3,4-二溴-1H-吡咯-2,5-二羧酸 二甲酯 | 473401-83-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 3,4-二溴-1H-吡咯-2,5-二羧酸 二甲酯
• 中文别名: 3,4-二溴-1H-吡咯-2,5-二羧酸二甲酯
• 英文名称: 3,4-dibromo-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl 3,4-dibromo-1H-pyrrole-2,5-dicarboxylate；3,4-dibromo-pyrrole-2,5-dicarboxylic acid dimethyl ester；3,4-Dibrom-pyrrol-2,5-dicarbonsaeure-dimethylester
• CAS: 473401-83-1
• 化学式: C₈H₇Br₂NO₄
• 分子量: 340.956
• InChiKey: NFAUQKWYXQETPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3,4-二溴-1H-吡咯-2,5-二羧酸 二甲酯 在 四(三苯基膦)钯 三溴化硼 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 6.5h， 生成 3,4-bis(4-hydroxyphenyl)-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Efficient relay syntheses and assessment of the DNA-cleaving properties of the pyrrole alkaloid derivatives permethyl storniamide A, lycogalic acid A dimethyl ester, and the halitulin core

  摘要：

  Palladium catalyzed Suzuki- and Negishi cross coupling reactions are used to convert the now readily available 3,4-dibromopyrrole derivatives 13 and 26 into the core structures of different pyrrole alkaloids. Several compounds of this series exhibit respectable cytotoxicity and resensitize multidrug resistant (MDR) cancer cell lines at non-toxic concentrations. Cytotoxicity and MDR reversal can be efficiently uncoupled by per-O-methylation of the peripheral hydroxyl groups. For the storniamide core structure 9 it is demonstrated that this chemical modification goes hand in hand with a complete loss of the DNA-cleaving capacity of the alkaloid. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00637-3
• 作为产物：
  描述：

  2-吡咯甲酸甲酯 在 iron(III)-acetylacetonate 、 溴 作用下， 以 四氯化碳 、 水 为溶剂， 生成 3,4-二溴-1H-吡咯-2,5-二羧酸 二甲酯
  参考文献：
  名称：

  (+)-spiroindimicin A 及其同系物的全合成揭示了它们的抗寄生虫活性

  摘要：

  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，

  DOI：

  10.1039/d1sc02838c

文献信息

• Lynamicin D an antimicrobial natural product affects splicing by inducing the expression of SR protein kinase 1
  作者：Ioanna Sigala、George Ganidis、Savvas Thysiadis、Alexandros L. Zografos、Thomas Giannakouros、Vasiliki Sarli、Eleni Nikolakaki

  DOI：10.1016/j.bmc.2017.01.025

  日期：2017.3

  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.
• Ciamician; Silber, Chemische Berichte, 1887, vol. 20, p. 2600
  作者：Ciamician、Silber

  DOI：——

  日期：——
• Efficient relay syntheses and assessment of the DNA-cleaving properties of the pyrrole alkaloid derivatives permethyl storniamide A, lycogalic acid A dimethyl ester, and the halitulin core
  作者：Alois Fürstner、Helga Krause、Oliver R Thiel

  DOI：10.1016/s0040-4020(02)00637-3

  日期：2002.8

  Palladium catalyzed Suzuki- and Negishi cross coupling reactions are used to convert the now readily available 3,4-dibromopyrrole derivatives 13 and 26 into the core structures of different pyrrole alkaloids. Several compounds of this series exhibit respectable cytotoxicity and resensitize multidrug resistant (MDR) cancer cell lines at non-toxic concentrations. Cytotoxicity and MDR reversal can be efficiently uncoupled by per-O-methylation of the peripheral hydroxyl groups. For the storniamide core structure 9 it is demonstrated that this chemical modification goes hand in hand with a complete loss of the DNA-cleaving capacity of the alkaloid. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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，