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

ID: ALA3108850

PubChem CID: 53255434

Max Phase: Preclinical

Molecular Formula: C20H21N3O4S

Molecular Weight: 399.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(NS(=O)(=O)c2ccc(NC(=O)Cc3ccc(C)c(C)c3)cc2)no1

Standard InChI:  InChI=1S/C20H21N3O4S/c1-13-4-5-16(10-14(13)2)12-20(24)21-17-6-8-18(9-7-17)28(25,26)23-19-11-15(3)27-22-19/h4-11H,12H2,1-3H3,(H,21,24)(H,22,23)

Standard InChI Key:  LQUGFZCZZYMZSI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    9.1277   -4.6539    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.5383   -5.3604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9449   -4.6516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5817   -5.8836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8715   -6.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1627   -5.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4572   -6.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7457   -5.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7465   -5.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4561   -4.6557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1609   -5.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2912   -6.2936    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9991   -5.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7017   -6.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4127   -5.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4127   -5.0684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7017   -4.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9991   -5.0684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1246   -3.8307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8079   -2.5358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9914   -2.6216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8266   -3.4190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5360   -3.8275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1403   -3.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9430   -3.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5809   -5.0664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0389   -4.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0384   -6.2958    0.0000 C   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  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  6 11  2  0
  5  6  1  0
 12  4  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 18  2  0
  1 19  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 20 24  1  0
 24 25  1  0
 19 22  1  0
 16  1  1  0
  4 26  2  0
  9 27  1  0
  8 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3108850

   2-(3,4-dimethylphenyl)-N-[4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]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: 399.47

Molecular Weight (Monoisotopic): 399.1253

AlogP: 3.58

#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: 5.88

CX Basic pKa: 0.38

CX LogP: 3.72

CX LogD: 2.86

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.66

Np Likeness Score: -2.18

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