1'H-1,3'-bipyrrole-2,2'-diylbis((2-methoxyphenyl)methanone) | 1227869-59-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1'H-1,3'-bipyrrole-2,2'-diylbis((2-methoxyphenyl)methanone)
• 英文别名: 1'H-1,3'-bipyrrole-2,2'-diylbis[(2-methoxyphenyl)methanone]；dechloro-O,O'-dimethylmarinopyrrole A；[1-[2-(2-methoxybenzoyl)-1H-pyrrol-3-yl]pyrrol-2-yl]-(2-methoxyphenyl)methanone
• CAS: 1227869-59-1
• 化学式: C₂₄H₂₀N₂O₄
• 分子量: 400.434
• InChiKey: LWKVRACKMKHYBX-UHFFFAOYSA-N

物化性质

• 熔点：
  175-176 °C
• 沸点：
  658.6±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  1'H-1,3'-bipyrrole-2,2'-diylbis((2-methoxyphenyl)methanone) 在 N-溴代丁二酰亚胺(NBS) 、 三溴化硼 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 [4,5-dibromo-1-[4,5-dibromo-2-(2-hydroxybenzoyl)-1H-pyrrol-3-yl]pyrrol-2-yl]-(2-hydroxyphenyl)methanone
  参考文献：
  名称：

  Total synthesis and biological evaluation of marinopyrrole A and analogs

  摘要：

  A five-step total synthesis of the antibiotic marinopyrrole A (1) is described. The developed synthetic technology enabled the synthesis of several marinopyrrole A analogs whose antibacterial properties against methicillin-resistant Staphylococcus aureus TCH1516 were evaluated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.059
• 作为产物：
  描述：

  ethyl 1'H-1,3'-bipyrrole-2'-carboxylate 在 aluminum (III) chloride 、 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.33h， 生成 1'H-1,3'-bipyrrole-2,2'-diylbis((2-methoxyphenyl)methanone)
  参考文献：
  名称：

  [EN] MCL-1 MODULATING COMPOSITIONS
  [FR] COMPOSITIONS DE MODULATION DE MCL-1

  摘要：

  本发明涉及海洋吡咯酮A衍生物和吡洛特霉素衍生物，以及治疗与Mcl-l误调节相关的疾病的方法，例如白血病、淋巴瘤、多发性骨髓瘤、黑色素瘤或胰腺癌。我们描述了一些示范性化合物，这些化合物可以包含在药物组合物中，并且它们可作为治疗剂单独使用或与其他抗癌治疗方法结合使用，例如抗Bcl-2剂。

  公开号：

  WO2013112878A1

文献信息

• [EN] MCL-1 MODULATING COMPOSITIONS<br/>[FR] COMPOSITIONS DE MODULATION DE MCL-1
  申请人：PENN STATE RES FOUND

  公开号：WO2013112878A1

  公开（公告）日：2013-08-01

  The present invention relates to marinopyrrole A derivatives and pyoluteorin derivatives and methods of treatment of disorders associated with misregulation of Mcl-l, e.g., leukemia, lymphoma, multiple myeloma, melanoma, or pancreatic cancer. We describe exemplary compounds, which may be contained in pharmaceutical compositions, and their use as therapeutic agents either alone or in combination with other anti-cancer treatments, e.g., anti-Bcl- 2 agents.

  本发明涉及海洋吡咯酮A衍生物和吡洛特霉素衍生物，以及治疗与Mcl-l误调节相关的疾病的方法，例如白血病、淋巴瘤、多发性骨髓瘤、黑色素瘤或胰腺癌。我们描述了一些示范性化合物，这些化合物可以包含在药物组合物中，并且它们可作为治疗剂单独使用或与其他抗癌治疗方法结合使用，例如抗Bcl-2剂。
• 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。
• Total Synthesis of (±)-Marinopyrrole A via Copper-Mediated N-Arylation
  作者：Argyrios A. Kanakis、Vasiliki Sarli

  DOI：10.1021/ol102035s

  日期：2010.11.5

  The total synthesis of the racemic form of the marine alkaloid marinopyrrole A is described. The characteristic 1,3'-bipyrrole core was constructed by a copper-mediated N-arylation process under microwave irradiation.
• [EN] (±)-MARINOPYRROLE A AND SYNTHESIZED DERIVATIVES THEREOF FOR RESISTING METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS<br/>[FR] (±)-MARINOPYRROLE A ET SES DÉRIVÉS SYNTHÉTIQUES POUR LUTTER CONTRE STAPHYLOCOCCUS AUREUS RÉSISTANT À LA MÉTHICILLINE
  申请人：CHONGQING ZHIEN PHARMACEUTICAL CO LTD

  公开号：WO2011103788A1

  公开（公告）日：2011-09-01

  Disclosed are synthesized derivatives of a natural product, (±)-marinopyrrole A, shown as structural formula I, which have inhibition activities on gram-positive bacteria, such as methicillin sensitive Staphylococcus aureus (MSSA), methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant Enterococcus (VRE), oxacilline-resistant Staphylococcus aureus (ORSA), methicillin-resistant Staphylococcus epidermidis (MRSE) and the like. Furthermore, the methods for preparing (±)-marinopyrrole A and the derivatives thereof are disclosed. According to the study of antibacterial activity in vitro, the synthesized derivatives of the natural product (±)-marinopyrrole A have excellent antibiotic activities on the gram-positive bacteria, such as methicillin sensitive Staphylococcus aureus (MSSA), methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant Enterococcus (VRE), oxacilline-resistant Staphylococcus aureus (ORSA), methicillin-resistant Staphylococcus epidermidis (MRSE) and the like, and have potential prospects in clinical application.