2-氰基-2-(2-硝基苯基)乙酸乙酯 | 65548-02-9

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氰基-2-(2-硝基苯基)乙酸乙酯
• 英文名称: (+/-)-ethyl cyano(2-nitrophenyl)acetate
• 英文别名: ethyl α-cyano-α-(o-nitrophenyl)acetate；ethyl 2-(2-nitrophenyl)-2-cyanoacetate；ethyl 2-cyano-2-(2-nitrophenyl)acetate；ethyl 2-cyano-2-(nitrophenyl)acetate；Ethyl cyano(2-nitrophenyl)acetate；ethyl 2-nitrophenylcyanoacetate
• CAS: 65548-02-9
• 化学式: C₁₁H₁₀N₂O₄
• 分子量: 234.211
• InChiKey: JUGQARWTQZEZRI-UHFFFAOYSA-N

物化性质

• 熔点：
  49-51°C
• 沸点：
  139-141 °C(Press: 0.09 Torr)
• 密度：
  1.292±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  95.9
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  2-氰基-2-(2-硝基苯基)乙酸乙酯 在 盐酸 作用下， 生成 3-methoxycarbonylbenzoisoxazole
  参考文献：
  名称：

  Zur Herstellung von Oxindol-Derivaten aus-o-Chlor-nitrobenzolen undCyanessigsäure-bzw。Malonsäure-estern

  摘要：

  在邻位丁醇中，氰基乙酸乙酯和丙二酸乙酯的钾盐在邻位丁醇中的邻位被单个硝基激活的氯苯进行平滑的亲核取代。这样得到的2-硝基苯基丙二酸酯衍生物（2a）和（2b）容易分别转化为2-硝基苯基乙酸和羟吲哚和吲哚的衍生物。

  DOI：

  10.1002/hlca.19610440630
• 作为产物：
  描述：

  硝基氯苯 生成 2-氰基-2-(2-硝基苯基)乙酸乙酯
  参考文献：
  名称：

  Tetrahydropyran derivatives

  摘要：

  公开号：

  EP1367058B1

文献信息

• [EN] HYDROXAMATE DERIVATIVES FOR HDAC INHIBITOR, AND THE PHARMACEUTICAL COMPOSITION COMPRISING THEREOF<br/>[FR] DÉRIVÉS HYDROXAMATE POUR UN INHIBITEUR DES HISTONE-DÉSACÉTYLASES (HDAC) ET COMPOSITION PHARMACEUTIQUE LES COMPRENANT
  申请人：CHONG KUN DANG PHARM CORP

  公开号：WO2013062344A1

  公开（公告）日：2013-05-02

  The present invention relates to a novel hydroxamate derivatives, more specifically, to novel hydroxamate derivatives having inhibitory activity against Histone Deacetylase (HDAC), isomers thereof, pharmaceutically acceptable salts thereof, hydrates or solvates thereof, use for preparing pharmaceutical compositions, pharmaceutical compositions comprising the same, treatment method using said composition, and a preparing method of novel hydroxamate derivatives. The novel selective hydroxamate derivatives having inhibitory activity against Histone Deacetylase (HDAC) compositions can be used for treatment of inflammatory disease, rheumatoid arthritis, or degenerative disease.

  本发明涉及一种新型羟肟酸衍生物，更具体地说，涉及一种具有对组蛋白去乙酰化酶（HDAC）具有抑制活性的新型羟肟酸衍生物，其异构体，其药学上可接受的盐，其水合物或溶剂合物，用于制备药物组合物的用途，包含其的药物组合物，使用该组合物的治疗方法，以及一种新型羟肟酸衍生物的制备方法。具有对组蛋白去乙酰化酶（HDAC）具有抑制活性的新型选择性羟肟酸衍生物组合物可用于治疗炎症性疾病、类风湿性关节炎或退行性疾病。
• HYDROXAMATE DERIVATIVES FOR HDAC INHIBITOR, AND THE PHARMACEUTICAL COMPOSITION COMPRISING THEREOF
  申请人：CHONG KUN DANG PHARMACEUTICAL CORP.

  公开号：US20140315889A1

  公开（公告）日：2014-10-23

  The present invention relates to a novel hydroxamate derivatives, more specifically, to novel hydroxamate derivatives having inhibitory activity against Histone Deacetylase (HDAC), isomers thereof, pharmaceutically acceptable salts thereof, hydrates or solvates thereof, use for preparing pharmaceutical compositions, pharmaceutical compositions comprising the same, treatment method using said composition, and a preparing method of novel hydroxamate derivatives. The novel selective hydroxamate derivatives having inhibitory activity against Histone Deacetylase (HDAC) compositions can be used for treatment of inflammatory disease, rheumatoid arthritis, or degenerative disease.

