6-((3,4-Difluorophenyl)thio)-5,7-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

ID: ALA4225535

PubChem CID: 145968997

Max Phase: Preclinical

Molecular Formula: C14H13F2N5S

Molecular Weight: 321.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(Sc2ccc(F)c(F)c2)n(C)c2nc(N)nc(N)c12

Standard InChI:  InChI=1S/C14H13F2N5S/c1-6-10-11(17)19-14(18)20-12(10)21(2)13(6)22-7-3-4-8(15)9(16)5-7/h3-5H,1-2H3,(H4,17,18,19,20)

Standard InChI Key:  DXAZMIQDBFVLSA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    2.7019  -28.1972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7008  -29.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4088  -29.4257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4070  -27.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9927  -29.4248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4046  -26.9711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1156  -28.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204  -29.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9005  -29.2607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3778  -28.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8927  -27.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1407  -27.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1950  -28.5907    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.6078  -29.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2008  -30.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6129  -30.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4309  -30.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8352  -29.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4208  -29.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1575  -30.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6523  -29.9825    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.8446  -31.4100    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  8  2  0
  7  4  2  0
  4  1  1  0
  2  5  1  0
  4  6  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11  7  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  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
  9 20  1  0
 18 21  1  0
 17 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4225535

   ---

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: 321.36

Molecular Weight (Monoisotopic): 321.0860

AlogP: 2.87

#Rotatable Bonds: 2

Polar Surface Area: 82.75

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.95

CX LogP: 3.43

CX LogD: 2.79

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.76

Np Likeness Score: -1.48

References

1. Shah K, Lin X, Queener SF, Cody V, Pace J, Gangjee A..  (2018)  Targeting species specific amino acid residues: Design, synthesis and biological evaluation of 6-substituted pyrrolo[2,3-d]pyrimidines as dihydrofolate reductase inhibitors and potential anti-opportunistic infection agents.,  26  (9): [PMID:29691153] [10.1016/j.bmc.2018.04.032]

Source

Source(1):

• Scientific Literature