Synthesis of new biologically active polyfunctional terpenoids based on industrial wastes
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ARICU, Aculina, LUNGU, Lidia, CIOCARLAN, Alexandru, BARBA, Alic, DRAGANCEA, Diana. Synthesis of new biologically active polyfunctional terpenoids based on industrial wastes. In: Ecological and environmental chemistry : - 2017, Ed. 6, 2-3 martie 2017, Chișinău. Chisinau, Republic of Moldova: Academy of Sciences of Moldova, 2017, Ediția 6, pp. 168-169.
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Ecological and environmental chemistry
Ediția 6, 2017
Conferința "Ecological and environmental chemistry 2017"
6, Chișinău, Moldova, 2-3 martie 2017

Synthesis of new biologically active polyfunctional terpenoids based on industrial wastes


Pag. 168-169

Aricu Aculina, Lungu Lidia, Ciocarlan Alexandru, Barba Alic, Dragancea Diana
 
Institute of Chemistry of the Academy of Sciences of Moldova
 
 
Disponibil în IBN: 15 martie 2019


Rezumat

Thiosemicarbazide derivatives are widely used in medicine in treating various types of diseases. All of them have a wide range of reactive atoms and form with metal ions coordination compounds with various composition, structure and properties. Many of these coordination compounds are biologicallly active substances. In this connection, we intend to use in condensation reactions with tiosemicarbazide, some ketones derived from naturally labdane diterpenoide (-)-sclareol (1). The key strengths of this research are: accessibility of the starting material, which can be extracted from renewable resources and high probability of their biological activities and low toxicity, due to their natural origin. These researches are devoted to synthesis, structure elucidation of new terpeno-thiosemicarbazone ligands and their transition metal complexes, starting from accessible material (-)-sclareol (1). The synthesis of the target compounds was done according to the scheme: Reagents: a. KOH, EtOH, 98%; b. NH2NHCSNH2, EtOH, 80-85%; c. CuCl2∙2H2O, MeOH, 67-70%. Scheme 1 As starting material for the synthesis of named compounds was used methyl 7-oxo-13,14,15,16-tetranorlabd-8-en-12oate (2) (obtained from naturally labdane diterpenoide (-)-sclareol (1)) in three steps with an overall yield 75%, scheme 1. After that coupling reaction of ketoester (2) with thiosemicarbazide was elaborated. In order to obtain drim-8(9)-en-7-one (3), saponification and decarboxilation of the ketoester (2) with KOH was performed. Drimenone (3) was coupled with thiosemicarbazide also as in the previous case. Subsequently, the complexation of thiosemicarbazones (4), (5) with Cu(II) salt was developed. In complexes (6), (7) ligands act as mono-deprotonated bases in the thioenolic form. Copper(II) ions exhibit a square planar configuration with two bidentate thiosemicarbazones bonded through the azomethinic nitrogen and thioenolic sulfur. The structure of all obtained compounds have been established using modern methods of analysis (ATR-FTIR, 1H, 13C and 15N RMN and MS spectroscopy).