Literature DB >> 31041687

Synthesis and anti-HIV activity of L-2',3'-Dideoxy-4'-selenonucleosides (L-4'-Se-ddNs).

Jinha Yu1, Gyudong Kim1,2, Dnyandev B Jarhad1, Hong-Rae Kim1, Lak Shin Jeong3.   

Abstract

Based on the potent anti-HIV activity of L-2',3'-dideoxycytidine (L-ddC), L-2',3'-dideoxy-4'-selenonucleosides (L-4'-Se-ddNs) have been synthesized from natural chiral template, L-glutamic acid, using Pummerer-type condensation as a key step. All synthesized compounds were assayed for anti-HIV-1 activity, but none of them did show any significant antiviral activity up to 100 μM, probably due to conformational differences between L-ddC and L-4'-Se-ddC, induced by the bulky selenium atom, which might play an important role in phosphorylation by cellular kinase.

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Keywords:  Antiviral; L-2′,3′-Dideoxy-4′-selenonucleosides; L-4′-Se-ddC; L-Nucleoside; Pummerer-type condensation

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Year:  2019        PMID: 31041687     DOI: 10.1007/s12272-019-01157-6

Source DB:  PubMed          Journal:  Arch Pharm Res        ISSN: 0253-6269            Impact factor:   4.946


  1 in total

1.  Synthesis of 4-Selenothreofuranose Derivatives via Pummerer-Type Reactions of trans-3,4-Dioxygenated Tetrahydroselenophenes Mediated by a Selenonium Intermediate.

Authors:  Michio Iwaoka; Yuta Hiyoshi; Shota Arai; Takeru Ito
Journal:  ACS Omega       Date:  2021-06-25
  1 in total

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