diethyl 1′H-[1,3′-bipyrrole]-2,2′-dicarboxylate | 1227869-53-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: diethyl 1′H-[1,3′-bipyrrole]-2,2′-dicarboxylate
• 英文别名: ethyl 1-(2-ethoxycarbonyl-1H-pyrrol-3-yl)pyrrole-2-carboxylate
• CAS: 1227869-53-5
• 化学式: C₁₄H₁₆N₂O₄
• 分子量: 276.292
• InChiKey: AKSPODOGIZJQOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  73.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 1′H-[1,3′-bipyrrole]-2,2′-dicarboxylate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以86%的产率得到diethyl 4,4',5,5'-tetrabromo-1'H-1,3'-bipyrrole-2,2'-dicarboxylate
  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：

  ethyl 2,5-dioxopentanoate 、 3-氨基-1H-吡咯-2-甲酸乙酯 在 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 以23%的产率得到diethyl 1′H-[1,3′-bipyrrole]-2,2′-dicarboxylate
  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

• Total Synthesis of (±)-Marinopyrrole A and Its Library as Potential Antibiotic and Anticancer Agents
  作者：Chunwei Cheng、Lili Pan、Yi Chen、Hao Song、Yong Qin、Rongshi Li

  DOI：10.1021/cc100052j

  日期：2010.7.12

  The first total synthesis of marine natural product, (±)-marinopyrrole A, has been accomplished via a nine-step synthesis in an overall yield of 30%. A small focused library based on marinopyrrole has been designed and synthesized. The scope of chemistry was investigated, and a robust chemistry suitable for library synthesis has been developed in the current study. The method that we have developed

  通过九步合成完成了海洋天然产物的第一个全合成，即（±）-marinopyrrole A，总收率为30％。设计并合成了一个基于marinopyrrole的小型库。研究了化学的范围，并且在当前的研究中已经开发了适用于文库合成的稳健化学。我们已经开发出的方法使基于结构新颖的海萘酚生成多种类似物用于研究潜在的抗生素和抗癌活性成为可能。
• Exploration of the Bis(thio)urea-Catalyzed Atropselective Synthesis of Marinopyrrole A
  作者：Maciej Stodulski、Stefanie V. Kohlhepp、Gerhard Raabe、Tanja Gulder

  DOI：10.1002/ejoc.201600147

  日期：2016.4

  The marinopyrroles are a new class of natural products with highly interesting biomedical and structural features. We herein provide a concise, nitrogen-protective-group-free synthesis of marinopyrrole A, constituting the as yet most efficient route. The presented studies elaborate a straightforward and mild chlorination protocol. Moreover, the first study towards the atropselective synthesis of marinopyrrole

  marinopyrroles 是一类新的天然产物，具有非常有趣的生物医学和结构特征。我们在此提供了一种简洁的、无氮保护基团的 marinopyrrole A 合成方法，构成了迄今为止最有效的路线。所提出的研究阐述了一个简单而温和的氯化方案。此外，还介绍了使用手性 C2 对称双硫脲催化剂阻滞选择性合成 marinopyrrole A 的第一项研究。
• Synthesis of 10,10′-bis(trifluoromethyl) marinopyrrole A derivatives and evaluation of their antiviral activities in vitro
  作者：Yaxin Xiao、Jingjing Yang、Liangjing Zou、Pingzhou Wu、Wei Li、Yunzheng Yan、Yuexiang Li、Song Li、Hao Song、Wu Zhong、Yong Qin

  DOI：10.1016/j.ejmech.2022.114436

  日期：2022.8

  emerge unexpectedly in human populations and cause a spectrum of potentially severe diseases or even death. Since effective vaccine is currently unavailable against most of these deadly viruses, antiviral chemical drugs remain in urgent need. To meet this unmet demand, we developed a series of 10,10′-bis(trifluoromethyl) marinopyrrole A derivates bearing various substituents at C5′-positions, which

  黄病毒和肠道病毒会在人群中意外出现，并导致一系列潜在的严重疾病甚至死亡。由于目前还没有针对大多数这些致命病毒的有效疫苗，因此仍然迫切需要抗病毒化学药物。为了满足这一未满足的需求，我们开发了一系列在 C5'-位置带有各种取代基的 10,10'-双（三氟甲基）marinopyrrole A 衍生物，它们在体外对黄病毒（ZIKV、DENV、YFV、JEV）和肠道病毒（EV71、CA6、CA16）。先导化合物 10,10'-双（三氟甲基）marinopyrrole A 3在培养细胞中对肠道病毒 EV71 和 CA16 非常有效，但对黄病毒的抑制活性较低。由化合物精心修饰如图3所示，具有巯基脂肪链的化合物32和33被发现是有希望的ZIKV和DENV抑制剂；含有吡嗪的化合物19是一种有效的广谱黄病毒抑制剂；除了广谱肠道病毒抑制作用外，噻吩化合物15对JEV-SA14、YFV-17D表现出显着的选择性抑制作用。因此，这些结果表明，10
• 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.