2,3-Dichloro-N-(3-hydroxy-1H-pyrazolo[3,4-d]pyrimidin-4-yl)benzenesulfonamide

ID: ALA4090166

PubChem CID: 137643503

Max Phase: Preclinical

Molecular Formula: C11H7Cl2N5O3S

Molecular Weight: 360.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(Nc1ncnc2[nH]nc(O)c12)c1cccc(Cl)c1Cl

Standard InChI:  InChI=1S/C11H7Cl2N5O3S/c12-5-2-1-3-6(8(5)13)22(20,21)18-10-7-9(14-4-15-10)16-17-11(7)19/h1-4H,(H3,14,15,16,17,18,19)

Standard InChI Key:  PGRGKRXPFYRQPM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   30.7944  -11.7290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2094  -11.0135    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.3824  -11.0119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9282  -11.4229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2108  -10.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9271   -9.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9260   -8.9503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2085   -8.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4905   -8.9563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4952   -9.7813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4147  -12.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4108  -13.7474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.8994  -13.0800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6251  -13.4888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6314  -12.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9227  -12.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2072  -12.6570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2049  -13.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9142  -13.8950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6427  -10.1913    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   32.6418   -8.5358    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.6704  -11.6222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  2  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 11 15  1  0
 14 12  1  0
 12 13  1  0
 13 11  2  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 16  4  1  0
  6 20  1  0
  7 21  1  0
 11 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4090166

   ---

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: 360.18

Molecular Weight (Monoisotopic): 358.9647

AlogP: 2.17

#Rotatable Bonds: 3

Polar Surface Area: 120.86

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.47

CX Basic pKa: 0.70

CX LogP: 2.32

CX LogD: -0.32

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.66

Np Likeness Score: -1.84

References

1. Miah AH, Champigny AC, Graves RH, Hodgson ST, Percy JM, Procopiou PA..  (2017)  Identification of pyrazolopyrimidine arylsulfonamides as CC-chemokine receptor 4 (CCR4) antagonists.,  25  (20): [PMID:28801066] [10.1016/j.bmc.2017.07.052]

Source

Source(1):

• Scientific Literature