2-Carbethoxy-4-(4-bromophenyl)pyrrole | 127572-57-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-Carbethoxy-4-(4-bromophenyl)pyrrole
• 英文别名: ethyl 4-(4-bromophenyl)pyrrole-2-carboxylate；ethyl 4-(4-bromophenyl)-1H-pyrrole-2-carboxylate
• CAS: 127572-57-0
• 化学式: C₁₃H₁₂BrNO₂
• 分子量: 294.148
• InChiKey: MRGHPPZAWZLQBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Carbethoxy-4-(4-bromophenyl)pyrrole 在 pyridinium hydrobromide perbromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2,4-dibromo-5-carbethoxy-3-(4-bromophenyl)pyrrole
  参考文献：
  名称：

  Developing novel C-4 analogues of pyrrole-based antitubulin agents: weak but critical hydrogen bonding in the colchicine site

  摘要：

  报告了一系列与 3,5-二溴-4-(3,4-二甲氧基苯基)-1H-吡咯-2-羧酸有关的吡咯化合物的合成、生物学评价和分子建模，对 C-4 取代基进行了评估和优化。微管解聚活性的关键因素似乎是在原本疏水性的子口袋 A 中存在一个位置适当的 Cys241β 受体。

  DOI：

  10.1039/c2md20320k
• 作为产物：
  描述：

  (4-溴苯基)乙炔 、 异氰基乙酸乙酯 在 nano-copper⁽⁰⁾ stabilized on alumina 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以72%的产率得到2-Carbethoxy-4-(4-bromophenyl)pyrrole
  参考文献：
  名称：

  Nano-copper catalysed highly regioselective synthesis of 2,4-disubstituted pyrroles from terminal alkynes and isocyanides

  摘要：

  从Cu-Al水滑石制备的氧化铝上稳定的纳米铜(0)已被报道用于从未活化的末端芳香/脂肪炔烃和异氰酸酯完全区域选择性合成2,4-二取代吡咯。

  DOI：

  10.1039/c5cc04166j

文献信息

• The application of vinylogous iminium salt derivatives and microwave accelerated Vilsmeier–Haack reactions to efficient relay syntheses of the polycitone and storniamide natural products
  作者：John T. Gupton、Edith J. Banner、Melissa D. Sartin、Matthew B. Coppock、Jonathan E. Hempel、Anastasia Kharlamova、Daniel C. Fisher、Ben C. Giglio、Kristin L. Smith、Matt J. Keough、Timothy M. Smith、Rene P.F. Kanters、Raymond N. Dominey、James A. Sikorski

  DOI：10.1016/j.tet.2008.03.038

  日期：2008.5

  vinylogous iminium salts and microwave accelerated Vilsmeier-Haack formylations are described. The successful strategy relies on the formation of a 2,4-disubstituted pyrrole or a 2,3,4-trisubstituted pyrrole from a vinamidinium salt or vinamidinium salt derivative followed by formylation at the 5-position of the pyrrole. Subsequent transformations of the selectively formylated pyrroles lead to efficient

  描述了通过乙烯基亚胺盐和微波加速 Vilsmeier-Haack 甲酰化合成聚氯乙烯和 storniamide 天然产物的研究。成功的策略依赖于从 vinamidinium 盐或 vinamidinium 盐衍生物形成 2,4-二取代的吡咯或 2,3,4-三取代的吡咯，然后在吡咯的 5-位进行甲酰化。选择性甲酰化吡咯的后续转化导致含有天然产物的相应吡咯的有效和区域控制的中继合成。
• Application of 2-substituted vinamidinium salts to the synthesis of 2,4-disubstituted pyrroles
  作者：John T. Gupton、Dale A. Krolikowski、Richard H. Yu、Steve W. Riesinger、James A. Sikorski

  DOI：10.1021/jo00302a047

  日期：1990.7
• Synthesis and Cytotoxicity of 2,4-Disubstituted and 2,3,4-Trisubstituted Brominated Pyrroles in Murine and Human Cultured Tumor Cells
  作者：John T. Gupton、Bruce S. Burham、Keith Krumpe、Karen Du、James A. Sikorski、Amy E. Warren、Cheryl R. Barnes、Iris. H. Hall

  DOI：10.1002/(sici)1521-4184(200001)333:1<3::aid-ardp3>3.0.co;2-4

  日期：2000.1

  The 2,4-disubstituted and 2,3,4-trisubstituted brominated pyrroles were successfully prepared and demonstrated potent cytotoxicity against the growth of suspended murine and human tumors, i.e. leukemia and lymphomas, acute monocytic leukemia, and HeLa-S-3 uterine carcinoma. The brominated compounds were more selective in inhibiting the growth of tumors derived from human solid tumors. Nevertheless activity with some of the derivatives occurred in the human KB nasopharynx, SW-480 colon, and HCT ileum adenocarcinoma, and lung A549 carcinoma screens. In Tmolt(4) T cell leukemia cells DNA synthesis was reduced over 60 min from 25 to 100 mu M followed by RNA synthesis reduction. De novo purine synthesis was retarded with the regulatory enzyme PRPP-amino transferase being markedly inhibited with less effects dehydrogenase, dihydrofolate reductase,, nucleoside kinases. After 60 min incubations d[TTP] and d[GTP] pools were marginally reduced. In vitro ct-DNA studies that the agents may affect the DNA molecule itself with DNA viscosity and the Tmolt(4) studies suggest that DNA cross-linking of DNA strands may be present.
• GUPTON, JOHN T.;KROLIKOWSKI, DALE A.;YU, RICHARD H.;RIESINGER, STEVE W.;S+, J. ORG. CHEM., 55,(1990) N5, C. 4735-4740
  作者：GUPTON, JOHN T.、KROLIKOWSKI, DALE A.、YU, RICHARD H.、RIESINGER, STEVE W.、S+

  DOI：——

  日期：——