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

ID: ALA3108855

PubChem CID: 53255423

Max Phase: Preclinical

Molecular Formula: C20H19Cl2N3O4S

Molecular Weight: 468.36

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H19Cl2N3O4S/c1-12-10-18(24-29-12)25-30(27,28)15-7-5-14(6-8-15)23-19(26)20(2,3)13-4-9-16(21)17(22)11-13/h4-11H,1-3H3,(H,23,26)(H,24,25)

Standard InChI Key:  DBKRAZSTNZDPHZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    4.5826   -7.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1756   -7.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9928   -7.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8388   -5.4710    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.2494   -6.1776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6560   -5.4688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2928   -6.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0023   -7.1108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7102   -6.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4128   -7.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1237   -6.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1237   -5.8856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4128   -5.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7102   -5.8856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8357   -4.6479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5190   -3.3530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7025   -3.4387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5377   -4.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2471   -4.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8514   -4.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6540   -4.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2920   -5.8836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8740   -6.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8776   -5.8909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1698   -5.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4621   -5.8942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4665   -6.7156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1749   -7.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7623   -7.1277    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7561   -5.4876    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  0
  5  4  2  0
  4  6  2  0
  7  1  1  0
  8  7  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  9 14  2  0
  4 15  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 16 20  1  0
 20 21  1  0
 15 18  1  0
 12  4  1  0
  7 22  2  0
  1 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
 27 29  1  0
 26 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3108855

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

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: 468.36

Molecular Weight (Monoisotopic): 467.0473

AlogP: 5.01

#Rotatable Bonds: 6

Polar Surface Area: 101.30

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.88

CX Basic pKa: 0.38

CX LogP: 5.00

CX LogD: 4.14

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.53

Np Likeness Score: -2.13

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