(Z)-2-(4-ethenyl-3-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide | 329314-75-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: (Z)-2-(4-ethenyl-3-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide
• 英文别名: 2-[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]acetamide；(2Z)-2-(4-ethenyl-3-methyl-5-oxopyrrol-2-ylidene)acetamide
• CAS: 329314-75-2
• 化学式: C₉H₁₀N₂O₂
• 分子量: 178.191
• InChiKey: JJDLLVZMTMEVBY-DAXSKMNVSA-N

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl (Z)-(4-bromo-3-methyl-5-oxofuran-2(5H)-ylidene)ethanoate 在 bis-triphenylphosphine-palladium(II) chloride 、 草酰氯 、 ammonium acetate 、 氨 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 cesium fluoride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 (Z)-2-(4-ethenyl-3-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide
  参考文献：
  名称：

  Total synthesis and characterization of the bilirubin oxidation product (Z)-2-(4-ethenyl-3-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide (Z-BOX B)

  摘要：

  Bilirubin oxidation end products (BOXes) show significant physiological effects and are connected to severe diseases such as subarachnoid hemorrhage induced cerebral vasospasm. BOX B (2-(4-ethenyl-3methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide) was prepared via a five-step synthesis starting from methyl (4-bromo-3-methyl-5-oxofuran-2(5H)-ylidene)ethanoate that was vinylated and then reacted with NH4OAc, LiOH, (COCl)(2), and finally with ammonia yielding Z-BOX B. Derivatives of Z-BOX A and Z-BOX B with [N-15]labeled lactam rings were synthesized accordingly. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.108

文献信息

• Isolation and Identification of Intermediates of the Oxidative Bilirubin Degradation
  作者：Marcel Ritter、Raphael A. Seidel、Peter Bellstedt、Bernd Schneider、Michael Bauer、Helmar Görls、Georg Pohnert

  DOI：10.1021/acs.orglett.6b02287

  日期：2016.9.2

  Four endogenous products of oxidative bilirubin degradation were isolated and fully characterized. The constitutional isomers belong to the propentdyopents (PDPs). Their structures and further oxidative transformations to biologically active bilirubin oxidation end products (Z-BOXes) are reported. Using liquid chromatography–mass spectrometry protocols, PDPs were detected in human bile and gallstones

  氧化胆红素降解的四个内源性产物被分离并得到充分表征。组成异构体属于propentdyopents（PDP）。据报道它们的结构和进一步的氧化转化为生物活性胆红素氧化终产物（Z- BOXes）。使用液相色谱-质谱联用规程，在人的胆汁和胆结石中检测到了PDP。鉴于最近对将BOX作为脑血管痉挛和肝功能障碍的效应子的兴趣，共同出现的PDP代表了要考虑的另一种潜在活性化合物。
• Degradation fragments
  申请人：——

  公开号：US20030162826A1

  公开（公告）日：2003-08-28

  A pharmaceutical composition comprising a compound of formula (I) wherein X is an electron withdrawing group, Y 1 is hydrogen, alkyl, alkenyl, alkynyl, aryl, heterocyclyl, —SO 2 R 4 , —CO 2 R 4 , —CONHR 4 or —COR 4 , and each of R 1 , R 2 and R 4 , which may be the same or different, is hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl or heterocyclyl, or a compound of formula (II) wherein each of Y 2 and Y 3 , which may be the same or different, is hydrogen, alkyl, alkenyl, alkynyl, aryl, heterocyclyl, —SO 2 R 9 , —CO 2 R 9 , —CONHR 9 or —COR 9 , Z is hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, heterocyclyl, —CH═C(NHR 10 )CH((CH 2 ) m CO 2 R 11 )(C═O)CH 3 or —CH 2 (C═O)CH((CH 2 ) m CO 2 R 11 )(C═O)CH 3 , R 8 is —(CH 2 ),CO 2 R 12 , each of R 5 to R 7 and R 9 to R 12 , which may be the same or different, is hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl or heterocyclyl, and each of m and n, which may be the same or different, is 1 to 6 or a compound of formula (III) wherein each of Y 4 to Y 6 , which may be the same or different, is hydrogen, alkyl, alkenyl, alkynyl, aryl, heterocyclyl, —SO 2 R 19 , —CO 2 R 19 , —CONHR 19 or —COR 19 , each of R 16 and R 17 , which may be the same or different, is —(CH 2 ) p CO 2 R 20 , each of R 13 TO R 15 and R 18 to R 20 , which may be the same or different, is hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl or heterocyclyl, and p is 1 to 6, or other photolabile degradation product of bilirubin or biliverdin or derivative of a photolabile degradation fragment of bilirubin or biliverdin, or a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable carrier or diluent. 1

  一种药物组合物，包含式 (I) 的化合物，其中 X 是一个电子僻取基团，Y 1 是氢、烷基、烯基、炔基、芳基、杂环基、-SO 2 R 4 、-CO 2 R 4 、-CONHR 4 或-COR 4 和每个 R 1 , R 2 和 R 4 可以相同或不同，为氢、烷基、环烷基、烯基、环烯基、炔基、芳基或杂环烷基，或式 (II) 的化合物，其中每个 Y 2 和 Y 3 可以相同或不同，为氢、烷基、烯基、环烷基、炔基、芳基、杂环基、-SO 2 R 9 、-CO 2 R 9 , -CONHR 9 或-COR 9 , Z 是氢、烷基、环烷基、烯基、环烯基、炔基、芳基、杂环基、-CH═C(NHR 10 )CH((CH 2 ) m CO 2 R 11 )(C═O)CH 3 或-CH 2 (C═O)CH((CH 2 ) m CO 2 R 11 )(C═O)CH 3 , R 8 是-(CH 2 ）、CO 2 R 12 ，R 5 至 R 7 和 R 9 至 R 12 可相同或不同，为氢、烷基、环烷基、烯基、环烯基、炔基、芳基或杂环基，且 m 和 n（可相同或不同）各为 1 至 6 或式 (III) 化合物，其中 Y 4 至 Y 6 可以相同或不同，为氢、烷基、烯基、炔基、芳基、杂环基、-SO 2 R 19 、-CO 2 R 19 、-CONHR 19 或-COR 19 ，每个 R 16 和 R 17 可以相同或不同，是-(CH 2 ) p CO 2 R 20 ，R 13 至 R 15 和 R 18 至 R 20 可以是相同或不同的氢、烷基、环烷基、烯基、环烯基、炔基、芳基或杂环烷基，且 p 为 1 至 6，或胆红素或胆绿素的其他光降解产物或胆红素或胆绿素的光降解片段的衍生物，或其药学上可接受的盐，连同药学上可接受的载体或稀释剂。 1
• BILIRUBIN OR BILIVERDIN DEGRADATION FRAGMENTS
  申请人：MEDICAL RESEARCH COUNCIL

  公开号：EP1272178B1

  公开（公告）日：2008-01-23
• US7098238B2
  申请人：——

  公开号：US7098238B2

  公开（公告）日：2006-08-29
• US7498421B2
  申请人：——

  公开号：US7498421B2

  公开（公告）日：2009-03-03