Chemical Modification of Plant Alkaloids. 7. T-Reaction of an Aloperine Derivative

N-(2-Carboxy-5-nitrophenyl)aloperine was prepared from aloperine and 2-fluoro-5-nitrobenzaldehyde and condensed with 1,3-dimethylbarbituric acid via a T-reaction with opening of the piperidine ring and formation of 1,3-dimethyl-5-{5-nitro-2-[3-(10-oxo-7-azatricyclo[7.3.1.02,7]trideca-11-en-12-yl)propylamino]} benzylhexahydro-2,4,6-pyrimidinetrione. The structure of the prepared compound was studied by an X-ray crystal structure analysis. © 2017, Springer Science+Business Media, LLC.

Authors
Krasnov K.A.1 , Kartsev V.G. 2 , Dobrokhotova E.V. 3 , Kultyshkina E.K. 3 , Timofeeva T.V.4 , Khrustalev V.N. 3, 5
Journal
Chemistry of Natural Compounds
Number of issue
4
Language
English
Pages
703-707
Status
Published
Link
External link
DOI
10.1007/S10600-017-2095-Z
Volume
53
Year
2017
Organizations
  • 1 Institute of Toxicology, Federal Medical and Biological Agency, 1 Bekhtereva St, St. Petersburg, 192019, Russian Federation
  • 2 ZAO Interbioscreen, 8 Institutskii Prosp, Moscow Oblast, Chernogolovka 142432, Russian Federation
  • 3 People’s Friendship University of Russia, 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation
  • 4 Department of Chemistry & Biology, New Mexico Highlands University, Las Vegas, NM 87701, United States
  • 5 Nesmeyanov Institute of Elementorganic Compounds, Russian Academy of Sciences, 28 Vavilova St, Moscow, 119991, Russian Federation
Keywords
1,3-dimethyl-5-{5-nitro-2-[3-(10-oxo-7-azatricyclo[7.3.1.02,7]trideca-11-en-12-yl)propylamino]}benzylhexahydro-2,4,6-pyrimidinetrione; 1,3-dimethylbarbituric acid; aloperine; hydride shift; N-(2-carboxy-5-nitrophenyl)aloperine; T-reaction; tert-amine effect
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