N-(4-(N-1,3,4-thiadiazol-2-ylsulfamoyl)phenyl)-2-(3-chloro-4-fluorophenyl)acetamide

ID: ALA3108870

PubChem CID: 73670805

Max Phase: Preclinical

Molecular Formula: C16H12ClFN4O3S2

Molecular Weight: 426.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cc1ccc(F)c(Cl)c1)Nc1ccc(S(=O)(=O)Nc2nncs2)cc1

Standard InChI:  InChI=1S/C16H12ClFN4O3S2/c17-13-7-10(1-6-14(13)18)8-15(23)20-11-2-4-12(5-3-11)27(24,25)22-16-21-19-9-26-16/h1-7,9H,8H2,(H,20,23)(H,21,22)

Standard InChI Key:  DDCAUPBWFJKZDY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   10.8419   -8.7094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4248   -8.7151    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.8321   -8.0066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0150   -8.0081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1687  -10.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8789   -9.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5884  -10.3548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2963   -9.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9989  -10.3568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7098   -9.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7098   -9.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9989   -8.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2962   -9.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8781   -9.1276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4601   -9.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4637   -9.1349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7559   -8.7279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0481   -9.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0526   -9.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7609  -10.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3484  -10.3717    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.1333   -9.1224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5872   -9.0414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1335   -8.4297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7205   -7.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9190   -7.8949    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3390   -8.7321    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  2  4  2  0
  6  5  1  0
  7  6  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  8 13  2  0
 11  2  1  0
  6 14  2  0
  5 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 19 21  1  0
  2 22  1  0
 22  1  1  0
  1 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26  1  1  0
 18 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3108870

   2-(3-chloro-4-fluorophenyl)-N-[4-(1,3,4-thiadiazol-2-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: 426.88

Molecular Weight (Monoisotopic): 426.0023

AlogP: 3.31

#Rotatable Bonds: 6

Polar Surface Area: 101.05

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.55

CX Basic pKa: ┄

CX LogP: 2.74

CX LogD: 2.09

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.63

Np Likeness Score: -2.68

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