2,4-Diamino-5-isopropyl-6-(3',4'-dichlorophenylsulfanyl)-7Hpyrrolo[2,3-d]pyrimidine

ID: ALA477151

PubChem CID: 24950854

Max Phase: Preclinical

Molecular Formula: C15H15Cl2N5S

Molecular Weight: 368.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1c(Sc2ccc(Cl)c(Cl)c2)[nH]c2nc(N)nc(N)c12

Standard InChI:  InChI=1S/C15H15Cl2N5S/c1-6(2)10-11-12(18)20-15(19)22-13(11)21-14(10)23-7-3-4-8(16)9(17)5-7/h3-6H,1-2H3,(H5,18,19,20,21,22)

Standard InChI Key:  ZANQFNCQCCPBKV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   13.6077  -12.4968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6065  -13.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3211  -13.7367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3193  -12.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0345  -12.4931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0348  -13.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8250  -13.5806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3133  -12.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8234  -12.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8918  -13.7358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3169  -11.2594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1346  -12.9042    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.5370  -13.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1117  -14.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5134  -15.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3390  -15.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7612  -14.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3571  -13.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1902  -11.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7330  -10.8104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0133  -11.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5860  -14.3579    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.7423  -15.7822    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  4 11  1  0
  8 12  1  0
  2  3  1  0
 12 13  1  0
  3  6  2  0
 13 14  2  0
  1  2  2  0
 14 15  1  0
  5  4  2  0
 15 16  2  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 17 18  2  0
 18 13  1  0
  8  9  2  0
  9 19  1  0
  9  5  1  0
 19 20  1  0
  4  1  1  0
 19 21  1  0
  2 10  1  0
 17 22  1  0
  5  6  1  0
 16 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA477151

   6-(3,4-dichlorophenyl)sulfanyl-5-propan-2-yl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

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: 368.29

Molecular Weight (Monoisotopic): 367.0425

AlogP: 4.70

#Rotatable Bonds: 3

Polar Surface Area: 93.61

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.13

CX Basic pKa: 8.33

CX LogP: 4.86

CX LogD: 3.90

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.62

Np Likeness Score: -0.85

References

1. Gangjee A, Jain HD, Queener SF, Kisliuk RL..  (2008)  The effect of 5-alkyl modification on the biological activity of pyrrolo[2,3-d]pyrimidine containing classical and nonclassical antifolates as inhibitors of dihydrofolate reductase and as antitumor and/or antiopportunistic infection agents.,  51  (15): [PMID:18605720] [10.1021/jm800244v]

Source

Source(1):

• Scientific Literature