2-(3,4-dichlorophenyl)-N-methyl-N-(4-(N-(5-methylisoxazol-3-yl)sulfamoyl)phenyl)acetamide

ID: ALA3108835

PubChem CID: 53255427

Max Phase: Preclinical

Molecular Formula: C19H17Cl2N3O4S

Molecular Weight: 454.34

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H17Cl2N3O4S/c1-12-9-18(22-28-12)23-29(26,27)15-6-4-14(5-7-15)24(2)19(25)11-13-3-8-16(20)17(21)10-13/h3-10H,11H2,1-2H3,(H,22,23)

Standard InChI Key:  FVYBYNAJZKLMMY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.1525   -6.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4423   -6.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1527   -5.3413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7334   -6.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0279   -6.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3165   -6.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3173   -5.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0269   -4.9322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7316   -5.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6037   -4.9252    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6027   -6.5773    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.8620   -6.5701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5699   -6.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6985   -4.9304    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.1090   -5.6369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5156   -4.9281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2725   -6.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9834   -6.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9834   -5.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2725   -4.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5699   -5.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6954   -4.1072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3786   -2.8123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5621   -2.8981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3974   -3.6955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1068   -4.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7111   -3.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5137   -3.7265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8617   -7.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  4  9  2  0
  7 10  1  0
  6 11  1  0
  2  4  1  0
 12  1  1  0
 12 13  1  0
 15 14  2  0
 14 16  2  0
 13 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 13 21  2  0
 14 22  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 23 27  1  0
 27 28  1  0
 22 25  1  0
 19 14  1  0
 12 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3108835

   2-(3,4-dichlorophenyl)-N-methyl-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: 454.34

Molecular Weight (Monoisotopic): 453.0317

AlogP: 4.30

#Rotatable Bonds: 6

Polar Surface Area: 92.51

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.87

CX Basic pKa: 0.38

CX LogP: 3.76

CX LogD: 2.91

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.60

Np Likeness Score: -2.21

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