THE CYCLOADDITION REACTION OF BENZOTHIAZOLIUM YLIDES WITH α-CYANOCINNAMAMIDES: THE SYNTHESIS OF STRUCTURAL ANALOGS OF INHIBITORS OF HIV-1 POST-INTEGRATIONAL REPAIR

Authors

  • Marina V. Molchanova Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997. Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow 119992
  • Viktoria А. Ikonnikova Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997
  • Andrey N. Anisenko Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow 119992. A.N. Belozresky Institute of Physico-Chemical Biology, Moscow State University, 1, Build. 40 Leninskie Gory, Moscow 119902
  • Marina B. Gottikh A.N. Belozresky Institute of Physico-Chemical Biology, Moscow State University, 1, Build. 40 Leninskie Gory, Moscow 119902
  • Mikhail S. Baranov Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997. Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997
  • Andrey A. Mikhaylov Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997. Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997

Keywords:

azomethine ylides, benzothiazoles, 1,3-dipolar cycloaddition, HIV-1 inhibitors, stereoselectivity

Abstract

Benzothiazolium ylides generated in situ from benzothiazolium salts by the action of triethylamine reacted stereoselectively with α-cyanocinnamamides to form 1,2,3,3a-tetrahydropyrrolo[2,1-b][1,3]benzothiazoles in 15–91% yields. The resulting compounds were significantly more stable than their analogs derived from quinolinium ylides (KuINin), inhibitors of HIV-1 post-integrational repair.

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Published

2024-12-13

Issue

Vol. 60 No. 9/10 (2024)

Section

Original Papers