dimethyl 3,4-bis(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxylate | 473401-85-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: dimethyl 3,4-bis(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxylate
• CAS: 473401-85-3
• 化学式: C₂₂H₂₁NO₆
• 分子量: 395.412
• InChiKey: FSWNFOYZPVRNDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  86.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 3,4-bis(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxylate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 0.75h， 以90%的产率得到methyl 3,4-bis(4-methoxyphenyl)-5-(hydroxymethyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Selective Mono-reduction of Pyrrole-2,5 and 2,4-Dicarboxylates

  摘要：

  吡咯-2,5-二羧酸酯在0°C下使用3倍等摩尔的二异丁基铝氢化物迅速且选择性地还原为相应的单醇。吡咯-2,4-二羧酸酯显示出相同的反应性；然而，吡咯-3,4-二羧酸酯的选择性有所降低。当吡咯-2,5-二羧酸酯的氮原子被苄基保护时，选择性单还原不再发生。考虑到在相同条件下呋喃-2,5-二羧酸酯并未产生相应的单醇，显然，未保护的吡咯氮原子在此选择性单还原反应中起着重要作用。

  DOI：

  10.1248/cpb.c16-00122
• 作为产物：
  描述：

  methyl 3-(4-methoxyphenyl)-2-oxopropanoate 在 碘 ammonium hydroxide 、 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 为溶剂， 以67%的产率得到dimethyl 3,4-bis(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxylate
  参考文献：
  名称：

  Synthesis of Simple 3,4-Diarylpyrrole-2,5-dicarboxylic Acids and Lukianol A by Oxidative Condensation of 3-Arylpyruvic Acids with Ammonia

  摘要：

  在氨存在下，通过芳基丙酮酸或芳基丙酮酸盐的氧化二聚，合成了 3,4- 二芳基和 3,4- 二吲哚基吡咯-2,5-二羧酸的几种衍生物，其中包括lukogalic 酸 A 和两种 Halomonas 代谢物。该反应可用于苜蓿醇 A 的短期合成。

  DOI：

  10.1055/s-2007-965876

文献信息

• Cu/Mn Co-oxidized Cyclization for the Synthesis of Highly Substituted Pyrrole Derivatives from Amino Acid Esters: A Strategy for the Biomimetic Syntheses of Lycogarubin C and Chromopyrrolic Acid
  作者：Nini Zhou、Tao Xie、Lin Liu、Zhixiang Xie

  DOI：10.1021/jo500740w

  日期：2014.7.3

  An effective and concise approach to synthesis of tetrasubstituted pyrroles from readily available amino acid esters by the promotion of Cu(OAc)2 in conjunction with Mn(OAc)3 has been developed. This reaction proceeds through multiple dehydrogenations, deamination, and oxidative cyclization. This oxidized system tolerates substrates bearing various electron-donating or electron-withdrawing groups.

  通过促进Cu（OAc）2与Mn（OAc）3的结合，已经开发了一种有效，简洁的方法，可以从容易获得的氨基酸酯中合成四取代的吡咯。该反应通过多次脱氢，脱氨基和氧化环化而进行。这种氧化的系统可以承受带有各种给电子或吸电子基团的底物。用这种方法，已经有效地制备了几种天然产物的关键中间体，并且高效地完成了糖木蛋白C和色吡咯酸的全部合成。
• 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。
• A General Method for the Synthesis of N-Unsubstituted 3,4-Diarylpyrrole-2,5-dicarboxylates
  作者：Masatomo Iwao、Tsutomu Fukuda、Yukie Hayashida

  DOI：10.3987/com-08-s(f)89

  日期：——

  A general method for the synthesis of N-unsubstituted 3,4-diarylpyrrole-2,5-dicarboxylates (3) has been developed. The key reactions involved are the Hinsberg-type synthesis of dimethyl N-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylate (6) followed by palladium-catalyzed Suzuki-Miyaura coupling of its bis-triflate derivative (7). The N-benzyl protecting group of the resulting 3,4-diarylpyrrole-2,5-dicarboxylates (8) is cleanly removed under hydrogenolytic or solvolytic conditions.
• 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.