Highly Potent Triazole-Based Tubulin Polymerization Inhibitors

Zhang, Qiang; Peng, Youyi; Wang, Xin I.; Keenan, Susan M.; Arora, Sonia; Welsh, William J.

doi:10.1021/jm061142s

Cited by 151 publications

(77 citation statements)

References 41 publications

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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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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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“…This mostly included either modification of the olefinic bond by the introduction of saturation, substituents and other functionalities or its replacement with a three to six membered ring system, which resulted in cis restricted analogues of CA4. 16,[19][20][21][22] Similar to CA4, a number of colchicine site binding ligands are known to inhibit tubulin polymerization and are considered as potential lead like molecules. One of them, E7010 is the first orally active antimitotic sulphonamide derivative that has received much interest in recent years and currently it is in clinical trials.…”

mentioning

confidence: 99%

Design and synthesis of cis-restricted benzimidazole and benzothiazole mimics of combretastatin A-4 as antimitotic agents with apoptosis inducing ability

Ashraf

Shaik

Malik

et al. 2016

Bioorganic & Medicinal Chemistry Letters

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“…Their cyclization with carbonyl compounds is one of the most important pathways to access 1,2,4-triazole derivatives [46][47][48].…”

Section: Amidrazonesmentioning

confidence: 99%

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Zhang¹,

Damu²,

Cai³

et al. 2014

COC

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Heterocyclic 1,2,4-triazole derivatives possess unusually spacious potentiality as medicinal agents, agricultural chemicals, functional materials, ionic liquids, supramolecular catalysts as well as artificial enzymes and receptors for supramolecular recognition and biomimetic catalysis, and their various researches and developments have been being a quite rapidly developing and active highlight topic with an infinite space. Numerous efforts have been directed toward various types of possible applications of 1,2,4-triazole-based compounds and a lot of important progress has been made, especially their preparations have attracted increasing attention. This review systematically summarized the recent advances in the syntheses of 1,2,4-triazole derivatives, including: (1) Cyclizations to form triazole ring; (2) Transformations of heterocyclic compounds to construct triazole ring; (3) Substitutions on 1,2,4-triazole ring; (4) Structural modifications in side chains of 1,2,4-triazole ring. It was hoped that this review would be helpful for the design and development of highly efficient preparation of 1,2,4-triazole derivatives with various sorts and varieties of extensively potential applications in medicine, agriculture, chemistry, materials, supramolecular sciences and so on.

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Highly Potent Triazole-Based Tubulin Polymerization Inhibitors

Cited by 151 publications

References 41 publications

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

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

Design and synthesis of cis-restricted benzimidazole and benzothiazole mimics of combretastatin A-4 as antimitotic agents with apoptosis inducing ability

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

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