4-(4-(3,4-Dichlorophenyl)piperazine-1-carboxamido)phenyl sulfamate

ID: ALA4589725

PubChem CID: 155568231

Max Phase: Preclinical

Molecular Formula: C17H18Cl2N4O4S

Molecular Weight: 445.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)Oc1ccc(NC(=O)N2CCN(c3ccc(Cl)c(Cl)c3)CC2)cc1

Standard InChI:  InChI=1S/C17H18Cl2N4O4S/c18-15-6-3-13(11-16(15)19)22-7-9-23(10-8-22)17(24)21-12-1-4-14(5-2-12)27-28(20,25)26/h1-6,11H,7-10H2,(H,21,24)(H2,20,25,26)

Standard InChI Key:  WCFRJEPDEBLNCB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   15.4812  -16.0756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8940  -16.7854    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.3024  -16.0731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3123  -15.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3112  -16.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0192  -17.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7289  -16.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7260  -15.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0174  -15.5593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6031  -17.1958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1877  -17.1947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4322  -15.5534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1414  -15.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8476  -15.5480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1445  -16.7765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5555  -15.9566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2595  -15.5489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2607  -14.7313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5516  -14.3232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8413  -14.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9684  -14.3227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6744  -14.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3816  -14.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3821  -13.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6694  -13.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9651  -13.5098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0891  -14.7350    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.0892  -13.0984    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  5 10  1  0
 10  2  1  0
  2 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 14 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 23 27  1  0
 24 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4589725

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 445.33

Molecular Weight (Monoisotopic): 444.0426

AlogP: 2.93

#Rotatable Bonds: 4

Polar Surface Area: 104.97

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.75

CX Basic pKa: 1.05

CX LogP: 2.92

CX LogD: 2.92

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.75

Np Likeness Score: -1.82

References

1. Moi D, Foster PA, Rimmer LG, Jaffri A, Deplano A, Balboni G, Onnis V, Potter BVL..  (2019)  Synthesis and in vitro evaluation of piperazinyl-ureido sulfamates as steroid sulfatase inhibitors.,  182  [PMID:31422224] [10.1016/j.ejmech.2019.111614]

2. Nocentini A,Moi D,Deplano A,Osman SM,AlOthman ZA,Balboni G,Supuran CT,Onnis V.  (2020)  Sulfonamide/sulfamate switch with a series of piperazinylureido derivatives: Synthesis, kinetic and in silico evaluation as carbonic anhydrase isoforms I, II, IV, and IX inhibitors.,  186  [PMID:31784185] [10.1016/j.ejmech.2019.111896]

Source

Source(1):

• Scientific Literature