Synthesis and biological activity of C-4 and C-15 Aryl azide derivatives of anguidine

Stewart K. Richardson, Alwarsamy Jeganathan, Rajarathnam S. Mani, Boyd E. Haley, David S. Watt, Lynn R. Trusal

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

Potential trichothecene photoaffinity reagents were prepared by coupling either the C-4 or C-15 alcohols derived from anguidine with (3-azido-5-methoxyphenoxy) acetic acid, 4-(3-azido-5-methoxyphenoxy)butyric acid, or N-(3-azido-5-methoxyphenyl) N'-(carboxymethyl) urea. The C-15 anguidine deriviatives of (3-azido-5-methoxyphenoxy)acetic acid and (3-azido-4-iodo-5-methoxyphenoxy) acetic acid possessed protein synthesis inhibition activity comparable to that of anguidine itself in Chinese hamster ovary and African Green Monkey kidney cell lines.

Original languageEnglish
Pages (from-to)2925-2934
Number of pages10
JournalTetrahedron
Volume43
Issue number13
DOIs
StatePublished - 1987

Bibliographical note

Funding Information:
This work was supported by a G-R-H Grant at the University of Kentucky and by the U. S. Army Medical Research Acquisition Agency, Contract No. DAMD17-85-C-5192. We thank Dr. Takushi Kaneko of Bristol-Myers Companyf or generous chemical gift, the Midwest Center for Mass Spectrometry for exact mass determinations, and David C. Hybner for technical assistance.

Funding

This work was supported by a G-R-H Grant at the University of Kentucky and by the U. S. Army Medical Research Acquisition Agency, Contract No. DAMD17-85-C-5192. We thank Dr. Takushi Kaneko of Bristol-Myers Companyf or generous chemical gift, the Midwest Center for Mass Spectrometry for exact mass determinations, and David C. Hybner for technical assistance.

FundersFunder number
U. S. Army Medical Research Acquisition Agency
University of Kentucky

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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