New Synthesis and Antiparasitic Activity of Model 5-Aryl-1-methyl-4-nitroimidazoles
A number of 5-aryl-1-methyl-4-nitroimidazoles 5a-f have been synthesized in good yields by the Suzuki coupling reaction between 5-chloro-1-methyl-4-nitroimidazole (3) and arylboronic acids 4a-f, aided by dichlorobis-(triphenylphosphine)palladium(II), K2CO3, and tetrabutylammonium bromide in water at...
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| Language: | English |
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MDPI AG
2009-07-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/14/8/2758/ |
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| author | Mustafa M. El-Abadelah Ibrahim M. Mosleh Haythem A. Saadeh |
| author_facet | Mustafa M. El-Abadelah Ibrahim M. Mosleh Haythem A. Saadeh |
| author_sort | Mustafa M. El-Abadelah |
| collection | DOAJ |
| description | A number of 5-aryl-1-methyl-4-nitroimidazoles 5a-f have been synthesized in good yields by the Suzuki coupling reaction between 5-chloro-1-methyl-4-nitroimidazole (3) and arylboronic acids 4a-f, aided by dichlorobis-(triphenylphosphine)palladium(II), K2CO3, and tetrabutylammonium bromide in water at 70-80 °C. Compounds 5a-f were characterized by elemental analysis, NMR and MS spectral data. On the basis of in vitro screening data, 5-(3-chlorophenyl)-1-methyl-4-nitro-1H-imidazole (5f)exhibited potent lethal activity against Entamoeba histolytica and Giardia intestinalis with IC50 = 1.47 µM/mL, a value lower by a factor of two than that of the standard drug, metronidazole. The boosted activity of 5f was not accompanied by any increased cytotoxicity.The rest of the series also exhibited potent antiparasitic activity with IC50 valuesin the 1.72-4.43 µM/mL range. The cytotoxicity of the derivatives 5c and 5e was increased compared to the precursor compound, metronidazole, although they remain non-cytotoxic at concentrations much higher than the antiparasitic concentration of the two derivatives. |
| first_indexed | 2024-12-17T06:01:37Z |
| format | Article |
| id | doaj.art-03f57a6bf0f543ec9482046d239ad566 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-17T06:01:37Z |
| publishDate | 2009-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-03f57a6bf0f543ec9482046d239ad5662022-12-21T22:00:51ZengMDPI AGMolecules1420-30492009-07-011482758276710.3390/molecules14082758New Synthesis and Antiparasitic Activity of Model 5-Aryl-1-methyl-4-nitroimidazolesMustafa M. El-AbadelahIbrahim M. MoslehHaythem A. SaadehA number of 5-aryl-1-methyl-4-nitroimidazoles 5a-f have been synthesized in good yields by the Suzuki coupling reaction between 5-chloro-1-methyl-4-nitroimidazole (3) and arylboronic acids 4a-f, aided by dichlorobis-(triphenylphosphine)palladium(II), K2CO3, and tetrabutylammonium bromide in water at 70-80 °C. Compounds 5a-f were characterized by elemental analysis, NMR and MS spectral data. On the basis of in vitro screening data, 5-(3-chlorophenyl)-1-methyl-4-nitro-1H-imidazole (5f)exhibited potent lethal activity against Entamoeba histolytica and Giardia intestinalis with IC50 = 1.47 µM/mL, a value lower by a factor of two than that of the standard drug, metronidazole. The boosted activity of 5f was not accompanied by any increased cytotoxicity.The rest of the series also exhibited potent antiparasitic activity with IC50 valuesin the 1.72-4.43 µM/mL range. The cytotoxicity of the derivatives 5c and 5e was increased compared to the precursor compound, metronidazole, although they remain non-cytotoxic at concentrations much higher than the antiparasitic concentration of the two derivatives.http://www.mdpi.com/1420-3049/14/8/2758/5-chloro-1-methyl-4-nitroimidazolearylboronic acidsSuzuki coupling5-aryl-1-methyl-4-nitroimidazolesantiparasitic activity |
| spellingShingle | Mustafa M. El-Abadelah Ibrahim M. Mosleh Haythem A. Saadeh New Synthesis and Antiparasitic Activity of Model 5-Aryl-1-methyl-4-nitroimidazoles Molecules 5-chloro-1-methyl-4-nitroimidazole arylboronic acids Suzuki coupling 5-aryl-1-methyl-4-nitroimidazoles antiparasitic activity |
| title | New Synthesis and Antiparasitic Activity of Model 5-Aryl-1-methyl-4-nitroimidazoles |
| title_full | New Synthesis and Antiparasitic Activity of Model 5-Aryl-1-methyl-4-nitroimidazoles |
| title_fullStr | New Synthesis and Antiparasitic Activity of Model 5-Aryl-1-methyl-4-nitroimidazoles |
| title_full_unstemmed | New Synthesis and Antiparasitic Activity of Model 5-Aryl-1-methyl-4-nitroimidazoles |
| title_short | New Synthesis and Antiparasitic Activity of Model 5-Aryl-1-methyl-4-nitroimidazoles |
| title_sort | new synthesis and antiparasitic activity of model 5 aryl 1 methyl 4 nitroimidazoles |
| topic | 5-chloro-1-methyl-4-nitroimidazole arylboronic acids Suzuki coupling 5-aryl-1-methyl-4-nitroimidazoles antiparasitic activity |
| url | http://www.mdpi.com/1420-3049/14/8/2758/ |
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