6-(3,4-dichlorophenylthio)-5-methyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

ID: ALA442702

PubChem CID: 23647977

Max Phase: Preclinical

Molecular Formula: C13H11Cl2N5S

Molecular Weight: 340.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(Sc2ccc(Cl)c(Cl)c2)[nH]c2nc(N)nc(N)c12

Standard InChI:  InChI=1S/C13H11Cl2N5S/c1-5-9-10(16)18-13(17)20-11(9)19-12(5)21-6-2-3-7(14)8(15)4-6/h2-4H,1H3,(H5,16,17,18,19,20)

Standard InChI Key:  ZDGXEJGHCJAUPD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    8.7444   -6.0583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7432   -6.8857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4581   -7.2985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4563   -5.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9659   -7.1350    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4493   -6.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9584   -5.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1716   -6.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1763   -6.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4500   -4.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2743   -6.4572    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.2089   -5.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0284   -7.2976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6908   -7.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2814   -7.8838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6973   -8.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5231   -8.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9314   -7.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5132   -7.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7564   -7.8619    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.9406   -9.3028    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  4 10  1  0
  8  9  1  0
  6 11  1  0
  7 12  1  0
  2  3  1  0
  2 13  1  0
  6  7  2  0
 11 14  1  0
  3  9  2  0
 14 15  2  0
  1  2  2  0
 15 16  1  0
  8  4  2  0
 16 17  2  0
  5  6  1  0
 17 18  1  0
  7  8  1  0
 18 19  2  0
 19 14  1  0
  9  5  1  0
 18 20  1  0
  4  1  1  0
 17 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA442702

   6-[(3,4-dichlorophenyl)sulfanyl]-5-methyl-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: 340.24

Molecular Weight (Monoisotopic): 339.0112

AlogP: 3.89

#Rotatable Bonds: 2

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: 12.35

CX Basic pKa: 8.36

CX LogP: 4.13

CX LogD: 3.15

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.66

Np Likeness Score: -1.06

References

1. Gangjee A, Zeng Y, Talreja T, McGuire JJ, Kisliuk RL, Queener SF..  (2007)  Design and synthesis of classical and nonclassical 6-arylthio-2,4-diamino-5-ethylpyrrolo[2,3-d]pyrimidines as antifolates.,  50  (13): [PMID:17552508] [10.1021/jm070165j]

Source

Source(1):

• Scientific Literature