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

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 Δ^8,9-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.

Graphical Abstract

Keywords:

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

Disclosure statement

No potential conflict of interest was reported by the authors.