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

ID: ALA227065

PubChem CID: 23647976

Max Phase: Preclinical

Molecular Formula: C17H15N5S

Molecular Weight: 321.41

Molecule Type: Small molecule

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES:  Cc1c(Sc2ccc3ccccc3c2)[nH]c2nc(N)nc(N)c12

Standard InChI:  InChI=1S/C17H15N5S/c1-9-13-14(18)20-17(19)22-15(13)21-16(9)23-12-7-6-10-4-2-3-5-11(10)8-12/h2-8H,1H3,(H5,18,19,20,21,22)

Standard InChI Key:  HYATWDPIRHVVDH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    3.3520   -5.6238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5270   -5.6238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1145   -4.9093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7645   -4.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1145   -6.3383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5895   -4.9093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3520   -4.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5270   -4.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720   -3.4103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9395   -2.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6069   -3.4103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3915   -3.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9395   -2.1003    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6540   -1.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6540   -0.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3684   -0.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3684   -2.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0829   -1.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0829   -0.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7974   -0.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5118   -0.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5118   -1.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7974   -2.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11  7  1  0
  2  5  1  0
 11 12  1  0
  2  3  1  0
 10 13  1  0
  4  6  1  0
 13 14  1  0
  7  8  1  0
 14 15  2  0
  3  8  2  0
 15 16  1  0
 16 19  2  0
 17 14  1  0
 17 18  2  0
  1  2  2  0
  7  4  2  0
  4  1  1  0
 18 19  1  0
 19 20  1  0
  8  9  1  0
 20 21  2  0
  9 10  1  0
 21 22  1  0
 10 11  2  0
 22 23  2  0
 23 18  1  0
M  END

Associated Targets(Human)

DHFR Tclin Dihydrofolate reductase (3072 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Dihydrofolate reductase (1239 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Dihydrofolate reductase (1637 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
folA Dihydrofolate reductase (350 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Dhfr Dihydrofolate reductase (2343 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DHFR Dihydrofolate reductase (20 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 321.41Molecular Weight (Monoisotopic): 321.1048AlogP: 3.74#Rotatable Bonds: 2
Polar Surface Area: 93.61Molecular Species: NEUTRALHBA: 5HBD: 3
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): 5#RO5 Violations (Lipinski):
CX Acidic pKa: 12.35CX Basic pKa: 8.36CX LogP: 3.91CX LogD: 2.93
Aromatic Rings: 4Heavy Atoms: 23QED Weighted: 0.52Np Likeness Score: -0.70

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]
2. Gangjee A, Lin X, Biondo LR, Queener SF..  (2010)  CoMFA analysis of tgDHFR and rlDHFR based on antifolates with 6-5 fused ring system using the all-orientation search (AOS) routine and a modified cross-validated r(2)-guided region selection (q(2)-GRS) routine and its initial application.,  18  (4): [PMID:20117005] [10.1016/j.bmc.2009.12.066]
3. 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