Literature DB >> 25514696

Syntheses and biological studies of marine terpenoids derived from inorganic cyanide.

Martin J Schnermann1, Ryan A Shenvi.   

Abstract

Isocyanoterpenes (ICTs) are marine natural products biosynthesized through an unusual pathway that adorns terpene scaffolds with nitrogenous functionality derived from cyanide. The appendage of nitrogen functional groups - isonitriles in particular - onto stereochemically-rich carbocyclic ring systems provides enigmatic, bioactive molecules that have required innovative chemical syntheses. This review discusses the challenges inherent to the synthesis of this diverse family and details the development of the field. We also present recent progress in isolation and discuss key aspects of the remarkable biological activity of these compounds.

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Year:  2015        PMID: 25514696      PMCID: PMC4414506          DOI: 10.1039/c4np00109e

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


  78 in total

1.  Drug development: Holding out for reinforcements.

Authors:  Michael Eisenstein
Journal:  Nature       Date:  2012-04-25       Impact factor: 49.962

2.  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

3.  Asymmetric synthesis of (+)-geranyllinaloisocyanide: assignment of absolute stereochemistry.

Authors:  Yoshiyasu Ichikawa; Yasunori Matsuda; Ken Okumura; Mitsuhiro Nakamura; Toshiya Masuda; Hiyoshizo Kotsuki; Keiji Nakano
Journal:  Org Lett       Date:  2011-04-14       Impact factor: 6.005

4.  The combining power of hemoglobin for alkyl isocyanides, and the nature of the heme-heme interactions in hemoglobin.

Authors:  R C C ST GEORGE; L PAULING
Journal:  Science       Date:  1951-12-14       Impact factor: 47.728

5.  Walden inversion in unimolecular reactions of secondary and tertiary alkyl halides.

Authors:  E D HUGHES; C K INGOLD; R J L MARTIN; D F MEIGH
Journal:  Nature       Date:  1950-10-21       Impact factor: 49.962

Review 6.  Naturally occurring isocyanides.

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

7.  Protein complex directs hemoglobin-to-hemozoin formation in Plasmodium falciparum.

Authors:  Monika Chugh; Vidhya Sundararaman; Saravanan Kumar; Vanga S Reddy; Waseem A Siddiqui; Kenneth D Stuart; Pawan Malhotra
Journal:  Proc Natl Acad Sci U S A       Date:  2013-03-05       Impact factor: 11.205

8.  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

9.  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

10.  Artemisinin resistance in Plasmodium falciparum malaria.

Authors:  Arjen M Dondorp; François Nosten; Poravuth Yi; Debashish Das; Aung Phae Phyo; Joel Tarning; Khin Maung Lwin; Frederic Ariey; Warunee Hanpithakpong; Sue J Lee; Pascal Ringwald; Kamolrat Silamut; Mallika Imwong; Kesinee Chotivanich; Pharath Lim; Trent Herdman; Sen Sam An; Shunmay Yeung; Pratap Singhasivanon; Nicholas P J Day; Niklas Lindegardh; Duong Socheat; Nicholas J White
Journal:  N Engl J Med       Date:  2009-07-30       Impact factor: 91.245

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  17 in total

1.  Synthesis and preliminary biological evaluation of a small library of hybrid compounds based on Ugi isocyanide multicomponent reactions with a marine natural product scaffold.

Authors:  Edward Avilés; Jacques Prudhomme; Karine G Le Roch; Scott G Franzblau; Kevin Chandrasena; Alejandro M S Mayer; Abimael D Rodríguez
Journal:  Bioorg Med Chem Lett       Date:  2015-09-15       Impact factor: 2.823

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

Authors:  Hai-Hua Lu; Sergey V Pronin; Yevgeniya Antonova-Koch; Stephan Meister; Elizabeth A Winzeler; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2016-05-31       Impact factor: 15.419

3.  Facile Discovery and Quantification of Isonitrile Natural Products via Tetrazine-Based Click Reactions.

Authors:  Yao-Bing Huang; Wenlong Cai; Antonio Del Rio Flores; Frederick F Twigg; Wenjun Zhang
Journal:  Anal Chem       Date:  2019-12-11       Impact factor: 6.986

Review 4.  Marine Isonitriles and Their Related Compounds.

Authors:  Jens Emsermann; Ulrich Kauhl; Till Opatz
Journal:  Mar Drugs       Date:  2016-01-14       Impact factor: 5.118

5.  Synthesis of the Privileged 8-Arylmenthol Class by Radical Arylation of Isopulegol.

Authors:  Steven W M Crossley; Ruben M Martinez; Sebastián Guevara-Zuluaga; Ryan A Shenvi
Journal:  Org Lett       Date:  2016-05-13       Impact factor: 6.005

6.  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

7.  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

8.  Probing the Mechanism of Isonitrile Formation by a Non-Heme Iron(II)-Dependent Oxidase/Decarboxylase.

Authors:  Antonio Del Rio Flores; David W Kastner; Yongle Du; Maanasa Narayanamoorthy; Yuanbo Shen; Wenlong Cai; Vyshnavi Vennelakanti; Nicholas A Zill; Luisa B Dell; Rui Zhai; Heather J Kulik; Wenjun Zhang
Journal:  J Am Chem Soc       Date:  2022-03-07       Impact factor: 15.419

9.  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

10.  Asmic: An Exceptional Building Block for Isocyanide Alkylations.

Authors:  Embarek Alwedi; J Armando Lujan-Montelongo; Bhaskar R Pitta; Allen Chao; Rodrigo Cortés-Mejía; Jorge M Del Campo; Fraser F Fleming
Journal:  Org Lett       Date:  2018-09-06       Impact factor: 6.005

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