Truncated Reverse Isoxazolidinyl Nucleosides: A New Class of Allosteric HIV‐1 Reverse Transcriptase Inhibitors

Abstract

Affairs of the HAART! The synthesis of HEPT‐derived, truncated reverse isoxazolidinyl nucleosides (shown) is reported. These compounds represent the first examples of isoxazolidines bearing a pyrimidine scaffold at the C‐3 position using a glycoside‐type linkage. Biological evaluation showed that some of the derivatives act as non‐nucleoside inhibitors of HIV‐1 reverse transcriptase, with an efficacy comparable to that of Nevirapine but with reduced toxicity.

Design and Development of Rilpivirine Nanoparticle Containing Chitosan Using Ionic Gelation Method for Hiv Infections

“…flow rate of nitrogen. Consistent with standard procedures, the machine was calibrated for temperature as well as sensitivity with indium [26,27].…”

Organocatalytic synthesis of 5‐hydroxyisoxazolidine catalyzed by camphor sulfonyl hydrazines through aza‐Michael addition/cyclization

“…Isoxazolidines are important skeletons that occur widely in drugs as well as bioactive compounds . For example, compound A, known as TRINs, has been reported to have anti‐HIV properties (Figure ) . Isoxazolidines could also be readily transformed into γ‐amino alcohols or β‐amino acids .…”

Synthesis and Biological Properties of 5-(1H-1,2,3-Triazol-4-yl)isoxazolidines: A New Class of C-Nucleosides

“…As part of ongoing efforts to identify new antiviral/antitumor agents, we were interested in the investigation of N,O -nucleosides, where the ribose moiety has been replaced by an isoxazolidine system, as mimetic of the sugar unit [ 19 , 20 , 21 , 22 , 23 ]. Phosphonated carbocyclic 2'-oxa-3'-azanucleosides 1 have shown to be potent inhibitors of RT of different retroviruses, following incubation with human PBMCs crude extract [ 24 , 25 , 26 ]; truncated phosphonated azanucleosides 2 are able to inhibit HIV and HTLV-1 viruses at concentration in the nanomolar range [ 27 ]; truncated phosphonated N,O -psiconucleosides 3 inhibit HIV in vitro infection with low or absent cytotoxicity ( Figure 2 ) [ 28 ].…”