N-(2,6-dimethylphenyl)-2-<4-(2-hydroxyethylpierazin-1-yl)>acetamide | 89169-43-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2,6-dimethylphenyl)-2-<4-(2-hydroxyethylpierazin-1-yl)>acetamide
• 英文别名: N-(2,6-dimethylphenyl)-2-(4-(2-hydroxyethyl)piperazin-1-yl)acetamide；N-<4-(2-Hydroxy-ethyl)-piperazinoacetyl>-2,6-dimethyl-anilin；N-(2,6-dimethylphenyl)-2-[4-(2-hydroxyethyl)piperazin-1-yl]acetamide
• CAS: 89169-43-7
• 化学式: C₁₆H₂₅N₃O₂
• 分子量: 291.393
• InChiKey: UMLXVRBBEZUKGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-二甲基-5-甲氧羰基-4-(3-硝基苯基)-1,4-二氢吡啶-3-羧酸 、 N-(2,6-dimethylphenyl)-2-<4-(2-hydroxyethylpierazin-1-yl)>acetamide 在 N,N'-羰基二咪唑 作用下， 生成
  参考文献：
  名称：

  1,4-Dihydropyridines bearing a pharmacophoric fragment of lidoflazine

  摘要：

  A series of 1,4-dihydropyridines bearing a pharmacophoric fragment of Iidoflazine was synthesized. The compounds were evaluated for inotropic, chronotropic, and calcium antagonist activities. All compounds behave as inotropic and chronotropic agents, except for compounds 4b, 5a, and 5b, which exibit a rather weak calcium antagonism in vascular smooth muscle (like aorta). Compound 5b is about twofold more potent in decreasing both chronotropy and inotropy, while compound 5c is about fivefold more potent in decreasing inotropy than nifedipine. Moreover, compound 5b is the most potent calcium antagonist derivative of the series. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00155-1

文献信息

• Cardiovascular Profile of Xanthone-Based 1,4 Dihydropyridines Bearing a Lidoflazine Pharmacophore Fragment
  作者：Alessandra Bisi、Matteo Micucci、Silvia Gobbi、Federica Belluti、Roberta Budriesi、Angela Rampa

  DOI：10.3390/molecules23123088

  日期：——

  As a follow-up to our previous studies on differently substituted 1,4-dihydropyridines endowed with a peculiar cardiac selectivity, in this paper, a small series of hybrid compounds bearing the pharmacophore fragment of lidoflazine in position 2 or 3 on a 4-(xanthen-9-one)-dihydropyridine core was reported. Lidoflazine was selected due to our promising previously reported data, and the xanthen-9-one substituent was introduced in position 4 of the dihydropyridine scaffold based on the cardiac selectivity observed in several of our studies. The new hybrid compounds were tested to assess cardiac and vascular activities, and the data were evaluated in comparison with those previously obtained for 4-(xanthen-9-one)-dihydropyridines and lidoflazine–nifedipine hybrid compounds. The functional studies indicated an interesting peculiar selectivity for the cardiac parameter inotropy, in particular when the lidoflazine fragment was introduced in position 2 of the dihydropyridine scaffold (4a–e), and thus a possible preferential binding with the Cav 1.2 isoform of l-type calcium channels, which are mainly involved in cardiac contractility.

  作为我们之前对不同取代的1,4-二氢吡啶具有特殊心脏选择性的研究的后续，本文报告了一系列小型混合化合物，这些化合物在4-(黄酮-9-酮)-二氢吡啶核心上携带了利多氟嗪的药效团片段，该片段位于位置2或3。利多氟嗪是由于我们之前报告的有希望的数据而被选择，而黄酮-9-酮取代基是基于我们几项研究中观察到的心脏选择性，在二氢吡啶骨架的位置4引入的。对新的混合化合物进行了测试以评估其对心血管活动的影响，并将数据与先前获得的4-(黄酮-9-酮)-二氢吡啶和利多氟嗪-硝苯地平混合化合物的数据进行比较。功能研究表明，在心脏参数肌力方面存在有趣的特殊选择性，特别是当利多氟嗪片段被引入到二氢吡啶骨架的位置2时（4a-e），因此可能与主要参与心脏收缩的l-型钙通道的Cav 1.2亚型发生优先结合。
• 1,4-Dihydropyridines bearing a pharmacophoric fragment of lidoflazine
  作者：A. Chiarini、A. Rampa、R. Budriesi、A. Bisi、G. Fabbri、P. Valenti

  DOI：10.1016/0968-0896(96)00155-1

  日期：1996.10

  A series of 1,4-dihydropyridines bearing a pharmacophoric fragment of Iidoflazine was synthesized. The compounds were evaluated for inotropic, chronotropic, and calcium antagonist activities. All compounds behave as inotropic and chronotropic agents, except for compounds 4b, 5a, and 5b, which exibit a rather weak calcium antagonism in vascular smooth muscle (like aorta). Compound 5b is about twofold more potent in decreasing both chronotropy and inotropy, while compound 5c is about fivefold more potent in decreasing inotropy than nifedipine. Moreover, compound 5b is the most potent calcium antagonist derivative of the series. Copyright (C) 1996 Elsevier Science Ltd