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Expert Opinion on Therapeutic Patents Volume 13, 2003 - Issue 6
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Review

Recent progress in the field of macrolide antibiotics

Todd C Henninger Johnson & Johnson Pharmaceutical Research & Development, LLC, 1000 Route 202, PO Box 300, Raritan, NJ 08869, USA. [email protected]
Pages 787-805 | Published online: 02 Mar 2005

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Ji-Dong Wang, Huan Qi, Ji Zhang, Jian-Song Li, Shao-Yong Zhang, Zhi-Kui Hao, Li-Qin Zhang & Wen-Sheng Xiang. (2021) Two new 13-hydroxylated milbemycin metabolites from the genetically engineered strain Streptomyces avermitilis AVE-H39. Journal of Asian Natural Products Research 23:9, pages 837-843.
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Zhe-Hui Zhao, Long-Long Jin, Yan-Peng Xu, Chao Liu, A-Peng Wang & Ping-Sheng Lei. (2017) Synthesis and antibacterial activities of some novel 17, 18-unsaturated carbonyl compounds derivated from josamycin. Journal of Asian Natural Products Research 19:4, pages 358-387.
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Georg Schitter & Tanja M Wrodnigg. (2009) Update on carbohydrate-containing antibacterial agents. Expert Opinion on Drug Discovery 4:3, pages 315-356.
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Lan Wu, Weige Zhang, Liang Tian, Kai Bao, Pengfei Li & Jie Lin. (2007) Immunomodulatory Effects of Erythromycin and its Derivatives on Human T-Lymphocyte In Vitro. Immunopharmacology and Immunotoxicology 29:3-4, pages 587-596.
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Bhaskar Chatterjee, Dhananjoy Mondal & Smritilekha Bera. (2023) Macrocyclization Strategies Towards the Synthesis of Amphidinolide Natural Products. Asian Journal of Organic Chemistry 12:4.
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Ivayla Pantcheva, Radoslava Stamboliyska, Nikolay Petkov, Alia Tadjer, Svetlana Simova, Radostina Stoyanova, Rositza Kukeva & Petar Dorkov. (2022) Dinuclear vs. Mononuclear Copper(II) Coordination Species of Tylosin and Tilmicosin in Non-Aqueous Solutions. Molecules 27:12, pages 3899.
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Phyo Phyo Kyaw Zin, Gavin Williams & Denis Fourches. (2020) SIME: synthetic insight-based macrolide enumerator to generate the V1B library of 1 billion macrolides. Journal of Cheminformatics 12:1.
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Wei Fu, Lianhui Wang, Zi Yang, Jiang-Shan Shen, Fei Tang, Jiayi Zhang & Xiuling Cui. (2020) Facile access to versatile aza-macrolides through iridium-catalysed cascade allyl-amination/macrolactonization. Chemical Communications 56:6, pages 960-963.
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Girija S. Singh. 2020. Carbohydrates in Drug Discovery and Development. Carbohydrates in Drug Discovery and Development 523 559 .
Ashutosh K. Dash, Nazar Hussain & Debaraj Mukherjee. 2020. Carbohydrates in Drug Discovery and Development. Carbohydrates in Drug Discovery and Development 481 522 .
Biljana Arsic, Jill Barber, Ana Čikoš, Milan Mladenovic, Nevena Stankovic & Predrag Novak. (2018) 16-membered macrolide antibiotics: a review. International Journal of Antimicrobial Agents 51:3, pages 283-298.
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Andrew N. Lowell, Matthew D. DeMarsIIII, Samuel T. Slocum, Fengan Yu, Krithika Anand, Joseph A. Chemler, Nisha Korakavi, Jennifer K. Priessnitz, Sung Ryeol Park, Aaron A. Koch, Pamela J. Schultz & David H. Sherman. (2017) Chemoenzymatic Total Synthesis and Structural Diversification of Tylactone-Based Macrolide Antibiotics through Late-Stage Polyketide Assembly, Tailoring, and C—H Functionalization. Journal of the American Chemical Society 139:23, pages 7913-7920.
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Ruben Vardanyan & Victor Hruby. 2016. Synthesis of Best-Seller Drugs. Synthesis of Best-Seller Drugs 573 643 .
Herbert A. Kirst. 2001. Kirk-Othmer Encyclopedia of Chemical Technology. Kirk-Othmer Encyclopedia of Chemical Technology 1 15 .
Zhehui Zhao, Longlong Jin, Yanpeng Xu, Di Zhu, Yi Liu, Chao Liu & Pingsheng Lei. (2014) Synthesis and antibacterial activity of a series of novel 9-O-acetyl- 4′-substituted 16-membered macrolides derived from josamycin. Bioorganic & Medicinal Chemistry Letters 24:2, pages 480-484.
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Yanpeng Xu, Xiaozhuo Chen, Di Zhu, Yi Liu, Zhehui Zhao, Longlong Jin, Chao Liu & Pingsheng Lei. (2013) Synthesis and antibacterial activity of novel modified 5-O-mycaminose 14-membered ketolides. European Journal of Medicinal Chemistry 69, pages 174-181.
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A. Parenty, X. Moreau, Gilles Niel & J.-M. Campagne. (2013) Update 1 of: Macrolactonizations in the Total Synthesis of Natural Products. Chemical Reviews 113:1, pages PR1-PR40.
