6-氨基-4-(4-氯苯基)-5-氰基-2-甲基烟酸乙酯 | 138566-00-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 6-氨基-4-(4-氯苯基)-5-氰基-2-甲基烟酸乙酯
• 英文名称: ethyl 6-amino-4-(4-chlorophenyl)-5-cyano-2-methylnicotinate
• 英文别名: Ethyl 6-amino-4-(4-chlorophenyl)-5-cyano-2-methylpyridine-3-carboxylate
• CAS: 138566-00-4
• 化学式: C₁₆H₁₄ClN₃O₂
• 分子量: 315.759
• InChiKey: ICPVGQUJPNNHLM-UHFFFAOYSA-N

物化性质

• 沸点：
  516.8±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  89
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-氨基-4-(4-氯苯基)-5-氰基-2-甲基烟酸乙酯 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以68%的产率得到(E)-diethyl 6,6'-(diazene-1,2-diyl)bis[4-(4chlorophenyl)-5-cyano-2-methylnicotinate]
  参考文献：
  名称：

  Synthesis of (E)-diethyl 6,6′-(diazene-1,2-diyl)bis(5-cyano-2-methyl-4-phenylnicotinates), a new type of 2,2′-azopyridine dyes

  摘要：

  An unexpected, but simple method for the efficient synthesis of new 2.2'-azopyridine dyes, such as (E)-diethyl 6,6'-(diazene-1,2-diyl)bis(5-cyano-2-methyl-4-phenylnicotinates) (2, 4, 6, 8, 10, and 12), based on the treatment of ethyl 6-amino-5-cyano-2-methyl-4-arylnicotinates (1, 3, 5, 7, 9, and 11) with NBS/benzoyl peroxide, is described. The X-ray diffraction analysis and the UV-vis absorption spectra of dye 2 are reported and discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.095
• 作为产物：
  描述：

  4-氯苄亚基丙二腈 在 哌啶 、 乙酸铵 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 6-氨基-4-(4-氯苯基)-5-氰基-2-甲基烟酸乙酯
  参考文献：
  名称：

  Zayed, Salem E.; Elmaged, Eiman I. Abou; Metwally, Saud A., Collection of Czechoslovak Chemical Communications, 1991, vol. 56, # 10, p. 2175 - 2182

  摘要：

  DOI：

文献信息

• 6-Amino-Nicotinsäurederivaten und ihre Verwendung als selektive Kaliumkanalmodulatoren
  申请人：BAYER AG

  公开号：EP0705820A1

  公开（公告）日：1996-04-10

  Die Anmeldung betrifft substituierte 4-Phenyl-6-amino-nicotinsäurederivate zur therapeutischen Anwendung, neue Wirkstoffe sowie deren Verwendung als cerebral wirksame Mittel. Die Wirkstoffe werden hergestellt, indem man entsprechend substituierte Dihydropyridine nach üblichen Methoden oxidiert.

  本申请涉及用于治疗的取代 4-苯基-6-氨基烟酸衍生物、新的活性成分及其作为脑活性 剂的用途。这些活性成分是根据传统方法，通过氧化相应取代的二氢吡啶而制备的。
• Synthesis, biological evaluation and molecular modelling of diversely functionalized heterocyclic derivatives as inhibitors of acetylcholinesterase/butyrylcholinesterase and modulators of Ca2+ channels and nicotinic receptors
  作者：José L Marco、Cristóbal de los Rı́os、Antonio G Garcı́a、Mercedes Villarroya、M.Carmo Carreiras、Carla Martins、Ana Eleutério、Antonio Morreale、M Orozco、F.Javier Luque

  DOI：10.1016/j.bmc.2004.02.017

  日期：2004.5

  The synthesis and the biological activity of compounds 5-40 as inhibitors of acetyleholinesterase (AChE) and butyrylcholinesterase (BuChE), as well as modulators of voltage-dependent Ca2+ channels and nicotinic receptors, are described. These molecules are tacrine analogues, which have been prepared from polyfunctionalized 6-amino-5-cyano-4H-pyrans, 6-amino-5-cyano-pyridines and 5-amino-2-aryl-3-cyano-1,3-oxazoles via Friedlander reaction with selected cycloalkanones. These compounds are moderate acetylcholinesterase and butyrylcholinesterase inhibitors, the BuChE/AChE selectivity of the most active molecules ranges from 10.0 (compound 29) to 76.9 (compound 16). Interestingly, the 'oxazolo-tacrine' derivatives are devoid of any activity. All compounds showed an important inhibitory effect on the nicotinic acetylcholine receptor. Most of them also blocked L-type Ca2+ channels, and three of them, 64, 19 and 67, the non-L type of Ca2+ channels. Molecular modelling studies suggest that these compounds might bind at the peripheral binding site of AChE, which opens the possibility to design inhibitors able to bind at both, the catalytic and peripheral binding sites of the enzyme. (C) 2004 Elsevier Ltd. All rights reserved.
• US5670525A
  申请人：——

  公开号：US5670525A

  公开（公告）日：1997-09-23
• Zayed, Salem E.; Elmaged, Eiman I. Abou; Metwally, Saud A., Collection of Czechoslovak Chemical Communications, 1991, vol. 56, # 10, p. 2175 - 2182
  作者：Zayed, Salem E.、Elmaged, Eiman I. Abou、Metwally, Saud A.、Elnagdi, Mohamed H.

  DOI：——

  日期：——
• Synthesis of (E)-diethyl 6,6′-(diazene-1,2-diyl)bis(5-cyano-2-methyl-4-phenylnicotinates), a new type of 2,2′-azopyridine dyes
  作者：Daniel Botelho da Silva、Abdelouahid Samadi、Lourdes Infantes、María do Carmo Carreiras、José Marco-Contelles

  DOI：10.1016/j.tetlet.2010.09.095

  日期：2010.12

  An unexpected, but simple method for the efficient synthesis of new 2.2'-azopyridine dyes, such as (E)-diethyl 6,6'-(diazene-1,2-diyl)bis(5-cyano-2-methyl-4-phenylnicotinates) (2, 4, 6, 8, 10, and 12), based on the treatment of ethyl 6-amino-5-cyano-2-methyl-4-arylnicotinates (1, 3, 5, 7, 9, and 11) with NBS/benzoyl peroxide, is described. The X-ray diffraction analysis and the UV-vis absorption spectra of dye 2 are reported and discussed. (C) 2010 Elsevier Ltd. All rights reserved.