3-(4,6-Diamino-2,2-dimethyl-2H-[1,3,5]triazin-1-yl)-benzonitrile

ID: ALA268914

Chembl Id: CHEMBL268914

Cas Number: 70743-55-4

PubChem CID: 271921

Max Phase: Preclinical

Molecular Formula: C12H14N6

Molecular Weight: 242.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)N=C(N)N=C(N)N1c1cccc(C#N)c1

Standard InChI:  InChI=1S/C12H14N6/c1-12(2)17-10(14)16-11(15)18(12)9-5-3-4-8(6-9)7-13/h3-6H,1-2H3,(H4,14,15,16,17)

Standard InChI Key:  NCLZDLNUFXETQQ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA268914

   Benzonitrile, 3-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1(2H)-yl)-

2. Alternative Forms:

   

   ALA268914

   3-(4,6-Diamino-2,2-dimethyl-1,3,5-triazin-1-yl)benzonitrile;ethanesulfonic acid

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: 242.29

Molecular Weight (Monoisotopic): 242.1280

AlogP: 0.74

#Rotatable Bonds: 1

Polar Surface Area: 103.79

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.10

CX LogP: 0.95

CX LogD: 0.18

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.76

Np Likeness Score: -0.92

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. Doweyko AM..  (1988)  The hypothetical active site lattice. An approach to modelling active sites from data on inhibitor molecules.,  31  (7): [PMID:3290487] [10.1021/jm00402a025]

4. 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]

5. 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]

6. 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]

7. 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]

8. Coats EA, Genther CS, Selassie CD, Strong CD, Hansch C..  (1985)  Quantitative structure-activity relationship of antifolate inhibition of bacteria cell cultures resistant and sensitive to methotrexate.,  28  (12): [PMID:3934385] [10.1021/jm00150a026]

9. 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]

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. 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]

12. Srinivasan B, Tonddast-Navaei S, Skolnick J..  (2015)  Ligand binding studies, preliminary structure-activity relationship and detailed mechanistic characterization of 1-phenyl-6,6-dimethyl-1,3,5-triazine-2,4-diamine derivatives as inhibitors of Escherichia coli dihydrofolate reductase.,  103  [PMID:26414808] [10.1016/j.ejmech.2015.08.021]

Source

Source(1):

• Scientific Literature