TY - JOUR
T1 - Design and synthesis via click chemistry of 8,9-anhydroerythromycin A 6,9-hemiketal analogues with anti-MRSA and -VRE activity
AU - Sugawara, Akihiro
AU - Sunazuka, Toshiaki
AU - Hirose, Tomoyasu
AU - Nagai, Kenichiro
AU - Yamaguchi, Yukie
AU - Hanaki, Hideaki
AU - Sharpless, K. Barry
AU - Omura, Satoshi
N1 - Funding Information:
This work was supported by a grant from the 21st Century COE Program, Ministry of Education, Culture, Sports, Science and Technology. We also thank Ms. A. Nakagawa, Ms. C. Sakabe, and Ms. N. Sato for the various instrumental analysis.
PY - 2007/11/15
Y1 - 2007/11/15
N2 - An erythromycin analogue, 11,12-di-O-iso-butyryl-8,9-anhydroerythromycin A 6,9-hemiketal (1b), was found to be a potential anti-MRSA and anti-VRE agent. The use of copper catalyzed azide-acetylene cycloaddition, and click chemistry, readily provided 10 types of triazole analogues of 1b in good to nearly quantitative yield. Among the library, 5b exhibited activity against MRSA and VRE bacterial strains, representing more than twice the potency of 1b.
AB - An erythromycin analogue, 11,12-di-O-iso-butyryl-8,9-anhydroerythromycin A 6,9-hemiketal (1b), was found to be a potential anti-MRSA and anti-VRE agent. The use of copper catalyzed azide-acetylene cycloaddition, and click chemistry, readily provided 10 types of triazole analogues of 1b in good to nearly quantitative yield. Among the library, 5b exhibited activity against MRSA and VRE bacterial strains, representing more than twice the potency of 1b.
KW - Anti-MRSA and -VRE agent
KW - Click chemistry
KW - Erythromycin A
KW - Macrolides
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U2 - 10.1016/j.bmcl.2007.08.068
DO - 10.1016/j.bmcl.2007.08.068
M3 - Article
C2 - 17869508
AN - SCOPUS:35248866227
VL - 17
SP - 6340
EP - 6344
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
SN - 0960-894X
IS - 22
ER -