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Directed synthesis and study of antimicrobial activity of polyfunctionalized norlabdane compounds


Author: Blaja Svetlana
Degree:doctor of chemistry
Speciality: 02.00.10 - Bioorganic chemistry; chemistry of natural and physiological active compounds
Year:2022
Scientific adviser: Aculina Aricu
doctor habilitat, associate professor (docent), Institute of Chemistry of the ASM
Institution: University of European Political and Economic Studies "Constantin Stere"

Status

The thesis was presented on the 5 May, 2022 at the meeting of the Scientific Council and now it is under consideration of the National Council.

Abstract

Adobe PDF document1.57 Mb / in romanian
Adobe PDF document1.50 Mb / in english

Thesis

CZU 547./-3.057(043.2)

Adobe PDF document 4.47 Mb / in romanian
148 pages


Keywords

synthesis, heterocyclization, (+)-sclareolide, norlabdane compound, thiosemicarbazide, 1,3-thiazole, 1,3,4-thiadiazole, benzothiazole, antimicrobial activity

Summary

Dissertation contents. The thesis was developed in the Institute of Chemistry, Laboratory of Chemistry of Natural and Biologically Active Compounds. The thesis was written in Romanian and consists of the introduction, three chapters, general conclusions and recomandations, bibliography of 197 references, 121 basic text pages, 72 figures and 5 tables. The obtained results were presented in 15 scientific publications.

The purpose and objectives of the study is devoted to the elaboration of the efficient methods for the directed synthesis of new optically active norlabdane compounds with thiosemicarbazone, 1,3-thiazole, 1,3,4-thiadiazole and benzothiazole fragments, based on the natural labdane diterpenoid sclareol; elucidation of the possible mechanisms of synthesis reactions of polyfunctionalized compounds that are endowed with promising biological activity.

Novelty and scientific originality consists in the elaboration of new, efficient and original methods of directed synthesis of a series of new optically active norlabdane compounds with thiosemicarbazone and heterocyclic structural units, which show a promising therapeutic potential; obtaining for the first time the chiral complex compounds with the use as ligands of the norlabdanic compounds functionalized with thiosemicarbazone structural unit.

The important scientific problem solved is the directed synthesis of new optically active norlabdanic compounds with hybrid skeleton based on the natural labdanic diterpenoid sclareol - a new concept in fine organic synthesis. These chiral compounds are important syntons for obtaining biologically active substances of high interest for applications in the pharmaceutical industry.

Theoretical significance. The research results contribute to the expansion of scientific knowledge on the study of structural and steric laws in the synthesis reactions of new chiral norlabdanic compounds with thiosemicarbazone and heterocyclic fragments, which show increased potential for biological activity.

Applicative value of the study: The antimicrobial activity of fifty new chiral compounds on five fungal strains and two bacterial species was tested. Four of the reported compounds showed pronounced antimicrobial activity. These developments may be of interest to pharmaceutical companies, which produce drugs containing chiral biologically active compounds, which may be replaced by norlabdane derivatives. The diminished impact on the environment is related to the use of unconventional methods (microwave, electrooxidation, sensitized photooxidation), which are the basis of non-polluting, non-aggressive and cheaper technologies.

Implementation of scientific results: The methods of synthesis and activity of two new tri- and tetranorlabdane compounds with thiosemicarbazone and 1,3,4-thiadiazole fragment have been patented, which may continue to be the subject of more detailed research, in order to be implemented in practice in the treatment of diseases caused by fungi.