Synthesis and antimicrobial activity of new 1,2,4-triazole-3-thiol metronidazole derivatives

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

doi:10.1007/s00706-010-0281-9

Synthesis and antimicrobial activity of new 1,2,4-triazole-3-thiol metronidazole derivatives

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

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

45 Citations (Scopus)

Abstract

New 1,2,4-triazole-3-thiol metronidazole derivatives have been synthesized by treating 1,2,4-triazole-3-thiols with metronidazole tosylate (toluene-4-sulfonic acid 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl ester) in DMF and in the presence of potassium carbonate as a base. S-alkylated and N-alkylated products were obtained, with the S-alkylated being the major products. All of the newly synthesized compounds were characterized by IR, ¹H NMR, ¹³C NMR, and high-resolution mass spectrometry. The antiparasitic activity of the compounds against Entamoeba histolytica and Giardia intestinalis was investigated. The antibacterial and antifungal activity of the compounds, assessed as minimal inhibitory concentration, was also investigated.

Original language	English
Pages (from-to)	471-478
Number of pages	8
Journal	Monatshefte fur Chemie
Volume	141
Issue number	4
DOIs	https://doi.org/10.1007/s00706-010-0281-9
Publication status	Published - Apr 2010
Externally published	Yes

Keywords

Antimicrobial activity
Antiparasitic activity
Metronidazole
Triazoles

ASJC Scopus subject areas

Chemistry(all)

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10.1007/s00706-010-0281-9

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title = "Synthesis and antimicrobial activity of new 1,2,4-triazole-3-thiol metronidazole derivatives",

abstract = "New 1,2,4-triazole-3-thiol metronidazole derivatives have been synthesized by treating 1,2,4-triazole-3-thiols with metronidazole tosylate (toluene-4-sulfonic acid 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl ester) in DMF and in the presence of potassium carbonate as a base. S-alkylated and N-alkylated products were obtained, with the S-alkylated being the major products. All of the newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR, and high-resolution mass spectrometry. The antiparasitic activity of the compounds against Entamoeba histolytica and Giardia intestinalis was investigated. The antibacterial and antifungal activity of the compounds, assessed as minimal inhibitory concentration, was also investigated.",

keywords = "Antimicrobial activity, Antiparasitic activity, Metronidazole, Triazoles",

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

note = "Funding Information: This work was financially supported by the Deanship of Scientific Research at the University of Jordan; this support is highly acknowledged.",

year = "2010",

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doi = "10.1007/s00706-010-0281-9",

language = "English",

volume = "141",

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AU - Saadeh, Haythem A.

AU - Mosleh, Ibrahim M.

AU - Al-Bakri, Amal G.

AU - Mubarak, Mohammad S.

N1 - Funding Information: This work was financially supported by the Deanship of Scientific Research at the University of Jordan; this support is highly acknowledged.

PY - 2010/4

Y1 - 2010/4

N2 - New 1,2,4-triazole-3-thiol metronidazole derivatives have been synthesized by treating 1,2,4-triazole-3-thiols with metronidazole tosylate (toluene-4-sulfonic acid 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl ester) in DMF and in the presence of potassium carbonate as a base. S-alkylated and N-alkylated products were obtained, with the S-alkylated being the major products. All of the newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR, and high-resolution mass spectrometry. The antiparasitic activity of the compounds against Entamoeba histolytica and Giardia intestinalis was investigated. The antibacterial and antifungal activity of the compounds, assessed as minimal inhibitory concentration, was also investigated.

AB - New 1,2,4-triazole-3-thiol metronidazole derivatives have been synthesized by treating 1,2,4-triazole-3-thiols with metronidazole tosylate (toluene-4-sulfonic acid 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl ester) in DMF and in the presence of potassium carbonate as a base. S-alkylated and N-alkylated products were obtained, with the S-alkylated being the major products. All of the newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR, and high-resolution mass spectrometry. The antiparasitic activity of the compounds against Entamoeba histolytica and Giardia intestinalis was investigated. The antibacterial and antifungal activity of the compounds, assessed as minimal inhibitory concentration, was also investigated.

KW - Antimicrobial activity

KW - Antiparasitic activity

KW - Metronidazole

KW - Triazoles

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DO - 10.1007/s00706-010-0281-9

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VL - 141

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JO - Monatshefte fur Chemie

JF - Monatshefte fur Chemie

IS - 4

ER -

Synthesis and antimicrobial activity of new 1,2,4-triazole-3-thiol metronidazole derivatives

Abstract

Keywords

ASJC Scopus subject areas

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