2-[2-(4-邻-甲苯基-哌嗪-1-基)-乙氧基]-苯甲醛 | 103076-76-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 2-[2-(4-邻-甲苯基-哌嗪-1-基)-乙氧基]-苯甲醛
• 英文名称: 2-[2-[4-(2-Methylphenyl)piperazin-1-yl]ethoxy]benzaldehyde
• CAS: 103076-76-2
• 化学式: C₂₀H₂₄N₂O₂
• 分子量: 324.423
• InChiKey: IGZZMLREHWSXQF-UHFFFAOYSA-N

物化性质

• 沸点：
  500.8±50.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  异硫氰酸甲酯 、 2-[2-(4-邻-甲苯基-哌嗪-1-基)-乙氧基]-苯甲醛 以68%的产率得到
  参考文献：
  名称：

  NATE, HIROYUKI;MATSUKI, KENJI;TSUNASHIMA, AKIRA;OHTSUKA, HISAO;SEKINE, YA+, CHEM. AND PHARM. BULL., 35,(1987) N 6, 2394-2411

  摘要：

  DOI：

文献信息

• Synthesis of 2-phenylthiazolidine derivatives as cardiotonic agents. II. 2-(Phenylpiperazinoalkoxyphenyl)thiazolidine-3-thiocarboxamides and the corresponding carboxamides.
  作者：HIROYUKI NATE、KENJI MATSUKI、AKIRA TSUNASHIMA、HISAO OHTSUKA、YASUO SEKINE、KUNIYUKI ODA、YASUSHI HONMA、AKIHIKO ISHIDA、HIDEO NAKAI、HIROSHI WADA、MIKIO TAKEDA、HIDEO YABANA、YUTAKA HINO、TAKU NAGAO

  DOI：10.1248/cpb.35.2394

  日期：——

  A large number of 2- (phenylpiperazinoalkoxyphenyl) thiazolidine-3-thiocarboxamides and the corresponding carboxamides (II) were synthesized and tested for inotropic activity in anesthetized dogs. Compounds II were prepared from a hydroxybenzaldehyde (III) through the intermediates (IV, V, and X). Structure-activity relationships (SAR) were investigated by varying the structural parameters. Transposition of the piperazinoalkoxyl group to the meta or para position from the ortho position caused a marked fall in activity. Conversion of the thiocarboxamido to a carboxamido group caused a marked increase in activity. This tendency was generally observed in this series of compounds and constitutes a major deviation from the SAR in the simple 2-phenylthiazolidine series. With regard to effects of the length of the aminoalkoxy chain, the ethoxy derivatives were generally more potent than higher analogues. Lengthening of the N-alkyl group in the (thio) carboxamido group generally caused a decrease in activity. Among the various derivatives synthesized, II15 was found to be approximately one hundred times more potent than amrinone with a long duration of action.

  大量2-（苯基哌嗪基烷氧苯基）噻唑烷-3-硫代羧酰胺及其相应羧酰胺（II）被合成并在麻醉犬中测试其强心活性。化合物II通过羟基苯甲醛（III）及其中间体（IV、V和X）制备。通过改变结构参数来研究结构-活性关系（SAR）。将哌嗪基烷氧基团从邻位位置移至间位或对位导致活性显著下降。将硫代羧酰胺转变为羧酰胺基团导致活性显著增加。这种趋势在这一系列化合物中普遍存在，并构成与简单2-苯基噻唑烷系列SAR的主要偏离。关于氨基烷氧链长度的影响，乙氧基衍生物通常比更高级的类似物更有效。在（硫代）羧酰胺基团中延长N-烷基通常导致活性下降。在合成的各种衍生物中，II15被发现其效力约为氨力农的一百倍，且作用时间较长。