The Synthesis, Antimicrobial Activity, and Molecular Docking of New 1, 2, 4-Triazole, 1, 2, 4-Triazepine, Quinoline, and Pyrimidine Scaffolds Condensed to Naturally Occurring Furochromones

• Main Authors: Ameen Ali Abu-Hashem (Author), Sami A. Al-Hussain (Author)
• Format: Book
• Published: MDPI AG, 2022-10-01T00:00:00Z.
• Subjects: article
• Online Access: Connect to this object online.

Summary

This study aims to synthesize a new series of furochromone derivatives, evaluate their antimicrobial properties, and improve the permeability of potent compounds to inhibit different types of bacteria and fungi. Hence, Substituted furo[3,2-<i>g</i>]chromene-6-carbonitrile (<b>3a,b</b>) readily form 7-amino-5-methyl-furo [3,2-<i>g</i>]chromene-6-carbonitrile (<b>4a</b>,<b>b</b>) via reduction using sodium borohydride in methanol. The same compounds of (<b>4a</b>,<b>b</b>) were used as starting materials for the synthesis of new furochromone derivatives such as furochromeno [2,3-<i>d</i>]pyrimidines, <i>N</i>- (6-cyano- 5-methyl-furochromene) acetamide, <i>N</i>-(6-cyano-5-methyl-furo chromene)-2-phenyl acetamide, <i>N</i>- (6-cyano-5-methyl-furochromene) formimidate, furochromeno[1,2,4]triazepin-5-amine, furochrom ene-6-carboxamide, furochromeno[1,2,4]triazolopyrimidines, and furochromeno[2,3-<i>b</i>]quinolin- 6-amine. The structures of the new compounds were determined using spectroscopy: Nuclear Magnetic Resonance (¹H, ¹³C), Mass spectra, Infrared, and elemental analysis. Molecular docking studies were conducted to investigate the binding patterns of the prepared compounds against DNA-gyrase (PDB 1HNJ). The results displayed that compounds furochromenotriazolopyrimidine (<b>20a</b>,<b>b</b>), furochromenoquinolin-6-amine (<b>21a</b>,<b>b</b>), furochromenotriazepin-amine (<b>9a</b>,<b>b</b>), and furo- chromenopyrimidine-amine (<b>19a</b>,<b>b</b>) were excellent antimicrobials.

Item Description

10.3390/ph15101232
1424-8247