4-(4-(4-phenylpyrimidin-2-yl)piperazine-1-carboxamido)phenyl sulfamate

ID: ALA4547402

PubChem CID: 155553321

Max Phase: Preclinical

Molecular Formula: C21H22N6O4S

Molecular Weight: 454.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)Oc1ccc(NC(=O)N2CCN(c3nccc(-c4ccccc4)n3)CC2)cc1

Standard InChI:  InChI=1S/C21H22N6O4S/c22-32(29,30)31-18-8-6-17(7-9-18)24-21(28)27-14-12-26(13-15-27)20-23-11-10-19(25-20)16-4-2-1-3-5-16/h1-11H,12-15H2,(H,24,28)(H2,22,29,30)

Standard InChI Key:  BMESPXWKAAGELO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   12.1423   -7.5157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5550   -6.8099    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.7333   -6.8012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7449   -2.2823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7438   -3.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4559   -3.5149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1656   -3.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1628   -2.2787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4541   -1.8693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8758   -3.5122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8751   -4.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5835   -4.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2971   -4.3356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2978   -3.5134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5849   -3.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0080   -4.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0062   -5.5712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7208   -4.3388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4317   -4.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4250   -5.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1350   -5.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8446   -5.5758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8438   -4.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1373   -4.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5561   -5.9850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2669   -7.2197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0335   -3.5143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3217   -3.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6100   -3.5108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6089   -4.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3254   -4.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0342   -4.3323    0.0000 C   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
 10 11  1  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  7 10  1  0
 13 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 22 25  1  0
 25  2  1  0
  2 26  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
  5 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4547402

   ---

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: 454.51

Molecular Weight (Monoisotopic): 454.1423

AlogP: 2.08

#Rotatable Bonds: 5

Polar Surface Area: 130.75

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.75

CX Basic pKa: 3.73

CX LogP: 2.50

CX LogD: 2.50

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.60

Np Likeness Score: -1.71

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