Literature DB >> 15869264

Toward understanding how the lactone moiety of discodermolide affects activity.

Simon J Shaw1, Kurt F Sundermann, Mark A Burlingame, David C Myles, B Scott Freeze, Ming Xian, Ignacio Brouard, Amos B Smith.   

Abstract

A series of simplified discodermolide analogues have been designed and synthesized in an attempt to understand the role of the lactone ring. These synthetic efforts have led to an unsubstituted butyrolactone 9 being generated, which shows improved activity over the natural product.

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Year:  2005        PMID: 15869264     DOI: 10.1021/ja051185i

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


  11 in total

1.  Structural Refinement of the Tubulin Ligand (+)-Discodermolide to Attenuate Chemotherapy-Mediated Senescence.

Authors:  Boying Guo; Alicia Rodriguez-Gabin; Andrea E Prota; Tobias Mühlethaler; Nan Zhang; Kenny Ye; Michel O Steinmetz; Susan Band Horwitz; Amos B Smith; Hayley M McDaid
Journal:  Mol Pharmacol       Date:  2020-06-26       Impact factor: 4.436

2.  (+)-Discodermolide: Total Synthesis, Construction of Novel Analogues, and Biological Evaluation.

Authors:  Amos B Smith; B Scott Freeze
Journal:  Tetrahedron       Date:  2007-01-07       Impact factor: 2.457

3.  Synthesis of a ring-expanded bryostatin analogue.

Authors:  Barry M Trost; Hanbiao Yang; Oliver R Thiel; Alison J Frontier; Cheyenne S Brindle
Journal:  J Am Chem Soc       Date:  2007-02-06       Impact factor: 15.419

4.  Catalytic, asymmetric reactions of ketenes and ketene enolates.

Authors:  Daniel H Paull; Anthony Weatherwax; Thomas Lectka
Journal:  Tetrahedron       Date:  2009-08-22       Impact factor: 2.457

Review 5.  Conformation-activity relationships of polyketide natural products.

Authors:  Erik M Larsen; Matthew R Wilson; Richard E Taylor
Journal:  Nat Prod Rep       Date:  2015-08       Impact factor: 13.423

6.  The quest for supernatural products: the impact of total synthesis in complex natural products medicinal chemistry.

Authors:  Zhi-Chen Wu; Dale L Boger
Journal:  Nat Prod Rep       Date:  2020-11-10       Impact factor: 13.423

Review 7.  Microtubule stabilizing agents as potential treatment for Alzheimer's disease and related neurodegenerative tauopathies.

Authors:  Carlo Ballatore; Kurt R Brunden; Donna M Huryn; John Q Trojanowski; Virginia M-Y Lee; Amos B Smith
Journal:  J Med Chem       Date:  2012-09-28       Impact factor: 7.446

8.  Design and synthesis of (+)-discodermolide-paclitaxel hybrids leading to enhanced biological activity.

Authors:  Amos B Smith; Keizo Sugasawa; Onur Atasoylu; Chia-Ping Huang Yang; Susan Band Horwitz
Journal:  J Med Chem       Date:  2011-08-26       Impact factor: 7.446

9.  Total syntheses of bryostatins: synthesis of two ring-expanded bryostatin analogues and the development of a new-generation strategy to access the C7-C27 fragment.

Authors:  Barry M Trost; Hanbiao Yang; Guangbin Dong
Journal:  Chemistry       Date:  2011-07-21       Impact factor: 5.236

10.  Human liver microsomal metabolism of (+)-discodermolide.

Authors:  Yun Fan; Emanuel M Schreiber; Billy W Day
Journal:  J Nat Prod       Date:  2009-10       Impact factor: 4.050

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