4-(3-(2-propenyloxy)propyl)-1H-imidazole | 184026-88-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(3-(2-propenyloxy)propyl)-1H-imidazole
• 英文别名: 4-[3-(allyloxy)propyl]-1H-imidazole；3-(1H-Imidazol-4-yl)propyl 2-propenyl ether；5-(3-prop-2-enoxypropyl)-1H-imidazole
• CAS: 184026-88-8
• 化学式: C₉H₁₄N₂O
• 分子量: 166.223
• InChiKey: JWHMIDZSSHJCJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(3-(2-propenyloxy)propyl)-1H-imidazole 在 sodium hydroxide 、 碘 、 silver nitrate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 13.0h， 生成 4-[3-(2,3-Bis-nitrooxy-propoxy)-propyl]-1H-imidazole
  参考文献：
  名称：

  A new class of NO-donor H3-antagonists

  摘要：

  Synthesis and pharmacological characterisation of a series of compounds obtained by joining, through appropriate spacers, NO-donor furoxan and nitrooxy moieties to the imidazole ring, as well as their structurally related analogues devoid of NO-donating properties are described. All the products were studied for their capacity to interact with H3-receptors present on the guinea-pig ileum and with H2-receptors present on guinea-pig right atrium. The whole series of products displayed reversible H3-antagonistic activity. No activity on H2-receptors was observed when the products were tested at 10 microM concentration. Many of the products were also able to induce partial relaxation when added to the bath after electrical contraction of the guinea-pig ileum during the study of their H3-antagonism. This phenomenon seems to be dependent on various factors; for some compounds it proved to be dependent on NO-mediated sGC activation, for other products it could be due to their weak M3-antagonism. The investigation of the lipophilic-hydrophilic balance of all the products indicates, for many of them, an ideal value to cross the blood-brain barrier.

  DOI：

  10.1016/j.farmac.2003.12.008
• 作为产物：
  描述：

  4-(3-Allyloxy-propyl)-1-trityl-1H-imidazole 在 盐酸 作用下， 反应 0.75h， 生成 4-(3-(2-propenyloxy)propyl)-1H-imidazole
  参考文献：
  名称：

  4-(ω-(Alkyloxy)alkyl)-1H-imidazole Derivatives as Histamine H₃ Receptor Antagonists/Agonists

  摘要：

  In an effort to develop new histamine H-3 receptor antagonists usable as pharmacological tools we present here novel unsymmetrical ether derivatives. Etherification of different omega-(1H-imidazol-4-yl)alkyl scaffolds led to compounds containing alkyl chains of increasing lengths either with or without unsaturated termini, cycloalkyl or arylalkyl moieties, or additional heteroatoms. When investigated in an in vitro assay on rat synaptosomes, the majority of compounds displayed potencies in the low nanomolar concentration range at the H-3 receptor, e.g., 4-(3-(3-cyclopentylpropyloxy)propyl)-1H-imidazole (27, K-i = 7 nM). FUB 465, 4-(3-(ethoxy)propyl)-1H-imidazole (14), a useful tool for the characterization of constitutive activity of H-3 receptors in vivo in rodents, proved to be of high oral in vivo potency in mice (ED50 = 0.26 mg/kg). Further, the influence of chosen compounds on specific [S-35]GTPgammaS binding was assayed on HEK293 cell membranes expressing the human histamine H-3 receptor revealing partial agonism of the compounds in this particular model. These distinct responses are further hints for "protean agonism" in this class of compounds. Additionally, selected compounds were functionally investigated in vitro on isolated organs of the guinea-pig at H-3, H-1, and H-2 receptors.

  DOI：

  10.1021/jm031065q

文献信息

• Imidazole derivatives as histamine receptor H3 (ANT) agonists
  申请人：Institut National de la Sante et de la Recherche Medical

  公开号：US06248765B1

  公开（公告）日：2001-06-19

  Novel imidazole derivatives as histamine receptor H3 antagonists and/or agonists, preparation thereof and therapeutical uses thereof. Chemical compounds for use as histamine receptor H3 agonists, partial agonists or antagonists, having general formula (Ia) or (Ib), the use thereof for making drugs, and methods for revealing the agonist, partial agonist or antagonist activity of such compounds in vivo, are disclosed.

  小说咪唑衍生物作为组胺受体H3的拮抗剂和/或激动剂，其制备方法和治疗用途。公开了用作组胺受体H3激动剂、部分激动剂或拮抗剂的化学化合物，其具有一般式（Ia）或（Ib），其用于制药，并公开了在体内揭示这些化合物的激动剂、部分激动剂或拮抗剂活性的方法。
• DERIVES D'IMIDAZOLE MODULATEURS DU RECEPTEUR H3 DE L'HISTAMINE
  申请人：INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM)

  公开号：EP0760811B1

  公开（公告）日：2009-11-18
• US6248765B1
  申请人：——

  公开号：US6248765B1

  公开（公告）日：2001-06-19