N-(3-((4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methyl)phenyl)-2,6-difluorobenzenesulfonamide

ID: ALA2386997

PubChem CID: 67219275

Max Phase: Preclinical

Molecular Formula: C24H23F2N5O2S

Molecular Weight: 483.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(Cc1cccc(NS(=O)(=O)c3c(F)cccc3F)c1)cn2C1CCCC1

Standard InChI:  InChI=1S/C24H23F2N5O2S/c25-19-9-4-10-20(26)22(19)34(32,33)30-17-6-3-5-15(12-17)11-16-13-31(18-7-1-2-8-18)24-21(16)23(27)28-14-29-24/h3-6,9-10,12-14,18,30H,1-2,7-8,11H2,(H2,27,28,29)

Standard InChI Key:  KHXWUFRFWLVSHJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   36.5831  -13.4530    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   36.7587  -14.2591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.3690  -13.7039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2030  -16.5923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2029  -17.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9182  -17.8317    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9143  -16.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6302  -16.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6315  -17.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4179  -17.6675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.9027  -16.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4159  -16.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6782  -18.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1944  -19.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6803  -19.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4646  -19.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4632  -18.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9108  -15.3537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6696  -15.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4763  -15.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0234  -15.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8294  -15.8138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0838  -15.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5260  -14.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7221  -14.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7770  -13.6286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.8340  -12.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6395  -12.4964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8905  -11.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3351  -11.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5254  -11.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2782  -12.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1928  -13.1083    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   35.4730  -12.2439    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 10 13  1  0
  7 18  1  0
 12 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 24 26  1  0
 26  1  1  0
  1 27  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
 28 33  1  0
 32 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2386997

   N-[3-[(4-amino-7-cyclopentylpyrrolo[2,3-d]pyrimidin-5-yl)methyl]phenyl]-2,6-difluorobenzenesulfonamide

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: 483.54

Molecular Weight (Monoisotopic): 483.1541

AlogP: 4.80

#Rotatable Bonds: 6

Polar Surface Area: 102.90

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.92

CX Basic pKa: 7.07

CX LogP: 3.60

CX LogD: 3.74

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.41

Np Likeness Score: -1.04

References

1. Arcari JT, Beebe JS, Berliner MA, Bernardo V, Boehm M, Borzillo GV, Clark T, Cohen BD, Connell RD, Frost HN, Gordon DA, Hungerford WM, Kakar SM, Kanter A, Keene NF, Knauth EA, Lagreca SD, Lu Y, Martinez-Alsina L, Marx MA, Morris J, Patel NC, Savage D, Soderstrom CI, Thompson C, Tkalcevic G, Tom NJ, Vajdos FF, Valentine JJ, Vincent PW, Wessel MD, Chen JM..  (2013)  Discovery and synthesis of novel 4-aminopyrrolopyrimidine Tie-2 kinase inhibitors for the treatment of solid tumors.,  23  (10): [PMID:23566514] [10.1016/j.bmcl.2013.03.012]

Source

Source(1):

• Scientific Literature