Literature DB >> 24076171

Total syntheses and cytotoxicity of kealiiquinone, 2-deoxy-2-aminokealiiquinone and analogs.

Jayanta Das1, Arunoday Bhan, Subhrangsu S Mandal, Carl J Lovely.   

Abstract

Concise syntheses of two Leucetta-derived naphthimidazole alkaloids, kealiiquinone and 2-deoxy-2-aminokealiiquinone, are described based on a biosynthetic-guided hypothesis. Advanced intermediates containing the full naphthimidazole framework are constructed through Friedel-Crafts chemistry followed by oxidation of the electron rich C-ring with hydrogen peroxide. The cytotoxicity of these alkaloids in a breast cancer cell line along with several closely related marine-derived natural products kealiinines A-C and analogs are reported.
Copyright © 2013 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Biomimetic; Cytotoxicity; Leucetta alkaloids; Naphthimidazole; Oxidation

Mesh：

Substances：

Year:  2013        PMID： 24076171      PMCID： PMC3876475          DOI： 10.1016/j.bmcl.2013.08.093

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


  14 in total

Review 1.  Marine natural products.

Authors:  John W Blunt; Brent R Copp; Robert A Keyzers; Murray H G Munro; Michèle R Prinsep
Journal:  Nat Prod Rep       Date:  2011-12-22       Impact factor: 13.423

Review 2.  Structure and synthesis of 2-aminoimidazole alkaloids from Leucetta and Clathrina sponges.

Authors:  Panduka B Koswatta; Carl J Lovely
Journal:  Nat Prod Rep       Date:  2010-10-28       Impact factor: 13.423

3.  A concise total synthesis of naamidine A.

Authors:  Nicholas S Aberle; Guillaume Lessene; Keith G Watson
Journal:  Org Lett       Date:  2006-02-02       Impact factor: 6.005

4.  Synthesis and biological evaluation of analogues of the anti-tumor alkaloid naamidine A.

Authors:  Nicholas Aberle; Jenny Catimel; Edouard C Nice; Keith G Watson
Journal:  Bioorg Med Chem Lett       Date:  2007-04-10       Impact factor: 2.823

5.  Synthesis of 2-imidazolones and 2-iminoimidazoles.

Authors:  Heather M Lima; Carl J Lovely
Journal:  Org Lett       Date:  2011-10-12       Impact factor: 6.005

6.  Naamidine A intensifies the phosphotransferase activity of extracellular signal-regulated kinases causing A-431 cells to arrest in G1.

Authors:  Robyn D James; David A Jones; William Aalbersberg; Chris M Ireland
Journal:  Mol Cancer Ther       Date:  2003-08       Impact factor: 6.261

7.  Total syntheses of kealiinines A-C.

Authors:  Jayanta Das; Panduka B Koswatta; J Daniel Jones; Muhammed Yousufuddin; Carl J Lovely
Journal:  Org Lett       Date:  2012-12-05       Impact factor: 6.005

8.  Naamidine A is an antagonist of the epidermal growth factor receptor and an in vivo active antitumor agent.

Authors:  B R Copp; C R Fairchild; L Cornell; A M Casazza; S Robinson; C M Ireland
Journal:  J Med Chem       Date:  1998-09-24       Impact factor: 7.446

9.  The marine alkaloid naamidine A promotes caspase-dependent apoptosis in tumor cells.

Authors:  Daniel V LaBarbera; Katarzyna Modzelewska; Amanda I Glazar; Phillip D Gray; Manjinder Kaur; Tong Liu; Douglas Grossman; Mary Kay Harper; Scott K Kuwada; Nadeem Moghal; Chris M Ireland
Journal:  Anticancer Drugs       Date:  2009-07       Impact factor: 2.248

10.  New imidazole alkaloids from the Indonesian sponge Leucetta chagosensis.

Authors:  Wafaa Hassan; RuAngelie Edrada; Rainer Ebel; Victor Wray; Albrecht Berg; Rob van Soest; Sumali Wiryowidagdo; Peter Proksch
Journal:  J Nat Prod       Date:  2004-05       Impact factor: 4.050
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  7 in total

1.  Total synthesis and cytotoxicity of Leucetta alkaloids.

Authors:  Panduka B Koswatta; Sabha Kasiri; Jayanta K Das; Arunoday Bhan; Heather M Lima; Beatriz Garcia-Barboza; Nicole N Khatibi; Muhammed Yousufuddin; Subhrangsu S Mandal; Carl J Lovely
Journal:  Bioorg Med Chem       Date:  2017-01-20       Impact factor: 3.641

Review 2.  Applications of Friedel-Crafts reactions in total synthesis of natural products.

Authors:  Majid M Heravi; Vahideh Zadsirjan; Pegah Saedi; Tayebeh Momeni
Journal:  RSC Adv       Date:  2018-12-03       Impact factor: 4.036

3.  Total synthesis of kealiiquinone: the regio-controlled strategy for accessing its 1-methyl-4-arylbenzimidazolone core.

Authors:  Velayudham Ramadoss; Angel J Alonso-Castro; Nimsi Campos-Xolalpa; Rafael Ortiz-Alvarado; Berenice Yahuaca-Juárez; César R Solorio-Alvarado
Journal:  RSC Adv       Date:  2018-08-31       Impact factor: 4.036

4.  Studies Towards the Leucetta-derived Alkaloids Spirocalcaridine A and B - Possible Biosynthetic Implications.

Authors:  Panduka B Koswatta; Jayanta Das; Muhammed Yousufuddin; Carl J Lovely
Journal:  European J Org Chem       Date:  2015-04

5.  Synthesis of Naamidine A and Selective Access to N(2)-Acyl-2-aminoimidazole Analogues.

Authors:  Joseph B Gibbons; Justin M Salvant; Rachel M Vaden; Ki-Hyeok Kwon; Bryan E Welm; Ryan E Looper
Journal:  J Org Chem       Date:  2015-09-24       Impact factor: 4.354

6.  Polyketides and Alkaloids from the Marine-Derived Fungus Dichotomomyces cejpii F31-1 and the Antiviral Activity of Scequinadoline A against Dengue Virus.

Authors:  Dong-Lan Wu; Hou-Jin Li; Duncan R Smith; Janejira Jaratsittisin; Xia-Fu-Kai-Ti Xia-Ke-Er; Wen-Zhe Ma; Yong-Wei Guo; Jun Dong; Juan Shen; De-Po Yang; Wen-Jian Lan
Journal:  Mar Drugs       Date:  2018-07-06       Impact factor: 5.118

7.  Total synthesis of 7'-desmethylkealiiquinone, 4'-desmethoxykealiiquinone, and 2-deoxykealiiquinone.

Authors:  Heather M Lima; Rasapalli Sivappa; Muhammed Yousufuddin; Carl J Lovely
Journal:  J Org Chem       Date:  2014-03-03       Impact factor: 4.354
  7 in total

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