Shivaji V. More
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ABSTRACT APPROACHES TOWARDS THE SYNTHESIS OF BIOLOGICALLY ACTIVE N-HETEROCYCLES AND SYNTHESIS OF ANTICANCER AGENTS Knowledge of heterocyclic chemistry is useful in biosynthesis and in drug metabolism as well. Nucleic acids are important in biological processes of heredity and evolution. There are a large number of synthetic heterocyclic compounds with other important applications and many are valuable intermediates in synthesis. Heterocyclic compounds hold a special place among pharmaceutically important natural and synthetic materials. The remarkable ability of heterocyclic nuclei to serve both as biomimetics and active pharmacophores has largely contributed to their unique value as traditional key elements of numerous drugs. The title of the thesis clearly indicates the objective that is to interface synthetic organic chemistry for the development of new methodologies and synthesize of anti-cancer agents. The thesis is divided into three chapters. The first chapter is divided into three sections, section I and II deals with the synthesis of quinoxaline using different Lewis acids such as molecular iodine and CAN under mild conditions. The section III deals with the synthesis of quinoxaline using Ionic Liquid as a green promoter and solvent. Second chapter is divided in to two sections, section I describe the synthesis of tetrahydroquinoline and section II which deals with the synthesis of benzodiazepines using TMSCl as a catalyst. Chapter third describes the synthesis of new anti-cancer agents. Chapter 1: Synthesis of Quinoxalines Among the various classes of nitrogen containing heterocyclic compounds, Quinoxalines are of interest because of the occurrence of their saturated and partially saturated derivatives in biologically active compounds and natural products. Section I: Synthesis of quinoxalines using molecular iodine as catalyst Compounds containing the quinoxaline ring system have been shown to possess anticancer, antituberculosis, antimicrobial, anti-HIV, antiprotozoal, antimalarial, anti-inflammatory, anticonvulsant and so many other activities. This section deals with the synthesis of quinoxaline using molecular iodine as a catalyst. Section II: Synthesis of quinoxalines using CAN as catalyst in tap water Green chemistry is the universally accepted term to describe the movement towards more environmentally acceptable chemical processes and products. Green chemistry can be achieved by applying environmentally friendly technologies. Hundreds of tons of hazardous waste are released to the air, water, and land by industry every hour of every day. So needs to develop new ecofriendly methodologies for the synthesis of important organic compounds. This section deals with the synthesis of quinoxaline using CAN as a catalyst in tap water. Section III: Synthesis of quinoxalines using Ionic Liquid The past few years has witnessed the evolution of a new era in chemical research by the entry of ionic liquids as potential ‘Green Designer Solvents’ as novel replacements for volatile organic compounds traditionally used as industrial solvents. Ionic liquids are systems consist of salts that are liquid at ambient conditions. This section describes the use of Ionic Liquid as a green promoter for the synthesis of Quinoxaline. Chapter 2: Synthesis of Tetrahydroquinolines and 1, 5-Benzodiazepines Section I: Synthesis of tetrahydroquinolines using TMSCl as catalyst Tetrahydroquinoline is an essential structural unit in many important natural products (alkaloids) such as veprisine, flindersine, oricine, simulenoline, huajiaosimuline, zanthodioline, teclealbine and flindersiamine and exhibits interesting biological activities in various field, such as psychotropic, antiallergenic, anti-inflammatory, antipyretic, analgesic, antiplatelet and estrogenic activity. This section deals with the synthesis of tetrahydroquinolines using TMSCl as a catalyst at room temperature. Section II: Synthesis of 1,5-benzodiazepines The benzodiazepine nucleus is a well-studied traditional pharmacophoric scaffold that has emerged as a core structural unit of various sedative hypnotic, muscle relaxant, anxiolytic, antistaminic, and anticonvulsant agents. Although the first benzodiazepine was introduced as a drug nearly 35 years ago the research in this area is still very active and is directed towards the synthesis of compounds with enhanced pharmacological activity. This section describes a TMSCl promoted simple and effective method for the synthesis of several 1,5-benzodiazepines at ambient temperature. Chapter 3: Synthesis of Furazan-3, 4-diamide derivatives More than century before furazan and its derivatives were synthesized. Their importance has much attracted due to their biological properties. Compounds with furazan ring system have many pharmacological properties. 3,4-Diphenylfuraoxan and other furaoxan derivatives have ability to release NO and act as a nonsteroidal anti- inflammatory drugs which are widely used to treat the effect of inflammation through inhibition of cyclooxygenase enzymes ( COX ). NO releasing moieties also display reversible histamine H3-antagonistic activity. This Section deals with the synthesis of some new furazanamide derivatives as an anticancer agent.