4-(3,4-dichlorophenethylamino)-N-(5-methylisoxazol-3-yl)benzenesulfonamide

ID: ALA3108836

PubChem CID: 53255426

Max Phase: Preclinical

Molecular Formula: C18H17Cl2N3O3S

Molecular Weight: 426.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(NS(=O)(=O)c2ccc(NCCc3ccc(Cl)c(Cl)c3)cc2)no1

Standard InChI:  InChI=1S/C18H17Cl2N3O3S/c1-12-10-18(22-26-12)23-27(24,25)15-5-3-14(4-6-15)21-9-8-13-2-7-16(19)17(20)11-13/h2-7,10-11,21H,8-9H2,1H3,(H,22,23)

Standard InChI Key:  DLSFAJHHDXJOAO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    4.8429   -6.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1328   -6.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4239   -6.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7184   -6.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0070   -6.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0077   -5.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7174   -4.9611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4221   -5.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2942   -4.9541    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2932   -6.6062    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5525   -6.5990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2603   -6.1907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3889   -4.9593    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.7995   -5.6658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2061   -4.9570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9630   -6.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6739   -6.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6739   -5.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9630   -4.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2603   -5.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3858   -4.1361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0691   -2.8412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2526   -2.9270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0878   -3.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7972   -4.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4015   -3.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2042   -3.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  3  8  2  0
  6  9  1  0
  5 10  1  0
  2  3  1  0
 11  1  1  0
 11 12  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
M  END

Alternative Forms

1. Parent:

   

   ALA3108836

   4-[2-(3,4-dichlorophenyl)ethylamino]-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide

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: 426.33

Molecular Weight (Monoisotopic): 425.0368

AlogP: 4.75

#Rotatable Bonds: 7

Polar Surface Area: 84.23

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.15

CX Basic pKa: 2.97

CX LogP: 4.31

CX LogD: 3.52

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.57

Np Likeness Score: -1.98

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