Novel Triester Derivative of Glycerol: Synthesis, Characterization & Bioactivity

Abstract

In this PhD thesis, synthesis of three biologically active novel triaryl triglycerides series has been reported through three synthetic routes. Thesis has six chapters in total which are further divided into two sections. Every chapter has its own numbering of compounds and references. Section I Section I contains two chapters, chapter 1 is introduction and chapter 2 is about literature survey. First chapter describes the general introduction to molecular structure of glycerol, methods of alcohol protection to bring selectivity in functional group’s reaction, structure of azo compounds and their synthetic methods. Some discussion on biological activities and molecular binding analysis i.e. molecular docking, is also given. Second chapter consists of literature survey and includes the details about the reactions involved in the synthesis of all three series of triaryl triglycerides (3a-3d, 11a-11i and 14a-14d) and also discusses application of these compounds. Section II Section II contains four chapters, synthesis of triaryl triglyceride (Chapter 3), structural elucidation and application of triaryl triglycerides (Chapter 4), results and discussion (Chapter 5), and conclusion (Chapter 6). Chapter 3 describes the synthetic schemes of all three series (3a-3d, 11a-11i and 14a-14d) in details including all synthetic steps involved in reactions and conditions with structures of reactants and products. First series includes four compounds (3a-3d) and these are formed from single step synthesis scheme. In this synthesis scheme, esterification of glycerol with benzoic acid derivatives is presented through the acyl addition elimination of activated form of benzoic acid through reaction with carbonyldiimidazole (CDI). Synthesis of second series of mixed triaryl triglycerids compound (11a-11i) consists of four step synthesis scheme. It comprises of selective acyl addition elimination reaction on the primary –OH of glycerol achieved through protection of rest two -OH by way solketal protection and subsequent deprotection. This afforded mixed triaryl triglycerides (11a-11i) XV products. Third series has four compounds (14a-14d) which are the azo chromophore containing derivatives of triaryl triglyceride (3b) synthesized in first series. In Chapter 4, characterization of the synthesized molecule i.e. molecular structural elucidation through EI-MS, 1H-NMR and FT-IR spectroscopic techniques are presented for the representative molecules (3a, 11a and 14a). It also contains the methodology of the biological assay in detail as well. Result and discussion about the structure data of all synthesized compounds, intermediates and their biological activities are combined in chapter 5. Finally, conclusion of the entire research thesis is presented in chapter 6.