New synthetic approaches towards analogues of bedaquiline

Abstract

Multi-drug resistant tuberculosis (MDR-TB) is of growing global concern and threatens to undermine increasing efforts to control the worldwide spread of tuberculosis (TB). Bedaquiline has recently emerged as a new drug developed to specifically treat MDR-TB. Despite being highly effective as a result of its unique mode of action, bedaquiline has been associated with significant toxicities and as such, safety concerns are limiting its clinical use. In order to access pharmaceutical agents that exhibit an improved safety profile for the treatment of MDR-TB, new synthetic pathways to facilitate the preparation of bedaquiline and analogues thereof have been discovered.

Color-tuning and manipulation of the aggregation-induced emission efficiency of o-carborane-tetraphenylethylene dyads through substituted o-carboranes

“…(2-(4-Ethynylphenyl)ethene-1,1,2-triyl)tribenzene was synthesized according to literature procedures. 11 B 10 H 12 (CH 3 CN) 2 was synthesized by a modified method according to literature reports. 12 The model compound M was also synthesized according to literature procedures.…”

Cross-Coupling Reactions of Double or Triple Electrophilic Templates for Alkene Synthesis

“…This approach has been used to synthesize bedaquiline analogues (Scheme S25). 50 The key intermediate S25-3 was prepared via a Suzuki reaction of bromovinyl acetate S25-2 followed by ester hydrolysis during column chromatographic purification.…”