[1-benzyl-3-hexyl-4-(methoxycarbonyl)-1H-pyrrol-2-yl]acetic acid | 738658-87-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: [1-benzyl-3-hexyl-4-(methoxycarbonyl)-1H-pyrrol-2-yl]acetic acid
• 英文别名: 2-(1-Benzyl-3-hexyl-4-methoxycarbonylpyrrol-2-yl)acetic acid
• CAS: 738658-87-2
• 化学式: C₂₁H₂₇NO₄
• 分子量: 357.45
• InChiKey: ZQRVUHVKMMTXOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [1-benzyl-3-hexyl-4-(methoxycarbonyl)-1H-pyrrol-2-yl]acetic acid 在 silica gel 作用下， 反应 0.25h， 以95%的产率得到methyl 1-benzyl-4-hexyl-5-methyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  A Diversity-Oriented Strategy for the Construction of Tetrasubstituted Pyrroles via Coupled Domino Processes

  摘要：

  A new microwave-assisted rearrangement of 1,3-oxazolidines scaffolds is the basis for a new, metal-free, direct, and modular construction of tetrasubstituted pyrroles from terminal-conjugated alkynes, aldehydes, and primary amines. This new reaction manifold entails two linked domino processes in a one-pot manner with both atom- and bond-efficiency and under very simple and environment-friendly experimental conditions.

  DOI：

  10.1021/ja047396p
• 作为产物：
  描述：

  methyl 4-{[(1E)-3-methoxy-3-oxo-1-propenyl]oxy}-2-decynoate 在 lithium hydroxide 、 silica gel 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 [1-benzyl-3-hexyl-4-(methoxycarbonyl)-1H-pyrrol-2-yl]acetic acid
  参考文献：
  名称：

  Antiproliferative activity in HL60 cells by tetrasubstituted pyrroles: a structure–activity relationship study

  摘要：

  A number of tetrasubstituted pyrrole derivatives have been synthesized and evaluated for their in vitro antiproliferative activities using the human promyelocytic leukemia cell line HL60. Tetrasubstituted pyrroles are obtained by irradiation of a silica gel absorbed mixture of a conjugated alkynoate and a primary amine. Active compounds exhibited GI(50) values in the range 445 mu M, and only six products showed TGI values within the evaluation range. A structure-activity relationship is also discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.069

文献信息

• A Diversity-Oriented Strategy for the Construction of Tetrasubstituted Pyrroles via Coupled Domino Processes
  作者：David Tejedor、David González-Cruz、Fernando García-Tellado、José Juan Marrero-Tellado、Matías López Rodríguez

  DOI：10.1021/ja047396p

  日期：2004.7.14

  A new microwave-assisted rearrangement of 1,3-oxazolidines scaffolds is the basis for a new, metal-free, direct, and modular construction of tetrasubstituted pyrroles from terminal-conjugated alkynes, aldehydes, and primary amines. This new reaction manifold entails two linked domino processes in a one-pot manner with both atom- and bond-efficiency and under very simple and environment-friendly experimental conditions.
• Antiproliferative activity in HL60 cells by tetrasubstituted pyrroles: a structure–activity relationship study
  作者：José M. Padrón、David Tejedor、Alicia Santos-Expósito、Fernando García-Tellado、Víctor S. Martín、Jesús Villar

  DOI：10.1016/j.bmcl.2005.03.069

  日期：2005.5

  A number of tetrasubstituted pyrrole derivatives have been synthesized and evaluated for their in vitro antiproliferative activities using the human promyelocytic leukemia cell line HL60. Tetrasubstituted pyrroles are obtained by irradiation of a silica gel absorbed mixture of a conjugated alkynoate and a primary amine. Active compounds exhibited GI(50) values in the range 445 mu M, and only six products showed TGI values within the evaluation range. A structure-activity relationship is also discussed. (c) 2005 Elsevier Ltd. All rights reserved.