1-cyano-2-[[N-(2-aminoethyl)]carbamoyl]indolizine | 825639-30-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 1-cyano-2-[[N-(2-aminoethyl)]carbamoyl]indolizine
• 英文别名: N-(2-Aminoethyl)-1-cyanoindolizine-2-carboxamide；N-(2-aminoethyl)-1-cyanoindolizine-2-carboxamide
• CAS: 825639-30-3
• 化学式: C₁₂H₁₂N₄O
• 分子量: 228.253
• InChiKey: ZIUUXTMAURRZOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  83.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-cyano-2-[[N-(2-aminoethyl)]carbamoyl]indolizine 、 N-cyano-S-methyl-N'-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]isothiourea 在 吡啶 作用下， 反应 3.0h， 以8%的产率得到1-cyano-indolizine-2-carboxylic acid (2-{N'-cyano-N''-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]-guanidino}ethyl)amide
  参考文献：
  名称：

  Fluorescent ligands for the histamine H2 receptor: synthesis and preliminary characterization

  摘要：

  -3-[3-(Pipesidinomethyl)pllenoxy]alkyl, N-cyano-N'-[omega-[3-(l-pipes-idinylinetllyl)phenoxy]alkyl]guanidine and 2-(5-methyl4-imidazolyl)nnethyl thioethyl derivatives containing fluorescent functionalities were synthesized and the histamine H-2, receptor affinity was evaluated using the H, antagonist [I-125]-aminopotentidine. The compounds exhibited weak to potent H-2, receptor affinity with pK(1) values ranging from <4 to 8.85. The highest H, receptor affinity was observed for N-cyailo-N'-[omega-[3-(1-piperidinylinethyl)phenoxy]alkyl]guanidines substituted with methylanthranilate (13), cyanoindolizine (6) and cyanoisoindole (11) moieties via an ethyl or propyl linker. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.018
• 作为产物：
  描述：

  ethyl 1-cyanoindolizine-2-carboxylate 、 乙二胺 反应 5.0h， 以41%的产率得到1-cyano-2-[[N-(2-aminoethyl)]carbamoyl]indolizine
  参考文献：
  名称：

  Fluorescent ligands for the histamine H2 receptor: synthesis and preliminary characterization

  摘要：

  -3-[3-(Pipesidinomethyl)pllenoxy]alkyl, N-cyano-N'-[omega-[3-(l-pipes-idinylinetllyl)phenoxy]alkyl]guanidine and 2-(5-methyl4-imidazolyl)nnethyl thioethyl derivatives containing fluorescent functionalities were synthesized and the histamine H-2, receptor affinity was evaluated using the H, antagonist [I-125]-aminopotentidine. The compounds exhibited weak to potent H-2, receptor affinity with pK(1) values ranging from <4 to 8.85. The highest H, receptor affinity was observed for N-cyailo-N'-[omega-[3-(1-piperidinylinethyl)phenoxy]alkyl]guanidines substituted with methylanthranilate (13), cyanoindolizine (6) and cyanoisoindole (11) moieties via an ethyl or propyl linker. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.018

文献信息

• Fluorescent ligands for the histamine H2 receptor: synthesis and preliminary characterization
  作者：Sarel F. Malan、Andre van Marle、Wiro M. Menge、Valentina Zuliana、Marcel Hoffman、Henk Timmerman、Rob Leurs

  DOI：10.1016/j.bmc.2004.09.018

  日期：2004.12

  -3-[3-(Pipesidinomethyl)pllenoxy]alkyl, N-cyano-N'-[omega-[3-(l-pipes-idinylinetllyl)phenoxy]alkyl]guanidine and 2-(5-methyl4-imidazolyl)nnethyl thioethyl derivatives containing fluorescent functionalities were synthesized and the histamine H-2, receptor affinity was evaluated using the H, antagonist [I-125]-aminopotentidine. The compounds exhibited weak to potent H-2, receptor affinity with pK(1) values ranging from <4 to 8.85. The highest H, receptor affinity was observed for N-cyailo-N'-[omega-[3-(1-piperidinylinethyl)phenoxy]alkyl]guanidines substituted with methylanthranilate (13), cyanoindolizine (6) and cyanoisoindole (11) moieties via an ethyl or propyl linker. (C) 2004 Elsevier Ltd. All rights reserved.