Synthesis, characterization, and biological activity of novel metronidazole-piperazine amides

Malath A. Al-Qtaitat, Haythem A. Saadeh, Amal G. Al-Bakri, Hargobinder Kaur, Kapil Goyal, Rakesh Sehgal, Mohammad S. Mubarak

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

A new series of metronidazole derivatives containing piperazine rings were prepared via the reaction of 2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetyl chloride with selected substituted piperazines in the presence of a base. Structures of the new compounds were confirmed by NMR and MS spectral data and by elemental analyses. The antibacterial and anti-parasitic activities of these compounds were evaluated in vitro. Some of the newly synthesized compounds exhibited superior activity against Clostridium sporogenes bacteria compared to the standard drug metronidazole. On the other hand, other derivatives exhibited remarkable antigiardial activity and were found to be more active than metronidazole with IC 50 ranging from 1.8 to 6.7 μg/dm3. 1-Ethyl-4-[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]piperazine also exhibited antigiardial activity with similar IC 50 value (7.6 μg/cm3) as compared to the reference drug metronidazole (IC 50 = 7.4 μg/cm3). Similarly, several of the new compounds exhibited significant antitrichomonal activity and found to be more active than metronidazole with IC 50 ranging from 6.7 to 8.65 μg/cm3 as compared to the reference drug metronidazole (8.9 μg/cm3). Graphical abstract: [Figure not available: see fulltext.]

Original languageEnglish
Pages (from-to)705-712
Number of pages8
JournalMonatshefte fur Chemie
Volume146
Issue number4
DOIs
Publication statusPublished - Apr 2015
Externally publishedYes

Keywords

  • Antibacterial activity
  • Antigiardial and antitrichomonal activity
  • Metronidazole
  • Piperazine
  • Synthesis

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint

Dive into the research topics of 'Synthesis, characterization, and biological activity of novel metronidazole-piperazine amides'. Together they form a unique fingerprint.

Cite this