Literature DB >> 10425099

Nucleosides and nucleotides. 185. Synthesis and biological activities of 4'alpha-C-branched-chain sugar pyrimidine nucleosides.

M Nomura1, S Shuto, M Tanaka, T Sasaki, S Mori, S Shigeta, A Matsuda.   

Abstract

A series of 4'alpha-C-branched-chain pyrimidine nucleosides was synthesized from 2'-deoxycytidine or uridine. In the 2'-deoxycytidine series, the substituent at the 4'alpha-position affected cytotoxicity against L1210 mouse leukemic cells in vitro in the order Me (23) > CN (22) > C(symbol)CH (21) > CH=CH(2) (19) > Et (24) > CH=CHCl (20). However, uridine and cytidine derivatives with ethynyl and cyano groups at the 4'alpha-position did not show any cytotoxicity. The antiviral activities of these nucleosides against HSV-1, HSV-2, and HIV-1 in vitro were also examined. Compounds 22 and 23 showed antiviral activities against HSV-1 and HSV-2 without showing significant toxicity to the host cells (MRC-5 cells). Although almost all of the nucleosides showed anti-HIV-1 activities, they were also cytotoxic to the host cells (MT-4).

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Year:  1999        PMID: 10425099     DOI: 10.1021/jm990050i

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  7 in total

1.  4'-Ethynyl nucleoside analogs: potent inhibitors of multidrug-resistant human immunodeficiency virus variants in vitro.

Authors:  E I Kodama; S Kohgo; K Kitano; H Machida; H Gatanaga; S Shigeta; M Matsuoka; H Ohrui; H Mitsuya
Journal:  Antimicrob Agents Chemother       Date:  2001-05       Impact factor: 5.191

Review 2.  From the chemistry of epoxy-sugar nucleosides to the discovery of anti-HIV agent 4'-ethynylstavudine-Festinavir.

Authors:  Kazuhiro Haraguchi; Shingo Takeda; Yutaka Kubota; Hiroki Kumamoto; Hiromichi Tanaka; Takayuki Hamasaki; Masanori Baba; Elijah Paintsil; Yung-Chi Cheng
Journal:  Curr Pharm Des       Date:  2013       Impact factor: 3.116

3.  The High Genetic Barrier of EFdA/MK-8591 Stems from Strong Interactions with the Active Site of Drug-Resistant HIV-1 Reverse Transcriptase.

Authors:  Yuki Takamatsu; Debananda Das; Satoru Kohgo; Hironori Hayashi; Nicole S Delino; Stefan G Sarafianos; Hiroaki Mitsuya; Kenji Maeda
Journal:  Cell Chem Biol       Date:  2018-08-30       Impact factor: 8.116

4.  Development of modified nucleosides that have supremely high anti-HIV activity and low toxicity and prevent the emergence of resistant HIV mutants.

Authors:  Hiroshi Ohrui
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2011       Impact factor: 3.493

Review 5.  The evolution of antiviral nucleoside analogues: A review for chemists and non-chemists. Part II: Complex modifications to the nucleoside scaffold.

Authors:  Mary K Yates; Katherine L Seley-Radtke
Journal:  Antiviral Res       Date:  2018-12-08       Impact factor: 10.103

Review 6.  Advance of structural modification of nucleosides scaffold.

Authors:  Xia Lin; Chunxian Liang; Lianjia Zou; Yanchun Yin; Jianyi Wang; Dandan Chen; Weisen Lan
Journal:  Eur J Med Chem       Date:  2021-01-30       Impact factor: 6.514

7.  Acetylated and methylated β-cyclodextrins as viable soluble supports for the synthesis of short 2′-oligodeoxyribo-nucleotides in solution.

Authors:  Alejandro Gimenez Molina; Vyacheslav Kungurtsev; Pasi Virta; Harri Lönnberg
Journal:  Molecules       Date:  2012-10-16       Impact factor: 4.411

  7 in total

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