1-butyl-4,5-dihydro-1H-imidazole-2-carbaldehyde oxime hydrochloride | 1353880-51-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 亚胺内酰胺
• 英文名称: 1-butyl-4,5-dihydro-1H-imidazole-2-carbaldehyde oxime hydrochloride
• 英文别名: N-[(1-butyl-4,5-dihydroimidazol-2-yl)methylidene]hydroxylamine;hydrochloride
• CAS: 1353880-51-9
• 化学式: C₈H₁₅N₃O*ClH
• 分子量: 205.688
• InChiKey: URIFTYUURHVWGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  48.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 tin(II) chloride dihdyrate 、 碳酸氢钠 、 盐酸 作用下， 以 二氯甲烷 、 甲醇 、 乙醚 为溶剂， 反应 24.0h， 以19%的产率得到1-butyl-4,5-dihydro-1H-imidazole-2-carbaldehyde oxime hydrochloride
  参考文献：
  名称：

  [EN] BLOOD BRAIN BARRIER-PENETRATING OXIMES FOR CHOLISTENERASES REACTIVATION
  [FR] OXIMES FRANCHISSANT LA BARRIÈRE HÉMATO-ENCÉPHALIQUE POUR RÉACTIVER DES CHOLINESTÉRASES

  摘要：

  该发明描述了一种能够穿越血脑屏障的药物，可以保护免受有机磷杀虫剂、神经毒剂或其他亲电性物质的侵害，通过重新激活被抑制的胆碱酯酶（即乙酰胆碱酯酶和丁酰胆碱酯酶）以及其他蛋白质在外周和中枢神经系统中的作用。

  公开号：

  WO2012083261A1

文献信息

• Nonquaternary Reactivators for Organophosphate-Inhibited Cholinesterases
  作者：Jarosław Kalisiak、Erik C. Ralph、John R. Cashman

  DOI：10.1021/jm201364d

  日期：2012.1.12

  A new class of amidine-oxime reactivators of organophosphate (OP)-inhibited cholinesterases (ChE) was synthesized and tested in vitro and in vivo. Compared with 2-PAM, the most promising cyclic amidine-oxime (i.e., 12e) showed comparable or greater reactivation of OP-inactivated AChE and OP-inactivated BChE. To the best of our knowledge, this is the first report of a nonquaternary oxime that has, comparable to 2-PAM, in vitro potency for reactivation of Sarin (GB)-inhibited AChE and BChE. Amidine-oximes were tested in vitro, and reactivation rates for OP-inactivated butyrylcholinesterase (BChE) were greater than those for 2-PAM or MINA. Amidine-oxime reactivation rates for OP-inactivated acetylcholinesterase (AChE) were lower compared to 2-PAM but greater compared with MINA. Amidine-oximes were tested in vivo for protection against the toxicity of nerve agent model compounds. (i.e., a model of Sarin). Post-treatment (i.e., 5 min after OP exposure, i.p,) with amidine oximes 7a-c and 12a, 12c, 12e, 12f, and 15b (145 mu mol/kg, i.p.) protected 100% of the mice challenged with the satin model compound. Even at 25% of the initial dose of amidine-oxime (i.e., a dose of 36 mu mol/kg, i.p.), 7b and 12e protected 100% of the animals challenged with the sarin nerve agent model compound that caused lethality in 6/11 animals without amidine-oxime.