Synthesis of N-Alkylated derivatives of imidazole as antibacterial agents

Khabnadideh, Soghra; Rezaei, Zahra; Khalafi-Nezhad, Ali; Bahrinajafi, R.; Mohamadi, R.; Farrokhroz, A.A.

doi:10.1016/s0960-894x(03)00591-2

Cited by 167 publications

(114 citation statements)

References 3 publications

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“…Thus, reaction of 2-mercapto-4,4-diphenyl-1H-imidazol-5(4H)-one (6) with 2-hydrazono-3,5-diphenyl-2,3-dihydro-1,3,4-thiadiazole (7) in ethanol under reflux, afforded a product which is typical in all respects with that obtained from the reaction of 2 with 3 (Chart 1).…”

Section: Resultsmentioning

confidence: 88%

“…There are plenty of imidazole containing drugs, such as angiotensin II antagonistic, [1][2][3][4] antimalarial, 5) antibacterial, 6,7) anticancer, 8) anti-inflammatory 9) and anticytokine agents. 10) Moreover, many literature reviews [11][12][13] showed that the 1,3,4-thiadiazole nuclei and annelated 1,3,4-thiadiazoles have antimicrobial, anti-inflammatory, anticancer, anticonvulsant, antidepressant, antioxidant, radio protective, and anti-leishmanial activities.…”

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confidence: 99%

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Synthesis and SAR Study of the Novel Thiadiazole–Imidazole Derivatives as a New Anticancer Agents

2016

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In the present study, a novel series of 2-(2-(3-aryl-5-substituted-1,3,4-thiadiazol-2(3H)-ylidene)-hydrazinyl)-4,4-diphenyl-1H-imidazol-5(4H)-one derivatives were designed and prepared via the reaction of the most versatile, hitherto unreported 2-(5-oxo-4,4-diphenyl-4,5-dihydro-1H-imidazol-2-yl)-N-phenylhydrazinecarbothioamide with the appropriate hydrazonoyl halides. In addition, some thiazole derivatives were prepared. The structures of the newly synthesized compounds were established based on spectroscopic evidences and their alternative syntheses. Some of the newly synthesized compounds have been evaluated for their anticancer activity against a liver carcinoma cell line HEPG2-1. Moreover, their structure-activity relationship (SAR) was explored for further development in this area. The results indicated that many of the tested compounds showed moderate to high anticancer activity with respective to doxorubicin as a reference drug. Consequently, the new synthesized series of thiadiazole-imidazole derivatives are considered as powerful anticancer agents.

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Section: Resultsmentioning

confidence: 88%

mentioning

confidence: 99%

Synthesis and SAR Study of the Novel Thiadiazole–Imidazole Derivatives as a New Anticancer Agents

2016

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“…Quantities of reagents were chosen for ease of work-up (13,15). The solvent was evaporated in vacuo and the crude product purified by column chromatography using methanol/dichloromethane (1/9) to give the final product.…”

Section: Synthesis Of Azole Compoundsmentioning

confidence: 99%

Effect of an Ionic Liquid [Bmim][Tf2N] on the Rate of Reaction in the Synthesis of some Azole Compounds as Antifungal Agents

Khabnadideh

Harper²

2014

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3-Butyl-1-methyl-1H-imidazol-3-iumbis((trifluoromethyl)sulfonyl)amide [Bmim][Tf 2 N] as an environmentalfriendly solvent was added to the reaction media for synthesis of some new azole compounds as antifungal agents. The effect of [Bmim][Tf 2 N] on the rate of reactions was studied using NMR analysis. The results show remarkable increasing in the progress of the reactions. As in recent years the developments of resistance to currently available antifungal azoles in Candida spp., as well as clinical failures in the treatment of fungal infections have been reported therefore intense efforts in antifungal drug discovery are still needed to develop more promising and effective antifungal agents for use in the clinical arena. We present a synthetic route for producing antifungal that is improved by using an ionic liquid.

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“…Khabnadideh et al, synthesized a series of alkylimidazole 8 and investigated the relationship between the length of the alkyl chain and its antibacterial activity (Fig. 1) [46]. The compound 8 were investigated for antibacterial activity against Staphylococcus aureus, Pseudomanas aeruginosa and Escherichia coli.…”

Section: Antibacterial Agentsmentioning

confidence: 99%

Synthetic Nitroimidazoles: Biological Activities and Mutagenicity Relationships

Mital

2009

Sci. Pharm.

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Parasitic and bacterial infections affecting the gastrointestinal tract represent a significant cause of morbidity and mortality worldwide. Nitroheterocyclic drugs have been available since the early 1960s for the treatment of anaerobic protozoa. The application of these drugs has widened and they are presently used to treat anaerobic pathogenic bacteria and protozoa. 5-nitroimidazoles are a well-established group of antiprotozoal and antibacterial agents that inhibit the growth of both anaerobic bacteria and certain anaerobic protozoa, such as Trichomonas vaginalis, Entamoeba histolytica and Giardia lamblia. The important antibacterial and antiprotozoal activities of nitroimidazoles are associated with reductive metabolism that has led to considerable interest in nitroimidazole reduction chemistry and the synthesis of new, highly effective drugs. The present review provides a brief account of various biological activities exhibited by synthetic nitroimidazole derivatives as well as their structure-mutagenicity relationships.

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Synthesis of N-Alkylated derivatives of imidazole as antibacterial agents

Cited by 167 publications

References 3 publications

Synthesis and SAR Study of the Novel Thiadiazole–Imidazole Derivatives as a New Anticancer Agents

Synthesis and SAR Study of the Novel Thiadiazole–Imidazole Derivatives as a New Anticancer Agents

Effect of an Ionic Liquid [Bmim][Tf2N] on the Rate of Reaction in the Synthesis of some Azole Compounds as Antifungal Agents

Synthetic Nitroimidazoles: Biological Activities and Mutagenicity Relationships

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