Síntese, avaliação antimicrobiana e estudo teórico em infravermelho de 2-(4-metoxifenil(alquil)amino)-2-oxoetiltereftalatos de alquila obtidos a partir de garrafas pet pós-consumo

Abstract

The present work describes the synthesis of alkyl 2-(4-methoxyphenyl(alkyl)amino)- 2-oxoethylterate (9g-o) through the alkylation reaction of 2-chloro-N-4- methoxyphenyl(alkyl)acetamides (8d-f) with potassium alkylterphthalates (5a-c), what are the effects after the depolymerization reaction of PET bottles (polyethylene terephthalate) post-consumption. The final nine compounds (9g-o), among which are eight credits, shown a simple and effective synthetic route, with variations between 70-80%. All compounds synthesized in this work were characterized by spectroscopic techniques of IR, 1H and 13C NMR (uni and bidimensional). The antimicrobial potential of the intermediate (8d-f) and final (9g-o) compounds was evaluated. The compounds 8d-f showed fungicidal activity against the yeast Prototheca zopfii and compound 8d showed fungistatic activity against the yeast Saccharomyces cerevisiae, and only the final compound 9n fungistatic activity against the yeast Cryptococcus gatti. Compound 8d exhibited fungistatic activity against filamentous fungi Aspergillus niger, A. flavus and A. fumigatus, and compound 8e exhibited fungistatic activity only for fungus A. fumigatus. The intermediate compounds (8d-f) and the final compounds (9g-o) did not show antibacterial activity in the reactions of 80-0.3 µg.mL-1 . To confirm stretches of functional groups in the infrared spectra, theoretical calculations were formed using the DFT (Density Funtional Theory), with a 6311++G(d, p) base set and B3LYP, Cam-B3LYP and BHandH-LYP functions. The method used was very efficient in the optimization and calculation of the harmful vibratory spectra of the final compounds, where the values of the theoretical stretches were close to the experiments.