2-[3-[4-(toluene-4-sulfonyl)-4,5-dihydrooxazol-5-yl]propyl]pyridine | 639089-33-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[3-[4-(toluene-4-sulfonyl)-4,5-dihydrooxazol-5-yl]propyl]pyridine
• 英文别名: 4-(4-Methylphenyl)sulfonyl-5-(3-pyridin-2-ylpropyl)-4,5-dihydro-1,3-oxazole
• CAS: 639089-33-1
• 化学式: C₁₈H₂₀N₂O₃S
• 分子量: 344.434
• InChiKey: QQJCKHLQKAGIAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[3-[4-(toluene-4-sulfonyl)-4,5-dihydrooxazol-5-yl]propyl]pyridine 在 palladium on activated charcoal 、 Rh on carbon 氨 、 氢溴酸 、 氢气 作用下， 以 乙醇 为溶剂， 90.0~110.0 ℃ 、10.13 MPa 条件下， 反应 72.0h， 生成 (+/-)-VUF 5683
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Conformationally Constrained Histamine H₃ Receptor Agonists

  摘要：

  Immepip, a conformationally constrained analogue of the histamine congener imbutamine, shows high affinity and functional activity on the human H-3 receptor. Using histamine and its homologues as prototypes, other rigid analogues containing either a piperidine or pyrrolidine ring in the side chain were synthesized and tested for their activities at the human H-3 receptor and the closely related H-4 receptor. In the series of piperidine containing analogues, immepip was found to be the most potent H-3 receptor agonist, whereas its propylene analogue 13a was identified as a high-affinity neutral antagonist for the human H-3 receptor. Moreover, replacement of the piperidine ring of immepip by a pyrrolidine ring led to a pair of enantiomers that show a distinct stereoselectivity at the human H-3 and H-4 receptor.

  DOI：

  10.1021/jm030905y
• 作为产物：
  描述：

  2-[3-(1,3-Dioxolan-2-yl)prop-1-enyl]pyridine 在 palladium on activated charcoal 盐酸 、 氰化钠 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 26.5h， 生成 2-[3-[4-(toluene-4-sulfonyl)-4,5-dihydrooxazol-5-yl]propyl]pyridine
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Conformationally Constrained Histamine H₃ Receptor Agonists

  摘要：

  Immepip, a conformationally constrained analogue of the histamine congener imbutamine, shows high affinity and functional activity on the human H-3 receptor. Using histamine and its homologues as prototypes, other rigid analogues containing either a piperidine or pyrrolidine ring in the side chain were synthesized and tested for their activities at the human H-3 receptor and the closely related H-4 receptor. In the series of piperidine containing analogues, immepip was found to be the most potent H-3 receptor agonist, whereas its propylene analogue 13a was identified as a high-affinity neutral antagonist for the human H-3 receptor. Moreover, replacement of the piperidine ring of immepip by a pyrrolidine ring led to a pair of enantiomers that show a distinct stereoselectivity at the human H-3 and H-4 receptor.

  DOI：

  10.1021/jm030905y

文献信息

• Identification of 4-(1<i>H</i>-Imidazol-4(5)-ylmethyl)pyridine (Immethridine) as a Novel, Potent, and Highly Selective Histamine H₃ Receptor Agonist
  作者：Ruengwit Kitbunnadaj、Obbe P. Zuiderveld、Bernard Christophe、Saskia Hulscher、Wiro M. P. B. Menge、Edith Gelens、Erwin Snip、Remko A. Bakker、Sylvain Celanire、Michel Gillard、Patrice Talaga、Henk Timmerman、Rob Leurs

  DOI：10.1021/jm049932u

  日期：2004.5.1

  In this study, the piperidine ring of immepip and its analogues was replaced by a rigid heterocyclic pyridine ring. Many compounds in the series exhibit high affinity and agonist activity at the human histamine H(3) receptor. Particularly, the 4-pyridinyl analogue of immepip (1c, immethridine) is identified as a novel potent and highly selective histamine H(3) receptor agonist (pK(i) = 9.07, pEC(50)

  在这项研究中，immepip及其类似物的哌啶环被刚性杂环吡啶环取代。该系列中的许多化合物在人类组胺H（3）受体上表现出高亲和力和激动剂活性。特别是，immepip（1c，immethridine）的4-吡啶基类似物被确定为一种新型的有效且高度选择性的组胺H（3）受体激动剂（pK（i）= 9.07，pEC（50）= 9.74），具有300倍的折叠率密切相关的H（4）受体的选择性。
• Synthesis and Structure−Activity Relationships of Conformationally Constrained Histamine H₃ Receptor Agonists
  作者：Ruengwit Kitbunnadaj、Obbe P. Zuiderveld、Iwan J. P. De Esch、Roeland C. Vollinga、Remko Bakker、Martin Lutz、Anthony L. Spek、Emile Cavoy、Marie-France Deltent、Wiro M. P. B. Menge、Henk Timmerman、Rob Leurs

  DOI：10.1021/jm030905y

  日期：2003.12.1

  Immepip, a conformationally constrained analogue of the histamine congener imbutamine, shows high affinity and functional activity on the human H-3 receptor. Using histamine and its homologues as prototypes, other rigid analogues containing either a piperidine or pyrrolidine ring in the side chain were synthesized and tested for their activities at the human H-3 receptor and the closely related H-4 receptor. In the series of piperidine containing analogues, immepip was found to be the most potent H-3 receptor agonist, whereas its propylene analogue 13a was identified as a high-affinity neutral antagonist for the human H-3 receptor. Moreover, replacement of the piperidine ring of immepip by a pyrrolidine ring led to a pair of enantiomers that show a distinct stereoselectivity at the human H-3 and H-4 receptor.