Literature DB >> 27244042

Synthesis of (+)-7,20-Diisocyanoadociane and Liver-Stage Antiplasmodial Activity of the Isocyanoterpene Class.

Hai-Hua Lu1, Sergey V Pronin1, Yevgeniya Antonova-Koch2, Stephan Meister2, Elizabeth A Winzeler2, Ryan A Shenvi1.   

Abstract

7,20-Diisocyanoadociane, a scarce marine metabolite with potent antimalarial activity, was synthesized as a single enantiomer in 13 steps from simple building blocks (17 linear steps). Chemical synthesis enabled identification of isocyanoterpene antiplasmodial activity against liver-stage parasites, which suggested that inhibition of heme detoxification does not exclusively underlie the mechanism of action of this class.

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Year:  2016        PMID： 27244042      PMCID： PMC5851774          DOI： 10.1021/jacs.6b03899

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  31 in total

1.  Stereoinversion of tertiary alcohols to tertiary-alkyl isonitriles and amines.

Authors:  Sergey V Pronin; Christopher A Reiher; Ryan A Shenvi
Journal:  Nature       Date:  2013-09-12       Impact factor: 49.962

Review 2.  A Longitudinal Study of Alkaloid Synthesis Reveals Functional Group Interconversions as Bad Actors.

Authors:  Steven W M Crossley; Ryan A Shenvi
Journal:  Chem Rev       Date:  2015-07-09       Impact factor: 60.622

Review 3.  Naturally occurring isocyanides.

Authors:  M S Edenborough; R B Herbert
Journal:  Nat Prod Rep       Date:  1988-06       Impact factor: 13.423

4.  Total synthesis of antimalarial diterpenoid (+)-kalihinol A.

Authors:  Hiroaki Miyaoka; Yasunori Abe; Nobuaki Sekiya; Hidemichi Mitome; Etsuko Kawashima
Journal:  Chem Commun (Camb)       Date:  2011-12-05       Impact factor: 6.222

5.  In vivo active antimalarial isonitriles.

Authors:  Chandan Singh; Naveen Chandra Srivastav; Sunil K Puri
Journal:  Bioorg Med Chem Lett       Date:  2002-09-02       Impact factor: 2.823

6.  Lewis acid-promoted ketene-alkene [2 + 2] cycloadditions.

Authors:  Christopher M Rasik; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2013-01-28       Impact factor: 15.419

7.  In silico activity profiling reveals the mechanism of action of antimalarials discovered in a high-throughput screen.

Authors:  David Plouffe; Achim Brinker; Case McNamara; Kerstin Henson; Nobutaka Kato; Kelli Kuhen; Advait Nagle; Francisco Adrián; Jason T Matzen; Paul Anderson; Tae-Gyu Nam; Nathanael S Gray; Arnab Chatterjee; Jeff Janes; S Frank Yan; Richard Trager; Jeremy S Caldwell; Peter G Schultz; Yingyao Zhou; Elizabeth A Winzeler
Journal:  Proc Natl Acad Sci U S A       Date:  2008-06-25       Impact factor: 11.205

8.  Investigations into an anionic oxy-cope/transannular conjugate addition approach to 7,20-diisocyanoadociane.

Authors:  Philipp C Roosen; Christopher D Vanderwal
Journal:  Org Lett       Date:  2014-08-08       Impact factor: 6.005

9.  High-Throughput Luciferase-Based Assay for the Discovery of Therapeutics That Prevent Malaria.

Authors:  Justine Swann; Victoria Corey; Christina A Scherer; Nobutaka Kato; Eamon Comer; Micah Maetani; Yevgeniya Antonova-Koch; Christin Reimer; Kerstin Gagaring; Maureen Ibanez; David Plouffe; Anne-Marie Zeeman; Clemens H M Kocken; Case W McNamara; Stuart L Schreiber; Brice Campo; Elizabeth A Winzeler; Stephan Meister
Journal:  ACS Infect Dis       Date:  2016-02-10       Impact factor: 5.084

10.  Simple, chemoselective hydrogenation with thermodynamic stereocontrol.

Authors:  Kotaro Iwasaki; Kanny K Wan; Alberto Oppedisano; Steven W M Crossley; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2014-01-15       Impact factor: 15.419
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  11 in total

1.  The High Chemofidelity of Metal-Catalyzed Hydrogen Atom Transfer.

Authors:  Samantha A Green; Steven W M Crossley; Jeishla L M Matos; Suhelen Vásquez-Céspedes; Sophia L Shevick; Ryan A Shenvi
Journal:  Acc Chem Res       Date:  2018-11-08       Impact factor: 22.384

2.  Stereocontrolled Synthesis of Kalihinol C.

Authors:  Christopher A Reiher; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2017-03-02       Impact factor: 15.419

3.  Concise Synthesis of the Antiplasmodial Isocyanoterpene 7,20-Diisocyanoadociane.

Authors:  Alexander S Karns; Bryan D Ellis; Philipp C Roosen; Zeinab Chahine; Karine G Le Roch; Christopher D Vanderwal
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-27       Impact factor: 15.336

4.  Antimalarial Natural Products.

Authors:  David G I Kingston; Maria Belen Cassera
Journal:  Prog Chem Org Nat Prod       Date:  2022

5.  Evolution of a Short and Stereocontrolled Synthesis of (+)-7,20-Diisocyanoadociane.

Authors:  Philipp C Roosen; Alexander S Karns; Bryan D Ellis; Christopher D Vanderwal
Journal:  J Org Chem       Date:  2022-01-06       Impact factor: 4.198

6.  Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins.

Authors:  Steven W M Crossley; Carla Obradors; Ruben M Martinez; Ryan A Shenvi
Journal:  Chem Rev       Date:  2016-07-27       Impact factor: 60.622

7.  Natural product-inspired aryl isonitriles as a new class of antimalarial compounds against drug-resistant parasites.

Authors:  Kwaku Kyei-Baffour; Dexter C Davis; Zarko Boskovic; Nobutaka Kato; Mingji Dai
Journal:  Bioorg Med Chem       Date:  2020-08-01       Impact factor: 3.641

8.  Antimalarial Properties of Simplified Kalihinol Analogues.

Authors:  Mary Elisabeth Daub; Jacques Prudhomme; Choukri Ben Mamoun; Karine G Le Roch; Christopher D Vanderwal
Journal:  ACS Med Chem Lett       Date:  2017-02-16       Impact factor: 4.345

Review 9.  Acetylene in Organic Synthesis: Recent Progress and New Uses.

Authors:  Vladimir V Voronin; Maria S Ledovskaya; Alexander S Bogachenkov; Konstantin S Rodygin; Valentine P Ananikov
Journal:  Molecules       Date:  2018-09-24       Impact factor: 4.411

10.  A general synthesis of dendralenes.

Authors:  Josemon George; Jas S Ward; Michael S Sherburn
Journal:  Chem Sci       Date:  2019-09-12       Impact factor: 9.825
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