Lithiation of Uracilnucleosides and its Application to the Synthesis of a New Class of Anti-HIV-1 Acyclonucleosides

Hiromichi Tanaka; Masanori Baba; Hiroyuki Hayakawa; Kazuhiro Haraguchi; Tadashi Miyasaka; Masaru Ubasawa; Hideaki Takashima; Kouichi Sekiya; Issei Nitta; Richard Walker; De Clercq Erik

doi:10.1080/07328319108046487

Abstract

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Abstract A highly general and regioselective modification of the base moiety of uracilnucleosides can be accomplished based on lithiation chemistry. An application of this approach to the synthesis of various acyclouridine derivatives, in which both C-5 and C-6 positions were substituted, was carried out to improve the HIV-1 specific inhibitory activity of a new lead compound, l-[(2-hydroxyethoxy)methyl]-6-phenylthiothymine (HEPT).

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Issei Nitta, Kohei Umezu, Hiroshi Nakashima, S Mori, Masanori Baba, De Clercq Erik, H. TANAKA, Masaru Ubasawa, Hideaki Takashima, Kouichi Sekiya

Lithiation of Uracilnucleosides and its Application to the Synthesis of a New Class of Anti-HIV-1 Acyclonucleosides

Abstract

Discussion(0)

Related publications

A new class of HIV-1 specific 6-substituted acyclouridine derivatives: synthesis and anti-HIV-1 activity of 5- or 6-substituted analogs of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT)

Anti-human immunodeficiency virus type 1 activities and pharmacokinetics of novel 6-substituted acyclouridine derivatives

Structure-activity relationships of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine analogs: effect of substitutions at the C-6 phenyl ring and at the C-5 position on anti-HIV-1 activity

Synthesis and anti-HIV activity of 2-, 3-, and 4-substituted analogs of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT)

Potent and selective inhibition of human immunodeficiency virus type 1 (HIV-1) by 5-ethyl-6-phenylthiouracil derivatives through their interaction with the HIV-1 reverse transcriptase.