Synthesis, characterization and biological activity of Schiff bases derived from metronidazole

Haythem A. Saadeh; Eman A.Abu Shaireh; Ibrahim M. Mosleh; Amal G. Al-Bakri; Mohammad S. Mubarak

doi:10.1007/s00044-011-9830-y

Synthesis, characterization and biological activity of Schiff bases derived from metronidazole

Haythem A. Saadeh, Eman A.Abu Shaireh, Ibrahim M. Mosleh, Amal G. Al-Bakri, Mohammad S. Mubarak

Research output: Contribution to journal › Article › peer-review

32 Citations (Scopus)

Abstract

A series of novel Schiff bases; compounds 3a- j were prepared by reacting 1-(2-aminoethyl)-2-methyl-5-nitroimidazole dihydrochloride monohydrate (1) with different aldehydes. The structures of these compounds were confirmed through different spectroscopic methods such as ¹H-NMR, ¹³C-NMR and mass spectrometry and also by elemental analyses. The prepared compounds were evaluated in vitro for their antigiardial, antibacterial and antifungal activities. Compounds 3h, 3b and 3d showed remarkable antigiardial activities and were found to be more active than metronidazole with IC ₅₀ of 0.83, 1.36 and 1.83 μM, respectively. Other compounds also exhibited antigiardial activity and were as good as or even more potent than metronidazole. Some of the newly synthesized Schiff bases exhibited more antifungal activities than the parent drug. In addition, a few of the prepared compounds exhibited modest antibacterial activity but were not as active as metronidazole.

Original language	English
Pages (from-to)	2969-2974
Number of pages	6
Journal	Medicinal Chemistry Research
Volume	21
Issue number	10
DOIs	https://doi.org/10.1007/s00044-011-9830-y
Publication status	Published - Oct 2012
Externally published	Yes

Keywords

Antigiardial activity
Metronidazole
Schiff bases

ASJC Scopus subject areas

General Pharmacology, Toxicology and Pharmaceutics
Organic Chemistry

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10.1007/s00044-011-9830-y

Cite this

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title = "Synthesis, characterization and biological activity of Schiff bases derived from metronidazole",

abstract = "A series of novel Schiff bases; compounds 3a- j were prepared by reacting 1-(2-aminoethyl)-2-methyl-5-nitroimidazole dihydrochloride monohydrate (1) with different aldehydes. The structures of these compounds were confirmed through different spectroscopic methods such as 1H-NMR, 13C-NMR and mass spectrometry and also by elemental analyses. The prepared compounds were evaluated in vitro for their antigiardial, antibacterial and antifungal activities. Compounds 3h, 3b and 3d showed remarkable antigiardial activities and were found to be more active than metronidazole with IC 50 of 0.83, 1.36 and 1.83 μM, respectively. Other compounds also exhibited antigiardial activity and were as good as or even more potent than metronidazole. Some of the newly synthesized Schiff bases exhibited more antifungal activities than the parent drug. In addition, a few of the prepared compounds exhibited modest antibacterial activity but were not as active as metronidazole.",

keywords = "Antigiardial activity, Metronidazole, Schiff bases",

author = "Saadeh, {Haythem A.} and Shaireh, {Eman A.Abu} and Mosleh, {Ibrahim M.} and Al-Bakri, {Amal G.} and Mubarak, {Mohammad S.}",

note = "Funding Information: Acknowledgments I.M. Mosleh was supported by a joint grant from the Deanship of Scientific Research, The University of Jordan, and Hamdi Manko Center for Scientific Research (HMCSR), The University of Jordan. We also wish to thank Miss Lina Al-Natsheh for the technical assistance and the maintenance of cultures.",

year = "2012",

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doi = "10.1007/s00044-011-9830-y",

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AU - Saadeh, Haythem A.

AU - Shaireh, Eman A.Abu

AU - Mosleh, Ibrahim M.

AU - Al-Bakri, Amal G.

AU - Mubarak, Mohammad S.

N1 - Funding Information: Acknowledgments I.M. Mosleh was supported by a joint grant from the Deanship of Scientific Research, The University of Jordan, and Hamdi Manko Center for Scientific Research (HMCSR), The University of Jordan. We also wish to thank Miss Lina Al-Natsheh for the technical assistance and the maintenance of cultures.

PY - 2012/10

Y1 - 2012/10

N2 - A series of novel Schiff bases; compounds 3a- j were prepared by reacting 1-(2-aminoethyl)-2-methyl-5-nitroimidazole dihydrochloride monohydrate (1) with different aldehydes. The structures of these compounds were confirmed through different spectroscopic methods such as 1H-NMR, 13C-NMR and mass spectrometry and also by elemental analyses. The prepared compounds were evaluated in vitro for their antigiardial, antibacterial and antifungal activities. Compounds 3h, 3b and 3d showed remarkable antigiardial activities and were found to be more active than metronidazole with IC 50 of 0.83, 1.36 and 1.83 μM, respectively. Other compounds also exhibited antigiardial activity and were as good as or even more potent than metronidazole. Some of the newly synthesized Schiff bases exhibited more antifungal activities than the parent drug. In addition, a few of the prepared compounds exhibited modest antibacterial activity but were not as active as metronidazole.

AB - A series of novel Schiff bases; compounds 3a- j were prepared by reacting 1-(2-aminoethyl)-2-methyl-5-nitroimidazole dihydrochloride monohydrate (1) with different aldehydes. The structures of these compounds were confirmed through different spectroscopic methods such as 1H-NMR, 13C-NMR and mass spectrometry and also by elemental analyses. The prepared compounds were evaluated in vitro for their antigiardial, antibacterial and antifungal activities. Compounds 3h, 3b and 3d showed remarkable antigiardial activities and were found to be more active than metronidazole with IC 50 of 0.83, 1.36 and 1.83 μM, respectively. Other compounds also exhibited antigiardial activity and were as good as or even more potent than metronidazole. Some of the newly synthesized Schiff bases exhibited more antifungal activities than the parent drug. In addition, a few of the prepared compounds exhibited modest antibacterial activity but were not as active as metronidazole.

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Synthesis, characterization and biological activity of Schiff bases derived from metronidazole

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Keywords

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