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

doi:10.1007/s00706-014-1352-0

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 journal › Article › peer-review

7 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 language	English
Pages (from-to)	705-712
Number of pages	8
Journal	Monatshefte fur Chemie
Volume	146
Issue number	4
DOIs	https://doi.org/10.1007/s00706-014-1352-0
Publication status	Published - Apr 2015
Externally published	Yes

Keywords

Antibacterial activity
Antigiardial and antitrichomonal activity
Metronidazole
Piperazine
Synthesis

ASJC Scopus subject areas

Chemistry(all)

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10.1007/s00706-014-1352-0

Cite this

@article{e16e9281debc4878a4c87963b5db935f,

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

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.]",

keywords = "Antibacterial activity, Antigiardial and antitrichomonal activity, Metronidazole, Piperazine, Synthesis",

author = "Al-Qtaitat, {Malath A.} and Saadeh, {Haythem A.} and Al-Bakri, {Amal G.} and Hargobinder Kaur and Kapil Goyal and Rakesh Sehgal and Mubarak, {Mohammad S.}",

note = "Publisher Copyright: {\textcopyright} 2014 Springer-Verlag Wien.",

year = "2015",

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doi = "10.1007/s00706-014-1352-0",

language = "English",

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TY - JOUR

T1 - Synthesis, characterization, and biological activity of novel metronidazole-piperazine amides

AU - Al-Qtaitat, Malath A.

AU - Saadeh, Haythem A.

AU - Al-Bakri, Amal G.

AU - Kaur, Hargobinder

AU - Goyal, Kapil

AU - Sehgal, Rakesh

AU - Mubarak, Mohammad S.

PY - 2015/4

Y1 - 2015/4

N2 - 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.]

AB - 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.]

KW - Antibacterial activity

KW - Antigiardial and antitrichomonal activity

KW - Metronidazole

KW - Piperazine

KW - Synthesis

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SN - 0026-9247

VL - 146

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EP - 712

JO - Monatshefte fur Chemie

JF - Monatshefte fur Chemie

IS - 4

ER -

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

Abstract

Keywords

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