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Wenping Cui, Lihong An, Chenchen Ma, Siti Ma, Chao Cong, Xin Li & Shutao Ma. (2012) Novel azithromycin derivatives with the C-4″ bisamide side chains: synthesis and biological evaluation against gram-positive bacteria. The Journal of Antibiotics.
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Dražen Pavlović, Andrea Fajdetić & Stjepan Mutak. (2010) Novel hybrids of 15-membered 8a- and 9a-azahomoerythromycin A ketolides and quinolones as potent antibacterials. Bioorganic & Medicinal Chemistry 18:24, pages 8566-8582.
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Dražen Pavlović & Stjepan Mutak. (2010) Synthesis and Structure−Activity Relationships of Novel 8a-Aza-8a-homoerythromycin A Ketolides. Journal of Medicinal Chemistry 53:15, pages 5868-5880.
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Arnold L. Demain. (2009) Antibiotics: Natural products essential to human health. Medicinal Research Reviews 29:6, pages 821-842.
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Ali Sadeghi-Khomami, Michael D. Lumsden & David L. Jakeman. (2008) Glycosidase Inhibition by Macrolide Antibiotics Elucidated by STD-NMR Spectroscopy. Chemistry & Biology 15:7, pages 739-749.
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C. Prasad Narasimhulu, Javed Iqbal, Khagga Mukkanti & Parthasarathi Das. (2008) Studies towards the total synthesis of narbonolide: stereoselective preparation of the C1–C10 fragment. Tetrahedron Letters 49:19, pages 3185-3188.
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Akihiro Sugawara, Toshiaki Sunazuka, Tomoyasu Hirose, Kenichiro Nagai, Yukie Yamaguchi, Hideaki Hanaki, K. Barry Sharpless & Satoshi Ōmura. (2007) Design and synthesis via click chemistry of 8,9-anhydroerythromycin A 6,9-hemiketal analogues with anti-MRSA and -VRE activity. Bioorganic & Medicinal Chemistry Letters 17:22, pages 6340-6344.
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Manomi A. Tennakoon, Todd C. Henninger, Darren Abbanat, Barbara D. Foleno, Jamese J. Hilliard, Karen Bush & Mark J. Macielag. (2006) Synthesis and antibacterial activity of C6-carbazate ketolides. Bioorganic & Medicinal Chemistry Letters 16:24, pages 6231-6235.
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Svetlana A. Borisova, Changsheng Zhang, Haruko Takahashi, Hua Zhang, Alexander W. Wong, Jon S. Thorson & Hung‐wen Liu. (2006) Substrate Specificity of the Macrolide‐Glycosylating Enzyme Pair DesVII/DesVIII: Opportunities, Limitations, and Mechanistic Hypotheses. Angewandte Chemie International Edition 45:17, pages 2748-2753.
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Svetlana A. Borisova, Changsheng Zhang, Haruko Takahashi, Hua Zhang, Alexander W. Wong, Jon S. Thorson & Hung‐wen Liu. (2006) Substrate Specificity of the Macrolide‐Glycosylating Enzyme Pair DesVII/DesVIII: Opportunities, Limitations, and Mechanistic Hypotheses. Angewandte Chemie 118:17, pages 2814-2819.
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A. Parenty, X. Moreau & J.-M. Campagne. (2006) Macrolactonizations in the Total Synthesis of Natural Products. Chemical Reviews 106:3, pages 911-939.
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Tomoyasu Hirose, Toshiaki Sunazuka, Yoshihiko Noguchi, Yukie Yamaguchi, Hideaki Hanaki, K. Barry Sharpless & Satoshi Omura. (2006) Rapid ‘SAR’ via Click Chemistry: An Alkyne-Bearing Spiramycin is fused with Diverse Azides to Yield New Triazole-Antibacterial Candidates. HETEROCYCLES 69:1, pages 55.
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Xiaodong Xu, Todd Henninger, Darren Abbanat, Karen Bush, Barbara Foleno, Jamese Hilliard & Mark Macielag. (2005) Synthesis and antibacterial activity of C2-fluoro, C6-carbamate ketolides, and their C9-oximes. Bioorganic & Medicinal Chemistry Letters 15:4, pages 883-887.
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Arnold L. Demain & Lixin Zhang. 2005. Natural Products. Natural Products 3 29 .
Todd C. Henninger, Xiaodong Xu, Darren Abbanat, Ellen Z. Baum, Barbara D. Foleno, Jamese J. Hilliard, Karen Bush, Dennis J. Hlasta & Mark J. Macielag. (2004) Synthesis and antibacterial activity of C-6 carbamate ketolides, a novel series of orally active ketolide antibiotics. Bioorganic & Medicinal Chemistry Letters 14:17, pages 4495-4499.
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Ly T. Phan, Tianying Jian, Zhigang Chen, Yao-Ling Qiu, Zhaolin Wang, Theresa Beach, Alex Polemeropoulos & Yat Sun Or. (2004) Synthesis and Antibacterial Activity of a Novel Class of 4‘-Substituted 16-Membered Ring Macrolides Derived from Tylosin. Journal of Medicinal Chemistry 47:12, pages 2965-2968.
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David C Myles. (2003) Novel biologically active natural and unnatural products. Current Opinion in Biotechnology 14:6, pages 627-633.
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