2-羟基乙基吡啶-3-羧酸酯 | 3612-80-4

• 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: 2-羟基乙基吡啶-3-羧酸酯
• 英文名称: 2-Hydroxyethyl nicotinate
• 英文别名: nicotinic acid monoglycolate；nicotinic acid 2-hydroxyethyl ester；nicotinic acid-(2-hydroxy-ethyl ester)；Nicotinsaeure-(2-hydroxy-aethylester)；ethyleneglycol mononicotinic acid ester；Etofibrate 2-hydroxymethylnicotinate；2-hydroxyethyl pyridine-3-carboxylate
• CAS: 3612-80-4
• 化学式: C₈H₉NO₃
• mdl: MFCD00870064
• 分子量: 167.164
• InChiKey: OMMRNSLAFWRKOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  2-羟基乙基吡啶-3-羧酸酯 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (S)-2-((1-(benzylsulfonyl)piperidine-2-carbonyl)oxy)ethyl nicotinate
  参考文献：
  名称：

  Development, synthesis and structure–activity-relationships of inhibitors of the macrophage infectivity potentiator (Mip) proteins of Legionella pneumophila and Burkholderia pseudomallei

  摘要：

  The bacteria Burkholderia pseudomallei and Legionella pneumophila cause severe diseases like melioidosis and Legionnaire's disease with high mortality rates despite antibiotic treatment. Due to increasing antibiotic resistances against these and other Gram-negative bacteria, alternative therapeutical strategies are in urgent demand. As a virulence factor, the macrophage infectivity potentiator (Mip) protein constitutes an attractive target. The Mip proteins of B. pseudomallei and L. pneumophila exhibit peptidyl-prolyl cis/trans isomerase (PPIase) activity and belong to the PPIase superfamily. In previous studies, the pipecolic acid moiety proved to be a valuable scaffold for inhibiting this PPIase activity. Thus, a library of pipecolic acid derivatives was established guided by structural information and computational analyses of the binding site and possible binding modes. Stability and toxicity considerations were taken into account in iterative extensions of the library. Synthesis and evaluation of the compounds in PPlase assays resulted in highly active inhibitors. The activities can be interpreted in terms of a common binding mode obtained by docking calculations. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.08.025
• 作为产物：
  描述：

  依托贝特 在 盐酸 、 水 作用下， 生成 2-羟基乙基吡啶-3-羧酸酯 、 氯贝酸
  参考文献：
  名称：

  药物制剂中稳定性的预测XIX：高压液相色谱法对氯纤维酸酯的稳定性评估和生物分析。

  摘要：

  已在水溶液和生物流体中开发了氯贝酸酯，氯贝特和依非贝特及其水解产物，氯贝酸及其单甘醇酸酯和烟酸及其单甘醇酸酯的特异性，灵敏的反相高压液相色谱测定法。据报道，注入的流动相的灵敏度为100 ng / ml，是现有方法的10倍。乙腈变性后，在混相中可轻松分析低至200 ng / ml的血浆浓度。该化合物及其产物可用卤代烷溶剂萃取。将提取物蒸发，重构并以最少量的流动相进行分析，从而产生10 ng / ml血浆的灵敏度。提出了使对等离子体成分的干扰最小化的条件。该测定法用于确定氯纤酸酯在水溶液中的稳定性，建立在各种温度下的log k-pH曲线以及评估Arrhenius参数。水解是通过特定的酸碱催化进行的。pH值大于6的依托贝特溶剂分解的初始产物是氯贝酸的单乙二醇酯。在pH小于3时，它是烟酸的单乙二醇酯。氯贝酸酯对弱碱（在pH 10和30度下1-3小时）极不稳定。即使在最大稳定性的估计pH范围内，它们

  DOI：

  10.1002/jps.2600710105

文献信息

• Cosmetic composition
  申请人：UNILEVER PLC

  公开号：EP0489581A2

  公开（公告）日：1992-06-10

  Compositions containing an ester of nicotinic acid and a cosmetically acceptable surfactant are provided. These compositions, when applied topically to the human body produce a response such as a sensory or therapeutic response, for example a tingling or warming sensation or an increase in blood flow, which persists after the composition is rinsed from the body. The compositions are particularly suitable for application to the hair and/or scalp where they may encourage hair growth. Compositions for application to the hair and/or scalp preferably additionally comprise hair benefit agents such as hair growth promoters.

