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Russian Chemical Bulletin

, Volume 67, Issue 11, pp 2127–2130 | Cite as

Synthesis of N,N-dialkyl-1-(2-alkylthiopyrimidin-4-yl)piperidin- 4-amines as potential heat shock protein inhibitors

  • V. N. Aldobaev
  • M. A. Prezent
  • I. V. ZavarzinEmail author
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Abstract

A new efficient method for synthesizing promising heat shock protein inhibitors, N,N-dialkyl- 1-(2-alkylthiopyrimidin-4-yl)piperidin-4-amines, by the reaction of 2-alkyl-4-chlorothiouracils with 4-(N-alkyl-N-methylamino)piperidines was developed. 2-Alkyl-4-chlorothiouracils were synthesized by alkylation of 2-thiouracil with alkyl iodides and subsequent treatment of the intermediates with POCl3. 4-(N-Alkyl-N-methylamino)piperidines were prepared by reductive amination of 1-(tert-butoxycarbonyl)-4-piperidinone with methylamine followed by treatment of the intermediate with the appropriate aldehydes.

Key words

thiouracil 1-(tert-butoxycarbonyl)-4-piperidinone piperidines reductive amination nucleophilic substitution pyrimidines heat shock protein inhibitors antitumor activity 

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • V. N. Aldobaev
    • 1
  • M. A. Prezent
    • 2
  • I. V. Zavarzin
    • 2
    Email author
  1. 1.Research Center for Toxicology and Hygienic Regulation of Biologics – Branch of the State Scientific Center “Institute of Immunology” of the Federal Medical and Biological Agency of RussiaBolshevik, Moscow RegionRussian Federation
  2. 2.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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