Synthesis and anthelmintic activity of some novel 2-substituted-4,5-diphenyl imidazoles.

Abstract

A series of 2-substituted-4,5-diphenyl imidazoles 1a-j were synthesized by refluxing benzil with different substituted aldehydes in the presence of ammonium acetate and glacial acetic acid. Structures of the synthesized compounds were confirmed on the basis of IR, 1H NMR and mass spectral data. Compounds 1a-j were screened for anthelmintic activity. Test results revealed that compounds showed paralysis time of 0.24 to 1.54 min and death time of 0.39 to 4.40 min while the standard drugs albendazole and piperazine citrate showed paralysis time of 0.54 and 0.58 min and death time of 2.16 and 2.47 min, respectively, at the same concentration of 1% (m/V). Five compounds, 2-[2-hydroxyphenyl]-4,5-diphenyl imidazole (1b), 2-[3-methoxyphenyl]-4,5-diphenyl imidazole (1c), 2-[2-phenylethenyl]-4,5-diphenyl imidazole (1e), 2-[4-fluorophenyl]-4,5-diphenyl imidazole (1g) and 2-[3-nitrophenyl]-4,5-diphenyl imidazole (1h) showed significant anthelmintic activity compared to the standard drugs.

• Authors: Satyajit Dutta
• Journal: Acta pharmaceutica (Zagreb, Croatia) (Acta Pharm) Vol. 60 Issue 2 Pg. 229-35 (Jun 2010) ISSN: 1846-9558 [Electronic] Poland
• PMID: 21134859 (Publication Type: Journal Article)

Chemical References

• Acetates
• Aldehydes
• Anthelmintics
• Imidazoles
• Phenylglyoxal
• Acetic Acid
• ammonium acetate
• benzil

Topics

• Acetates (chemistry)
• Acetic Acid (chemistry)
• Aldehydes (chemistry)
• Animals
• Anthelmintics (chemical synthesis, chemistry, pharmacology)
• Imidazoles (chemical synthesis, chemistry, pharmacology)
• Magnetic Resonance Spectroscopy
• Mass Spectrometry
• Oligochaeta (drug effects)
• Phenylglyoxal (analogs & derivatives, chemistry)
• Structure-Activity Relationship