Benzimidazole-2-carboxylic acid amides and esters: a new structural class of 5-HT3 ligands

Design and Synthesis of Benzimidazole-Chalcone Derivatives as Potential Anticancer Agents

“…Benzimidazole derivative 16 was synthesized in high yield [45] through a reaction of o -phenylenediamine with lactic acid (1.1 equiv) in hydrochloric acid (4.0 N concentration) under reflux for 6.0 h, which underwent oxidation in the presence of potassium permanganate (2.5 equiv) and solid aluminium oxide to afford the intermediate compound 17 , which was prepared from the oxidation products. After being ground with a pestle and mortar and then purified, compound 17 was obtained in 72% yield as a white solid [46]. We prepared the benzimidazolyl-chalcones 18a – 18d in 82–95% overall yields by reacting compound 17 with substituted aromatic aldehydes possessing 4-methyl- ( 18b ), 4-methoxy- ( 18c ), and 4-chloro- ( 18d ) groups in the presence of a base, through conventional Claisen-Schmidt condensations.…”

Similarity Searching and Scaffold Hopping in Synthetically Accessible Combinatorial Chemistry Spaces

“…Using 22 as a query revealed distinct solutions with variations of the query’s indazole scaffold. The structure of 27 shows a benzimidazole ring, whereas 28 contains a pyrrazolopyridine heterocycle instead. , In the case of solutions 29 and 30 , the indazole scaffold of query 22 is replaced by an oxobenzimidazole and indole ring, respectively. , At the same time, the synthetic access to the products compared to the query differs (amide to urea chemistry). The observation that most of the hits in Figure do not replace the azabicyclic tropanyl ring in both queries is due to the fact that almost allof the 5-HT3 antagonists in the data set contain this very distinctive ring system.…”

“…The structure of 27 shows a benzimidazole ring, whereas 28 contains a pyrrazolopyridine heterocycle instead. 92,93 In the case of solutions 29 and 30, the indazole scaffold of query 22 is replaced by an oxobenzimidazole and indole ring, respectively. 94,95 At the same time, the synthetic access to the products compared to the query differs (amide to urea chemistry).…”

Cytotoxicity of Substituted Benzimidazolyl Curcumin Mimics Against Multi-Drug Resistance Cancer Cell

“…The reaction of variously substituted 1,2-phenylenediamine (7a-7g) with glycolic acid (3 eq) in 4 N hydrochloric acid produced substituted benzimidazolyl methanol (8a-8g) after reflux for 6 h. 20 The benzimidazolyl methanols 8a-8g were reacted with iodomethane (3 eq) in the presence of tetrabutylammonium bromide (TBAB, 0.2 eq) and potassium hydroxide (KOH, 1.1 eq) in tetrahydrofuran (THF) at 0 o C to afford 1-methylbenzimidazolyl compounds (9a-9g), 21 which were subsequently oxidized with the Dess-Martin periodinane in methylene chloride at 0 o C to produce substituted benzimidazolyl 2-carbaldehyde (10a-10g).…”