Literature DB >> 20161135

Antineoplastic agents. 565. Synthesis of combretastatin D-2 phosphate and dihydro-combretastatin D-2.

George R Pettit1, Peter D Quistorf, Jeremy A Fry, Delbert L Herald, Ernest Hamel, Jean-Charles Chapuis.   

Abstract

A modified synthetic route to combretastatin D-2 (5) was devised in order to further evaluate its biological activity, for its conversion to phosphate prodrugs (25-28), and as a route to obtaining dihydro-combretastatin D-2 (42). A parallel first total synthesis of dihydro-combretastatin D-2 was completed, proceeding from a saturated 3-phenylpropionic ester intermediate via the Ullmann biaryl ether reaction (39-41). In contrast to the cancer cell growth inhibitory activity exhibited by combretastatin D-2, relatively minor structural modifications (41, 42) caused elimination of those properties.

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Year:  2009        PMID： 20161135      PMCID： PMC2729559          DOI： 10.1021/np800635h

Source DB:  PubMed          Journal:  J Nat Prod        ISSN： 0163-3864            Impact factor:   4.050


  15 in total

1.  Stabilization of microtubules by Combretastatin D derivatives.

Authors:  E A Couladouros; T Li; V I Moutsos; E N Pitsinos; I C Soufli
Journal:  Bioorg Med Chem Lett       Date:  1999-10-18       Impact factor: 2.823

Review 2.  Novel vascular targeting/disrupting agents: combretastatin A4 phosphate and related compounds.

Authors:  Matthew M Cooney; Jose Ortiz; Ronald M Bukowski; Scot C Remick
Journal:  Curr Oncol Rep       Date:  2005-03       Impact factor: 5.075

3.  An empirical correction for absorption anisotropy.

Authors:  R H Blessing
Journal:  Acta Crystallogr A       Date:  1995-01-01       Impact factor: 2.290

4.  Vancomycin CD and DE Macrocyclization and Atropisomerism Studies.

Authors:  Dale L. Boger; Steven L. Castle; Susumu Miyazaki; Jason H. Wu; Richard T. Beresis; Olivier Loiseleur
Journal:  J Org Chem       Date:  1999-01-08       Impact factor: 4.354

5.  Design, synthesis, and biological evaluation of combretastatin nitrogen-containing derivatives as inhibitors of tubulin assembly and vascular disrupting agents.

Authors:  Keith A Monk; Rogelio Siles; Mallinath B Hadimani; Benon E Mugabe; J Freeland Ackley; Scott W Studerus; Klaus Edvardsen; Mary Lynn Trawick; Charles M Garner; Monte R Rhodes; George R Pettit; Kevin G Pinney
Journal:  Bioorg Med Chem       Date:  2006-01-25       Impact factor: 3.641

6.  Mechanistic study of the Mitsunobu reaction.

Authors:  Chuljin Ahn; Reuben Correia; Philip DeShong
Journal:  J Org Chem       Date:  2002-03-22       Impact factor: 4.354

7.  An approach to the stereoselective synthesis of syn- and anti-1,3-diol derivatives. Retention of configuration in the Mitsunobu reaction.

Authors:  Chuljin Ahn; Philip DeShong
Journal:  J Org Chem       Date:  2002-03-22       Impact factor: 4.354

8.  Antineoplastic agents. 487. Synthesis and biological evaluation of the antineoplastic agent 3,4-methylenedioxy-5,4'-dimethoxy-3'-amino-Z-stilbene and derived amino acid amides.

Authors:  George R Pettit; Collin R Anderson; Delbert L Herald; M Katherine Jung; Debbie J Lee; Ernest Hamel; Robin K Pettit
Journal:  J Med Chem       Date:  2003-02-13       Impact factor: 7.446

9.  Isolation, structure, and synthesis of combretastatins A-1 and B-1, potent new inhibitors of microtubule assembly, derived from Combretum caffrum.

Authors:  G R Pettit; S B Singh; M L Niven; E Hamel; J M Schmidt
Journal:  J Nat Prod       Date:  1987 Jan-Feb       Impact factor: 4.050

10.  The tubulin-binding agent combretastatin A-4-phosphate arrests endothelial cells in mitosis and induces mitotic cell death.

Authors:  Chryso Kanthou; Olga Greco; Anna Stratford; Ian Cook; Richard Knight; Omar Benzakour; Gillian Tozer
Journal:  Am J Pathol       Date:  2004-10       Impact factor: 4.307
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  1 in total

1.  Components from the Leaves and Twigs of Mangrove Lumnitzera racemosa with Anti-Angiogenic and Anti-Inflammatory Effects.

Authors:  Szu-Yin Yu; Shih-Wei Wang; Tsong-Long Hwang; Bai-Luh Wei; Chien-Jung Su; Fang-Rong Chang; Yuan-Bin Cheng
Journal:  Mar Drugs       Date:  2018-10-25       Impact factor: 5.118
  1 in total

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