Pyrazoline bearing benzimidazoles: Search for anticancer agent

• Published in: European journal of medicinal chemistry 2010, Vol.45 (1), p.114-119
• Main Authors: Shaharyar, Mohammad, Abdullah, M.M., Bakht, M.A., Majeed, Jaseela
• Format: Article
• Language: English
• Subjects: Anticancer activity; Antineoplastic agents; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Antiproliferative activity; Benzimidazole; Benzimidazoles - chemistry; Benzimidazoles - pharmacology; Biological and medical sciences; Cell Line, Tumor; Dose-Response Relationship, Drug; Drug Discovery; General aspects; Humans; Medical sciences; NCI; Pharmacology. Drug treatments; Pyrazoles - chemistry; Pyrazoline
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2009.09.032

2-acetyl benzimidazole was allowed to react with substituted aromatic aldehydes to get desired intermediate chalcones ( 2a– g), the cyclocondensation of these intermediates with hydrazine hydrate and phenyl hydrazine in two separate reactions yielded pyrazoline derivatives ( 3a– g & 4a– g respectively). Among the synthesize compounds, six compounds were granted NSC code and screened at National Cancer Institute (NCI), USA for anticancer activity at a single high dose (10 −5 M) in full NCI 60 cell panel. Among the selected compounds, ( 4f) 2-[5-(3,4-dimethoxyphenyl)-1-phenyl-4,5-dihydro-1 H-3-pyrazolyl]-1 H-benzimidazole (NSC 748326) was found to be the most active candidate of the series and selected for further evaluation at five dose level screening. 2-acetyl benzimidazole derived chalcones ( 2a– g) on cyclocondensation with hydrazine hydrate and phenyl hydrazine yielded pyrazolines ( 3a– g & 4a– g). Compound 2-[5-(3,4-dimethoxyphenyl)-1-phenyl-4,5-dihydro-1 H-3-pyrazolyl]-1 H-benzimidazole (NSC 748326) was most active candidate of the series. [Display omitted]