Literature DB >> 28159485

Total synthesis and cytotoxicity of Leucetta alkaloids.

Panduka B Koswatta1, Sabha Kasiri1, Jayanta K Das1, Arunoday Bhan1, Heather M Lima1, Beatriz Garcia-Barboza1, Nicole N Khatibi1, Muhammed Yousufuddin1, Subhrangsu S Mandal1, Carl J Lovely2.   

Abstract

The total synthesis of a number of representative natural products isolated from Leucetta and Clathrina sponges containing a polysubstituted 2-aminoimidazole are described. These syntheses take advantage of the site specific metallation reactions of 4,5-diiodoimidazoles resulting in the syntheses of three different classes of Leucetta derived natural products. The cytotoxicities of these natural products, along with several precursors in MCF7 cells were determined through an MTT growth assay. For comparative purposes a series of naphthimidazole-containing family members are included.
Copyright © 2017 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  2-Aminoimidazole; Heterocycles; Metallation; Naphthimidazole; Reduction

Mesh:

Substances:

Year:  2017        PMID: 28159485      PMCID: PMC5596918          DOI: 10.1016/j.bmc.2017.01.024

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  34 in total

1.  Full functionalization of the imidazole scaffold by selective metalation and sulfoxide/magnesium exchange.

Authors:  Christoph Sämann; Estibaliz Coya; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-18       Impact factor: 15.336

2.  4,5-Di-substituted benzyl-imidazol-2-substituted amines as the structure template for the design and synthesis of reversal agents against P-gp-mediated multidrug resistance breast cancer cells.

Authors:  Nan Zhang; Zhaohui Zhang; Iris L K Wong; Shengbiao Wan; Larry M C Chow; Tao Jiang
Journal:  Eur J Med Chem       Date:  2014-06-10       Impact factor: 6.514

3.  Preparation of new polyfunctional magnesiated heterocycles using a chlorine-, bromine-, or iodine-magnesium exchange

Authors: 
Journal:  J Org Chem       Date:  2000-07-28       Impact factor: 4.354

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

Authors:  Jayanta Das; Arunoday Bhan; Subhrangsu S Mandal; Carl J Lovely
Journal:  Bioorg Med Chem Lett       Date:  2013-09-06       Impact factor: 2.823

5.  Total Syntheses of Naamidine G and 14-Methoxynaamidine G.

Authors:  Panduka B Koswatta; Carl J Lovely
Journal:  Tetrahedron Lett       Date:  2010-01-06       Impact factor: 2.415

6.  Total synthesis of (+/-)-calcaridine A and (+/-)-epi-calcaridine A.

Authors:  Panduka B Koswatta; Rasapalli Sivappa; H V Rasika Dias; Carl J Lovely
Journal:  Org Lett       Date:  2008-09-25       Impact factor: 6.005

7.  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

8.  Structure revision of spiroleucettadine, a sponge alkaloid with a bicyclic core meager in H-atoms.

Authors:  Kimberly N White; Taro Amagata; Allen G Oliver; Karen Tenney; Philip J Wenzel; Phillip Crews
Journal:  J Org Chem       Date:  2008-10-17       Impact factor: 4.354

9.  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

10.  Synthesis of substituted 2-aminoimidazoles via Pd-catalyzed alkyne carboamination reactions. Application to the synthesis of preclathridine natural products.

Authors:  Blane P Zavesky; Nicholas R Babij; John P Wolfe
Journal:  Org Lett       Date:  2014-09-08       Impact factor: 6.005

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  1 in total

1.  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

  1 in total

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