methyl 3-(1-(N,N-dimethylsulfamoyl)imidazol-4-yl)-2-propenoate | 220378-46-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 3-(1-(N,N-dimethylsulfamoyl)imidazol-4-yl)-2-propenoate
• 英文别名: Methyl 3-[1-(dimethylsulfamoyl)imidazol-4-yl]prop-2-enoate
• CAS: 220378-46-1
• 化学式: C₉H₁₃N₃O₄S
• 分子量: 259.286
• InChiKey: UGYDKMIARYXNQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-(1-(N,N-dimethylsulfamoyl)imidazol-4-yl)-2-propenoate 在 氯化亚砜 、 二异丁基氢化铝 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (2E)-3-(1-dimethylsulfamoyl-1H-imidazol-4-yl)prop-2-en-1-amine
  参考文献：
  名称：

  4-乙烯基咪唑的分子内 Diels-Alder 化学†

  摘要：

  描述了在分子内 Diels-Alder 反应中作为二烯组分的 4-乙烯基咪唑的研究。在这些研究过程中，评估了影响环加成反应的几个参数，包括咪唑保护基团的性质、亲二烯体的类型和连接基团。这些研究确定氨基接头通常比醚或酯更有效。在大多数情况下，环加成是高度立体选择性的，导致形成源自反过渡态的产物。吡咯-咪唑生物碱ageliferin的多取代四氢苯并咪唑核可以通过使用假二聚体4-乙烯基咪唑构建。

  DOI：

  10.1039/c0ob00657b
• 作为产物：
  描述：

  二甲胺基磺酰氯 、 3-(1H-咪唑-4-基)丙烯酸甲酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以61%的产率得到methyl 3-(1-(N,N-dimethylsulfamoyl)imidazol-4-yl)-2-propenoate
  参考文献：
  名称：

  Antiviral effect of ribonuclease conjugated oligodeoxynucleotides targeting the IRES RNA of the hepatitis C virus

  摘要：

  Hepatitis C virus (HCV) translation initiation is mediated by a highly structured and conserved RNA, termed the Internal Ribosome Entry Site (IRES), located at the 5'-end of its single stranded RNA genome. It is a key target for the development of new antiviral compounds. Here we made use of the recently developed HCV cell culture system to test the antiviral activity of artificial ribonucleases consisting of imidazole(s) linked to antisense oligodeoxynucleotides targeting the HCV IRES. Results from the cell culture model indicate that the naked antisense oligodeoxynucleotide displayed an efficient antiviral activity. Despite the increased activity observed with the addition of imidazole moieties when tested with the cell-free system, it appears that these improvements were not reproduced in the cellular model. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.139

文献信息

• Efficient Preparation of Urocanic Acid Derivatives from Histidine
  作者：Carl J. Lovely、Rasapalli Sivappa、Sabuj Mukherjee、Thomas Doundoulakis、Heather M. Lima、Muhammed Yousufuddin

  DOI：10.3987/com-09-s(s)127

  日期：——

  Urocanic acid derivatives have served as useful starting materials in several total synthesis endeavors in our lab. This paper describes a convenient, large-scale synthesis of several derivatives of urocanic acid via the net elimination of ammonia from histidine.

  在我们实验室的几项全合成工作中，尿刊酸衍生物已作为有用的起始材料。本文描述了通过从组氨酸中净消除氨来方便、大规模地合成尿刊酸的几种衍生物。
• Intramolecular Diels–Alder chemistry of 4-vinylimidazoles
  作者：Yong He、Pasupathy Krishnamoorthy、Heather M. Lima、Yingzhong Chen、Haiyan Wu、Rasapalli Sivappa、H. V. Rasika Dias、Carl J. Lovely

  DOI：10.1039/c0ob00657b

  日期：——

  An investigation of 4-vinylimidazoles as diene components in the intramolecular Diels–Alder reaction is described. In the course of these studies several parameters affecting the cycloaddition were evaluated including the nature of the imidazole protecting group, the type of dienophile and the linking group. These investigations established that amino linkers were generally more effective than either

  描述了在分子内 Diels-Alder 反应中作为二烯组分的 4-乙烯基咪唑的研究。在这些研究过程中，评估了影响环加成反应的几个参数，包括咪唑保护基团的性质、亲二烯体的类型和连接基团。这些研究确定氨基接头通常比醚或酯更有效。在大多数情况下，环加成是高度立体选择性的，导致形成源自反过渡态的产物。吡咯-咪唑生物碱ageliferin的多取代四氢苯并咪唑核可以通过使用假二聚体4-乙烯基咪唑构建。
• Antiviral effect of ribonuclease conjugated oligodeoxynucleotides targeting the IRES RNA of the hepatitis C virus
  作者：Carly Gamble、Maud Trotard、Jacques Le Seyec、Valérie Abreu-Guerniou、Nicolas Gernigon、Fabienne Berrée、Bertrand Carboni、Brice Felden、Reynald Gillet

  DOI：10.1016/j.bmcl.2009.04.139

  日期：2009.7

  Hepatitis C virus (HCV) translation initiation is mediated by a highly structured and conserved RNA, termed the Internal Ribosome Entry Site (IRES), located at the 5'-end of its single stranded RNA genome. It is a key target for the development of new antiviral compounds. Here we made use of the recently developed HCV cell culture system to test the antiviral activity of artificial ribonucleases consisting of imidazole(s) linked to antisense oligodeoxynucleotides targeting the HCV IRES. Results from the cell culture model indicate that the naked antisense oligodeoxynucleotide displayed an efficient antiviral activity. Despite the increased activity observed with the addition of imidazole moieties when tested with the cell-free system, it appears that these improvements were not reproduced in the cellular model. (C) 2009 Elsevier Ltd. All rights reserved.