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

ID: ALA4091069

PubChem CID: 137644970

Max Phase: Preclinical

Molecular Formula: C13H11Cl2N5O3S

Molecular Weight: 388.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1n[nH]c2ncnc(NS(=O)(=O)c3cccc(Cl)c3Cl)c12

Standard InChI:  InChI=1S/C13H11Cl2N5O3S/c1-2-23-13-9-11(18-19-13)16-6-17-12(9)20-24(21,22)8-5-3-4-7(14)10(8)15/h3-6H,2H2,1H3,(H2,16,17,18,19,20)

Standard InChI Key:  VDRMWPDDONONGM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   30.8381  -11.2754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2524  -10.5611    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.4267  -10.5595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9699  -10.9698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2538   -9.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9687   -9.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9676   -8.5013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2514   -8.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5347   -8.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5392   -9.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4537  -11.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4499  -13.2902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.9376  -12.6240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6655  -13.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6719  -12.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9643  -11.7957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2500  -12.2018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2477  -13.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9558  -13.4377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6831   -9.7403    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   32.6822   -8.0875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.7091  -11.1688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.5168  -10.9972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7720  -10.2120    0.0000 C   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
 22 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4091069

   ---

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: 388.24

Molecular Weight (Monoisotopic): 386.9960

AlogP: 2.86

#Rotatable Bonds: 5

Polar Surface Area: 109.86

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.60

CX Basic pKa: 0.58

CX LogP: 2.82

CX LogD: 1.90

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.70

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