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Journal of Asian Natural Products Research Volume 19, 2017 - Issue 4
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Original Articles

Synthesis and antibacterial activities of some novel 17, 18-unsaturated carbonyl compounds derivated from josamycin

Zhe-Hui ZhaoState Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Department of Medicinal Chemistry, Institute of Materia Medica, Peking Union Medical College & Chinese Academy of Medical Sciences, Beijing 100050, China
,
Long-Long JinState Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Department of Medicinal Chemistry, Institute of Materia Medica, Peking Union Medical College & Chinese Academy of Medical Sciences, Beijing 100050, China
,
Yan-Peng XuState Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Department of Medicinal Chemistry, Institute of Materia Medica, Peking Union Medical College & Chinese Academy of Medical Sciences, Beijing 100050, China
,
Chao LiuState Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Department of Medicinal Chemistry, Institute of Materia Medica, Peking Union Medical College & Chinese Academy of Medical Sciences, Beijing 100050, China
,
A-Peng WangState Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Department of Medicinal Chemistry, Institute of Materia Medica, Peking Union Medical College & Chinese Academy of Medical Sciences, Beijing 100050, China
&
Ping-Sheng LeiState Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Department of Medicinal Chemistry, Institute of Materia Medica, Peking Union Medical College & Chinese Academy of Medical Sciences, Beijing 100050, ChinaCorrespondence[email protected]
Pages 358-387 | Received 20 May 2016, Accepted 24 May 2016, Published online: 26 Sep 2016
 
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Abstract

Some novel josamycin derivatives bearing an arylalkyl-type side chain were designed and synthesized. By HWE or Wittig reaction, 16-aldehyde group of josamycin analogs were converted into unsaturated carbonyl compounds. They were evaluated for their in vitro antibacterial activities against a panel of respiratory pathogens. 8b and 8e exhibited comparable activities against a panel of respiratory pathogens, especially to resistant ones in the series of desmycarosyl josamycin analogs. Among of all the target molecules, 21 showed the best antibacterial activities.

Acknowledgments

We are grateful to Professor Xuefu You for the antibacterial activity test.

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