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Resolution of a CPzl precursor, synthesis and biological evaluation of (+) and (-)-NBoc-CPzl: a further validation of the relationship between chemical solvolytic stability and cytotoxicity

Academic Article
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Overview

related to degree

  • Boyce, Christopher William, Ph.D. in Organic Chemistry, Medicinal Chemistry, Scripps Research 1994 - 1999

authors

  • Baraldi, P. G.
  • Cacciari, B.
  • Romagnoli, R.
  • Spalluto, G.
  • Boyce, Christopher William
  • Boger, Dale

publication date

  • November 1999

journal

  • Bioorganic & Medicinal Chemistry Letters  Journal

abstract

  • The chemical resolution, using N-tosyl-L-proline as a chiral auxiliary, of a racemate of the pyrazole analog (+/-)-N-Boc-CPzI of the left hand segment (CPI) of the antitumor agent CC-1065, and the cytotoxic evaluation of both enantiomers are described. The reported results further validate the direct relationship between chemical solvolytic stability of the cyclopropane ring and cytotoxicity proposed by Boger and coworkers.

subject areas

  • Animals
  • Antibiotics, Antineoplastic
  • Antineoplastic Agents, Alkylating
  • Indoles
  • Leucomycins
  • Leukemia L1210
  • Mice
  • Molecular Structure
  • Proline
  • Pyrazoles
  • Stereoisomerism
  • Streptomyces
  • Tumor Cells, Cultured
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Identity

International Standard Serial Number (ISSN)

  • 0960-894X

Digital Object Identifier (DOI)

  • 10.1016/s0960-894x(99)00533-8

PubMed ID

  • 10560730
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Additional Document Info

start page

  • 3087

end page

  • 3092

volume

  • 9

issue

  • 21

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