THE SPECIFIC CHARACTER OF THE REACTION OF DERIVATIVES OF 2-THIOXO-2,3-DIHYDROPYRIMIDIN-4(1<i>H</i>)-ONE WITH IODOMETHANE AND ALKYL CHLOROMETHYL SULFIDES

Authors

  • И. А. Новаков Volgograd State Technical University
  • Б. С. Орлинсон Volgograd State Technical University
  • М. Б. Навроцкий Volgograd State Technical University
  • A. Маи Istituto Pasteur – Fondazione Cenci Bolognetti, Dipartimento di Studi Farmaceutici, Università degli Studidi Roma "La Sapienza"
  • М. Артико Istituto Pasteur – Fondazione Cenci Bolognetti, Dipartimento di Studi Farmaceutici, Università degli Studidi Roma "La Sapienza"
  • Д. Ротили Istituto Pasteur – Fondazione Cenci Bolognetti, Dipartimento di Studi Farmaceutici, Università degli Studidi Roma "La Sapienza"
  • А. С. Еремийчук Volgograd State Technical University
  • Е. А. Гордеева Volgograd State Technical University
  • Л. Л. Брунилина Volgograd State Technical University
  • Х. Эсте Retrovirology Laboratory IrsiCaixa, Hospital Universitari Germans Trias i Pujol, Universitat Autònoma de Barcelona

DOI:

https://doi.org/10.1007/2804

Keywords:

5-alkyl-6-(2, 6-dihalobenzyl)-2-thioxo-2, 3-dihydropyrimidin-4(1H)-ones, allyl chloromethyl sulfide, iodomethane, methyl chloromethyl sulfide, SN1- and SN2-substitution, anti-HIV-1 agents

Abstract

The alkylation of 5-alkyl-6-(2,6-dihalobenzyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-ones with MeI, AllSCH2Cl, and MeSCH2Cl in the K2CO3–DMF, NaOMe–MeOH, and KOH–EtOH systems was investigated. A hypothetical mechanism for the reaction is examined, and an explanation is proposed for the composition of the reaction products. The presence of high anti-HIV-1 activity was established in the obtained derivatives of 2-{[(allylsulfanyl)methyl]sulfanyl}pyrimidin-4(3H)-one.

How to Cite
Novakov, I. A.; Orlinson, B. S.; Nawrozkij, M. B.; Mai, A.; Artico, M.; Rotili, D.; Eremiychuk, A. S.; Gordeeva, E. A.; Brunilina, L. L.; Este, J. A. Chem. Heterocycl. Compd. 2010, 46, 200. [Khim. Geterotsikl. Soedin. 2010, 248.]

For this article in the English edition see DOI 10.1007/s10593-010-0492-3

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Published

2015-11-26

Issue

No. 2 (2010)

Section

Original Papers