Synthesis and cytotoxicity studies of 1-propenyl-1,3-dihydro-benzimidazol-2-one
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ORIGINAL ARTICLE
Synthesis and cytotoxicity studies of 1-propenyl-1,3-dihydro-benzimidazol-2-one Biswadip Banerji 1 & Sumit Kumar Pramanik 1
Received: 13 January 2015 / Accepted: 24 March 2015 # Springer-Verlag Berlin Heidelberg 2015
Abstract A heterocyclic compound 1-propenyl-1,3dihydro-benzimidazol-2-one was synthesized by a palladium-catalyzed rearrangement reaction. Anticancer activities were confirmed by 3-(4,5-dimethylthiazol-2-yl)2,5-diphenyltetrazolium bromide (MTT) assay against Neura 2a (neuroblastoma cell), HEK 293 (kidney cancer) and MCF-7 (breast cancer) cell lines at low micromolar range. Furthermore, clear images from phase-contrast and fluorescence microscopes and confocal images unambiguously confirm the cancer cell death. The single X-ray crystal structure of the compound unambiguously proves the structure of the benzimidazolone compound. Keywords Benzimidazolone . Palladium catalyzed . MTT assay . Confocal microasopy
Introduction Worldwide cancer is one of the most common and fatal diseases that cause deaths [1, 2]. The existing anticancer drugs are not sufficient enough to combat this serious problem [3, 4]. Hence, identification of new, selective molecules which have low toxicity and their easy synthesis remain a challenging task
CCDC-776996 contains the supplementary crystallographic data for this paper. This data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.Ccdc.cam.ac.uk/data_request/cif * Biswadip Banerji [email protected] 1
Department of Chemistry, CSIR-Indian Institute of Chemical Biology, 4, Raja S.C. Mullick Road, Kolkata 700032, India
for the cancer therapy [5–7]. Benzimidazolone scaffold is one of the key scaffolds of a variety of heterocyclic compounds that play crucial roles in the modulation of a number of biologically important pathways [8–11]. Thus, benzimidazole and its derivatives representing a major class of nitrogencontaining heterocycles have gained an important role in the drug discovery [12–15]. The biological importance of benzimidazole derivatives is due to their structural resemblance to the naturally occurring nucleotides. This has allowed them to interact with the biopolymers of the living system [16]. Substituted benzimidazole derivatives have lots of therapeutic applications in the areas including antimicrobial [17], antioxidant [18], antiviral [19], antihypertensive [20], antiprotozoal [21], anti-inflammatory [22], and molluscicidal [23] agents. Many benzimidazole derivatives were reported to selectively inhibit endothelial cell growth and suppress angiogenesis both in vitro and in vivo [24]. Some potential anticancer activities were also reported with compounds having benzimidazolone scaffold [25]. Such characteristics have made this scaffold a synthetic target, and therefore, its synthesis and derivatization become an important and challenging job. In an ongoing project in our laboratory on the synthesis of Bnew chemical entity^ (NCE) having anticancer activity, we were interested to synthesize benzimidaz
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