1-(2-(3,4-dichlorophenyl)acetyl)-N-(5-methylisoxazol-3-yl)piperidine-4-sulfonamide

ID: ALA3108832

PubChem CID: 53255380

Max Phase: Preclinical

Molecular Formula: C17H19Cl2N3O4S

Molecular Weight: 432.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(NS(=O)(=O)C2CCN(C(=O)Cc3ccc(Cl)c(Cl)c3)CC2)no1

Standard InChI:  InChI=1S/C17H19Cl2N3O4S/c1-11-8-16(20-26-11)21-27(24,25)13-4-6-22(7-5-13)17(23)10-12-2-3-14(18)15(19)9-12/h2-3,8-9,13H,4-7,10H2,1H3,(H,20,21)

Standard InChI Key:  HFVJZFXVBPWOTF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   12.3593  -12.0127    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.7699  -12.7193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1765  -12.0104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6429  -12.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2307  -13.2448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9334  -13.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6443  -13.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9334  -12.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2307  -12.4280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3562  -11.1903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0395   -9.8939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2230   -9.9796    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0582  -10.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7676  -11.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3719  -10.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1746  -10.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5157  -13.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5157  -14.4802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8089  -13.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0980  -13.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3953  -13.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6844  -13.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6844  -14.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3953  -14.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0980  -14.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9694  -14.8989    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9694  -13.2407    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  4  1  0
  4  8  1  0
  8  9  1  0
  5  9  1  0
  1 10  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 11 15  1  0
 15 16  1  0
 10 13  1  0
 17 18  2  0
 17 19  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 20 25  2  0
 23 26  1  0
 22 27  1  0
 19 20  1  0
  5 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3108832

   1-[2-(3,4-dichlorophenyl)acetyl]-N-(5-methyl-1,2-oxazol-3-yl)piperidine-4-sulfonamide

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: 432.33

Molecular Weight (Monoisotopic): 431.0473

AlogP: 3.27

#Rotatable Bonds: 5

Polar Surface Area: 92.51

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.55

CX Basic pKa: 0.42

CX LogP: 2.11

CX LogD: 1.46

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.78

Np Likeness Score: -1.93

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