Literature DB >> 24930832

Efficient synthesis of eudistomin U and evaluation of its cytotoxicity.

Chad M Roggero1, Jennifer M Giulietti1, Seann P Mulcahy2.   

Abstract

Eudistomin U is a member of a subclass of naturally occurring indole alkaloids known as β-carbolines. These molecules are reported to have diverse biological activity and high binding affinity to DNA, which make them attractive targets for total synthesis. We describe an efficient, five-step synthesis of eudistomin U by employing two key reactions: a Bischler-Napieralski cyclization and a Suzuki cross coupling. We also describe the cytotoxicity of eudistomin U against various cancer cell lines and human pathogens, in which we observed potent antibacterial activity against Gram-positive bacteria.
Copyright © 2014 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Antibacterial; Eudistomin U; Palladium catalysis; Suzuki cross coupling; β-Carboline

Mesh:

Substances:

Year:  2014        PMID: 24930832      PMCID: PMC4116134          DOI: 10.1016/j.bmcl.2014.05.049

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  10 in total

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Journal:  J Nat Prod       Date:  1998-07       Impact factor: 4.050

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Journal:  J Nat Prod       Date:  1994-04       Impact factor: 4.050

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4.  Small molecules with antimicrobial activity against E. coli and P. aeruginosa identified by high-throughput screening.

Authors:  R De La Fuente; N D Sonawane; D Arumainayagam; A S Verkman
Journal:  Br J Pharmacol       Date:  2006-09-18       Impact factor: 8.739

Review 5.  beta-Carboline alkaloids: biochemical and pharmacological functions.

Authors:  Rihui Cao; Wenlie Peng; Zihou Wang; Anlong Xu
Journal:  Curr Med Chem       Date:  2007       Impact factor: 4.530

6.  Synthesis of β- and γ-carbolines via ruthenium and rhodium catalysed [2+2+2] cycloadditions of yne-ynamides with methylcyanoformate.

Authors:  Felix Nissen; Vincent Richard; Carole Alayrac; Bernhard Witulski
Journal:  Chem Commun (Camb)       Date:  2011-04-19       Impact factor: 6.222

7.  Eudistomins W and X, two new beta-carbolines from the micronesian tunicate Eudistoma sp.

Authors:  Peter Schupp; Timo Poehner; RuAngelie Edrada; Rainer Ebel; Albrecht Berg; Victor Wray; Peter Proksch
Journal:  J Nat Prod       Date:  2003-02       Impact factor: 4.050

8.  Room-temperature aromatization of tetrahydro-β-carbolines by 2-iodoxybenzoic acid: utility in a total synthesis of eudistomin U.

Authors:  Joseph D Panarese; Stephen P Waters
Journal:  Org Lett       Date:  2010-09-17       Impact factor: 6.005

9.  Antiviral and antitumor structure-activity relationship studies on tetracyclic eudistomines.

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Journal:  J Med Chem       Date:  1992-08-21       Impact factor: 7.446

10.  [Synthesis of 1-indole substituted beta-carboline alkaloid and its derivatives and evaluation of their preliminary antitumor activities].

Authors:  Xiao-chun Dong; Ren Wen; Jian-bin Zheng
Journal:  Yao Xue Xue Bao       Date:  2004-04
  10 in total
  3 in total

1.  Development of Kinase-Selective, Harmine-Based DYRK1A Inhibitors that Induce Pancreatic Human β-Cell Proliferation.

Authors:  Kunal Kumar; Peng Wang; Roberto Sanchez; Ethan A Swartz; Andrew F Stewart; Robert J DeVita
Journal:  J Med Chem       Date:  2018-08-21       Impact factor: 7.446

2.  DNA-binding studies of the natural β-carboline eudistomin U.

Authors:  Jennifer M Giulietti; Patrick M Tate; Ang Cai; Bongsup Cho; Seann P Mulcahy
Journal:  Bioorg Med Chem Lett       Date:  2016-08-18       Impact factor: 2.823

Review 3.  Recent Advances in the Synthesis of β-Carboline Alkaloids.

Authors:  Tímea Szabó; Balázs Volk; Mátyás Milen
Journal:  Molecules       Date:  2021-01-27       Impact factor: 4.411

  3 in total

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