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.
• [EN] BLOOD BRAIN BARRIER-PENETRATING OXIMES FOR CHOLISTENERASES REACTIVATION<br/>[FR] OXIMES FRANCHISSANT LA BARRIÈRE HÉMATO-ENCÉPHALIQUE POUR RÉACTIVER DES CHOLINESTÉRASES
  申请人：HUMAN BIOMOLECULAR RES INST

  公开号：WO2012083261A1

  公开（公告）日：2012-06-21

  The invention describes pharmaceutical agents capable of crossing the blood brain barrier to protect against organophosphate pesticides and nerve agents or other electrophiles by reactivating inhibited cholinesterase (i.e., acetylcholinesterase and butyrylcholinesterase) and other proteins in the peripheral and central nervous system.

  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。