Computational study of naphthylisoquinoline alkaloids with antimalarial activity from Dioncophyllaceae and Ancistrodaceae in vacuo

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• 作者：Liliana Mammino ; Mireille K. Bilonda
• 关键词：Alkaloids ; Antimalarials ; Intramolecular hydrogen bonding ; Mutual orientations of aromatic moieties ; Naphthylisoquinoline alkaloids
• 刊名：Theoretical Chemistry Accounts: Theory, Computation, and Modeling (Theoretica Chimica Acta)
• 出版年：2016
• 出版时间：April 2016
• 年：2016
• 卷：135
• 期：4
• 全文大小：1,258 KB
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• 作者单位：Liliana Mammino (1)
  Mireille K. Bilonda (1)
  
  1. Department of Chemistry, University of Venda, Thohoyandou, South Africa
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Theoretical and Computational Chemistry
  Inorganic Chemistry
  Organic Chemistry
  Physical Chemistry
  
• 出版者：Springer Berlin / Heidelberg
• ISSN：1432-2234

文摘

This study investigates 33 naphthylisoquinoline alkaloids with antimalarial activity isolated from different tropical plants belonging to the Dioncophyllaceae and Ancistrodaceae families. All these molecules have two moieties, a naphthalene moiety and an isoquinoline moiety. A thorough conformational study was carried in vacuo at two levels of theory, HF/6-31G(d,p) and DFT/B3LYP/6-31+G(d,p). Frequency calculations were also performed in vacuo for all the calculated conformers, at both levels of theory. The major stabilizing factors are the intramolecular hydrogen bonds. The mutual orientation of the two moieties also has considerable influence, with marked preference for the naphthalene moiety to be perpendicular to the isoquinoline moiety.