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Title: QSAR analysis of 2,4-diaminopyrido[2,3-d]pyrimidines and 2,4-diaminopyrrolo[2,3-d]pyrimidines as dihydrofolate reductase inhibitors
Authors: Jain, P
Soni, L K
Gupta, A K
Kashkedikar, S G
Keywords: Dihydrofolate reductase
Quantitative structure-activity relationship analysis
2,4-diaminopyrido [2,3-d] pyrimidine
2,4-diaminopyrrolo [2,3-d] pyrimidine
Lowest unoccupied molecular orbital (LUMO)
Dipole moment
Issue Date: Oct-2005
Publisher: CSIR
Series/Report no.: C12Q1/00,C12Q1/68
Abstract: Dihydrofolate reductase (DHFR) plays a ubiquitous role in the biosynthesis of DNA, RNA and essential amino acid methionine, and exhibits potential application in the treatment and prophylaxis of AIDS-associated opportunistic microbial infections. In this study, a series of DHFR analogs of 2,4-diaminopyrido[2,3-d]pyrimidines and 2,4-diaminopyrrolo[2,3-d]pyrimidines were subjected to quantitative structure-activity relationship (QSAR) analysis. The results showed that the electronic properties, energy of lowest unoccupied molecular orbital (LUMO) and Z-component of dipole moment (DPL₃) of the molecule could be explored to design the potent DHFR inhibitors. LUMO is indicative of π-bonding interaction of species crucial for the electrophilicity of the molecules. This suggests that molecules are able to interact with electron-rich area at the receptor site. DPL₃ is related to the molecular charge distribution in Z-component. These electronic parameters can be altered through the incorporation of electronegative groups. The QSAR study provides important structural insights for designing the potent DHFR inhibitors.
Description: 315-320
ISSN: 0301-1208
Appears in Collections:IJBB Vol.42(5) [October 2005]

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