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Abstract <p>Pyranocoumarins—a mixture of (+)-visnadine and (+)-dihydrosamidine—isolated from the roots of <i>Phlojodicarpus sibiricus</i> were subjected to chemical modification. The reactions of halogenation and selenylation of natural pyranocoumarins were studied, and a mechanism for the observed transformations was proposed. Selective methods for the synthesis of the corresponding 3- and 3,6-halogen- and -organylselanyl-substituted derivatives were developed, and their neuroprotective activity (inhibition of butyrylcholinesterase) was studied. Despite moderate activity, the synthesized 3- and 3,6-substituted pyranocoumarins are promising synthons for further functionalization, aimed at obtaining new neuroprotective drugs based on chemically modified plant material.</p>

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Synthesis of 3- and 3,6-Substituted Pyranocoumarins as Starting Structures Towards Compounds Having Neuroprotective Activity

  • 期刊论文

  • 发表日期：

    2025年12月1日

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  • Alexey R. Romanov,
  • Yuriy N. Nikolaev,
  • Vyacheslav V. Filatov,
  • Alexandra O. Bazhanova,
  • Sergey V. Zinchenko,
  • Vasiliy V. Taraskin,
  • Elvira E. Shults

摘要

Abstract

Pyranocoumarins—a mixture of (+)-visnadine and (+)-dihydrosamidine—isolated from the roots of Phlojodicarpus sibiricus were subjected to chemical modification. The reactions of halogenation and selenylation of natural pyranocoumarins were studied, and a mechanism for the observed transformations was proposed. Selective methods for the synthesis of the corresponding 3- and 3,6-halogen- and -organylselanyl-substituted derivatives were developed, and their neuroprotective activity (inhibition of butyrylcholinesterase) was studied. Despite moderate activity, the synthesized 3- and 3,6-substituted pyranocoumarins are promising synthons for further functionalization, aimed at obtaining new neuroprotective drugs based on chemically modified plant material.