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Microwave assisted synthesis and cytotoxic activity evaluations of new benzimidazole derivatives
Umeå University, Faculty of Medicine, Umeå Centre for Microbial Research (UCMR). Umeå University, Faculty of Science and Technology, Department of Chemistry.
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2016 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 57, no 8, 887-891 p.Article in journal (Refereed) PublishedText
Abstract [en]

Twelve new 2-quinolizinylbenzimidazole and 2-naphthalylbenzimidazole derivatives with various 5- and 6-positioned substituents (aza, H, CH3, Cl, NO2, NH2, OCH3), have been synthesized in moderate to excellent yields via the condensation of 4-oxo-4H-quinolizinecarbaldehyde or naphthalenecarbaldehyde with substituted o-phenylenediamines, o-nitroaniline, and 2,3-pyridinediamine using sodium metabisulfite or sodium hydrosulfite under microwave irradiation. The new benzimidazole derivatives were screened for their cytotoxic activity against the human breast cancer cell line (MCF-7). The results showed on one hand that 2-(substituted quinolizinyl)-1H-benzimidazoles (12bf) were less active (3–6 fold) than the positive control Tamoxifen (CC50 = 6.52 μM), and on the other hand, among the 2-(substituted naphthalyl)-1H-benzimidazoles series (13af), compounds 6,7,8-trimethoxy-3-(5-chloro-1H-benzo[d]imidazol-2-yl)naphthalen-1-ol (13c) (CC50 = 7.48 μM) and 6,7,8-trimethoxy-3-(5-methoxy-1H-benzo[d]imidazol-2-yl)naphthalen-1-ol (13f) (CC50 = 6.43 μM) were found to be as active as Tamoxifen.

Place, publisher, year, edition, pages
Elsevier, 2016. Vol. 57, no 8, 887-891 p.
Keyword [en]
4-Oxo-4H-quinolizine, Naphthalene, Benzimidazole, Stobbe condensation, Microwave assisted ganic synthesis, Human breast cancer cell line
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:umu:diva-118245DOI: 10.1016/j.tetlet.2016.01.042ISI: 000370307800014OAI: oai:DiVA.org:umu-118245DiVA: diva2:912775
Available from: 2016-03-17 Created: 2016-03-14 Last updated: 2016-03-17Bibliographically approved

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Vo, Duy Duc
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Umeå Centre for Microbial Research (UCMR)Department of Chemistry
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