Synthesis of 4'-modified noraristeromycins to clarify the effect of the 4'-hydroxyl groups for inhibitory activity against S-adenosyl-L-homocysteine hydrolase

Takayuki Ando; Kenji Kojima; Praveen Chahota; Atsushi Kozaki; Nikalje D Milind; Yukio Kitade

doi:10.1016/j.bmcl.2008.03.029

Synthesis of 4'-modified noraristeromycins to clarify the effect of the 4'-hydroxyl groups for inhibitory activity against S-adenosyl-L-homocysteine hydrolase

Bioorg Med Chem Lett. 2008 Apr 15;18(8):2615-8. doi: 10.1016/j.bmcl.2008.03.029. Epub 2008 Mar 14.

Authors

Takayuki Ando¹, Kenji Kojima, Praveen Chahota, Atsushi Kozaki, Nikalje D Milind, Yukio Kitade

Affiliation

¹ Center for Emerging Infectious Diseases, Department of Biomolecular Science, Gifu University, Yanagido 1-1, Gifu 501-1193, Japan.

PMID: 18374570
DOI: 10.1016/j.bmcl.2008.03.029

Abstract

4'-Modified noraristeromycin (NAM) analogs, 4'-sulfo-, 4'-sulfamoy, 4'-azido and 4'-amino-NAM, were systematically synthesized. The inhibitory activities of these analogs and related compounds against Plasmodium falciparum and human S-adenosyl-L-homocysteine hydrolase were investigated.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Adenosine / chemical synthesis*
Adenosine / chemistry
Adenosine / pharmacology*
Adenosylhomocysteinase / antagonists & inhibitors*
Adenosylhomocysteinase / metabolism
Animals
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / pharmacology*
Humans
Hydroxylation
Molecular Structure
Plasmodium falciparum / enzymology
Structure-Activity Relationship

Substances

Enzyme Inhibitors
Adenosylhomocysteinase
Adenosine