1-(3-Methoxy-phenyl)-6,6-dimethyl-1,6-dihydro-[1,3,5]triazine-2,4-diamine

ID: ALA266319

Chembl Id: CHEMBL266319

PubChem CID: 427328

Max Phase: Preclinical

Molecular Formula: C12H17N5O

Molecular Weight: 247.30

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms from Alternative Forms(1): GNF-Pf-4467

Canonical SMILES:  COc1cccc(N2C(N)=NC(N)=NC2(C)C)c1

Standard InChI:  InChI=1S/C12H17N5O/c1-12(2)16-10(13)15-11(14)17(12)8-5-4-6-9(7-8)18-3/h4-7H,1-3H3,(H4,13,14,15,16)

Standard InChI Key:  IANXQZFGCPHWLQ-UHFFFAOYSA-N

Associated Targets(non-human)

folA Dihydrofolate reductase (1415 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Dihydrofolate reductase (126 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Dhfr Dihydrofolate reductase (2343 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
folA Dihydrofolate reductase (640 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Lacticaseibacillus casei (578 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
L5178Y (1809 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
folA Dihydrofolate reductase (66 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
dhfrI Dihydrofolate reductase type 1 (145 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Dhfr Dihydrofolate reductase (711 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DHFR Dihydrofolate reductase (392 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: 247.30Molecular Weight (Monoisotopic): 247.1433AlogP: 0.88#Rotatable Bonds: 2
Polar Surface Area: 89.23Molecular Species: NEUTRALHBA: 6HBD: 2
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 4#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 8.30CX LogP: 0.94CX LogD: 0.00
Aromatic Rings: 1Heavy Atoms: 18QED Weighted: 0.81Np Likeness Score: -0.52

References

1. Ghose AK, Crippen GM..  (1983)  Combined distance geometry analysis of dihydrofolate reductase inhibition by quinazolines and triazines.,  26  (7): [PMID:6864738] [10.1021/jm00361a012]
2. Booth RG, Selassie CD, Hansch C, Santi DV..  (1987)  Quantitative structure-activity relationship of triazine-antifolate inhibition of Leishmania dihydrofolate reductase and cell growth.,  30  (7): [PMID:3599028] [10.1021/jm00390a017]
3. Coats EA, Genther CS, Dietrich SW, Guo ZR, Hansch C..  (1981)  Comparison of the inhibition of methotrexate-sensitive and -resistant Lactobacillus casei cell cultures with purified Lactobacillus casei dihydrofolate reductase by 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-(3-substituted-phenyl)-s-triazines. Use of quantitative structure-activity relationships in making inferences about the mechanism of resistance and the structure of the enzyme is situ compared with the enzyme in vitro.,  24  (12): [PMID:6796688] [10.1021/jm00144a010]
4. Hansch C, Hathaway BA, Guo ZR, Selassie CD, Dietrich SW, Blaney JM, Langridge R, Volz KW, Kaufman BT..  (1984)  Crystallography, quantitative structure-activity relationships, and molecular graphics in a comparative analysis of the inhibition of dihydrofolate reductase from chicken liver and Lactobacillus casei by 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-(substituted-phenyl)-s-triazine s.,  27  (2): [PMID:6420569] [10.1021/jm00368a006]
5. Khwaja TA, Pentecost S, Selassie CD, Guo Z, Hansch C..  (1982)  Comparison of quantitative structure-activity relationships of the inhibition of leukemia cells in culture with the inhibition of dihydrofolate reductase from leukemia cells and other cell types.,  25  (2): [PMID:7057420] [10.1021/jm00344a012]
6. Selassie CD, Guo Z, Hansch C, Khwaja TA, Pentecost S..  (1982)  A comparison of the inhibition of growth of methotrexate-resistant and -sensitive leukemia cells in culture by triazines. Evidence for a new mechanism of cell resistance to methotrexate.,  25  (2): [PMID:7057421] [10.1021/jm00344a013]
7. Andrea TA, Kalayeh H..  (1991)  Applications of neural networks in quantitative structure-activity relationships of dihydrofolate reductase inhibitors.,  34  (9): [PMID:1895302] [10.1021/jm00113a022]
8. Crippen GM..  (1997)  Validation of EGSITE2, a mixed integer program for deducing objective site models for experimental binding data.,  40  (20): [PMID:9379435] [10.1021/jm970211n]
9. Ghose AK, Crippen GM..  (1985)  Use of physicochemical parameters in distance geometry and related three-dimensional quantitative structure-activity relationships: a demonstration using Escherichia coli dihydrofolate reductase inhibitors.,  28  (3): [PMID:3882967] [10.1021/jm00381a013]
10. Selassie CD, Hansch C, Khwaja TA, Dias CB, Pentecost S..  (1984)  Comparative structure-activity relationships of antifolate triazines inhibiting murine tumor cells sensitive and resistant to methotrexate.,  27  (3): [PMID:6699880] [10.1021/jm00369a019]
11. Ghose AK, Crippen GM..  (1984)  General distance geometry three-dimensional receptor model for diverse dihydrofolate reductase inhibitors.,  27  (7): [PMID:6737433] [10.1021/jm00373a016]
12. Marlowe CK, Selassie CD, Santi DV..  (1995)  Quantitative structure-activity relationships of the inhibition of Pneumocystis carinii dihydrofolate reductase by 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-(X-phenyl)-s-triazines.,  38  (6): [PMID:7699713] [10.1021/jm00006a016]

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