FUB 349 | 184023-52-7

• 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: FUB 349
• 英文别名: 4-(4-phenylbutyl)-1H-imidazole；4-(4-phenylbutyl)-3H-imidazole；5-(4-phenylbutyl)-1H-imidazole
• CAS: 184023-52-7
• 化学式: C₁₃H₁₆N₂
• 分子量: 200.283
• InChiKey: BQTXNCXSCSNHGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-苯基戊酸 在 sodium cyanide 、 lithium aluminium tetrahydride 、 草酰氯 、 氨 、 二甲基亚砜 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 25.42h， 生成 FUB 349
  参考文献：
  名称：

  Synthesis and histamine H3 receptor activity of 4-(n-alkyl)-1H-imidazoles and 4-(ω-phenylalkyl)-1H-imidazoles

  摘要：

  The influence of lipophilic moieties attached to a 4-1H-imidazole ring on the histamine H-3 receptor activity was systematically investigated. Series of 4-(n-alkyl)-1H-imidazoles and 4-(omega-phenylalkyl)-1H-imidazoles were prepared, with an alkyl chain varying from 2-9 methylene groups and from 1-9 methylene groups, respectively. The compounds were tested for their activity on the H-3 receptor under in vitro conditions. For the 4-(n-alkyl)-1H-imidazoles the activity is proportional to chain length, ranging from a pA(2) value of 6.3 +/- 0.2 for 4-(n-propyl)-1H-imidazoIe to a pA(2) value of 7.2 +/- 0.1 for 4-(n-decyl)-1H-imidazole. For the series 4-(omega-phenylalkyl)-4H-imidazoles an optimum in H-3 activity was found for the pentylene spacer: 4-(omega-phenylpentyl)-1H-imidazole has a pA(2) value of 7.8 +/- 0.1. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00253-9

文献信息

• General construction pattern of histamine H3-receptor antagonists: Change of a paradigm
  作者：H. Stark、X. Ligneau、J.-M. Arrang、J.-C. Schwartz、W. Schunack

  DOI：10.1016/s0960-894x(98)00342-4

  日期：1998.8

  unsubstituted alkyl and alkenyl imidazole derivatives were prepared and tested for their antagonist activity in vitro and in vivo at histamine H3-receptors. Some compounds showed high in vitro and in vivo H3-receptor activity despite their structure bearing no polar moiety in the centre of the molecule which is a common structural feature of all other antagonists known. Quite probably there are further

  制备了新的ω-苯基取代的和未取代的烷基和链烯基咪唑衍生物，并在组胺H3-受体的体内和体外测试了它们的拮抗剂活性。尽管某些化合物的结构在分子中心不带有极性部分，但这是所有其他已知拮抗剂的共同结构特征，因此某些化合物在体外和体内均显示出很高的H3受体活性。某些化合物可能会由于其他受体相互作用而进一步产生体内效应。
• An Efficient and Convenient Synthesis of 4-Vinylimidazoles Using a Novel Horner-Wadsworth-Emmons (HWE) Reagent: Synthetic Studies Toward Novel Histamine H3-Ligands
  作者：Shinya Harusawa、Shuji Koyabu、Yasutoshi Inoue、Yasuhiko Sakamoto、Lisa Araki、Takushi Kurihara

  DOI：10.1055/s-2002-31951

  日期：——

  A novel Horner-Wadsworth-Emmons (HWE)-type reagent 1 reacted readily with various aldehydes and ketones to produce (E)-vinylimidazoles 2 in good yields. The synthetic utility of 1 was demonstrated by the efficient preparation of four histamine H 3 ligands 3 by simple hydrogenation of 2.

  一种新型的 Horner-Wadsworth-Emmons (HWE) 型试剂 1 很容易与各种醛和酮反应，以良好的收率生产 (E)-乙烯基咪唑 2。1 的合成效用通过简单氢化 2 有效制备四种组胺 H 3 配体 3 得到证明。