The concise synthesis of chalcone, indanone and indenone analogues of combretastatin A4

Kerr, Daniel J.; Hamel, Ernest; Jung, Katherine; Flynn, Bernard L.

doi:10.1016/j.bmc.2007.02.006

Cited by 85 publications

(40 citation statements)

References 32 publications

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“…In principle, it is desirable to maximize the difference between the dose required to affect cell proliferation and/or viability and that required to disrupt other cellular cytoskeletal functions. [25] …”

Section: Biological Evaluation Of the Inhibition Of Tubulin Polymerizmentioning

confidence: 97%

Synthesis of 2‐(1‐Phenylvinyl)benzofurans and 2‐(1‐Phenylvinyl)indoles as Antimitotic Agents by a Tandem Palladium‐Assisted Coupling‐Cyclization Reaction between 1‐Phenylvinyl Iodides and ortho‐Substituted Arylalkynes

et al. 2011

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A series of functionalized 2‐(1‐phenylvinyl)benzofurans 2 and 2‐(1‐phenylvinyl)indoles 3 were prepared from 1‐phenylvinyl iodides and silylated alkynes in a one‐pot reaction. After a desilylation step, the Sonogashira coupling reaction between the resulting terminal alkynes and 1‐phenylvinyliodide derivatives 6 gave enyne intermediates, which underwent a 5‐endo‐dig cyclization to afford 2‐(1‐phenylvinyl) heterocycles 2 and 3 in good yields. This method provides a rapid and efficient approach to build up benzoheterocycle‐based isocombretastatin A‐4 analogues of biological interest. From this series of compounds, the indoles 3o and 3r inhibited tubulin assembly at a micromolar level comparable to that of isoCA‐4.

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Section: Biological Evaluation Of the Inhibition Of Tubulin Polymerizmentioning

confidence: 97%

Synthesis of 2‐(1‐Phenylvinyl)benzofurans and 2‐(1‐Phenylvinyl)indoles as Antimitotic Agents by a Tandem Palladium‐Assisted Coupling‐Cyclization Reaction between 1‐Phenylvinyl Iodides and ortho‐Substituted Arylalkynes

et al. 2011

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“…These compounds have a particular value due to their broad spectrum of biological activity 2 and their wide-ranging utility as synthetic tools in the design of various bioactive molecules 3 . Furthermore, some indenol-based natural products 4 have shown analgesic and myorelaxation activity 2 and have been also used for the treatment of Alzheimer's disease 5 . Despite the synthetic and pharmacological importance of indenols, few methods are known for the synthesis of these indene skeletons 6 .…”

Section: Introductionmentioning

confidence: 99%

A facile approach towards the synthesis of functionalized indenol derivatives identified as potent anti-oxidant and anti-bacterial agents

et al. 2014

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An elegant one-pot synthesis of new indenols 2 was successfully carried out, starting from 1-hydroxy-1H-indene-2-carboxylic acid 1. Thus, esterification of acid 1 with aliphatic alcohols in toluene at reflux and a catalytic amount of para-toluenesulfonic acid afforded the corresponding alkyl esters 2 in moderate to good yields. This classical esterification process enables an efficient entry to a variety of new indenol-based molecular models 2, which could be adapted to a range of drug candidates. All the synthesized compounds 2a-e were subjected to the preliminary evaluation for their potential anti-oxidant and anti-bacterial activities. The assessment of radical scavenging capacity of the compounds 2a-e towards the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) was measured and these compounds were found to scavenge DPPH free radical efficiently. Moreover, the in vitro antibacterial activity of derivatives 2a-e has been tested against a panel of pathogenic agents to show potent activity against all sensitive and resistant ones.

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“…Combrestatin A-4 (a natural cis-stilbene) and its analogs [28][29][30][31][32] are characterized by high cytotoxic activity in vitro relative to several types of human tumor cells. Hence we have carried out the condensation of lactam 1 with benzaldehyde to give the novel lactam -6,6-dimethyl-2-oxo-4-styryl-1,2,5,6-tetrahydropyridine-3-carbonitrile (2) which contains all three of the discussed groups (δ-lactam, cyanovinyl, and β-styryl) in its molecule.…”

mentioning

confidence: 99%

Synthesis and cytotoxicity of phenyl-vinyl derivatives of 4,6,6-trimethyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonitrile

Lukevics

Jansone

Leite

et al. 2009

Chem Heterocycl Comp

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2-bromophenyl derivatives showed high cytotoxic activity towards both cell lines. The toxicity towards NIH 3T3 normal mouse embryonic fibroblasts depends on the nature and position of the substituent in the phenyl ring. The greatest selectivity of cytotoxic effect was seen in the 2-bromophenyl derivative.In the synthesis of novel antitumor compounds the method of introducing a δ-lactam [1][2][3][4] or cyanovinyl group [5-9] into the starting molecule has been successfully used. A δ-lactam ring is included in camptothecin series antitumor preparations (inhibitors of topoisomerase I [10] -irinotecan [10, 11], rubitecan [12], topotecan [10, 13], exatecan [14], and its metabolite 9-aminocamptothecin [15], silatecan [16], and also inhibitors of dihydrofolate reductase (pemetrexed [17]), thymidyl synthetase (raltitrexed [18]), and farnesyl transferase (tipifarnib [19]). A δ-lactam ring occurs in the structure of an immunoregulator [20] and the antiangiogenic agent roquinimex [21]. N H Me Me O Me N N H Me O Me N H O R 1 2-26 R EtOH, NaOH , 25-78°C

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The concise synthesis of chalcone, indanone and indenone analogues of combretastatin A4

Cited by 85 publications

References 32 publications

Synthesis of 2‐(1‐Phenylvinyl)benzofurans and 2‐(1‐Phenylvinyl)indoles as Antimitotic Agents by a Tandem Palladium‐Assisted Coupling‐Cyclization Reaction between 1‐Phenylvinyl Iodides and ortho‐Substituted Arylalkynes

Synthesis of 2‐(1‐Phenylvinyl)benzofurans and 2‐(1‐Phenylvinyl)indoles as Antimitotic Agents by a Tandem Palladium‐Assisted Coupling‐Cyclization Reaction between 1‐Phenylvinyl Iodides and ortho‐Substituted Arylalkynes

A facile approach towards the synthesis of functionalized indenol derivatives identified as potent anti-oxidant and anti-bacterial agents

Synthesis and cytotoxicity of phenyl-vinyl derivatives of 4,6,6-trimethyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonitrile

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