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

ID: ALA3108831

PubChem CID: 53255402

Max Phase: Preclinical

Molecular Formula: C18H15Cl2N3O4S

Molecular Weight: 440.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(NS(=O)(=O)c2cccc(NC(=O)Cc3ccc(Cl)c(Cl)c3)c2)no1

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

Standard InChI Key:  RLCMOWQLTYBXCC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    5.6436   -5.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9334   -4.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6438   -6.1943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2246   -5.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5191   -4.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8076   -5.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8084   -6.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5180   -6.6034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2228   -6.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0949   -6.6104    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0939   -4.9583    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.0610   -6.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1896   -4.9593    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.6002   -5.6658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0068   -4.9570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7637   -6.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4746   -6.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4746   -5.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7637   -4.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0610   -5.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1865   -4.1361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8698   -2.8412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0533   -2.9270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8885   -3.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5979   -4.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2022   -3.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0049   -3.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3531   -4.9655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  4  9  2  0
  7 10  1  0
  6 11  1  0
  2  4  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
 20 28  1  0
 28  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3108831

   2-(3,4-dichlorophenyl)-N-[3-[(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: 440.31

Molecular Weight (Monoisotopic): 439.0160

AlogP: 4.27

#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: 5.79

CX Basic pKa: 0.38

CX LogP: 3.90

CX LogD: 3.03

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.60

Np Likeness Score: -2.47

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