Synthesis of a series of boronated unnatural cyclic amino acids as potential boron neutron capture therapy agents

George Kabalka, Zhongzhi Wu, Min Liang Yao

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

New boronated unnatural cyclic amino acids, 1-6, were synthesized for potential use in neutron capture therapy. In order to understand the effect of molecular lipophilicity on the biological activity, different linkers were introduced between the boronic acid and 1-aminocycloalkanecarboxylic acid moieties. The key step in the syntheses was the preparation of a series of alkenyl-substituted cycloalkanones, which were subsequently converted to amino acids via the Bücherer-Strecker reaction. The introduction of the boronic acid function into hydrantoins 19-24 was realized by hydroboration reactions using diisopinocampheylborane (Ipc2BH). The target boronated amino acids were modeled after 1-aminocyclobutanecarboxylic acid and 1-amino-3-boronocyclopentanecarboxylic acid, which have previously demonstrated high uptake in tumors.

Original languageEnglish (US)
Pages (from-to)516-522
Number of pages7
JournalApplied Organometallic Chemistry
Volume22
Issue number9
DOIs
StatePublished - Sep 1 2008

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Cyclic Amino Acids
Boronic Acids
Boron
Neutrons
Amino Acids
Acids
Bioactivity
Tumors

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Inorganic Chemistry

Cite this

Synthesis of a series of boronated unnatural cyclic amino acids as potential boron neutron capture therapy agents. / Kabalka, George; Wu, Zhongzhi; Yao, Min Liang.

In: Applied Organometallic Chemistry, Vol. 22, No. 9, 01.09.2008, p. 516-522.

Research output: Contribution to journalArticle

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