Synthesis and Modeling Study of Some Potential Pyrimidine Derivatives as HIV Inhibitors
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Najim A. Al-Masoudi
,
Yossra A. Marich
A new series of 2-amino-6-((4-aryldiazenyl)benzyloxy)-4-chloropyrimidine derivatives 4 - 13 and 2,6-diamino-5-arylazo-4-chloro-pyrimidine analogs 15 - 20 were synthesized from the pyrimidine scaffolds 3 and 14, respectively, via diazotization with various amines. Nucleophilic displacement at the 2,4-diamino-5-arylazo-6-chloro-pyrimidine 16 by different amines afforded the 4-alkylamino analogs 21 - 27. All new compounds were evaluated for their in vitro anti-HIV activity in MT-4 cells as non-nucleoside reverse transcriptase inhibitors on the basis of our previous work. Screening results indicated that 10 and 11 were found to be the only compounds in the series inhibiting HIV-1 replication in cell cultures with EC50 of >1:23 and >2:92 μg mL-1 of a CC50 of 12.30 and 17.52 μg mL-1, resulting in a selectivity index of 10 and 6, respectively. In addition, preliminary structure-activity relationships and molecular modeling of these new analogs are detailed in this manuscript.
Graphical Abstract
Synthesis and Modeling Study of Some Potential Pyrimidine Derivatives as HIV Inhibitors
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- A New Wells-Dawson-based Organic-Inorganic Honeycomb Hybrid Compound with Cadmium Bis(2,2´-biimidazole) Spacers
- Anion Effect on the Structural Diversity of 1-D and 2-D Zinc(II) Coordination Polymers with a Flexible Fluorinated Bis(imidazole) Ligand
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- Synthesis and Crystal Structures of the P,N-Substituted Ferrocenes [Fe{η5-C5H4–P(S)Ph2}(η5-C5H4–NHCH2tBu)] and [Fe(η5-C5H4– PPh2)(η5-C5H4–NHCH2tBu)]
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