marinopyrrole F | 1228555-52-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: marinopyrrole F
• 英文别名: 4,9,10-trichloro-6-(2-hydroxybenzoyl)-2-oxa-7,11-diazatetracyclo[12.4.0.03,7.08,12]octadeca-1(18),3,5,8(12),9,14,16-heptaen-13-one
• CAS: 1228555-52-9
• 化学式: C₂₂H₁₁Cl₃N₂O₄
• 分子量: 473.699
• InChiKey: UMSYRMLQVAKNRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  marinopyrrole F 、 二甲胺 以 四氢呋喃 为溶剂， 反应 48.0h， 以100%的产率得到(4,4',5'-trichloro-5-(dimethylamino)-1'H-1,3'-bipyrrole-2,2'-diyl)bis((2-hydroxyphenyl)methanone)
  参考文献：
  名称：

  Structures, Reactivities, and Antibiotic Properties of the Marinopyrroles A−F

  摘要：

  Cultivation of actinomycete strain CNQ-418, retrieved from a deep ocean sediment sample off the coast of La Jolla, CA, has provided marinopyrroles A F. Sharing just 98% 16S rRNA gene sequence identity with S. sannurensis, the strain likely represents a new Streptomyces species. The metabolites contain an unusual 1,3'-bipyrrole core decorated with several chlorine and bromine substituents and possess marked antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). The congested N,C-biaryl bond establishes an axis of chirality that, for marinopyrroles A-E, is configurationally stable at room temperature. Moreover, the natural products are fashioned strictly in the M-configuration. The Paal-Knorr condensation was adapted for the synthesis of the 1,3'-bipyrrole core. Halogenation of this material with N-bromosuccinimide cleanly furnished the 4,4',5,5'-tetrahalogenated core that characterizes this class of marine-derived metabolites.

  DOI：

  10.1021/jo1002054
• 作为产物：
  描述：

  marinopyrrole A 以 N,N-二甲基乙酰胺 为溶剂， 反应 72.0h， 以62%的产率得到marinopyrrole F
  参考文献：
  名称：

  Structures, Reactivities, and Antibiotic Properties of the Marinopyrroles A−F

  摘要：

  Cultivation of actinomycete strain CNQ-418, retrieved from a deep ocean sediment sample off the coast of La Jolla, CA, has provided marinopyrroles A F. Sharing just 98% 16S rRNA gene sequence identity with S. sannurensis, the strain likely represents a new Streptomyces species. The metabolites contain an unusual 1,3'-bipyrrole core decorated with several chlorine and bromine substituents and possess marked antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). The congested N,C-biaryl bond establishes an axis of chirality that, for marinopyrroles A-E, is configurationally stable at room temperature. Moreover, the natural products are fashioned strictly in the M-configuration. The Paal-Knorr condensation was adapted for the synthesis of the 1,3'-bipyrrole core. Halogenation of this material with N-bromosuccinimide cleanly furnished the 4,4',5,5'-tetrahalogenated core that characterizes this class of marine-derived metabolites.

  DOI：

  10.1021/jo1002054

文献信息

• Marinopyrrole derivatives and methods of making and using same
  申请人：H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.

  公开号：US10358454B2

  公开（公告）日：2019-07-23

  Marinopyrrole derivatives and methods for their synthesis and use are described herein. Novel cyclic and symmetric marinopyrroles with triazole substituents having antibacterial activity against resistant bacterial strains, such as MRSA are introduced. Also provided are methods of using the compounds for treating or preventing cancer and/or microbial infections.

  本文介绍了马林吡咯衍生物及其合成和使用方法。本文介绍了具有三唑取代基的新型环状和对称卤代吡咯，它们对耐药细菌菌株（如 MRSA）具有抗菌活性。还提供了使用这些化合物治疗或预防癌症和/或微生物感染的方法。
• MARINOPYRROLE DERIVATIVES AND METHODS OF MAKING AND USING SAME
  申请人：H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.

  公开号：US20170050981A1

  公开（公告）日：2017-02-23

  Marinopyrrole derivatives and methods for their synthesis and use are described herein. Novel cyclic and symmetric marinopyrroles with triazole substituents having antibacterial activity against resistant bacterial strains, such as MRSA are introduced. Also provided are methods of using the compounds for treating or preventing cancer and/or microbial infections.
• Structures, Reactivities, and Antibiotic Properties of the Marinopyrroles A−F
  作者：Chambers C. Hughes、Christopher A. Kauffman、Paul R. Jensen、William Fenical

  DOI：10.1021/jo1002054

  日期：2010.5.21

  Cultivation of actinomycete strain CNQ-418, retrieved from a deep ocean sediment sample off the coast of La Jolla, CA, has provided marinopyrroles A F. Sharing just 98% 16S rRNA gene sequence identity with S. sannurensis, the strain likely represents a new Streptomyces species. The metabolites contain an unusual 1,3'-bipyrrole core decorated with several chlorine and bromine substituents and possess marked antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). The congested N,C-biaryl bond establishes an axis of chirality that, for marinopyrroles A-E, is configurationally stable at room temperature. Moreover, the natural products are fashioned strictly in the M-configuration. The Paal-Knorr condensation was adapted for the synthesis of the 1,3'-bipyrrole core. Halogenation of this material with N-bromosuccinimide cleanly furnished the 4,4',5,5'-tetrahalogenated core that characterizes this class of marine-derived metabolites.