N-(4-(N-1H-pyrazol-3-ylsulfamoyl)phenyl)-2-(3,4-dichlorophenyl)acetamide

ID: ALA3108859

PubChem CID: 53255393

Max Phase: Preclinical

Molecular Formula: C17H14Cl2N4O3S

Molecular Weight: 425.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cc1ccc(Cl)c(Cl)c1)Nc1ccc(S(=O)(=O)Nc2cc[nH]n2)cc1

Standard InChI:  InChI=1S/C17H14Cl2N4O3S/c18-14-6-1-11(9-15(14)19)10-17(24)21-12-2-4-13(5-3-12)27(25,26)23-16-7-8-20-22-16/h1-9H,10H2,(H,21,24)(H2,20,22,23)

Standard InChI Key:  SDBXCGIPGMBOSJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   11.4517   -3.0674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6352   -3.1532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4705   -3.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1798   -4.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7842   -3.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0534   -3.9564    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.4607   -3.2479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6435   -3.2494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7972   -5.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5074   -5.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2170   -5.5961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9248   -5.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6275   -5.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3384   -5.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3384   -4.3709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6275   -3.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9248   -4.3709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5066   -4.3689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0886   -5.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0922   -4.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3844   -3.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6767   -4.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6811   -5.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3895   -5.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9769   -5.6130    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9707   -3.9729    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.7619   -4.3637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  1  5  1  0
  7  6  2  0
  6  8  2  0
 10  9  1  0
 11 10  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  2  0
 15  6  1  0
 10 18  2  0
  9 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 23 25  1  0
 22 26  1  0
  6 27  1  0
 27  3  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3108859

   2-(3,4-dichlorophenyl)-N-[4-(1H-pyrazol-5-ylsulfamoyl)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: 425.30

Molecular Weight (Monoisotopic): 424.0164

AlogP: 3.70

#Rotatable Bonds: 6

Polar Surface Area: 103.95

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.25

CX Basic pKa: 2.68

CX LogP: 3.64

CX LogD: 2.88

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.56

Np Likeness Score: -2.14

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