5,5-dimethyl-1-pentyl-1,4,5,6-tetrahydropyrimidine-2-carbaldehyde oxime | 1353940-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 5,5-dimethyl-1-pentyl-1,4,5,6-tetrahydropyrimidine-2-carbaldehyde oxime
• 英文别名: N-[(5,5-dimethyl-1-pentyl-4,6-dihydropyrimidin-2-yl)methylidene]hydroxylamine
• CAS: 1353940-94-9
• 化学式: C₁₂H₂₃N₃O
• 分子量: 225.334
• InChiKey: FAFOJSDIPNFWOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  48.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,5-dimethyl-1-pentyl-1,4,5,6-tetrahydropyrimidine-2-carbaldehyde oxime 在 盐酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 生成 5,5-dimethyl-1-pentyl-1,4,5,6-tetrahydropyrimidine-2-carbaldehyde oxime hydrochloride
  参考文献：
  名称：

  Nonquaternary Reactivators for Organophosphate-Inhibited Cholinesterases

  摘要：

  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.

  DOI：

  10.1021/jm201364d
• 作为产物：
  描述：

  二甲基丙二胺 在 tin(II) chloride dihdyrate 、 sodium hydride 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.67h， 生成 5,5-dimethyl-1-pentyl-1,4,5,6-tetrahydropyrimidine-2-carbaldehyde oxime
  参考文献：
  名称：

  Nonquaternary Reactivators for Organophosphate-Inhibited Cholinesterases

  摘要：

  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.

  DOI：

  10.1021/jm201364d