Synthesis, anti-bacterial, anti-asthmatic and anti-diabetic activities of novel N-substituted-2-(4-phenylethynyl-phenyl)-1H-benzimidazoles and N-substituted 2[4-(4,4-dimethyl-thiochroman-6-yl-ethynyl)-phenyl-1H-benzimidazoles

• Published in: European journal of medicinal chemistry 2008-05, Vol.43 (5), p.986-995
• Main Authors: VINODKUMAR, Ramanatham, SANJAY DASHRATH VAIDYA, BOBBA VENKATA SIVA KUMAR, UMESH NANASAHEB BHISE, SHEKHAR BHASKAR BHIRUD, UDAY CHANDRAKANT MASHELKAR
• Format: Article
• Language: English
• Subjects: Alkynes - chemical synthesis; Alkynes - chemistry; Alkynes - pharmacology; Anti-Asthmatic Agents - chemical synthesis; Anti-Asthmatic Agents - chemistry; Anti-Asthmatic Agents - pharmacology; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Benzimidazoles - chemical synthesis; Benzimidazoles - chemistry; Benzimidazoles - pharmacology; Biological and medical sciences; Dipeptidyl-Peptidase IV Inhibitors; General and cellular metabolism. Vitamins; Heterocyclic Compounds, 2-Ring - chemical synthesis; Heterocyclic Compounds, 2-Ring - chemistry; Heterocyclic Compounds, 2-Ring - pharmacology; Humans; Hypoglycemic Agents - chemical synthesis; Hypoglycemic Agents - chemistry; Hypoglycemic Agents - pharmacology; Medical sciences; Pharmacology. Drug treatments; Phosphodiesterase 4 Inhibitors; Protein Tyrosine Phosphatase, Non-Receptor Type 1 - antagonists & inhibitors; Respiratory system; Structure-Activity Relationship
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2007.06.013

Synthesis of a series of novel and functionalized benzimidazole derivatives by the condensation of OPDA with 4-bromobenzoic acid and subsequent reactions of the product obtained with phenylacetylene and 6-ethynyl-4,4-dimethylthiochroman utilising Sonogashira coupling has been reported. The Sonogashira coupling products were then alkylated at the benzimidazole -NH with different electrophilic reagents leading to functionalized derivatives. All the compounds synthesized were screened for their potential anti-bacterial, anti-asthmatic and anti-diabetic properties, which exhibited moderate activities in screening studies in vitro.