Literature DB >> 19140149

Enantioselective synthesis of (+)-chamaecypanone C: a novel microtubule inhibitor.

Suwei Dong1, Ernest Hamel, Ruoli Bai, David G Covell, John A Beutler, John A Porco.   

Abstract

A bicycle built for tubulin: The total synthesis of (+)-chamaecypanone C has been achieved by using a tandem retro-Diels-Alder/Diels-Alder cascade reaction (see scheme). Initial biological studies demonstrate that (+)-chamaecypanone C is an inhibitor of tubulin assembly and binds at the colchicine site.

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Year:  2009        PMID： 19140149      PMCID： PMC2747729          DOI： 10.1002/anie.200805486

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  13 in total

Review 1.  Evaluation of antimitotic agents by quantitative comparisons of their effects on the polymerization of purified tubulin.

Authors:  Ernest Hamel
Journal:  Cell Biochem Biophys       Date:  2003       Impact factor: 2.194

Review 2.  Chemistry and biology of biosynthetic Diels-Alder reactions.

Authors:  Emily M Stocking; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2003-07-14       Impact factor: 15.336

3.  Cyclohexadienone ketals and quinols: four building blocks potentially useful for enantioselective synthesis.

Authors:  D Magdziak; S J Meek; T R R Pettus
Journal:  Chem Rev       Date:  2004-03       Impact factor: 60.622

4.  Domino retro Diels-Alder/Diels-Alder reaction: an efficient protocol for the synthesis of highly functionalized bicyclo[2.2.2]octenones and bicyclo[2.2.2]octadienones.

Authors:  Santhosh Kumar Chittimalla; Hui-Yi Shiao; Chun-Chen Liao
Journal:  Org Biomol Chem       Date:  2006-05-04       Impact factor: 3.876

Review 5.  2,3-dichloro-5,6-dicyanobenzoquinone and its reactions.

Authors:  D Walker; J D Hiebert
Journal:  Chem Rev       Date:  1967-04       Impact factor: 60.622

6.  Identification of novel antimitotic agents acting at the tubulin level by computer-assisted evaluation of differential cytotoxicity data.

Authors:  K D Paull; C M Lin; L Malspeis; E Hamel
Journal:  Cancer Res       Date:  1992-07-15       Impact factor: 12.701

7.  Structure-activity analysis of the interaction of curacin A, the potent colchicine site antimitotic agent, with tubulin and effects of analogs on the growth of MCF-7 breast cancer cells.

Authors:  P Verdier-Pinard; J Y Lai; H D Yoo; J Yu; B Marquez; D G Nagle; M Nambu; J D White; J R Falck; W H Gerwick; B W Day; E Hamel
Journal:  Mol Pharmacol       Date:  1998-01       Impact factor: 4.436

8.  Cyclopentadienone synthesis by rhodium(I)-catalyzed [3 + 2] cycloaddition reactions of cyclopropenones and alkynes.

Authors:  Paul A Wender; Thomas J Paxton; Travis J Williams
Journal:  J Am Chem Soc       Date:  2006-11-22       Impact factor: 15.419

9.  Ruthenium-catalyzed cycloisomerization of cis-3-en-1-ynes to cyclopentadiene and related derivatives through a 1,5-sigmatropic hydrogen shift of ruthenium-vinylidene intermediates.

Authors:  Swarup Datta; Arjan Odedra; Rai-Shung Liu
Journal:  J Am Chem Soc       Date:  2005-08-24       Impact factor: 15.419

10.  Enantioselective synthesis of bicyclo[2.2.2]octenones using a copper-mediated oxidative dearomatization/[4 + 2] dimerization cascade.

Authors:  Suwei Dong; Jianglong Zhu; John A Porco
Journal:  J Am Chem Soc       Date:  2008-02-12       Impact factor: 15.419
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  8 in total

1.  Microwave-based reaction screening: tandem retro-Diels-Alder/Diels-Alder cycloadditions of o-quinol dimers.

Authors:  Suwei Dong; Katharine J Cahill; Moon-Il Kang; Nancy H Colburn; Curtis J Henrich; Jennifer A Wilson; John A Beutler; Richard P Johnson; John A Porco
Journal:  J Org Chem       Date:  2011-10-07       Impact factor: 4.354

Review 2.  Aerobic copper-catalyzed organic reactions.

Authors:  Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal:  Chem Rev       Date:  2013-06-20       Impact factor: 60.622

3.  Selective Oxidation of Exogenous Substrates by a Bis-Cu(III) Bis-Oxide Complex: Mechanism and Scope.

Authors:  Tao A G Large; Viswanath Mahadevan; William Keown; T Daniel P Stack
Journal:  Inorganica Chim Acta       Date:  2018-11-22       Impact factor: 2.545

Review 4.  Dearomatization strategies in the synthesis of complex natural products.

Authors:  Stéphane P Roche; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

5.  Synthesis of chamaecypanone C analogues from in situ-generated cyclopentadienones and their biological evaluation.

Authors:  Suwei Dong; Tian Qin; Ernest Hamel; John A Beutler; John A Porco
Journal:  J Am Chem Soc       Date:  2012-11-20       Impact factor: 15.419

6.  High-throughput Screening in Larval Zebrafish Identifies Novel Potent Sedative-hypnotics.

Authors:  Xiaoxuan Yang; Youssef Jounaidi; Jennifer B Dai; Francisco Marte-Oquendo; Elizabeth S Halpin; Lauren E Brown; Richard Trilles; Wenqing Xu; Renee Daigle; Buwei Yu; Scott E Schaus; John A Porco; Stuart A Forman
Journal:  Anesthesiology       Date:  2018-09       Impact factor: 7.892

7.  Organocatalytic Enantioselective Synthesis of Bicyclo[2.2.2]octenones via Oxaziridinium Catalysed ortho-Hydroxylative Phenol Dearomatization.

Authors:  Tom D D'Arcy; Mark R J Elsegood; Benjamin R Buckley
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-10       Impact factor: 16.823

8.  Multidimensional reaction screening for photochemical transformations as a tool for discovering new chemotypes.

Authors:  Véronique I Martin; John R Goodell; Oscar J Ingham; John A Porco; Aaron B Beeler
Journal:  J Org Chem       Date:  2014-04-16       Impact factor: 4.354
  8 in total

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