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

doi:10.1016/S0040-4020(01)86831-9

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

Molecular and Cellular Biochemistry

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	2925-2934
Number of pages	10
Journal	Tetrahedron
Volume	43
Issue number	13
DOIs	https://doi.org/10.1016/S0040-4020(01)86831-9
State	Published - 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.

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4020(01)86831-9

Cite this

@article{fc7daa93d4f54f8a8e172f41f7cdd225,

title = "Synthesis and biological activity of C-4 and C-15 Aryl azide derivatives of anguidine",

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.",

author = "Richardson, {Stewart K.} and Alwarsamy Jeganathan and Mani, {Rajarathnam S.} and Haley, {Boyd E.} and Watt, {David S.} and Trusal, {Lynn R.}",

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.",

year = "1987",

doi = "10.1016/S0040-4020(01)86831-9",

language = "English",

volume = "43",

pages = "2925--2934",

number = "13",

}

TY - JOUR

T1 - Synthesis and biological activity of C-4 and C-15 Aryl azide derivatives of anguidine

AU - Richardson, Stewart K.

AU - Jeganathan, Alwarsamy

AU - Mani, Rajarathnam S.

AU - Haley, Boyd E.

AU - Watt, David S.

AU - Trusal, Lynn R.

N1 - 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.

PY - 1987

Y1 - 1987

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0023239158&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0023239158&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(01)86831-9

DO - 10.1016/S0040-4020(01)86831-9

M3 - Article

AN - SCOPUS:0023239158

SN - 0040-4020

VL - 43

SP - 2925

EP - 2934

JO - Tetrahedron

JF - Tetrahedron

IS - 13

ER -

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

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this