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Synthesis and Antibacterial Activity of Acylides (3-<i>O</i>-Acyl-erythromycin Derivatives): A Novel Class of Macrolide Antibiotics
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- Tetsuya Tanikawa
- Medicinal Research Laboratories, Taisho Pharmaceutical Co. Ltd., 1-403 Yoshino-cho, Saitama-shi 330-8530, Japan, and Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba-shi 263-8522, Japan
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- Toshifumi Asaka
- Medicinal Research Laboratories, Taisho Pharmaceutical Co. Ltd., 1-403 Yoshino-cho, Saitama-shi 330-8530, Japan, and Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba-shi 263-8522, Japan
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- Masato Kashimura
- Medicinal Research Laboratories, Taisho Pharmaceutical Co. Ltd., 1-403 Yoshino-cho, Saitama-shi 330-8530, Japan, and Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba-shi 263-8522, Japan
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- Yoko Misawa
- Medicinal Research Laboratories, Taisho Pharmaceutical Co. Ltd., 1-403 Yoshino-cho, Saitama-shi 330-8530, Japan, and Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba-shi 263-8522, Japan
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- Keiko Suzuki
- Medicinal Research Laboratories, Taisho Pharmaceutical Co. Ltd., 1-403 Yoshino-cho, Saitama-shi 330-8530, Japan, and Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba-shi 263-8522, Japan
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- Masakazu Sato
- Medicinal Research Laboratories, Taisho Pharmaceutical Co. Ltd., 1-403 Yoshino-cho, Saitama-shi 330-8530, Japan, and Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba-shi 263-8522, Japan
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- Kazuya Kameo
- Medicinal Research Laboratories, Taisho Pharmaceutical Co. Ltd., 1-403 Yoshino-cho, Saitama-shi 330-8530, Japan, and Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba-shi 263-8522, Japan
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- Shigeo Morimoto
- Medicinal Research Laboratories, Taisho Pharmaceutical Co. Ltd., 1-403 Yoshino-cho, Saitama-shi 330-8530, Japan, and Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba-shi 263-8522, Japan
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- Atsushi Nishida
- Medicinal Research Laboratories, Taisho Pharmaceutical Co. Ltd., 1-403 Yoshino-cho, Saitama-shi 330-8530, Japan, and Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba-shi 263-8522, Japan
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Description
Introduction of an acyl group to the 3-O-position of erythromycin A derivatives instead of L-cladinose led to a novel class of macrolide antibiotics that we named "acylides". The 3-O-nitrophenylacetyl derivative TEA0777 showed significantly potent activity against not only erythromycin-susceptible Gram-positive pathogens but also inducibly macrolides-lincosamides-streptogramin B (MLS(B))-resistant Staphylococcus aureus and efflux-resistant Streptococcus pneumoniae. These results indicated that acylides have potential as next-generation macrolide antibiotics.
Journal
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- Journal of Medicinal Chemistry
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Journal of Medicinal Chemistry 44 (24), 4027-4030, 2001-10-27
American Chemical Society (ACS)