Propenal O-(3-methoxy-benzyl)-oxime

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Propenal O-(3-methoxy-benzyl)-oxime
• 英文别名: (E)-N-[(3-methoxyphenyl)methoxy]prop-2-en-1-imine
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: AZSRWGVKMFFEPV-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  O-m-methoxybenzylhydroxylamine hydrochloride 、 丙烯醛 以 氯仿 、 水 为溶剂， 反应 24.0h， 生成 Propenal O-(3-methoxy-benzyl)-oxime 、 Propenal O-(3-methoxy-benzyl)-oxime
  参考文献：
  名称：

  Synthesis and β-adrenergic properties of (E)-N-[3-(alkylamino)-2-hydroxypropylidene](methyloxy)amines substituted with an aromatic group on their [(methyloxy)imino]methyl moiety (MOIMM): an investigation into the biopharmacological effects of an aryl substitution in the class of MOIM β-blocking drugs

  摘要：

  N-Isopropyl-(5a-g) and N-t-butyl-substituted(6a-g) (E)-N-[3-(amino)-2-hydroxypropylidene](arylmethyloxy)amines, which present an aromatic ring (Ar) linked to the CH2 carbon of the [(methyloxy)imino]methyl moiety (MOIMM), were synthesized with the aim of comparing their beta-adrenergic properties with those of the previously studied completely aliphatic analogs 1,2 and 3,4. Compounds 5 and 6 were tested for their affinity towards beta(1)- and beta(2)-adrenoceptors by radioligand binding experiments; the compounds with the highest affinity were also assayed for their beta(1) and beta(2)-adrenergic activity by functional tests on isolated preparations. The biopharmacological results show that, for the MOIM derivatives studied (1-6), the presence of an Ar substituent linked to the MOIM, as in 5 and 6, does not have any appreciable effect on the beta(1)-adrenergic properties in terms of affinity and activity; this type of substituent, on the contrary, appears to be capable of improving the beta(2)-adrenergic properties, as far as the receptor affinity is concerned. These results are discussed on the basis of a comparison of the conformational and electronic characteristics.

  DOI：

  10.1016/0223-5234(96)88293-6

文献信息

• Synthesis and β-Adrenergic Properties of (Z)-N-[3-(Alkylamino)-2-hydroxypropylidene](aryl-methyloxy)amines: Effects of the Configuration Around the Methyloxyiminomethyl (MOIM) Double Bond on the Biopharmacological Properties of MOIM-type β-Blocking Agents
  作者：Aldo Balsamo、Maria C. Breschi、Grazia Chiellini、Annalina Lapucci、Nicola Lazzeri、Marco Macchia、Adriano Martinelli、Eugenio Micali、Susanna Nencetti、Armando Rossello

  DOI：10.1016/s0968-0896(98)00172-2

  日期：1998.11

  The N-isopropyl- (3a-g) and N-tert-butyl-substituted (4a-g) (Z)-N-(3-(amino)-2-hydroxypropylidene)(arylmethyloxy)amines were synthesized in order to compare their beta(1)- and beta(2)-adrenergic properties with those of their previously studied corresponding analogues with the E configuration (la-g and 2a-g). Compounds 3 and 4 were tested for their affinity for beta(1)- and beta(2)-adrenoceptors by radioligand binding experiments, and the compounds with the highest affinity were also assayed for their activity towards the same types of beta-adrenoceptors by functional tests on isolated preparations. The Z-methyloxyiminomethyl (Z-MOIM) compounds 3 and 4 proved to possess, on the whole, affinity (K-i) and activity (pIC(50)) indices similar to those of the E isomers 1 and 2, thus indicating that for the MOIM-type beta-adrenergic antagonists 1-4, the type of configuration around the MOIM double bond does not have any appreciable effect either on the affinity or on the activity towards beta-adrenoceptors. These results are rationalized on the basis of the steric and electronic analogies existing between the MOIM groups of 1-4 in the two types of configurations (E and Z). (C) 1998 Elsevier Science Ltd. All rights reserved.