Síntese orgânica aplicada à ecologia química e à química medicinal

Abstract

The advent of synthetic organic chemistry is one of the most profound scientific developments in the history of human species. The creative nature of this area has earned this discipline a reputation for precise art and science, and can be applicable to a wide range of purposes. The first chapter of this thesis attempts to explore the application of organic synthesis to medicinal chemistry. The importance of inflammation as a disease-triggering factor is no longer restricted to autoimmune and infectious diseases since it has been increasingly associated with chronic and degenerative diseases. Based on the identification of the aminoguanidine moiety in several compounds that have anti-cytokine activity, the first chapter aimed at the synthesis of a series of aminoguanidine derivatives and their isosteric analogues from a strategy of molecular simplification of documented nitrogen heterocycles. The synthesis of derivatives was carried out in yields ranging from 58 to 99%. The second chapter covers the application of synthetic organic chemistry to chemical ecology. By taking into account the economic damage caused by insect pest damage on several important crops as well as the public health problem arisen from the use of pesticides to control the presence of these pests in crops, the use of pheromones comprises an attractive strategy for the control and monitoring of the same insects. Thus, we aimed at the application of synthetic procedures for the elaboration of the pheromonal components of economically interesting pests, namely Hyponeuma taltula, Anthistarcha binocularis and Rhynchophorus palmarum, which respectively affect sugarcane, cashew and coconut crops. Based on the established routes, the components of H. taltula and A. binocularis could be obtained with overall yields of 6.8% and 21.59%, respectively. We also compared the synthetic reference compounds with the extracts of the sex glands of these species and we thus confirmed the structure proposals of their components, which in turn will allow our research group to perform future studies on the electrophysiology and the attractivity of these components in the field.