2-benzoyl-3-phenylpyrrole-4-carboxylic acid ethyl ester | 246868-72-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-benzoyl-3-phenylpyrrole-4-carboxylic acid ethyl ester
• 英文别名: ethyl 5-benzoyl-4-phenyl-1H-pyrrole-3-carboxylate
• CAS: 246868-72-4
• 化学式: C₂₀H₁₇NO₃
• 分子量: 319.36
• InChiKey: YMFZPHTVQIFYRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 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：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzoyl-3-phenylpyrrole-4-carboxylic acid ethyl ester 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以85%的产率得到2-benzoyl-5-bromo-3-phenylpyrrole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  乙烯基亚胺盐衍生物在有效合成含生物碱Rigidin和Rigidin E的吡咯中的应用

  摘要：

  描述了关于经由乙烯基亚胺盐合成含有海洋天然产物Rigidin和Rigidin E的吡咯的研究。成功的策略依赖于从钒胺盐形成2，4-二取代的吡咯，然后在吡咯的5位进行酰化。吡咯3位的卤代和氨基羰基化，然后C-2处的酯基水解，然后Curtius重排生成吡咯并嘧啶骨架。最后的脱保护步骤完成了Rigidin和Rigidin E的合成。

  DOI：

  10.1016/j.tet.2006.06.047
• 作为产物：
  描述：

  ethyl (E)-2-(((4-methylphenyl)sulfonamido)methyl)-3-phenylacrylate 在 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 48.0h， 生成 2-benzoyl-3-phenylpyrrole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  从Baylis-Hillman加合物开始合成多取代的吡咯

  摘要：

  我们通过苯甲酰溴与氮杂-Baylis-Hillman加合物1a - d或其重排衍生物5a - e的反应合成了多取代的吡咯衍生物4a - e，7a - c和10a - d。通过连续的N-烷基化，迈克尔加成，消除对甲苯亚磺酸和氧化芳构化过程来合成吡咯。

  DOI：

  10.1016/j.tetlet.2007.04.022

文献信息

• 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; Burham; Byrd, Pharmazie, 1999, vol. 54, # 9, p. 691 - 697
  作者：Gupton、Burham、Byrd、Krumpe、Stokes、Shuford、Winkle、Webb、Warren、Barnes、Henry、Hall

  DOI：——

  日期：——
• Synthesis of poly-substituted pyrroles starting from the Baylis–Hillman adducts
  作者：Hyun Seung Lee、Jeong Mi Kim、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2007.04.022

  日期：2007.6

  We synthesized poly-substituted pyrrole derivatives 4a–e, 7a–c and 10a–d from the reaction of phenacyl bromide and the aza-Baylis–Hillman adducts 1a–d or their rearranged derivatives 5a–e. The pyrroles were synthesized via the successive N-alkylation, Michael addition, elimination of p-toluenesulfinic acid and oxidative aromatization processes.

  我们通过苯甲酰溴与氮杂-Baylis-Hillman加合物1a - d或其重排衍生物5a - e的反应合成了多取代的吡咯衍生物4a - e，7a - c和10a - d。通过连续的N-烷基化，迈克尔加成，消除对甲苯亚磺酸和氧化芳构化过程来合成吡咯。
• The application of vinylogous iminium salt derivatives to an efficient synthesis of the pyrrole containing alkaloids Rigidin and Rigidin E
  作者：John T. Gupton、Edith J. Banner、Austin B. Scharf、Bradley K. Norwood、Rene P.F. Kanters、Raymond N. Dominey、Jonathan E. Hempel、Anastasia Kharlamova、Itta Bluhn-Chertudi、Charles R. Hickenboth、Barrett A. Little、Melissa D. Sartin、Matthew B. Coppock、Keith E. Krumpe、Bruce S. Burnham、Herman Holt、Karen X. Du、Kartik M. Keertikar、Anthony Diebes、Shahnaz Ghassemi、James A. Sikorski

  DOI：10.1016/j.tet.2006.06.047

  日期：2006.8

  Studies directed on the synthesis of the pyrrole containing marine natural products Rigidin and Rigidin E via vinylogous iminium salts are described. The successful strategy relies on the formation of a 2,4-disubstituted pyrrole from a vinamidinium salt followed by acylation at the 5-position of pyrrole. Halogenation and aminocarbonylation at the 3-position of pyrrole followed by hydrolysis of the ester

  描述了关于经由乙烯基亚胺盐合成含有海洋天然产物Rigidin和Rigidin E的吡咯的研究。成功的策略依赖于从钒胺盐形成2，4-二取代的吡咯，然后在吡咯的5位进行酰化。吡咯3位的卤代和氨基羰基化，然后C-2处的酯基水解，然后Curtius重排生成吡咯并嘧啶骨架。最后的脱保护步骤完成了Rigidin和Rigidin E的合成。