Literature DB >> 21651467

Epipolythiodioxopiperazines from fungi: chemistry and bioactivities.

C-S Jiang1, Y-W Guo.   

Abstract

Epipolythiodioxopiperazines (ETPs), characterized by a unique bridged disulfide or polysulfide dioxopiperazine six-membered ring, occur in many fungi. Due to its broad spectra of bioactivities, ETPs have drawn wide attention in recent years. This review covers diverse natural sources that produce ETPs, the synthetic chemistry of ETPs and an overview of promising bioactivities exhibited by some well studied ETPs. The plausible biosynthetic hypotheses of ETPs and some new results on antitumor activity of ETPs are also reviewed.

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Year:  2011        PMID: 21651467     DOI: 10.2174/138955711796355276

Source DB:  PubMed          Journal:  Mini Rev Med Chem        ISSN: 1389-5575            Impact factor:   3.862


  18 in total

1.  n→π* Interactions Modulate the Disulfide Reduction Potential of Epidithiodiketopiperazines.

Authors:  Henry R Kilgore; Chase R Olsson; Kyan A D'Angelo; Mohammad Movassaghi; Ronald T Raines
Journal:  J Am Chem Soc       Date:  2020-08-21       Impact factor: 15.419

2.  Enantioselective total syntheses of plectosphaeroic acids B and C.

Authors:  Salman Y Jabri; Larry E Overman
Journal:  J Org Chem       Date:  2013-08-27       Impact factor: 4.354

3.  Enantioselective total synthesis of (-)-acetylaranotin, a dihydrooxepine epidithiodiketopiperazine.

Authors:  Julian A Codelli; Angela L A Puchlopek; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2011-10-28       Impact factor: 15.419

4.  General approach for preparing epidithiodioxopiperazines from trioxopiperazine precursors: enantioselective total syntheses of (+)- and (-)-gliocladine C, (+)-leptosin D, (+)-T988C, (+)-bionectin A, and (+)-gliocladin A.

Authors:  John E DeLorbe; David Horne; Richard Jove; Steven M Mennen; Sangkil Nam; Fang-Li Zhang; Larry E Overman
Journal:  J Am Chem Soc       Date:  2013-03-01       Impact factor: 15.419

5.  Concise Total Synthesis of (+)-Luteoalbusins A and B.

Authors:  Timothy C Adams; Joshua N Payette; Jaime H Cheah; Mohammad Movassaghi
Journal:  Org Lett       Date:  2015-08-25       Impact factor: 6.005

6.  Synthesis and Anticancer Activity of Epipolythiodiketopiperazine Alkaloids.

Authors:  Nicolas Boyer; Karen C Morrison; Justin Kim; Paul J Hergenrother; Mohammad Movassaghi
Journal:  Chem Sci       Date:  2013-04-01       Impact factor: 9.825

7.  Quantitative Modeling of Bis(pyridine)silver(I) Permanganate Oxidation of Hydantoin Derivatives: Guidelines for Predicting the Site of Oxidation in Complex Substrates.

Authors:  Amanda J Bischoff; Brandon M Nelson; Zachary L Niemeyer; Matthew S Sigman; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2017-10-18       Impact factor: 15.419

8.  Mechanism of Permanganate-Promoted Dihydroxylation of Complex Diketopiperazines: Critical Roles of Counter-cation and Ion-Pairing.

Authors:  Brandon E Haines; Brandon M Nelson; Jessica M Grandner; Justin Kim; K N Houk; Mohammad Movassaghi; Djamaladdin G Musaev
Journal:  J Am Chem Soc       Date:  2018-10-08       Impact factor: 15.419

9.  Biogenetically-inspired total synthesis of epidithiodiketopiperazines and related alkaloids.

Authors:  Justin Kim; Mohammad Movassaghi
Journal:  Acc Chem Res       Date:  2015-04-06       Impact factor: 22.384

10.  Tricyclic Analogues of Epidithiodioxopiperazine Alkaloids with Promising In Vitro and In Vivo Antitumor Activity.

Authors:  Marcus Baumann; André P Dieskau; Brad M Loertscher; Mary C Walton; Sangkil Nam; Jun Xie; David Horne; Larry E Overman
Journal:  Chem Sci       Date:  2015       Impact factor: 9.825

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