Literature DB >> 18703334

Synthesis of a natural product-inspired eight-membered ring lactam library via ring-closing metathesis.

Neil Brown1, Baohan Xie, Nataliya Markina, David Vandervelde, Jean-Pierre H Perchellet, Elisabeth M Perchellet, Kyle R Crow, Keith R Buszek.   

Abstract

We have prepared a novel speculative eight-membered lactam demonstration library based on the skeletal structure of the potent antitumor marine natural product octalactin A. The basic scaffold was readily constructed in a convergent fashion via ring-closing metathesis chemistry from the corresponding diene amides. A cursory examination of the biological properties of the library validates the relevance and significance of these structures.

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Year:  2008        PMID： 18703334      PMCID： PMC2723794          DOI： 10.1016/j.bmcl.2008.07.074

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  10 in total

1.  A diastereoselective synthesis of 2,4-disubstituted piperidines: scaffolds for drug discovery.

Authors:  P S Watson; B Jiang; B Scott
Journal:  Org Lett       Date:  2000-11-16       Impact factor: 6.005

2.  A systematic SAR study of C10 modified paclitaxel analogues using a combinatorial approach.

Authors:  Yanbin Liu; Syed M Ali; Thomas C Boge; Gunda I Georg; Samuel Victory; Jan Zygmunt; Rebecca T Marquez; Richard H Himes
Journal:  Comb Chem High Throughput Screen       Date:  2002-02       Impact factor: 1.339

3.  Enantioselective total synthesis of octalactin a using asymmetric aldol reactions and a rapid lactonization to form a medium-sized ring.

Authors:  Isamu Shiina; Minako Hashizume; Yu-suke Yamai; Hiromi Oshiumi; Takahisa Shimazaki; Yu-ji Takasuna; Ryoutarou Ibuka
Journal:  Chemistry       Date:  2005-11-04       Impact factor: 5.236

Review 4.  Comprehensive survey of combinatorial library synthesis: 2005.

Authors:  Roland E Dolle; Bertrand Le Bourdonnec; Guillermo A Morales; Kevin J Moriarty; Joseph M Salvino
Journal:  J Comb Chem       Date:  2006 Sep-Oct

5.  An Evans-Tishchenko-ring-closing metathesis approach to medium-ring lactones.

Authors:  Jennifer I Aird; Alison N Hulme; John W White
Journal:  Org Lett       Date:  2007-01-27       Impact factor: 6.005

6.  Natural products in combinatorial chemistry: an andrographolide-based library.

Authors:  Christian Mang; Sven Jakupovic; Stefan Schunk; Horst-Dieter Ambrosi; Oliver Schwarz; Jasmin Jakupovic
Journal:  J Comb Chem       Date:  2006 Mar-Apr

7.  Synthesis and evaluation of paclitaxel C7 derivatives: solution phase synthesis of combinatorial libraries.

Authors:  L Bhat; Y Liu; S F Victory; R H Himes; G I Georg
Journal:  Bioorg Med Chem Lett       Date:  1998-11-17       Impact factor: 2.823

8.  Antitumor activity of novel octalactin A analogs in murine leukemia cells in vitro.

Authors:  J P Perchellet; E M Perchellet; S W Newell; J A Freeman; J B Ladesich; Y Jeong; N Sato; K Buszek
Journal:  Anticancer Res       Date:  1998 Jan-Feb       Impact factor: 2.480

9.  Synthesis of beta-amino acids based on oxidative cleavage of dihydropyridone derivatives.

Authors:  Markus Ege; Klaus T Wanner
Journal:  Org Lett       Date:  2004-09-30       Impact factor: 6.005

10.  A concise synthesis of the octalactins.

Authors:  Paul T O'Sullivan; Wilm Buhr; Mary Ann M Fuhry; Justin R Harrison; John E Davies; Neil Feeder; David R Marshall; Jonathan W Burton; Andrew B Holmes
Journal:  J Am Chem Soc       Date:  2004-02-25       Impact factor: 15.419
  10 in total
  3 in total

1.  A Practical, Multi-gram Synthesis of (±)-Herbindole A, (±)-Herbindole B, and (±)-Herbindole C from a Common Intermediate via 6,7-Indole Aryne Cycloaddition and Pd(0)-Catalyzed Cross-Coupling Reactions.

Authors:  Nalin Chandrasoma; Sivadarshini Pathmanathan; Keith R Buszek
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

2.  Application of 6,7-indole aryne cycloaddition and Pd(0)-catalyzed Suzuki-Miyaura and Buchwald-Hartwig cross-coupling reactions for the preparation of annulated indole libraries.

Authors:  Paul D Thornton; Neil Brown; David Hill; Ben Neuenswander; Gerald H Lushington; Conrad Santini; Keith R Buszek
Journal:  ACS Comb Sci       Date:  2011-06-30       Impact factor: 3.784

3.  Novel synthetic inhibitors of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase activity that inhibit tumor cell proliferation and are structurally unrelated to existing statins.

Authors:  Jean-Pierre H Perchellet; Elisabeth M Perchellet; Kyle R Crow; Keith R Buszek; Neil Brown; Sampathkumar Ellappan; Ge Gao; Diheng Luo; Machiko Minatoya; Gerald H Lushington
Journal:  Int J Mol Med       Date:  2009-11       Impact factor: 4.101
  3 in total

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