63330-75-6

Upstream product

• 100-63-0 phenylhydrazine 
• 515824-31-4 (E)-1-(1H-benzo[d]imidazol-2-yl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 20224-09-3 1-(1H-benzo[d]imidazol-2-yl)-3-(4-methoxyphenyl)prop-2-en-1-one 

Downstream Products

• 1152184-31-0 C₃₃H₂₇N₅O₄ 
• 1152184-35-4 C₃₅H₃₁N₅O₄ 

Relevant academic research and scientific papers

Microwave assisted transformation of benzimidazolyl chalcones into N 1-substituted pyrazolines and evaluation of their antimicrobial activities

1-Benzimidazolyl-3-aryl-prop-2-ene-1-ones 2 have been transformed into N1-substituted pyrazoline derivatives by the interaction with phenyl hydrazine, thiosemicarbazide and hydrazine hydrate in the presence of formic acid under solvent microwave induced protocol. The structure of newly synthesized compounds have been confirmed on the basis of their elemental analysis and spectral data. Newly synthesized compounds have been evaluated for their antimicrobial activity in against E. coli, K. pneumonae, P. aeruginosa and B. subtilis using paper disc method. Some of the compounds have shown significant activity against the pathogens.

Pyrazoline bearing benzimidazoles: Search for anticancer agent

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-1H-3-pyrazolyl]-1H-benzimidazole (NSC 748326) was found to be the most active candidate of the series and selected for further evaluation at five dose level screening.

Facile synthesis of alkoxyphthalimide derivatized benzimidazole assembled pyrazoles, pyrimidines and isoxazoles, via common intermediate chalcone

In the present investigation, synthesis of 2-(3-aryl-2-phenyl-3,4- dihydropyrazol-5-yl)-1-N-alkoxyphthalimidobenzimidazole 9a-h, 4-(1-N-alkoxyphthalimidobenzimidazol-2-yl)-6-arylpyrimidin-2-amine 10a-h and 2-(5-aryl-4,5-dihydroisoxazol-3-yl)-1-N-alkoxyphthalimidobenzimidazole 11a-h are described. Mild dichromate oxidation of 1-benzimidazol-2-yl-ethanol 1 gives 1-benzimidazol-2-yl-ethanone 2 which on Clasien condensation with various aromatic aldehydes yields the corresponding 3-aryl-1-(benzimidazol-2-yl)-prop-2- en-1-one 3a-d derivatives. Compound 3a-d act as key intermediates for all the three series of final compounds. In one pathway 3a-d is converted to its alkoxyphthalimide derivatives 5a-h by condensation with ω- bromoalkoxyphthalimides 4a-b, which cyclize with PhNHNH2/pyridine, guanidine nitrate/10% NaOH and hydroxylamine hydrochloride/CH3COOH to give 9a-h, 10a-h and 11a-h respectively. In an alternative route, reaction of 3a-d with all the three reagents affords 2-(3-aryl-2-phenyl-3,4-dihydropyrazol- 5-yl)benzimidazole 6a-d, 4-(benzimidazol-2-yl)-6-arylpyrimidin-2-amine 7a-d and 2-(5-aryl-4,5-dihydroisoxazol-3-yl)benzimidazole 8a-d which on condensation with co-bromoalkoxyphthalimides 4a-b give the final compounds 9a-h, 10a-h and 11a-h. Structure elucidations of all the compounds have been accomplished by elemental analysis, IR, 1H NMR and mass spectral data.