  提供含有烟酸酯和化妆品可接受的表面活性剂的组合物。这些组合物在局部涂抹到人体时会产生一种感官或治疗反应，例如刺痛或温热感觉，或者增加血液流动，这种反应在组合物被冲洗后仍然持续。这些组合物特别适用于涂抹到头发和/或头皮，可以促进头发生长。用于涂抹到头发和/或头皮的组合物最好还包括头发益处剂，如促进头发生长的剂。
• Synthesis, characterization and in vitro hydrolysis of a gemfibrozil-nicotinic acid codrug for improvement of lipid profile
  作者：Amjad M. Qandil、Meriem M. Rezigue、Bassam M. Tashtoush

  DOI：10.1016/j.ejps.2011.03.012

  日期：2011.6

  therapy of fibrates and nicotinic acid has been reported to be synergistic. Herein, we describe a covalent codrug of gemfibrozil (GEM) and nicotinic acid (NA) that was synthesized and characterized by 1H NMR, 13C NMR, FT-IR, MS analysis and elemental analysis. A validated HPLC method was developed that allows for the accurate quantitative determination of the codrug and its hydrolytic products that

  据报道，贝特类药物和烟酸的联合治疗具有协同作用。在这里，我们描述了吉非贝齐（GEM）和烟酸（NA）的共价共价药物，该药物通过1 H NMR合成并表征，1313 C NMR，FT-IR，MS分析和元素分析。开发了一种经过验证的HPLC方法，可以准确定量测定在体外化学水解和酶促水解过程中形成的共同药物及其水解产物。相较于其母体药物，在水溶性和分配系数方面，共同药物的理化性质得到了改善。在高温下于pH 1.2、6.8和7.4的磷酸盐缓冲水溶液中使用加速水解实验研究了共药的水解动力学。使用Arrhenius方程，在37°C时外推的半衰期在cod的pH值为1.2时为289天，在codrug和吉非贝齐2-羟乙基酯（GHEE）的pH值为6.8时分别为130和20,315天。最短的半衰期是在pH 7.4上。共同用药42天，GHEE 5837天。仅在80°C和pH 1.2下研究了后者的水解，并将其与在相似条
• Disposition of Etofibrate, Clofibric and Nicotinic Acid Esters, and Their Products in Dogs
  作者：Edward R. Garrett、Paul Altmayer

  DOI：10.1002/jps.2600740314

  日期：1985.3

  transformation product, nicotinic acid, shows saturable or dose-dependent pharmacokinetics in dogs that conform to the Michaelis-Menten equation with a terminal half-life of 4.4 min at low concentrations (less than 6.9 microM/kg). Three distinct metabolites of nicotinic acid can be identified and assayed chromatographically in the urine. The partition properties were similar to nicotinic acid. Nicotinic acid

  依托贝酸，一种由纤维蛋白和烟酸制成的乙二醇二酯，经静脉输注到狗中后，终末半衰期为2分钟。中间半酸酯，烟酸酯和氯贝酸酯，各自的终末半衰期分别为4.6和1.7分钟，并在给予依托贝特时短暂出现。与clofibric acid的42小时终末半衰期相反，另一种最终转化产物烟酸在狗中显示出符合Michaelis-Menten方程的饱和或剂量依赖性药代动力学，终末半衰期为4.4 min低浓度（小于6.9 microM / kg）。烟酸的三种不同代谢产物可以通过尿液色谱法进行鉴定和分析。分配特性类似于烟酸。
• Photoredox-Nickel Dual-Catalyzed <i>C</i>-Alkylation of Secondary Nitroalkanes: Access to Sterically Hindered α-Tertiary Amines
  作者：Sina Rezazadeh、Maxwell I. Martin、Raphael S. Kim、Glenn P. A. Yap、Joel Rosenthal、Donald A. Watson

  DOI：10.1021/jacs.2c13174

  日期：2023.3.1

  The preparation of tertiary nitroalkanes via the nickel-catalyzed alkylation of secondary nitroalkanes using aliphatic iodides is reported. Previously, catalytic access to this important class of nitroalkanes via alkylation has not been possible due to the inability of catalysts to overcome the steric demands of the products. However, we have now found that the use of a nickel catalyst in combination

  据报道，通过使用脂肪族碘化物对仲硝基烷烃进行镍催化烷基化来制备叔硝基烷烃。此前，由于催化剂无法克服产物的空间需求，通过烷基化催化获得这一类重要的硝基烷烃是不可能的。然而，我们现在发现，将镍催化剂与光氧化还原催化剂和光结合使用会产生活性更高的烷基化催化剂。这些现在可以接触叔硝基烷烃。这些条件是可扩展的以及耐空气和耐湿气的。重要的是，叔硝基烷产物的还原可以快速获得α-叔胺。
• Gas-free alkoxycarbonylation of aryl iodides in a phosphonium-based deep eutectic solvent with Mo(CO)₆ as a solid CO source
  作者：Francesco Messa、Andrea Nicola Paparella、Serena Perrone、Antonio Salomone

  DOI：10.1039/d3ob00596h

  日期：——

  been explored, for the first time, in phosphonium-based deep eutectic solvents under gas-free conditions, by using Mo(CO)6 as the CO source. The method allows the preparation of ethylene glycol and glycerol esters in high yields (up to 99%), short reaction times and under mild reaction conditions with a very low catalyst loading (0.5 mol%).

  首次探索了在无气体条件下，使用 Mo(CO) 6作为 CO 源，在鏻基低共熔溶剂中进行 Pd 催化的芳基碘化物的烷氧基羰基化反应。该方法可以以高收率（高达 99%）、短反应时间、温和的反应条件以及极低的催化剂负载量（0.5 mol%）制备乙二醇和甘油酯。