2,3-Dichloro-N-(6-(dimethylamino)-3-methoxy-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)benzenesulfonamide

ID: ALA4093509

PubChem CID: 137654717

Max Phase: Preclinical

Molecular Formula: C15H16Cl2N6O3S

Molecular Weight: 431.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1nn(C)c2nc(N(C)C)nc(NS(=O)(=O)c3cccc(Cl)c3Cl)c12

Standard InChI:  InChI=1S/C15H16Cl2N6O3S/c1-22(2)15-18-12(10-13(19-15)23(3)20-14(10)26-4)21-27(24,25)9-7-5-6-8(16)11(9)17/h5-7H,1-4H3,(H,18,19,21)

Standard InChI Key:  ZOHDYXXLRJTJRV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   30.1500  -12.8684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5643  -12.1541    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.7386  -12.1525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2818  -12.5628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5657  -11.3274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2807  -10.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2797  -10.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5633   -9.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8466  -10.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8511  -10.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7657  -13.5470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7618  -14.8832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.2495  -14.2170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9774  -14.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9838  -13.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2762  -13.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5620  -13.7948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5596  -14.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2677  -15.0308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.0210  -12.7618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1393  -11.3423    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   29.1293   -9.6914    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.8287  -12.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0141  -15.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8436  -15.0310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8414  -15.8567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1295  -14.6163    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
 11 20  1  0
 10 21  1  0
  9 22  1  0
 20 23  1  0
 12 24  1  0
 18 25  1  0
 25 26  1  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4093509

   ---

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: 431.31

Molecular Weight (Monoisotopic): 430.0382

AlogP: 2.55

#Rotatable Bonds: 5

Polar Surface Area: 102.24

Molecular Species: ACID

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.59

CX Basic pKa: 0.29

CX LogP: 3.38

CX LogD: 2.48

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.66

Np Likeness Score: -1.94

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