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LUNGU, Lidia; CIOCARLAN, Alexandru; ARICU, Aculina; ILKER, Ozer; BARBA, Alic. Synthesis of new potential active homodrimane sesquiterpenoids with 1,3,4-thiadiazole units. In: Achievements and perspectives of modern chemistry. 9-11 octombrie 2019, Chişinău. Chisinau, Republic of Moldova: Tipografia Academiei de Ştiinţe a Moldovei, 2019, p. 225. ISBN 978-9975-62-428-2.
|Achievements and perspectives of modern chemistry 2019|
Conferința "International Conference "Achievements and perspectives of modern chemistry"" |
Chişinău, Moldova, 9-11 octombrie 2019
Sesquiterpenoids, especially those with a homodrimane skeleton, are natural compounds with a wide range of pharmaceutical and biological activities . The 1,3,4-thiadiazole and its derivatives are considered interesting heterocycles since they possess important pharmacological activities . As starting material for the synthesis of new title compounds 11-homodrim-6,8-dien-12-oic acid 2 was used. It was obtained before from commercially available sclareolide 1in 5 steps, with an overall yield of 47%, as depicted in Scheme . After that coupling reaction of acid 2 with hydrazine hydrate was performed. Subsequently, was used one-pot method, that includes the interaction of the hydrazide 3 with a series of substituted isothiocyanates, without isolation of the intermediate compounds. This reaction was carried out in the presence of triethylamine (Et3N) in water, giving desired homodrimane compounds bearing 1,3,4-thiadiazole units in 72-78% yields .formulaReagents: a. NH2-NH2·H2O, EtOH, delta, 5h, 85%; b. R-NCS, Et3N, H2O, delta, 18h, 72-78%. Scheme.Thesynthesis of homodrimane sesquiterpenoids with 1,3,4-thiadiazole units. The structures of compounds 4a-c were fully confirmed based on their 1H, 13C, 15N and 2D NMR data.