Synthesis, structural elucidation and biological evaluations of new guanidine-containing terpenoids as anticancer agents

Gheorghe Duca, Aculina Aricu, Kaleria Kuchkova, Elena Secara, Alic Barba, Ion Dragalin, Nicon Ungur, G. Spengler

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Abstract

Using sclareol and sclareolide as starting materials, the guanidine derivatives of 12-amino-11-dihomodrimane-8α-ol and 13-amino-14,15-bis-dinorlabd-8(9)-ene were synthesized by the reaction of the corresponding amines with sodium hydrogencyanamide in ethanol–water solution. Monoacyl- and diacylguanidines were prepared from activated with N,N-carbonyldiimidazole Δ8,9-bicyclohomofarnesenoic acid by the reaction with guanidine. Their structures were confirmed by the 1H and 13C NMR, IR spectral and elemental analysis data. The compounds 12, 13 and 15 were screened for their antiproliferative and cytotoxicity activities against Colo 205, Colo 320 and MRC 5 human lung fibroblasts with respect to standard drug, Cisplatin. The compounds 12 and 15 exhibits excellent results than positive control. Hence these two compounds may be act as drug lead molecules in cancer chemotherapy.

Original languageEnglish
JournalNatural Product Research
DOIs
Publication statusAccepted/In press - Jan 1 2018

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Keywords

  • 14,15-Bis-norlabdane
  • antiproliferative activity
  • dihomodrimane
  • Guanidines
  • synthesis
  • terpenoids

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Plant Science
  • Organic Chemistry

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