Literature DB >> 12517440

Semisynthesis of DB-67 and other silatecans from camptothecin by thiol-promoted addition of silyl radicals.

Wu Du1, Bashir Kaskar, Peter Blumbergs, P-K Subramanian, Dennis P Curran.   

Abstract

Thiol- or acid-promoted additions of silyl radicals to camptothecin are reported. At 105 degrees C, mixtures of 7-silyl (favored) and 12-silyl camptothecins are formed alongside substantial amounts of recovered camptothecin. At 160 degrees C, 12-silyl isomers are formed preferentially, but the total mass balance is substantially reduced. The silyl radical addition is featured in short semi-syntheses of DB-67 (7-tert-butyldimethylsilyl-10-hydroxy camptothecin) from both camptothecin and 10-hydroxycamptothecin.

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Year:  2003        PMID: 12517440     DOI: 10.1016/s0968-0896(02)00437-6

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  5 in total

Review 1.  Plant-derived natural product research aimed at new drug discovery.

Authors:  Hideji Itokawa; Susan L Morris-Natschke; Toshiyuki Akiyama; Kuo-Hsiung Lee
Journal:  J Nat Med       Date:  2008-04-22       Impact factor: 2.343

2.  An Electroreductive Approach to Radical Silylation via the Activation of Strong Si-Cl Bond.

Authors:  Lingxiang Lu; Juno C Siu; Yihuan Lai; Song Lin
Journal:  J Am Chem Soc       Date:  2020-12-08       Impact factor: 15.419

3.  Silylation of C-H bonds in aromatic heterocycles by an Earth-abundant metal catalyst.

Authors:  Anton A Toutov; Wen-Bo Liu; Kerry N Betz; Alexey Fedorov; Brian M Stoltz; Robert H Grubbs
Journal:  Nature       Date:  2015-02-05       Impact factor: 49.962

4.  A phase I study of 7-t-butyldimethylsilyl-10-hydroxycamptothecin in adult patients with refractory or metastatic solid malignancies.

Authors:  Susanne M Arnold; John J Rinehart; Eleftheria Tsakalozou; John R Eckardt; Scott Z Fields; Brent J Shelton; Philip A DeSimone; Bryan K Kee; Jeffrey A Moscow; Markos Leggas
Journal:  Clin Cancer Res       Date:  2010-01-12       Impact factor: 12.531

5.  Computational study of the rate constants and free energies of intramolecular radical addition to substituted anilines.

Authors:  Andreas Gansäuer; Meriam Seddiqzai; Tobias Dahmen; Rebecca Sure; Stefan Grimme
Journal:  Beilstein J Org Chem       Date:  2013-08-08       Impact factor: 2.883

  5 in total

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