Antineoplastic Agents. 487. Synthesis and Biological Evaluation of the Antineoplastic Agent 3,4-Methylenedioxy-5,4‘-dimethoxy-3‘-amino-<i>Z</i>-stilbene and Derived Amino Acid Amides

The design of novel anticancer agents based on the combretastatins, a group of antimitotic agents isolated from the bark of the South African willow tree Combretum caffrum Kuntz, is of considerable contemporary interest. Combretastatin A-4, the most active compound in the group, due to its unique dual features of antitubulin and antivascular properties, has drawn significant attention of medicinal chemists for the design of analogues as novel antitumor agents. To date, 252 references have been published since 1982 and 187 references have been published since 1998 related to combretastatins research. The 102 references related to chemistry efforts can be classified into three different categories including one-atom, two-atom, and three-atom bridgeheads as linker between two aryl rings of combretastatins. This review will particularly elucidate the rationale and strategic tactics towards the development of novel classes of antimitotic agents, based upon combretastatin A-4 as a promising lead.

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“…Compound 9 also showed a potent inhibition of tubulin polymerization. Compounds 10 and 11 are under further development [52].…”

Section: Combretastatinsmentioning

confidence: 99%

Pharmaceutical Design of Antimitotic Agents Based on Combretastatins

Hsieh

Liou²,

Mahindroo

2005

CPD

149

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“…Due to its structural simplicity, ease of synthesis, and potent antitumor activity, this class of molecules is widely studied to find potent anticancer agents. [11][12][13] Recently, conjugates bearing imidazo [2,1-b]thiazole scaffolds have become of interest due to their broad spectrum of pharmacological activities, such as antifungal, [14,15] antibacterial, [16][17][18] anti-inflammatory, [19] and antihypertensive properties. [20] It has been reported that they possess antitumor properties against a variety of human cancer cell lines.…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Imidazo[2,1‐b]thiazole–Chalcone Conjugates: Microtubule‐Destabilizing Agents

et al. 2014

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A series of chalcone conjugates featuring the imidazo[2,1-b]thiazole scaffold was designed, synthesized, and evaluated for their cytotoxic activity against five human cancer cell lines (MCF-7, A549, HeLa, DU-145 and HT-29). These new hybrid molecules have shown promising cytotoxic activity with IC50 values ranging from 0.64 to 30.9 μM. Among them, (E)-3-(6-(4-fluorophenyl)-2,3-bis(4-methoxyphenyl)imidazo[2,1-b]thiazol-5-yl)-1-(pyridin-2-yl)prop-2-en-1-one (11 x) showed potent antiproliferative activity with IC50 values ranging from 0.64 to 1.44 μM in all tested cell lines. To investigate the mechanism of action, the detailed biological aspects of this promising conjugate (11 x) were carried out on the A549 lung cancer cell line. The tubulin polymerization assay and immunofluoresence analysis results suggest that this conjugate effectively inhibits microtubule assembly in A549 cells. Flow cytometric analysis revealed that this conjugate induces cell-cycle arrest in the G2/M phase and leads to apoptotic cell death. This was further confirmed by Hoechst staining, activation of caspase-3, DNA fragmentation analysis, and Annexin V-FITC assay. Moreover, molecular docking studies indicated that this conjugate (11 x) interacts and binds efficiently with the tubulin protein.

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“…The most important intermediates for several biologically active molecules [56,57], fluoro compounds [58] have been synthesized through Wittig reaction.…”

Section: Wittig Reactionsmentioning

confidence: 99%

Recent Developments on Catalytic Applications of Nano-Crystalline Magnesium Oxide

Chintareddy

Kantam

2011

Catal Surv Asia

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Nanocrystalline metal oxides, MgO, CuO, ZnO, TiO 2 as catalysts or catalyst supports have been received much attention in the recent years, especially nanocrystalline magnesium oxide (NAP-MgO) has been used as a recyclable catalyst for Wittig, WadsworthEmmons, aza-Michael, Baylis-Hillman, Strecker, Aldol, Claisen-Schmidt condensation and other useful organic reactions. In general, it is reported that nanocrystalline magnesium oxide shows better activity in many organic reactions. These high reactivities are due to high surface areas combined with unusually reactive morphologies. The nanomaterials were also explored as supports to make supported metal catalysts for the organic reactions. The higher activity of these catalysts was studied partly to understand the mechanism of the reaction, the putative reaction pathways were preliminarily presented with the help of spectroscopic support, XPS, silicon, and phosphorus NMR spectroscopy. The catalysts are recovered and reused for several cycles. These catalytic systems are expected to contribute to the development of benign chemical processes.

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Antineoplastic Agents. 487. Synthesis and Biological Evaluation of the Antineoplastic Agent 3,4-Methylenedioxy-5,4‘-dimethoxy-3‘-amino-Z-stilbene and Derived Amino Acid Amides

Cited by 57 publications

References 19 publications

Pharmaceutical Design of Antimitotic Agents Based on Combretastatins

Pharmaceutical Design of Antimitotic Agents Based on Combretastatins

Design and Synthesis of Imidazo[2,1‐b]thiazole–Chalcone Conjugates: Microtubule‐Destabilizing Agents

Recent Developments on Catalytic Applications of Nano-Crystalline Magnesium Oxide

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