lynamicin D

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: lynamicin D
• 英文别名: dimethyl 3,4-bis(5-chloro-1H-indol-3-yl)-1H-pyrrole-2,5-dicarboxylate
• 化学式: C₂₄H₁₇Cl₂N₃O₄
• 分子量: 482.323
• InChiKey: YYBKJQDTRQASSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  100
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  lynamicin D 在 N,N’-difluoro-2,2’-bipyridinium bis(tetrafluoroborate) 、 水 作用下， 以 乙腈 、 乙酸乙酯 为溶剂， 反应 0.33h， 以57%的产率得到C₂₄H₁₅Cl₂N₃O₅
  参考文献：
  名称：

  天然产物螺菌素家族的仿生全合成

  摘要：

  通过仿生“二聚和转移”策略实现了具有 [5,5] 和 [5,6] 螺环骨架的天然产物螺菌素家族的全合成。开发了一种用于 L-色氨酸氧化二聚化的生物催化方法，用于制备双吲哚中间体，该中间体通过区域选择性氧化 C3'-C2'' 和 C3'-C4'' 偶联转化为螺茚霉素。

  DOI：

  10.1002/anie.202208802
• 作为产物：
  描述：

  5-氯-3-碘吡啶 在 4-二甲氨基吡啶 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 palladium diacetate 、 sodium carbonate 、 三乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 10.0h， 生成 lynamicin D
  参考文献：
  名称：

  Lynamicin D an antimicrobial natural product affects splicing by inducing the expression of SR protein kinase 1

  摘要：

  The first total synthesis of the antimicrobial natural product lynamicin D has been developed using a Suzuki coupling to construct the bisindole pyrrole skeleton. An evaluation of the biological activity of lynamicin D reveals that it has a minor effect on cell viability but it can modulate splicing of pre-mRNAs. We provide evidence that this effect is mainly due to the ability of lynamicin D to alter the levels of SRPK1, the key kinase involved in both constitutive and alternative splicing. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.01.025

文献信息

• Total synthesis of (+)-spiroindimicin A and congeners unveils their antiparasitic activity
  作者：Zhen Zhang、Sneha Ray、Leah Imlay、Lauren T. Callaghan、Hanspeter Niederstrasser、Prema Latha Mallipeddi、Bruce A. Posner、Dawn M. Wetzel、Margaret A. Phillips、Myles W. Smith

  DOI：10.1039/d1sc02838c

  日期：——

  heteroaromatic rings structured around a congested spirocyclic stereocenter. Here, we report the first total synthesis of (+)-spiroindimicin A, which bears a challenging C-3′/C-5′′-linked spiroindolenine. We detail our initial efforts to effect a biomimetic oxidative spirocyclization from its proposed natural precursor, lynamicin D, and describe how these studies shaped our final abiotic 9-step solution

  螺茚霉素是一类独特的氯化吲哚生物碱，其特征在于围绕拥挤的螺环立体中心构造的三个杂芳环。在这里，我们报告了 (+)-spiroindimicin A 的首次全合成，它具有具有挑战性的 C-3'/C-5'-连接的螺二氢吲哚。我们详细介绍了我们从其提出的天然前体lynamicin D 实现仿生氧化螺环化的初步努力，并描述了这些研究如何塑造我们最终的非生物9 步解决方案，以围绕关键的Pd 催化不对称螺环化构建这种复杂的生物碱。对螺菌素 A、H 及其同源物的可扩展性访问使人们能够发现它们对与人类健康相关的几种寄生虫的活性，
• Functional characterization of the halogenase SpmH and discovery of new deschloro-tryptophan dimers
  作者：Zhiwen Liu、Liang Ma、Liping Zhang、Wenjun Zhang、Yiguang Zhu、Yuchan Chen、Weimin Zhang、Changsheng Zhang

  DOI：10.1039/c8ob02775g

  日期：——

  Inactivation of the halogenase gene spmH led to discovery of four new deschloro-tryptophan dimers. SpmH was further biochemically characterized in vitro as an l-tryptophan 5-halogenase.

  禁用卤素酶基因spmH导致发现四种新的去氯色氨酸二聚体。在体外，SpmH进一步被生化特征化为一个l-色氨酸5-卤素酶。
• A biomimetic approach to lycogarubin C, lynamicin D and related analogues
  作者：Wenxue Li、Sheng Liu

  DOI：10.1039/d4ob00033a

  日期：——

  An efficient and biomimetic synthetic approach to 3,4-diindolylpyrrole-2,5-dicarboxylate derivatives, including lycogarubin C, lynamicin D and related analogues, was discovered. The crucial transformation included the one-pot formation of two C–N bonds and one C–C bond to construct characteristic pyrrole rings.

  发现了一种有效的仿生合成方法来合成 3,4-二吲哚基吡咯-2,5-二羧酸酯衍生物，包括 lycogarubin C、lynamicin D 和相关类似物。关键的转变包括一锅法形成两个 C-N 键和一个 C-C 键以构建特征吡咯环。
• BIS-INDOLE PYRROLES USEFUL AS ANTIMICROBIAL AGENTS
  申请人：Nereus Pharmaceuticals, Inc.

  公开号：EP1711486B1

  公开（公告）日：2011-05-11
• Bis-indole pyrroles useful as antimicrobials agents
  申请人：Mitchell S. Scott

  公开号：US20070149601A1

  公开（公告）日：2007-06-28

  Compounds of Formula I, commonly referred to as bis-indole pyrroles, including isolated naturally-occurring compounds, synthetic and semi-synthetic derivatives thereof having antimicrobial properties and to antimicrobial compositions that include one or more of bis-indole pyrroles and their derivatives or analogs having antimicrobial properties are disclosed. Pharmaceutical compositions comprising such compounds and methods of treating bacterial infections with the disclosed compounds or the disclosed pharmaceutical compositions are also disclosed.