Synthesis, structural elucidation and biological evaluations of new guanidine-containing terpenoids as anticancer agents
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DUCA, Gheorghe; ARICU, Aculina; KUCHKOVA, Kaleria; SECARA, Elena; BARBĂ, Alic; DRAGALIN, Ion; UNGUR, Nicon; SPENGLER, Gabriella. Synthesis, structural elucidation and biological evaluations of new guanidine-containing terpenoids as anticancer agents. In: Natural Product Research. 2019, nr. 21(33), pp. 3052-3056. ISSN 1478-6419.
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Natural Product Research
Numărul 21(33) / 2019 / ISSN 1478-6419 /ISSNe 1478-6427

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


DOI: 10.1080/14786419.2018.1516658
Pag. 3052-3056

Duca Gheorghe1, Aricu Aculina1, Kuchkova Kaleria1, Secara Elena1, Barbă Alic1, Dragalin Ion1, Ungur Nicon1, Spengler Gabriella2
 
1 Institute of Chemistry,
2 University of Szeged
 
Disponibil în IBN: 6 octombrie 2019


Rezumat

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.

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