2-(3-chloro-4-fluorophenyl)-N-(4-(N-(5-methylisoxazol-3-yl)sulfamoyl)phenyl)acetamide

ID: ALA3108848

PubChem CID: 53255428

Max Phase: Preclinical

Molecular Formula: C18H15ClFN3O4S

Molecular Weight: 423.85

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H15ClFN3O4S/c1-11-8-17(22-27-11)23-28(25,26)14-5-3-13(4-6-14)21-18(24)10-12-2-7-16(20)15(19)9-12/h2-9H,10H2,1H3,(H,21,24)(H,22,23)

Standard InChI Key:  PHMRRWNGTSNAOQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    8.3889   -4.5589    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.7995   -5.2655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2061   -4.5566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8429   -5.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1328   -6.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4239   -5.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7184   -6.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0070   -5.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0077   -4.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7174   -4.5608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4221   -4.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5525   -6.1987    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2603   -5.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9630   -6.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6739   -5.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6739   -4.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9630   -4.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2603   -4.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3858   -3.7358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0691   -2.4408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2526   -2.5266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0878   -3.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7972   -3.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4015   -3.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2042   -3.3551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8422   -4.9715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3001   -6.1991    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3001   -4.5620    0.0000 F   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
  8 27  1  0
  9 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3108848

   2-(3-chloro-4-fluorophenyl)-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: 423.85

Molecular Weight (Monoisotopic): 423.0456

AlogP: 3.76

#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: 3.44

CX LogD: 2.58

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.63

Np Likeness Score: -2.54

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