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Azinomycin bisepoxides containing rigid aromatic linkers: synthesis, cytotoxicity and DNA interstrand cross-linking activity
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Finerty, Matthew J., Bingham, John P., Hartley, John A. and Shipman, Michael (2009) Azinomycin bisepoxides containing rigid aromatic linkers: synthesis, cytotoxicity and DNA interstrand cross-linking activity. Tetrahedron Letters, Vol.50 (No.26 Sp. Iss. SI). pp. 3648-3650. doi:10.1016/j.tetlet.2009.03.123 ISSN 0040-4039.
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Official URL: http://dx.doi.org/10.1016/j.tetlet.2009.03.123
Abstract
The synthesis of a series of azinomycin bisepoxides containing rigid linkers is achieved through two different strategies. Double copper-mediated C-N bond formation under Buchwald-type conditions can be realised but yields are poor with fully intact epoxide substrates. The bisepoxides are made in improved yields through the simultaneous formation of two amide bonds. Bioassays reveal that 5, containing a 1,3-diaminobenzene linker, is a potent in vitro DNA interstrand cross-linking agent with significant cytotoxicity in the NCl 60-human cancer cell panel (Gl(50) = 0.15 mu M). (C) 2009 Elsevier Ltd. All rights reserved.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
Journal or Publication Title: | Tetrahedron Letters | ||||
Publisher: | Elsevier | ||||
ISSN: | 0040-4039 | ||||
Official Date: | 1 July 2009 | ||||
Dates: |
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Volume: | Vol.50 | ||||
Number: | No.26 Sp. Iss. SI | ||||
Number of Pages: | 3 | ||||
Page Range: | pp. 3648-3650 | ||||
DOI: | 10.1016/j.tetlet.2009.03.123 | ||||
Status: | Peer Reviewed | ||||
Publication Status: | Published | ||||
Access rights to Published version: | Restricted or Subscription Access | ||||
Funder: | University of Warwick, CRUK, EPSRC National Mass Spectroscopic service (Swansea), Engineering and Physical Sciences Research Council (EPSRC) | ||||
Grant number: | C22591A3083, EP/C007999/1 (EPSRC) |
Data sourced from Thomson Reuters' Web of Knowledge
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