Rapid Access to Conformational Analogues of (+)-Peloruside A

Zhao, Zhiming; Taylor, Richard E.

doi:10.1021/ol203268t

Cited by 14 publications

(12 citation statements)

References 22 publications

(19 reference statements)

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“…In 2010, Altmann et al [164] reported the stereoselective synthesis of monocyclic peloruside A analog and discovered that the compound is several-hundred-fold less potent than peloruside A in three human cancer cell lines. In 2012, Taylor et al [165] synthesized a set of conformational analogs of peloruside A just in 18 steps from commercial materials by a simple esterification-based fragments coupling and a late stage RCM reaction. This efficient synthetic strategy is significant for the further research, though they didn't make activity evaluation of conformational peloruside A M A N U S C R I P T…”

Section: Fig 14 Total Synthesis Strategies Of Peloruside Amentioning

confidence: 99%

Recent advances in microtubule-stabilizing agents

Cao

Zheng

Wang

et al. 2018

European Journal of Medicinal Chemistry

142

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Highly dynamic mitotic spindle microtubules are superb therapeutic targets for a group of chemically diverse and clinically successful anticancer drugs. Microtubule-targeted drugs disrupt microtubule dynamics in distinct ways, and they are primarily classified into two groups: microtubule destabilizing agents (MDAs), such as vinblastine, colchicine, and combretastatin-A4, and microtubule stabilizing agents (MSAs), such as paclitaxel and epothilones. Systematic discovery and development of new MSAs have been aided by extensive research on paclitaxel, yielding a large number of promising anticancer compounds. This review focuses on the natural sources, structural features, mechanisms of action, structure-activity relationship (SAR) and chemical synthesis of MSAs. These MSAs mainly include paclitaxel, taccalonolides, epothilones, FR182877 (cyclostreptin), dictyostatin, discodermolide, eleutherobin and sarcodictyins, zampanolide, dactylolide, laulimalides, peloruside and ceratamines from natural sources, as well as small molecular microtubule stabilizers obtained via chemical synthesis. Then we discuss the application prospect and development of these anticancer compounds.

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Section: Fig 14 Total Synthesis Strategies Of Peloruside Amentioning

confidence: 99%

Recent advances in microtubule-stabilizing agents

Cao

Zheng

Wang

et al. 2018

European Journal of Medicinal Chemistry

142

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“…Few analogues have been published since 2003 11,12. Among them, conformationally constrained analogues such as natural peloruside C 3 12a or synthetic compound 4 obtained by replacement of the C11 and C13 stereogenic centers with a set of olefinic Z and E isomers12b [compounds ( E )‐ 4 and ( Z )‐ 4 , Figure 1] have been recently characterized. At the same time, a stereoselective synthesis of monocyclic peloruside A analogue 5 has allowed the importance of the pyranose ring in the bicyclic core structure of the macrocycle to be outlined (Figure 1, IC 50 = 16.4 μ M on A549 cells) 13…”

Section: Introductionmentioning

confidence: 99%

Combination of Carbon Nitride and Carbon Nanotubes: Synergistic Catalysts for Energy Conversion

et al. 2014

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Due to their versatile features and environmental friendliness, functionalized carbon materials show great potential in practical applications, especially in energy conversion. Developing carbon composites with properties that can be modulated by simply changing the ratio of the original materials is an intriguing synthetic strategy. Here, we took cyanamide and multiwalled carbon nanotubes as precursors and introduced a facile method to fabricate a series of graphitic carbon nitride/carbon nanotubes (g-C3 N4 /CNTs) composites. These composites demonstrated different practical applications with different weight ratios of the components, that is, they showed synergistic effects in optoelectronic conversion when g-C3 N4 was the main ingredient and in oxygen reduction reaction (ORR) when CNTs dominated the composites. Our experiments indicated that the high electrical conductivity of carbon nanotubes promoted the transmission of the charges in both cases.

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“…While previous studies with these compounds have centered on determining their mode of action and molecular interactions with tubulin 4 there’s been little focus on understanding their conformational behavior in solution, which we believe is crucial in the process of designing bioactive analogues. 9 Herein, we report the conformational analysis of zampanolide and dactylolide’s shared macrolide core.…”

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confidence: 99%

Conformational Preferences of Zampanolide and Dactylolide

et al. 2013

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The solution conformation behavior of the macrolide core of microtubule-stabilizing agents (−)-zampanolide and (−)-dactylolide has been determined through a combination of high-field NMR experiments and computational modeling. Taken together, the results demonstrate that in solution both molecules exist as a mixture of three interconverting conformational families, one of which bears strong resemblance to zampanolide’s tubulin-bound conformation.

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Rapid Access to Conformational Analogues of (+)-Peloruside A

Cited by 14 publications

References 22 publications

Recent advances in microtubule-stabilizing agents

Recent advances in microtubule-stabilizing agents

Combination of Carbon Nitride and Carbon Nanotubes: Synergistic Catalysts for Energy Conversion

Conformational Preferences of Zampanolide and Dactylolide

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