2-[3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydro-4-pyridinyl]benzoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydro-4-pyridinyl]benzoic acid
• 英文别名: 4-(2-carboxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester；lacidipine acid；2-[3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridin-4-yl]benzoic acid
• 化学式: C₂₀H₂₃NO₆
• 分子量: 373.406
• InChiKey: WFWBIIFGTPBCHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-氨基巴豆酸乙酯 、 邻羧基苯甲醛 在 三氟乙酸 、 碳酸氢钠 作用下， 以 异丙醇 、 水 、 乙酸乙酯 为溶剂， 反应 1.08h， 生成 2-[3,5-bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydro-4-pyridinyl]benzoic acid
  参考文献：
  名称：

  PROCESS FOR PREPARING LACIDIPINE

  摘要：

  一种制备拉西地平的方法，包括将叔丁氧羰基甲基芳基磷銨鹽与邻苯二甲醛反应，进一步将产物（E）-3-(2-甲酰基苯基)-2-丙烯酸，1,1-二甲基乙基酯与乙基-3-氨基巴豆酸酯在不经过分离的情况下反应。

  公开号：

  US20070043088A1

文献信息

• Synthesis and Spectral Characterization of Related Substances of Lacidipine, an Antihypertensive Drug
  作者：V. V. N. K. V. Prasada Raju、Ganta Madhusudhan Reddy、Vedantham Ravindra、Vijayavitthal T. Mathad、P. K. Dubey、Padi Pratap Reddy

  DOI：10.1080/00397910802638560

  日期：2009.5.22

  Abstract Five related substances (impurities) were detected in lacidipine bulk drug substance by a simple high-performance liquid chromatographic method (HPLC) and were identified by liquid chromatography–mass spectrometry (LC-MS). These related substances were independently synthesized, characterized, and co-injected with the sample containing impurities.

  摘要 采用简单的高效液相色谱法 (HPLC) 检测拉西地平原料药中的 5 种相关物质（杂质），并通过液相色谱-质谱法 (LC-MS) 进行鉴定。这些相关物质是独立合成、表征的，并与含有杂质的样品共同进样。
• Synthesis of diethyl 4-substituted-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylates as a new series of inhibitors against yeast α-glucosidase
  作者：Huma Niaz、Hamdy Kashtoh、Jalaluddin A.J. Khan、Ajmal Khan、Atia-tul- Wahab、Muhammad Tanveer Alam、Khalid Mohammed Khan、Shahnaz Perveen、M. Iqbal Choudhary

  DOI：10.1016/j.ejmech.2015.03.018

  日期：2015.5

  1,4-Dihydropyridine-3,5-dicarboxylate derivatives (1-25) were synthesized in high yields via Hantzsch reaction and evaluated for their a-glucosidase inhibitory activity. Compounds 1, 2, 6-8, 11, 13-15, and 23-25 showed a potent inhibitory activity against yeast alpha-glucosidase with IC50 values in the range of 35.0-273.7 mu M, when compared with the standard drug acarbose (IC50 = 937 +/- 1.60 mu M). Their structures were characterized by different spectroscopic techniques. The kinetics, selectivity, and toxicity studies on these compounds were also carried out. The kinetic studies on most active compounds 14 and 25 determined their modes of inhibition and dissociation constants K-i. Compound 14 was found to be a noncompetitive inhibitor with K-i = 25.0 +/- 0.06, while compound 25 was identified as a competitive inhibitor with K-i = 66.0 +/- 0.07 mu M. (C) 2015 Elsevier Masson SAS. All rights reserved.