N-(4-(N-(5-methylisoxazol-3-yl)sulfamoyl)phenyl)-2-(naphthalen-2-yl)acetamide

ID: ALA3108852

PubChem CID: 53255376

Max Phase: Preclinical

Molecular Formula: C22H19N3O4S

Molecular Weight: 421.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(NS(=O)(=O)c2ccc(NC(=O)Cc3ccc4ccccc4c3)cc2)no1

Standard InChI:  InChI=1S/C22H19N3O4S/c1-15-12-21(24-29-15)25-30(27,28)20-10-8-19(9-11-20)23-22(26)14-16-6-7-17-4-2-3-5-18(17)13-16/h2-13H,14H2,1H3,(H,23,26)(H,24,25)

Standard InChI Key:  IGZIWEJRUCQXBT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    9.7674   -4.6993    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.1780   -5.4058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5846   -4.6970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2214   -5.9290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5112   -6.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8024   -5.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0969   -6.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958   -4.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8006   -5.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9310   -6.3390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6388   -5.9306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3415   -6.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0524   -5.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0524   -5.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3415   -4.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6388   -5.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7643   -3.8761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4476   -2.5812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6311   -2.6670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4663   -3.4644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1757   -3.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7800   -3.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5827   -3.4954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2207   -5.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3880   -5.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3862   -5.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6745   -4.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9640   -5.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9698   -5.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6821   -6.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  5  1  0
  6  7  1  0
  7 25  2  0
 26  8  2  0
  8  9  1  0
  6  9  2  0
  5  6  1  0
 10  4  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
  1 17  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 18 22  1  0
 22 23  1  0
 17 20  1  0
 14  1  1  0
  4 24  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3108852

   N-[4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]-2-naphthalen-2-ylacetamide

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: 421.48

Molecular Weight (Monoisotopic): 421.1096

AlogP: 4.12

#Rotatable Bonds: 6

Polar Surface Area: 101.30

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.88

CX Basic pKa: 0.38

CX LogP: 3.68

CX LogD: 2.83

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.49

Np Likeness Score: -1.88

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