Cyclodidepsipeptides with a promising scaffold in medicinal chemistry

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• 作者：Andrija Smelcerovic (1)
  Predrag Dzodic (2)
  Voja Pavlovic (3)
  Emiliya Cherneva (4)
  Denitsa Yancheva (5)
  
• 关键词：Biological activities ; Cyclodidepsipeptides ; Docking ; Drug ; likeness ; Structure–activity relationships ; Synthesis
• 刊名：Amino Acids
• 出版年：2014
• 出版时间：April 2014
• 年：2014
• 卷：46
• 期：4
• 页码：825-840
• 全文大小：752 KB
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• 作者单位：Andrija Smelcerovic (1)
  Predrag Dzodic (2)
  Voja Pavlovic (3)
  Emiliya Cherneva (4)
  Denitsa Yancheva (5)
  
  1. Department of Chemistry, Faculty of Medicine, University of Nis, Bulevar Dr Zorana Djindjica 81, 18000, Nis, Serbia
  2. Department of Pharmacy, Faculty of Medicine, University of Nis, Bulevar Dr Zorana Djindjica 81, 18000, Nis, Serbia
  3. Faculty of Medicine, Institute of Physiology, University of Nis, Bulevar Dr Zorana Djindjica 81, 18000, Nis, Serbia
  4. Department of Chemistry, Faculty of Pharmacy, Medical University of Sofia, 2 Dunav Str., 1000, Sofia, Bulgaria
  5. Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str., Build. 9, 1113, Sofia, Bulgaria
  
• ISSN：1438-2199

文摘

Among the large family of cyclodepsipeptides, the simplest members are the cyclodidepsipeptides which have an ester group and an amide group in the same six-membered ring. To point out the pharmacological potential of this class of compounds, the present article reviews structure, isolation, synthesis and biological properties of the known cyclodidepsipeptides. Synthesis of cyclodidepsipeptides is achieved by two general approaches—by initial formation of the amide bond, or initial formation of the ester bond; and subsequent intermolecular cyclization to cyclodidepsipeptide structure. It is closely related to the condensation and ring-closure strategies applied in the preparation of the larger members of the cyclodepsipeptide family. However, due to synthesis of the smaller heretocycles it allows for the use of more versatile building blocks. There are data on antimicrobial, antioxidant and immunomodulatory activities of cyclodidepsipeptides as well as their inhibitory activities toward α-glucosidase, acyl-CoA:cholesterol acyltransferase, xanthine oxidase and platelet aggregation. Because we have recently found that two 6-(propan-2-yl)-4-methyl-morpholine-2,5-diones, as novel non-purine xanthine oxidase inhibitors, may give promise to be used in the treatment of gout, in this review we have included a study of molecular interactions of the selected cyclodidepsipeptides with xanthine oxidase using idTarget web server. Cyclodidepsipeptides showed promising pharmacological activities and meet all criteria for good solubility and permeability. However, further research of their medical application is necessary. In addition to this, the diversity of natural cyclodidepsipeptides, simplicity for synthesis and convenience for rational drug design indicate the cyclodidepsipeptide as promising scaffold in medicinal chemistry.