Literature DB >> 25580910

Nitrosopurines en route to potently cytotoxic asmarines.

Kanny K Wan1, Kotaro Iwasaki, Jeffrey C Umotoy, Dennis W Wolan, Ryan A Shenvi.   

Abstract

A nitrosopurine ene reaction easily assembles the asmarine pharmacophore and transmits remote stereochemistry to the diazepine-purine hetereocycle. This reaction generates potent cytotoxins which exceed the potency of asmarine A (1.2 μM IC50) and supersede the metabolites as useful leads for biological discovery.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkaloids; ene reaction; natural products; structure-activity relationships; terpenoids

Mesh：

Substances：

Year:  2015        PMID： 25580910      PMCID： PMC4470469          DOI： 10.1002/anie.201411493

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  11 in total

Review 1.  The nitroso ene reaction: a regioselective and stereoselective allylic nitrogen functionalization of mechanistic delight and synthetic potential.

Authors:  Waldemar Adam; Oliver Krebs
Journal:  Chem Rev       Date:  2003-10       Impact factor: 60.622

2.  Efficient construction of the clerodane decalin core by an asymmetric Morita-Baylis-Hillman reaction/Lewis acid promoted annulation strategy.

Authors:  Stacy A Rodgen; Scott E Schaus
Journal:  Angew Chem Int Ed Engl       Date:  2006-07-24       Impact factor: 15.336

3.  Efficient pi-facial control in the ene reaction of nitrosoarene, triazolinedione, and singlet oxygen with tiglic amides of the bornane-derived sultam as chiral auxiliary: an economical synthesis of enantiomerically pure nitrogen- and oxygen-functionalized acrylic acid derivatives.

Authors:  Waldemar Adam; Hans-Georg Degen; Oliver Krebs; Chantu R Saha-Möller
Journal:  J Am Chem Soc       Date:  2002-11-06       Impact factor: 15.419

4.  The ene reactions of nitroso compounds involve polarized diradical intermediates.

Authors:  Andrew G Leach; K N Houk
Journal:  J Am Chem Soc       Date:  2002-12-18       Impact factor: 15.419

5.  The marine sponge toxin agelasine B increases the intracellular Ca(2+) concentration and induces apoptosis in human breast cancer cells (MCF-7).

Authors:  Adriana A Pimentel; Pimali Felibertt; Felipe Sojo; Laura Colman; Adriana Mayora; May Li Silva; Hector Rojas; Reinaldo Dipolo; Alírica I Suarez; Reinaldo S Compagnone; Francisco Arvelo; Ivan Galindo-Castro; Juan B De Sanctis; Perla Chirino; Gustavo Benaim
Journal:  Cancer Chemother Pharmacol       Date:  2011-05-21       Impact factor: 3.333

6.  Asmarines A-F, novel cytotoxic compounds from the marine sponge Raspailia species.

Authors:  T Yosief; A Rudi; Y Kashman
Journal:  J Nat Prod       Date:  2000-03       Impact factor: 4.050

7.  Synthesis of 9-substituted tetrahydrodiazepinopurines: studies toward the total synthesis of asmarines.

Authors:  Doron Pappo; Shiri Shimony; Yoel Kashman
Journal:  J Org Chem       Date:  2005-01-07       Impact factor: 4.354

8.  Some pharmacological activities of novel adenine-related compounds isolated from a marine sponge Agelas mauritiana.

Authors:  R Fathi-Afshar; T M Allen; C A Krueger; D A Cook; A S Clanachan; R Vriend; H P Baer; C E Cass
Journal:  Can J Physiol Pharmacol       Date:  1989-04       Impact factor: 2.273

9.  Antimicrobial and cytotoxic activity of agelasine and agelasimine analogs.

Authors:  Anders Vik; Erik Hedner; Colin Charnock; Linda W Tangen; Ørjan Samuelsen; Rolf Larsson; Lars Bohlin; Lise-Lotte Gundersen
Journal:  Bioorg Med Chem       Date:  2007-04-02       Impact factor: 3.641

10.  An X- (X=I, Br)-triggered ring-opening cyclization of cyclopropenyl-substituted alkyl halides or mesylates: an efficient and highly regio- and stereoselective approach to (E)-haloalkylidene 4-7-membered cyclic compounds.

Authors:  Jie Chen; Shengming Ma
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354
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  7 in total

1.  Mechanism of Action of the Cytotoxic Asmarine Alkaloids.

Authors:  Michael J Lambrecht; Jeffery W Kelly; Ryan A Shenvi
Journal:  ACS Chem Biol       Date:  2018-04-19       Impact factor: 5.100

2.  Asymmetric Total Synthesis of the Indole Diterpene Alkaloid Paspaline.

Authors:  Robert J Sharpe; Jeffrey S Johnson
Journal:  J Org Chem       Date:  2015-10-02       Impact factor: 4.354

3.  A global and local desymmetrization approach to the synthesis of steroidal alkaloids: stereocontrolled total synthesis of paspaline.

Authors:  Robert J Sharpe; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2015-04-09       Impact factor: 15.419

4.  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

Review 5.  Marine Alkylpurines: A Promising Group of Bioactive Marine Natural Products.

Authors:  Pablo A García; Elena Valles; David Díez; María-Ángeles Castro
Journal:  Mar Drugs       Date:  2018-01-01       Impact factor: 5.118

6.  Unexpected Racemization in the Course of the Acetalization of (+)-(S)-5-Methyl-Wieland-Miescher Ketone with 1,2-Ethanediol and TsOH under Classical Experimental Conditions.

Authors:  Francesca Leonelli; Irene Piergentili; Giulio Lucarelli; Luisa Maria Migneco; Rinaldo Marini Bettolo
Journal:  Int J Mol Sci       Date:  2019-12-05       Impact factor: 5.923

7.  Formal Total Synthesis of Salvinorin A.

Authors:  Marc Halang; Martin E Maier
Journal:  ChemistryOpen       Date:  2022-02-26       Impact factor: 2.630
  7 in total

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