7-(2-Chloro-2-phenylethyl)-2-(methylthio)-N-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

ID: ALA4103914

PubChem CID: 137657483

Max Phase: Preclinical

Molecular Formula: C21H19ClN4S

Molecular Weight: 394.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1nc(Nc2ccccc2)c2ccn(CC(Cl)c3ccccc3)c2n1

Standard InChI:  InChI=1S/C21H19ClN4S/c1-27-21-24-19(23-16-10-6-3-7-11-16)17-12-13-26(20(17)25-21)14-18(22)15-8-4-2-5-9-15/h2-13,18H,14H2,1H3,(H,23,24,25)

Standard InChI Key:  FJQQPDTVQFJFJW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    9.9102  -17.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6285  -17.6324    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3356  -17.2105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3245  -16.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6063  -15.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8949  -16.4048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1259  -17.4518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1080  -16.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6016  -16.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5952  -15.1579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8728  -14.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8617  -13.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1394  -13.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4322  -13.9494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4433  -14.7743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1657  -15.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1989  -17.6516    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.4806  -17.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3925  -18.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2027  -18.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4265  -19.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8530  -19.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0768  -20.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8740  -20.7764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4515  -20.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2278  -19.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7463  -17.7732    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  2  0
  8  9  2  0
  7  9  1  0
  3  7  1  0
  4  8  1  0
  5 10  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
 10 11  1  0
 17 18  1  0
  1 17  1  0
 19 20  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 21 26  2  0
 20 21  1  0
 20 27  1  0
  7 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4103914

   ---

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: 394.93

Molecular Weight (Monoisotopic): 394.1019

AlogP: 5.88

#Rotatable Bonds: 6

Polar Surface Area: 42.74

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.46

CX LogP: 6.53

CX LogD: 6.52

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.25

Np Likeness Score: -1.35

References

1. Musumeci F, Fallacara AL, Brullo C, Grossi G, Botta L, Calandro P, Chiariello M, Kissova M, Crespan E, Maga G, Schenone S..  (2017)  Identification of new pyrrolo[2,3-d]pyrimidines as Src tyrosine kinase inhibitors in vitro active against Glioblastoma.,  127  [PMID:28076826] [10.1016/j.ejmech.2016.12.036]

Source

Source(1):

• Scientific Literature