Abstract
The global health concern of antimicrobial resistance has harnessed research interest to find new classes of antibiotics to combat disease-causing pathogens. In our studies, 3-halobenzo[b]thiophene derivatives were synthesized and tested for their antimicrobial activities using the broth microdilution susceptibility method. The 3-halo substituted benzo[b]thiophenes were synthesized starting from 2-alkynyl thioanisoles using a convenient electrophilic cyclization methodology that utilizes sodium halides as the source of electrophilic halogens when reacted along with copper(II) sulfate. This environmentally benign methodology is facile, uses ethanol as the solvent, and results in 3-halo substituted benzo[b]thiophene structures in very high yields. The cyclohexanol-substituted 3-chloro and 3-bromobenzo[b]thiophenes resulted in a low MIC of 16 µg/mL against Gram-positive bacteria and yeast. Additionally, in silico absorption, distribution, metabolism, and excretion (ADME) properties of the compounds were determined. The compounds with the lowest MIC values showed excellent drug-like properties with no violations to Lipinski, Veber, and Muegge filters. The time-kill curve was obtained for cyclohexanol-substituted 3-chlorobenzo[b]thiophenes against Staphylococcus aureus, which showed fast bactericidal activity at MIC.
Highlights
There has been an increasing concern over the rapidly spreading resistance to existing antibiotics and antifungal drugs [1,2]
The antimicrobial resistance has been driven by antimicrobial exposure via underuse, overuse, and misuse in health care, agriculture, aquaculture, and the environment [3]
According to the Centers for Disease Control (CDC), 2.8 million people in the United States are infected with antibiotic-resistant bacteria or fungi each year, and over 35,000 of them die
Summary
There has been an increasing concern over the rapidly spreading resistance to existing antibiotics and antifungal drugs [1,2]. The antimicrobial resistance has been driven by antimicrobial exposure via underuse, overuse, and misuse in health care (human and veterinary medicine), agriculture, aquaculture, and the environment [3]. Antibiotic resistance threats report at least 18 antibiotic-resistant strains of bacteria and fungi. According to the Centers for Disease Control (CDC), 2.8 million people in the United States are infected with antibiotic-resistant bacteria or fungi each year, and over 35,000 of them die. The estimated national cost to treat infections in the USA alone is more than USD 4.6 billion annually [4]. The resistant microorganisms rapidly develop to evade antimicrobial effects by a wide range of complex biochemical and physiological mechanisms [5]. There has not been a new class of antibiotics approved since the discovery of daptomycin in
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