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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related to degree

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

publication date

  • 1999

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.