Literature DB >> 23110297

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

Suwei Dong1, Tian Qin, Ernest Hamel, John A Beutler, John A Porco.   

Abstract

A rhodium-catalyzed dehydrogenation protocol for the conversion of 3,5-diarylcyclopentenones to the corresponding 2,4-diarylcyclopentadienones has been developed. With this protocol, analogues of the cytotoxic agent chamaecypanone C have been synthesized via Diels-Alder cycloaddition between the cyclopentadienones and in situ-generated o-quinols. Biological evaluation of these analogues revealed a compound with higher activity as a microtubule inhibitor and cytotoxic agent in comparison with the parent structure.

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Year:  2012        PMID： 23110297      PMCID： PMC3542833          DOI： 10.1021/ja3084708

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  17 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

2.  Deantiaromatization as a driving force in an electrocyclic reaction.

Authors:  Michael Harmata; Pinguan Zheng; Peter R Schreiner; Armando Navarro-Vázquez
Journal:  Angew Chem Int Ed Engl       Date:  2006-03-13       Impact factor: 15.336

3.  Gold supported on hydroxyapatite as a versatile multifunctional catalyst for the direct tandem synthesis of imines and oximes.

Authors:  Hao Sun; Fang-Zheng Su; Ji Ni; Yong Cao; He-Yong He; Kang-Nian Fan
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  A general method for the synthesis of 3,5-diarylcyclopentenones via friedel-crafts acylation of vinyl chlorides.

Authors:  Yingju Xu; Mark McLaughlin; Cheng-yi Chen; Robert A Reamer; Peter G Dormer; Ian W Davies
Journal:  J Org Chem       Date:  2009-07-17       Impact factor: 4.354

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.  Molecular complexity via C-H activation: a dehydrogenative Diels-Alder reaction.

Authors:  Erik M Stang; M Christina White
Journal:  J Am Chem Soc       Date:  2011-09-01       Impact factor: 15.419

7.  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

8.  Direct Aerobic α, β-Dehydrogenation of Aldehydes and Ketones with a Pd(TFA)(2)/4,5-Diazafluorenone Catalyst().

Authors:  Tianning Diao; Tyler J Wadzinski; Shannon S Stahl
Journal:  Chem Sci       Date:  2011-10-31       Impact factor: 9.825

9.  N-heterocyclic carbene catalyzed ring expansion of formylcyclopropanes: synthesis of 3,4-dihydro-alpha-pyrone derivatives.

Authors:  Gong-Qiang Li; Li-Xin Dai; Shu-Li You
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005

10.  Chamaecypanone C, a novel skeleton microtubule inhibitor, with anticancer activity by trigger caspase 8-Fas/FasL dependent apoptotic pathway in human cancer cells.

Authors:  Cheng-Chih Hsieh; Yueh-Hsiung Kuo; Ching-Chuan Kuo; Li-Tzong Chen; Chun-Hei Antonio Cheung; Tsu-Yi Chao; Chi-Hung Lin; Wen-Yu Pan; Chi-Yen Chang; Shih-Chang Chien; Tung-Wei Chen; Chia-Chi Lung; Jang-Yang Chang
Journal:  Biochem Pharmacol       Date:  2009-12-23       Impact factor: 5.858
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  3 in total

1.  Asymmetric Syntheses of the Flavonoid Diels-Alder Natural Products Sanggenons C and O.

Authors:  Chao Qi; Yuan Xiong; Vincent Eschenbrenner-Lux; Huan Cong; John A Porco
Journal:  J Am Chem Soc       Date:  2016-01-19       Impact factor: 15.419

2.  Biomimetic dehydrogenative Diels-Alder cycloadditions: total syntheses of brosimones A and B.

Authors:  Chao Qi; Huan Cong; Katharine J Cahill; Peter Müller; Richard P Johnson; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-01       Impact factor: 15.336

3.  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
  3 in total

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