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Total synthesis and biological properties of novel antineoplastic (chloromethyl)furanoindolines - an asymmetric hydroboration mediated synthesis of the alkylation subunits

Academic Article
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Overview

authors

  • Mohamadi, F.
  • Spees, M. M.
  • Staten, G. S.
  • Marder, P.
  • Kipka, J. K.
  • Johnson, D. A.
  • Boger, Dale
  • Zarrinmayeh, H.

publication date

  • January 1994

journal

  • Journal of Medicinal Chemistry  Journal

abstract

  • 1,2-Dihydro-1-(chloromethyl)-5-hydroxy-8-methyl-3H-furano[3,2-e]in dole (CFI) as a novel replacement of the cyclopropylpyrroloindoline (CPI) alkylation subunit of CC-1065, U-71184, and U-73975 (adozelesin) has been synthesized and incorporated into a series of efficacious antineoplastic agents. A partial solution to an asymmetric synthesis of the CFI alkylation subunit has been achieved by the implementation of an asymmetric hydroboration reaction of an intermediate 3-methyleneindoline (13). Extension to the asymmetric synthesis of the CBI and CI alkylation subunits is presented. The demonstration and comparative study of the sequence-selective DNA alkylation properties of the CFI-based agents are detailed, and the preliminary in vitro and in vivo antineoplastic properties of these agents in the human epidermoid cell lung carcinoma (T222) are described.

subject areas

  • Alkylation
  • Animals
  • Antineoplastic Agents
  • Base Sequence
  • Boron Compounds
  • Carcinoma, Squamous Cell
  • Cyclohexanecarboxylic Acids
  • Cyclohexenes
  • DNA
  • Drug Screening Assays, Antitumor
  • Female
  • Furans
  • Humans
  • Indoles
  • Leucomycins
  • Lung Neoplasms
  • Mice
  • Mice, Nude
  • Molecular Sequence Data
  • Tumor Cells, Cultured
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Identity

International Standard Serial Number (ISSN)

  • 0022-2623

Digital Object Identifier (DOI)

  • 10.1021/jm00028a005

PubMed ID

  • 8295210
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Additional Document Info

start page

  • 232

end page

  • 239

volume

  • 37

issue

  • 2

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