SYNTHESIS OF 2-[(ω-PHTHALIMIDOALKYL)SULFANYL]PYRIMIDIN-4(3<i>H</i>)-ONES, THEIR CYTOTOXICITY AND <i>in vitro</i> ACTIVITY AGAINST HIV-1/2

Authors

  • Иван А. Новаков Volgograd State Technical University, 28 Lenina Ave., Volgograd 400005, Russia
  • Дмитрий С. Шейкин Volgograd State Technical University, 28 Lenina Ave., Volgograd 400005, Russia
  • Виктор В. Чапуркин Volgograd State Technical University, 28 Lenina Ave., Volgograd 400005, Russia
  • Максим Б. Навроцкий Volgograd State Technical University, 28 Lenina Ave., Volgograd 400005, Russia
  • Александр С. Бабушкин Volgograd State Technical University, 28 Lenina Ave., Volgograd 400005, Russia
  • Ярослав П. Кузнецов Volzhsky Polytechnic Institute (branch of the Volgograd State Technical University), 42a Engelsa St., Volzhsky 404121, Russia
  • Евсей А. Ручко Closed Joint Stock Company Farm-Sintez, 2-46 2-ya Kabelnaya St., Moscow 111024, Russia
  • Вадим В. Качала N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Антон Ю. Марышев LUKOIL-Volgogradneftepererabotka Ltd., 55 40 let VLKSM St., Volgograd 400029, Russia
  • Доминик Шольц Rega Institute for Medical Research, 10 Minderbroedersstraat, Leuven B1030 3000, Belgium

DOI:

https://doi.org/10.1007/5303

Keywords:

2-thiouracil, uracil, phthalimidoalkylation, antiHIV-1/2 activity, antiviral activity.

Abstract

The interaction of N-(2-bromoethyl)- and N-(3-bromopropyl)phthalimides with 2-thiouracils substituted at position 6 was studied in alkaline medium, providing S-monoamidoalkylation products and, depending on the substituents, the products of S,O(4)- and S,N(3)-diamidoalkylation. Among the obtained compounds, only 2-[2-(phthalimidoethyl)sulfanyl]-6-(trifluoromethyl)pyrimidin-4(3H)-one showed in vitro antiHIV-1 and antiHIV-2 activity at micromolar concentration range.

 

Downloads

Published

2020-01-31

Issue

Vol. 56 No. 1 (2020)

Section

Original Papers