ethyl (isonicotinamid-4-yl)acetate | 574715-93-8

• 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: ethyl (isonicotinamid-4-yl)acetate
• 英文别名: N-(4-pyridyl)glycine ethyl ester；N-isonicotinoyl-glycine ethyl ester；N-Isonicotinoyl-glycin-aethylester；N-Isonicotinoyl-glycin-ethylester；[(Pyridine-4-carbonyl)-amino]-acetic acid, ethyl ester；ethyl 2-(pyridine-4-carbonylamino)acetate
• CAS: 574715-93-8
• 化学式: C₁₀H₁₂N₂O₃
• 分子量: 208.217
• InChiKey: UKSITIYNEBPVGV-UHFFFAOYSA-N

物化性质

• 熔点：
  84.5 °C
• 沸点：
  420.8±25.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (isonicotinamid-4-yl)acetate 在 乙醇 、 一水合肼 作用下， 生成 2-(isonicotinamid-4-yl)acetohydrazide
  参考文献：
  名称：

  Kametani; Iwakata, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1951, vol. 71, p. 1002

  摘要：

  DOI：
• 作为产物：
  描述：

  甘氨酸乙酯盐酸盐 、 氯化异氰盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 ethyl (isonicotinamid-4-yl)acetate
  参考文献：
  名称：

  Structure selectivity relationship studies of 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-[(4′-pyridyl)carboxamido]morphinan derivatives toward the development of the mu opioid receptor antagonists

  摘要：

  Mu opioid receptor antagonists have been applied to target a variety of diseases clinically. The current study is designed to explore the structure selectivity relationship (SSR) of 17-cyclopropylmethyl-3,14 beta-dihydroxy-4,5 alpha-epoxy-6 beta-[(4'-pyridyl)carboxamido]morphinan (NAP), a lead compound identified as a selective mu opioid receptor antagonist based on the previous study. Among a series of NAP derivatives synthesized, compounds 6 (NMP) and 9 (NGP) maintained comparable binding affinity, selectivity and efficacy to the lead compound. Particularly, the mu opioid receptor selectivity over kappa opioid receptor of NGP was considerably enhanced compared to that of NAP. Overall, the preliminary SSR supported our original hypothesis that an alternate 'address' domain may exist in the mu opioid receptor, which favors the ligands carrying a hydrogen bond acceptor and an aromatic system to selectively recognize the mu opioid receptor. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.06.135

文献信息

• Design, Synthesis, and Biological Evaluation of 17-Cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-[(4′-pyridyl)carboxamido]morphinan Derivatives as Peripheral Selective μ Opioid Receptor Agents
  作者：Yunyun Yuan、Orgil Elbegdorj、Jianyang Chen、Shashidhar K. Akubathini、Feng Zhang、David L. Stevens、Irina O. Beletskaya、Krista L. Scoggins、Zhenxian Zhang、Phillip M. Gerk、Dana E. Selley、Hamid I. Akbarali、William L. Dewey、Yan Zhang

  DOI：10.1021/jm301247n

  日期：2012.11.26

  MOR antagonist mainly acting within the peripheral nervous system. The noticeable diarrhea associated with it prompted the design and synthesis of its analogues in order to study its structure–activity relationship. Among them, compound 8 showed improved pharmacological profiles compared to the original lead, acting mainly at peripheral while increasing the intestinal motility in morphine-pelleted mice

  外周选择性μ阿片受体（MOR）拮抗剂可以减轻阿片类药物引起的便秘（OIC）的症状，而不会影响阿片类药物的镇痛作用。然而，与它们相关的各种不利影响，部分是由于它们相对较低的 MOR 选择性。NAP 是一种6β- N -4'-吡啶基取代的纳曲胺衍生物，以前被鉴定为主要作用于外周神经系统的有效且高度选择性的 MOR 拮抗剂。与之相关的明显腹泻促使设计和合成其类似物以研究其结构-活性关系。其中，化合物8与原始铅相比，显示出改善的药理学特征，主要作用于外周，同时增加吗啡颗粒小鼠的肠蠕动（ED 50 = 0.03 mg/kg）。与原始铅相比，ED 50的轻微下降被未观察到的不利影响很好地补偿了。因此，该化合物似乎是开发针对 OIC 的新型治疗剂的更有希望的线索。
• Photochromic and Reductive Electrochemical Switching of a Dithiazolylethene with Large Redox Modulation
  作者：Anne Léaustic、Elodie Anxolabéhère-Mallart、François Maurel、Stéphanie Midelton、Régis Guillot、Rémi Métivier、Keitaro Nakatani、Pei Yu

  DOI：10.1002/chem.201002451

  日期：2011.2.11

  characterized. Due to the N‐methylation of the pyridyl rings, 2 a displays not only very different photochromic properties, but also undergoes a reductive ring‐closing reaction to generate its closed‐ring isomer 2 b. Careful electrochemical studies coupled with EPR spectroscopy show that this reductive ring‐closing reaction takes place when 2 a is two‐electron reduced. DFT calculations suggest that

  一个新的dipyridylthiazolylethene（1）和它的双阳离子类似物（2），具有两个N-甲基吡啶环，已被合成和结构表征。由于吡啶环的N-甲基化，2只不仅显示非常不同的光致变色特性，而且还经历还原性闭环反应，以生成其闭合环异构体2b中。仔细的电化学研究以及EPR光谱分析表明，这种还原性闭环反应是在2 a被两电子还原时发生的。DFT计算表明，这种基态电环化是由还原的闭环异构体2 b的非常大的稳定性驱动的相对于还原的开环异构体2 a。此外，2b在半波电势为0.04和-0.14 V时相对于SCE表现出两个连续且可逆的单电子降低，当从2 a传递到2 b时，实现了高达1 V的氧化还原调制。
• Chemotherapy of Experimental Tuberculosis. VIII. The Synthesis of Acid Hydrazides, their Derivatives and Related Compounds^1,2
  作者：Harry L. Yale、Kathryn Losee、Joseph Martins、Mary Holsing、Frances M. Perry、Jack Bernstein

  DOI：10.1021/ja01104a046

  日期：1953.4
• Meyer; Graf, Biochemische Zeitschrift, 1930, vol. 229, p. 154,156
  作者：Meyer、Graf

  DOI：——

  日期：——
• Upadhyay, Apoorva; Srivastava; Srivastava, Journal of the Indian Chemical Society, 2011, vol. 88, # 7, p. 1025 - 1031
  作者：Upadhyay, Apoorva、Srivastava、Srivastava、Upadhyay, Navneeta

  DOI：——

  日期：——