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Studies on the synthesis of dihydrofolate reductase inhibitor 5 substituted phenylthioseleno 2 4 diaminopyrimidines and their inhibitory activity to lactobacillus casei and chicken liver dhfr






Yaoxue Xuebao 22(2): 136-140

Studies on the synthesis of dihydrofolate reductase inhibitor 5 substituted phenylthioseleno 2 4 diaminopyrimidines and their inhibitory activity to lactobacillus casei and chicken liver dhfr

According to the principle of isosterism the -CH2-group of 5-(substituted benzyl)-2,4-diaminopyrimidine was modified by-S-and-Se-and some 5-(substituted phenyl)thio-2,4-diaminopyrimidines and 5-(substituted phenyl)seleno-2,4-diaminopyrimidines were synthesized. Their inhibitory activities on L. casei and chicken liver dihydrofolate reductase were determined. Preliminary data showed that the inhibitory activities of these compounds were less than those of the corresponding 5-(substituted benzyl)-2, 4-diaminopyrimidines. Their selectivities are also decreased.


Accession: 006522339



Related references

Zhang, W.S.; Li, R.L.; Wang, Q.J., 1987: Studies on the synthesis of dihydrofolate reductase inhibitor, 5-(substituted phenyl)-thio(seleno)-2, 4-diaminopyrimidines and their inhibitory activity on L. casei and chicken liver DHFR. Yao Xue Xue Bao 22(2): 136-140

Fang Z.X.; L.R.L.; Jiang Y.M.; Gao J.N., 1988: The synthesis of dihydrofolate reductase inhibitor 2 4 diamino 5 substituted benzylpyrimidines and their inhibition on lactobacillus casei dhfr and chicken liver dhfr. Eighteen 5-(substituted benzyl) -2,4-diamino -pyrimidine with groups of various sizes on the benzene ring were designed and synthesized for investigating the inhibition of dihydrofolate reductase (DHFR). The pyrimidines were prepared by the conden...

Fang, Z.X.; Li, R.L.; Jiang, Y.M.; Gao, J.N., 1988: The synthesis of the dihydrofolate reductase inhibitors 2,4-diamino-5-substituted-benzylpyrimidines and their inhibition on L. casei DHFR and chicken liver DHFR. Yao Xue Xue Bao 23(2): 108-114

Li, R.; Hansch, C.; Kaufman, B.T., 1982: A comparison of the inhibitory action of 5-(substituted-benzyl)-2,4-diaminopyrimidines on dihydrofolate reductase from chicken liver with that from bovine liver. Forty-four 5-(substituted-benzyl)-2,4-diaminopyrimidines have been tested as inhibitors of chicken and bovine liver dihydrofolate reductase. The chicken enzyme is, on the average, about 10 times less easily inhibited than bovine enzyme. Substituen...

Hansch, C.; Hathaway, B.A.; Guo, Z.R.; Selassie, C.D.; Dietrich, S.W.; Blaney, J.M.; Langridge, R.; Volz, K.W.; Kaufman, B.T., 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. The inhibition of dihydrofolate reductase from chicken liver and from Lactobacillus casei has been studied with 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-(substituted-phenyl)-s-triazines. It was found that for the chicken enzyme, inhibitor potency fo...

Selassie, C.D.; Fang, Z.X.; Li, R.L.; Hansch, C.; Klein, T.; Langridge, R.; Kaufman, B.T., 1986: Inhibition of chicken liver dihydrofolate reductase by 5-(substituted benzyl)-2,4-diaminopyrimidines. A quantitative structure-activity relationship and graphics analysis. The inhibition of chicken liver dihydrofolate reductase by a series of substituted benzylpyrimidines has been investigated. From the inhibition constants a quantitative structure-activity relationship has been formulated. This mathematical model i...

Coats, E.A.; Genther, C.S.; Dietrich, S.W.; Guo, Z.R.; 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. The inhibitory action of a set of 4,5-diamino-1,2-dihydro-2,2-dimethyl-1-(3-substituted-phenyl)-s-triazines on Lactobacillus casei dihydrofolate reductase is compared with their action on methotrexate-resistant and methotrexate-sensitive cell cult...

Hood, K.; Roberts, G.C., 1978: Ultraviolet difference-spectroscopic studies of substrate and inhibitor binding to Lactobacillus casei dihydrofolate reductase. The u.v. difference spectra generated when methotrexate, trimethoprim or folate bind to Lactobacillus casei dihydrofolate reductase were analysed. The difference spectrum producted by methotrexate binding is shown to consist of three components: (...

L.R.L.; Fang Z X., 1986: Investigation of the selectivity of dihydrofolate reductase inhibitor 5 substituted benzyl 2 4 diaminopyrimidines. The apparent inhibitory constants (Ki app) obtained from the action on dihydrofolate reductases from Lactobacillus casei bacteria and chicken liver of forty-seven 5-subtituted-benzyl-2,4-diaminopyrimidines (among them 4 compounds are newly synthes...

Birdsall, B.; Griffiths, D.V.; Roberts, G.C.; Feeney, J.; Burgen, A., 1977: 1H nuclear magnetic resonance studies of Lactobacillus casei dihydrofolate reductase: effects of substrate and inhibitor binding on the histidine residues. Proceedings of the Royal Society of London. Series B, Biological Sciences 196(1124): 251-265