3,4-bis(4-hydroxyphenyl)-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3,4-bis(4-hydroxyphenyl)-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl 3,4-di(4-hydroxyphenyl)pyrrol-2,5-dicarboxylate；dimethyl 3,4-bis(4-hydroxyphenyl)-1H-pyrrole-2,5-dicarboxylate
• 化学式: C₂₀H₁₇NO₆
• 分子量: 367.358
• InChiKey: UIALHYNVMBHEBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氧代-3-(4-羟基苯基)丙酸甲酯 在 重氮甲烷 、 碘 、 sodium methylate 作用下， 生成 3,4-bis(4-hydroxyphenyl)-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  粘液霉菌石Ly中3,4-双（吲哚-3-基）吡咯-2,5-二羧酸衍生物的分离与合成

  摘要：

  粘液粘液表皮的子实体含有标题化合物1a–c和2，星形孢菌素（3）和痕量的双辛基马来酰亚胺。乙醇酸通过一锅反应由3-（吲哚-3-基）丙酮酸甲酯合成了二甲酯（1a）。

  DOI：

  10.1016/0040-4039(94)88320-3

文献信息

• Design and Synthesis of 3,4-diarylpyrrole Analogues as Potent Topoisomerase Inhibitors
  作者：Wang Chen、Zili Feng、Xu He、Qiang Zhao、Qi Liang

  DOI：10.2174/1573406414666180226164049

  日期：2018.7.6

  inhibitory activities. OBJECTIVE We present the design, synthesis and antitumor studies of 3,4-diarylprrole derivatives. Their antitumor activities and inhibitory activities against Topo I and Topo IIα of these compounds were assayed. METHODS A series of 3,4-diarylpyrrole analogues have been designed and synthesized. Their antiproliferation activities were evaluated by sulforhodamine B assay on human breast

  背景技术由于具有独特的结构和多重生物活性，含有共同的3，4-二芳基吡咯骨架的天然产物引起了相当大的关注。在我们之前的研究中，合成了糖寡糖C，并显示出对MDAMB-231，A549，PC3和HeLa细胞系的细胞毒性以及拓扑异构酶II的抑制活性。目的我们介绍3,4-二芳基吡咯衍生物的设计，合成和抗肿瘤研究。测定了它们对这些化合物的Topo I和TopoIIα的抗肿瘤活性和抑制活性。方法已设计并合成了一系列3,4-二芳基吡咯类似物。通过磺基罗丹明B测定法对人乳腺癌MDAMB-231，MDA-MB-435和人宫颈癌HeLa细胞的抗增殖活性进行了评估。结果四种化合物对三种细胞系的生长均表现出适度的抑制活性，IC50低于50μM。DNA弛豫分析表明，化合物19o在体外显示出对TopoIIα的有效抑制活性。19o还诱导了MDA-MB-435细胞的DNA断裂，这由彗尾和γ-H2AX病灶的积累证明。19o诱
• Development of novel pyrrole synthesis for the preparation of intermediates of bioactive pyrrole alkaloids
  作者：Eiko Yasui、Masao Wada、Norio Takamura

  DOI：10.1016/j.tetlet.2009.06.012

  日期：2009.8

  We have developed a novel method for the synthesis of 3,4-diarylpyrrole-2,5-dicarboxylates via α-diazo esters, which are easily obtained from phenylalanine derivatives. Utilizing this method, intermediates of bioactive compounds having the structure of 3,4-diarylpyrrole-2,5-dicarboxylates were synthesized.

  我们已经开发了一种通过α-重氮酯合成3,4-二芳基吡咯-2,5-二羧酸酯的新颖方法，该酯很容易从苯丙氨酸衍生物中获得。使用该方法，合成了具有3，4-二芳基吡咯-2，5-二羧酸酯结构的生物活性化合物的中间体。
• 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.
• Isolation and synthesis of 3,4-bis(indol-3-yl)pyrrole-2,5-dicarboxylic acid derivatives from the slime mould Lycogala epidendrum
  作者：Rita Fröde、Claudia Hinze、Ingrid Josten、Bettina Schmidt、Bert Steffan、Wolfgang Steglich

  DOI：10.1016/0040-4039(94)88320-3

  日期：1994.3

  Fruit bodies of the myxomycete Lycogala epidendrum contain the title compounds 1a–c and 2, staurosporinone (3) and traces of bisindolylmaleimides. Lycogalic acid A dimethyl ester (1a) has been synthesized from methyl 3-(indol-3-yl)pyruvate in a one-pot reaction.

  粘液粘液表皮的子实体含有标题化合物1a–c和2，星形孢菌素（3）和痕量的双辛基马来酰亚胺。乙醇酸通过一锅反应由3-（吲哚-3-基）丙酮酸甲酯合成了二甲酯（1a）。