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

ID: ALA3108869

PubChem CID: 53255392

Max Phase: Preclinical

Molecular Formula: C16H12Cl2N4O3S2

Molecular Weight: 443.34

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H12Cl2N4O3S2/c17-13-6-1-10(7-14(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:  KZSYKOLWVMHZHD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   10.5324   -3.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1153   -3.3662    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.5226   -2.6577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7054   -2.6592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8591   -5.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5693   -4.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2789   -5.0059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9867   -4.5976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6894   -5.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4003   -4.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4003   -3.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6894   -3.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9867   -3.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5686   -3.7787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1505   -4.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1541   -3.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4464   -3.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7386   -3.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7430   -4.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4514   -5.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0388   -5.0228    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.8238   -3.7735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2777   -3.6925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8240   -3.0808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4110   -2.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6095   -2.5460    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0294   -3.3832    0.0000 Cl  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:

   

   ALA3108869

   2-(3,4-dichlorophenyl)-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: 443.34

Molecular Weight (Monoisotopic): 441.9728

AlogP: 3.83

#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: 3.20

CX LogD: 2.55

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.60

Np Likeness Score: -2.41

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