  0
 17 21  1  0
  1 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3108857

   2-(3,4-dichlorophenyl)-N-[4-(phenylsulfamoyl)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: 435.33

Molecular Weight (Monoisotopic): 434.0259

AlogP: 4.98

#Rotatable Bonds: 6

Polar Surface Area: 75.27

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.95

CX Basic pKa: ┄

CX LogP: 4.74

CX LogD: 4.65

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.57

Np Likeness Score: -1.81

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