Literature DB >> 21556392

Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids.

Ali Al-Mourabit1, Manuel A Zancanella, Supriya Tilvi, Daniel Romo.   

Abstract

The pyrrole-2-aminoimidazole (P-2-AI) alkaloids are a growing family of marine alkaloids, now numbering well over 150 members, with high topographical and biological information content. Their intriguing structural complexity, rich and compact stereochemical content, high N to C ratio (~1 : 2), and increasingly studied biological activities are attracting a growing number of researchers from numerous disciplines world-wide. This review surveys advances in this area with a focus on the structural diversity, biosynthetic hypotheses with increasing, but still rare, verifying experimental studies, asymmetric syntheses, and biological studies, including cellular target receptor isolation studies, of this stimulating and exciting alkaloid family.

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Year:  2011        PMID: 21556392      PMCID: PMC5596510          DOI: 10.1039/c0np00013b

Source DB:  PubMed          Journal:  Nat Prod Rep        ISSN: 0265-0568            Impact factor:   13.423


  119 in total

1.  Enantiospecific formal total synthesis of the tumor and GSK-3 beta inhibiting alkaloid, (-)-agelastatin A.

Authors:  Karl J Hale; Mathias M Domostoj; Derek A Tocher; Ed Irving; Feodor Scheinmann
Journal:  Org Lett       Date:  2003-08-07       Impact factor: 6.005

2.  Extending Pummerer reaction chemistry: application to the assembly of the pentacyclic core of dibromopalau'amine.

Authors:  Ken S Feldman; Ahmed Yimam Nuriye
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

3.  EVALUATION OF STRATEGIES FOR THE SYNTHESIS OF THE GUANIDINE HEMIAMINAL PORTION OF PALAU'AMINE.

Authors:  Brian A Lanman; Larry E Overman
Journal:  Heterocycles       Date:  2006-12-31       Impact factor: 0.831

4.  Stable 5-substituted cyclopentadienes for the Diels-Alder cycloaddition and their application to the synthesis of palau'amine.

Authors:  Jonathan Hudon; Timothy A Cernak; James A Ashenhurst; James L Gleason
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Revisiting the Kinnel-Scheuer hypothesis for the biosynthesis of palau'amine.

Authors:  Zhiqiang Ma; Jianming Lu; Xiao Wang; Chuo Chen
Journal:  Chem Commun (Camb)       Date:  2010-09-16       Impact factor: 6.222

6.  Total synthesis of all (-)-Agelastatin alkaloids.

Authors:  Mohammad Movassaghi; Dustin S Siegel; Sunkyu Han
Journal:  Chem Sci       Date:  2010-01-01       Impact factor: 9.825

7.  Enantioselective total synthesis of (+)-dibromophakellstatin.

Authors:  Karine G Poullennec; Daniel Romo
Journal:  J Am Chem Soc       Date:  2003-05-28       Impact factor: 15.419

8.  Density functional theory guided design of exo-selective dehydroalanine dienophiles for application toward the synthesis of palau'amine.

Authors:  Timothy A Cernak; James L Gleason
Journal:  J Org Chem       Date:  2007-12-08       Impact factor: 4.354

Review 9.  Preparation of hymenialdisine, analogues and their evaluation as kinase inhibitors.

Authors:  T N T Nguyen; J J Tepe
Journal:  Curr Med Chem       Date:  2009       Impact factor: 4.530

10.  Oxidative rearrangement of imidazoles with dimethyldioxirane.

Authors:  Carl J Lovely; Hongwang Du; Yong He; H V Rasika Dias
Journal:  Org Lett       Date:  2004-03-04       Impact factor: 6.005

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  42 in total

1.  A new small molecule inhibits Streptococcus mutans biofilms in vitro and in vivo.

Authors:  W Pan; M Fan; H Wu; C Melander; C Liu
Journal:  J Appl Microbiol       Date:  2015-09-24       Impact factor: 3.772

2.  Rapid access to the core skeleton of the [3 + 2]-type dimeric pyrrole-imidazole alkaloids by triplet ketone-mediated C-H functionalization.

Authors:  Lin You; Chuo Chen
Journal:  Tetrahedron       Date:  2017-12-15       Impact factor: 2.457

3.  Asymmetric synthesis of ageliferin.

Authors:  Xiao Wang; Zhiqiang Ma; Jianming Lu; Xianghui Tan; Chuo Chen
Journal:  J Am Chem Soc       Date:  2011-09-08       Impact factor: 15.419

4.  Precursor-Guided Mining of Marine Sponge Metabolomes Lends Insight into Biosynthesis of Pyrrole-Imidazole Alkaloids.

Authors:  Ipsita Mohanty; Samuel G Moore; Dongqi Yi; Jason S Biggs; David A Gaul; Neha Garg; Vinayak Agarwal
Journal:  ACS Chem Biol       Date:  2020-07-29       Impact factor: 5.100

5.  Pyrrole aminoimidazole alkaloid metabiosynthesis with marine sponges Agelas conifera and Stylissa caribica.

Authors:  E Paige Stout; Yong-Gang Wang; Daniel Romo; Tadeusz F Molinski
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-04       Impact factor: 15.336

6.  Microbial and Functional Biodiversity Patterns in Sponges that Accumulate Bromopyrrole Alkaloids Suggest Horizontal Gene Transfer of Halogenase Genes.

Authors:  Cintia P J Rua; Louisi S de Oliveira; Adriana Froes; Diogo A Tschoeke; Ana Carolina Soares; Luciana Leomil; Gustavo B Gregoracci; Ricardo Coutinho; Eduardo Hajdu; Cristiane C Thompson; Roberto G S Berlinck; Fabiano L Thompson
Journal:  Microb Ecol       Date:  2018-03-15       Impact factor: 4.552

7.  Derivatization of agelastatin A leading to bioactive analogs and a trifunctional probe.

Authors:  Morgan Jouanneau; Brandon McClary; Jeremy Chris P Reyes; Rong Chen; Yuling Chen; William Plunkett; Xin Cheng; Andrew Z Milinichik; Earl F Albone; Jun O Liu; Daniel Romo
Journal:  Bioorg Med Chem Lett       Date:  2016-02-23       Impact factor: 2.823

8.  A biomimetic route for construction of the [4+2] and [3+2] core skeletons of dimeric pyrrole-imidazole alkaloids and asymmetric synthesis of ageliferins.

Authors:  Xiao Wang; Xiaolei Wang; Xianghui Tan; Jianming Lu; Kevin W Cormier; Zhiqiang Ma; Chuo Chen
Journal:  J Am Chem Soc       Date:  2012-11-02       Impact factor: 15.419

9.  Methods for direct alkene diamination, new & old.

Authors:  Sam de Jong; Daniel G Nosal; Duncan J Wardrop
Journal:  Tetrahedron       Date:  2012-03-21       Impact factor: 2.457

10.  Oxidative Coupling of Enolates, Enol Silanes and Enamines: Methods and Natural Product Synthesis.

Authors:  Fenghai Guo; Michael D Clift; Regan J Thomson
Journal:  European J Org Chem       Date:  2012-07-16
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