Catalytic synthesis of α-amino chromone phosphonates and their antimicrobial, toxicity and potential HIV-1 RT inhibitors based on silico screening

Abstract

The α-amino phosphonates exhibit a wide range of biological properties which create demand for simple and efficient synthetic routes of new molecules. In this study synthesis of a new series of derivatives of α-amino chromone phosphonates (ACPs) was reported using RhBT catalyst. The RhBT was first prepared by simply mixing boron nitride in a solution of rhodium acetate, under inert atmosphere for a week followed by filtration (yield: 92%). The catalyst can be re-used for up to four times and showed minimal loss of activity. The ACPs was prepared in a one pot reaction containing chromone based aldehydes, aniline derivatives and diethyl phosphite. The structures of these compounds were characterized by IR, 1H NMR, 13C NMR, 31P NMR and high resolution mass spectral analysis. The synthesized ACPs were evaluated for their antimicrobial activities against three bacteria B. cereus, M. luteus, E. coli and one fungus C. albicans. The ACPs displayed selective toxicity toward the brine shrimp (Artemia salina). Compounds 8j and 8m was found to be less toxic to the brine shrimp and may have more valuable biological application. Furthermore, molecular docking studies were conducted to predict the possible therapeutic potential of ACPs. The compounds (8i, 8j, 8k and 8m) were predicted as highly active HIV-1 reverse transcriptase inhibitors.