Microwave-assisted synthesis and biological evaluation of 3,4-diaryl maleic anhydride/N-substituted maleimide derivatives as combretastatin A-4 analogues

Guan, Qı; Zuo, Daiying; Jiang, Nan; Qi, Huan; Zhai, Yanpeng; Bai, Zhaoshi; Feng, Dan; Yang, Lei; Jiang, Mingyang; Bao, Kai; Li, Chang; Wu, Yingliang; Zhang, Weige

doi:10.1016/j.bmcl.2014.12.004

Cited by 31 publications

(16 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Amongst them, 19 was the most promising compound, showing excellent IC 50 values of 1.3, 0.65 and 1.1 μM against SGC-7901, HT-1080 and KB cell lines, respectively. 41 In another study, the cis-olefinic bond was also replaced by NH attached imidazo-pyridine/pyrazine rings and four of such compounds significantly inhibited tubulin polymerization and were found to be potent against kidney (HEK 293T), breast (MCF 7) and cervical cancer (SiHa and HeLa) cell lines. 42 4.1.2 Other replacements and substitutions of the cis-olefinic bond.…”

Section: Recent Developments In Ca-4 Based Analoguesmentioning

confidence: 99%

“…72 In an earlier report, O'Boyle and coworkers synthesized water soluble amino acid and phosphate derivatives of β-lactam combretastatins followed by evaluation of antiproliferative and inhibition of tubulin polymerization properties. The phosphate derivatives (41)(42)(43), though exhibiting good antiproliferative ability, could not disrupt the microtubule assembly in MCF-7 breast cancer cells. Another series of CA-4 derivatives, β-lactam amino acid amides (44,45) displayed both potent anticancer and tubulin polymerization inhibition properties by binding to the colchicine domain.…”

Section: Recent Developments In Ca-4 Based Prodrugsmentioning

confidence: 99%

See 1 more Smart Citation

Recent advances in combretastatin based derivatives and prodrugs as antimitotic agents

et al. 2017

View full text Add to dashboard Cite

The dynamic and crucial role of tubulin in different cellular functions rendered it a promising target in anticancer drug development. Combretastatin A-4 (CA-4), an inhibitor of tubulin polymerization isolated from natural sources, is a lead molecule with significant cytotoxicity against tumour cells. Owing to its non polar nature it exhibits low solubility in natural biological fluids, thereby prompting the development of new CA-4 based derivatives. The modification of this lead molecule was mostly carried out by keeping the crucial -orientation of the double bond intact, along with a trimethoxyphenyl aromatic ring, by employing different approaches. The issue of solubility was also addressed by the development of water soluble prodrugs of CA-4. The present review highlights the investigations into the parallel development of both new CA-4 based derivatives and prodrugs in the past few years.

show abstract

Section: Recent Developments In Ca-4 Based Analoguesmentioning

confidence: 99%

Section: Recent Developments In Ca-4 Based Prodrugsmentioning

confidence: 99%

Recent advances in combretastatin based derivatives and prodrugs as antimitotic agents

et al. 2017

View full text Add to dashboard Cite

show abstract

“…Among those analogues, heterocyclic rings were often exchanged for the benzene B-ring. Thus, compound libraries were prepared with indole [44], benzoxazolone [45], benzothiophene [46] and naphthalene [47] as the B-rings. These analogues maintained the ability to bind tubulin and inhibit microtubule polymerization.…”

Section: Combretastatin A-4 Analoguesmentioning

confidence: 99%

Novel Natural Product- and Privileged Scaffold-Based Tubulin Inhibitors Targeting the Colchicine Binding Site

et al. 2016

View full text Add to dashboard Cite

Tubulin inhibitors are effective anticancer agents, however, there are many limitations to the use of available tubulin inhibitors in the clinic, such as multidrug resistance, severe side-effects, and generally poor bioavailability. Thus, there is a constant need to search for novel tubulin inhibitors that can overcome these limitations. Natural product and privileged structures targeting tubulin have promoted the discovery and optimization of tubulin inhibitors. This review will focus on novel tubulin inhibitors derived from natural products and privileged structures targeting the colchicine binding site on tubulin.

show abstract

“…Under conventional heating conduction, the reaction of 8 with PPh 3 in CCl 4 to generate (E)-ethyl 2-chloro-2-(arylimino)acetates (9) suffered from long reaction time and low yields (Table 1, entries 1-5). Microwave irradiation offered many advantages, such as rate enhancements and higher yields, over conventional heating and had become a popular technique that was widely used in organic synthesis today [15][16][17][18] . When microwave irradiation was incorporated into synthesis of 9-8, we found that the reaction rate was greatly improved.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and biological evaluation of 1-Aryl-5-(4-arylpiperazine-1-carbonyl)-1H-tetrazols as novel microtubule destabilizers

Wang

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

Self Cite

View full text Add to dashboard Cite

A series of 1-aryl-5-(4-arylpiperazine-1-carbonyl)-1H-tetrazols as microtubule destabilizers were designed, synthesised and evaluated for anticancer activity. Based on bioisosterism, we introduced the tetrazole moiety containing the hydrogen-bond acceptors as B-ring of XRP44X analogues. The key intermediates ethyl 1-aryl-1H-tetrazole-5-carboxylates 10 can be simply and efficiently prepared via a microwave-assisted continuous operation process. Among the compounds synthesised, compound 6-31 showed noteworthy potency against SGC-7901, A549 and HeLa cell lines. In mechanism studies, compound 6-31 inhibited tubulin polymerisation and disorganised microtubule in SGC-7901 cells by binding to tubulin. Moreover, compound 6-31 arrested SGC-7901cells in G2/M phase. This study provided a new perspective for development of antitumor agents that target tubulin.

show abstract

Microwave-assisted synthesis and biological evaluation of 3,4-diaryl maleic anhydride/N-substituted maleimide derivatives as combretastatin A-4 analogues

Cited by 31 publications

References 21 publications

Recent advances in combretastatin based derivatives and prodrugs as antimitotic agents

Recent advances in combretastatin based derivatives and prodrugs as antimitotic agents

Novel Natural Product- and Privileged Scaffold-Based Tubulin Inhibitors Targeting the Colchicine Binding Site

Design, synthesis and biological evaluation of 1-Aryl-5-(4-arylpiperazine-1-carbonyl)-1H-tetrazols as novel microtubule destabilizers

Contact Info

Product

Resources

About