Literature DB >> 21739942

Total synthesis of (-)-CP2-disorazole C1.

Chad D Hopkins1, John C Schmitz, Edward Chu, Peter Wipf.   

Abstract

The total synthesis of a bis-cyclopropane analog of the antimitotic natural product (-)-disorazole C(1) was accomplished in 23 steps and 1.1% overall yield. A vinyl cyclopropane cross-metathesis reaction generated a key (E)-alkene segment of the target molecule. IC(50) determinations of (-)-CP(2)-disorazole C(1) in human colon cancer cell lines indicated low nanomolar cytotoxic properties. Accordingly, this synthetic bioisostere represents the first biologically active disorazole analog not containing a conjugated diene or polyene substructure element.
© 2011 American Chemical Society

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Year:  2011        PMID： 21739942      PMCID： PMC3160746          DOI： 10.1021/ol2015994

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  26 in total

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Authors:  T M Trnka; R H Grubbs
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2.  Studies on the total synthesis of disorazole C1. An advanced macrocycle intermediate.

Authors:  M C Hillier; A T Price; A I Meyers
Journal:  J Org Chem       Date:  2001-09-07       Impact factor: 4.354

Review 3.  Myxobacterial secondary metabolites: bioactivities and modes-of-action.

Authors:  Kira J Weissman; Rolf Müller
Journal:  Nat Prod Rep       Date:  2010-06-03       Impact factor: 13.423

4.  Total synthesis of (-)-disorazole C1.

Authors:  Peter Wipf; Thomas H Graham
Journal:  J Am Chem Soc       Date:  2004-12-01       Impact factor: 15.419

5.  Synthesis and biological evaluation of structurally highly modified analogues of the antimitotic natural product curacin A.

Authors:  Peter Wipf; Jonathan T Reeves; Raghavan Balachandran; Billy W Day
Journal:  J Med Chem       Date:  2002-04-25       Impact factor: 7.446

6.  Mitotic slippage in non-cancer cells induced by a microtubule disruptor, disorazole C1.

Authors:  Fengfeng L Xu; Youssef Rbaibi; Kirill Kiselyov; John S Lazo; Peter Wipf; William S Saunders
Journal:  BMC Chem Biol       Date:  2010-02-11

7.  Cellular analysis of disorazole C and structure-activity relationship of analogs of the natural product.

Authors:  Peter Wipf; Thomas H Graham; Andreas Vogt; Rachel P Sikorski; Alexander P Ducruet; John S Lazo
Journal:  Chem Biol Drug Des       Date:  2006-01       Impact factor: 2.817

8.  Synthesis and biological evaluation of synthetic viridins derived from C(20)-heteroalkylation of the steroidal PI-3-kinase inhibitor wortmannin.

Authors:  Peter Wipf; Daniel J Minion; Robert J Halter; Margareta I Berggren; Caroline B Ho; Gary G Chiang; Lynn Kirkpatrick; Robert Abraham; Garth Powis
Journal:  Org Biomol Chem       Date:  2004-06-14       Impact factor: 3.876

9.  Microtubule binding and disruption and induction of premature senescence by disorazole C(1).

Authors:  Marni Brisson Tierno; Carolyn A Kitchens; Bethany Petrik; Thomas H Graham; Peter Wipf; Fengfeng L Xu; William S Saunders; Brianne S Raccor; Raghavan Balachandran; Billy W Day; Jane R Stout; Claire E Walczak; Alexander P Ducruet; Celeste E Reese; John S Lazo
Journal:  J Pharmacol Exp Ther       Date:  2008-12-09       Impact factor: 4.030

10.  Total synthesis, assignment of the relative and absolute stereochemistry, and structural reassignment of phostriecin (aka Sultriecin).

Authors:  Christopher P Burke; Nadia Haq; Dale L Boger
Journal:  J Am Chem Soc       Date:  2010-02-24       Impact factor: 15.419
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  7 in total

1.  The newly synthesized thiazole derivatives as potential antifungal compounds against Candida albicans.

Authors:  Anna Biernasiuk; Anna Berecka-Rycerz; Anna Gumieniczek; Maria Malm; Krzysztof Z Łączkowski; Jolanta Szymańska; Anna Malm
Journal:  Appl Microbiol Biotechnol       Date:  2021-08-19       Impact factor: 4.813

2.  Self-Assembly of Disorazole C1 through a One-Pot Alkyne Metathesis Homodimerization Strategy.

Authors:  Kevin J Ralston; H Clinton Ramstadius; Richard C Brewster; Helen S Niblock; Alison N Hulme
Journal:  Angew Chem Int Ed Engl       Date:  2015-04-29       Impact factor: 15.336

3.  Catalytic Z-selective cross-metathesis in complex molecule synthesis: a convergent stereoselective route to disorazole C1.

Authors:  Alexander W H Speed; Tyler J Mann; Robert V O'Brien; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2014-11-07       Impact factor: 15.419

4.  Synthesis of heterocyclic triads by Pd-catalyzed cross-couplings and evaluation of their cell-specific toxicity profile.

Authors:  Joseph Salamoun; Shelby Anderson; James C Burnett; Rick Gussio; Peter Wipf
Journal:  Org Lett       Date:  2014-03-18       Impact factor: 6.005

5.  Bis-cyclopropane analog of disorazole C1 is a microtubule-destabilizing agent active in ABCB1-overexpressing human colon cancer cells.

Authors:  Shaoyu Wu; Zhijian Guo; Chad D Hopkins; Ning Wei; Edward Chu; Peter Wipf; John C Schmitz
Journal:  Oncotarget       Date:  2015-12-01

6.  Small Molecule Antagonists of the Nuclear Androgen Receptor for the Treatment of Castration-Resistant Prostate Cancer.

Authors:  James K Johnson; Erin M Skoda; Jianhua Zhou; Erica Parrinello; Dan Wang; Katherine O'Malley; Benjamin R Eyer; Mustafa Kazancioglu; Kurtis Eisermann; Paul A Johnston; Joel B Nelson; Zhou Wang; Peter Wipf
Journal:  ACS Med Chem Lett       Date:  2016-05-27       Impact factor: 4.345

7.  Self-Assembly of Disorazole C1 through a One-Pot Alkyne Metathesis Homodimerization Strategy.

Authors:  Kevin J Ralston; H Clinton Ramstadius; Richard C Brewster; Helen S Niblock; Alison N Hulme
Journal:  Angew Chem Weinheim Bergstr Ger       Date:  2015-04-29
  7 in total

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