  本发明涉及一种新型羟肟酸衍生物，更具体地说，涉及一种具有对组蛋白去乙酰化酶（HDAC）抑制活性的新型羟肟酸衍生物，其异构体，其药学上可接受的盐，其水合物或溶剂合物，用于制备药物组合物的用途，包含其的药物组合物，使用该组合物的治疗方法，以及一种新型羟肟酸衍生物的制备方法。具有对组蛋白去乙酰化酶（HDAC）抑制活性的新型选择性羟肟酸衍生物组合物可用于治疗炎症性疾病、类风湿性关节炎或变性疾病。
• Construction of 1,2,5-Tricarbonyl Compounds using Methyl Cyanoacetate as a Glyoxylate Anion Synthon Combined with Copper(I) Iodide-Catalyzed Aerobic Oxidation
  作者：Se Hee Kim、Ko Hoon Kim、Jae Nyoung Kim

  DOI：10.1002/adsc.201100431

  日期：2011.12

  A practical and efficient synthesis of various 1,2,5-tricarbonyl compounds is described. The synthesis has been carried out by a conjugate addition of methyl cyanoacetate to the β-position of α,β-unsaturated carbonyl compounds and a subsequent copper(I) iodide-catalyzed aerobic oxidation. In addition, various α-aryl- and α-alkyl-α-keto esters have been synthesized using a similar approach.

  描述了一种实用而有效的合成各种1,2,5-三羰基化合物的方法。合成是通过将氰基乙酸甲酯共轭加到α，β-不饱和羰基化合物的β-位上进行的，然后进行碘化铜（I）催化的需氧氧化。另外，已经使用类似的方法合成了各种α-芳基-和α-烷基-α-酮酯。
• Studies on the synthesis and analgesic and anti-inflammatory activities of 2-thiazolylamino- and 2-thiazolyloxy-arylacetic acid derivatives.
  作者：RYOZO MAEDA、EIICHI OHSUGI、TOSHIHIRO FUJIOKA、KATSUMI HIROSE

  DOI：10.1248/cpb.31.3424

  日期：——

  A series of 2-thiazolylamino-, 2-thiazolyloxy- and 2-thiazolylthio-arylacetic acid derivatives was prepared by condensation of thioamides with halo-acetals according to Hantzsch's method, and thioamides having the α-methylarylacetic acid moiety were conveniently obtained from haloaromatic nitro compounds by a combination of known methods. In the model reaction of O-phenyl thiocarbamate (XVIII) with chloro-diethylacetal, isolation of intermediates such as acyclic halo-compound (XIX) and 4-ethoxy-2-phenoxy-2-thiazoline (XX) clarified the reaction path for the formation of 2-phenoxythiazole (XXI). The analgesic and anti-inflammatory effects of the compounds studied were evaluated by using the acetic acid-induced writhing method in mice and the rat carrageenin paw edema method, respectively. 2- [4- (2-Thiazolyloxy) phenyl] propionic acid (XIVa) had the most favorable therapeutic ratio between activity and toxicity (in mice).

  根据Hantzsch方法，通过硫酰胺与卤代乙缩醛的缩合反应制备了一系列2-噻唑基氨基、2-噻唑基氧和2-噻唑基硫代芳基乙酸衍生物，而具有α-甲基芳基乙酸部分的硫酰胺则通过结合已知方法从卤代芳香硝基化合物中方便地获得。在O-苯基硫代氨基甲酸酯（XVIII）与氯代二乙缩醛的模型反应中，分离出无环卤代化合物（XIX）和4-乙氧基-2-苯氧基-2-噻唑啉（XX）等中间体，阐明了苯氧噻唑（XXI）的生成反应途径。通过小鼠的醋酸引起的扭体法和大鼠的角叉菜胶引起的足跖肿胀法，分别评估了所研究化合物的镇痛和抗炎作用。2-[4-（2-噻唑氧基）苯基]丙酸（XIVa）在活性与毒性之间具有最佳的治疗比（在小鼠中）。
• Discovery of a Highly Selective Cell-Active Inhibitor of the Histone Lysine Demethylases KDM2/7
  作者：Philip A. Gerken、Jamie R. Wolstenhulme、Anthony Tumber、Stephanie B. Hatch、Yijia Zhang、Susanne Müller、Shane A. Chandler、Barbara Mair、Fengling Li、Sebastian M. B. Nijman、Rebecca Konietzny、Tamas Szommer、Clarence Yapp、Oleg Fedorov、Justin L. P. Benesch、Masoud Vedadi、Benedikt M. Kessler、Akane Kawamura、Paul E. Brennan、Martin D. Smith

  DOI：10.1002/anie.201706788

  日期：2017.12.4

  Small but mighty: A new class of inhibitor was discovered that is highly potent towards the histone lysine demethylases (KDMs) KDM2A/7A. A modular synthetic approach was used to explore chemical space and accelerate the investigation of key structure–activity relationships, leading to the development of a small molecule with more than 75-fold selectivity towards KDM2A/7A versus other KDMs, as well

  体积小巧但功能强大：发现了一种新型抑制剂，对组蛋白赖氨酸脱甲基酶（KDM）KDM2A / 7A非常有效。模块化合成方法用于探索化学空间并加快对关键结构与活性之间关系的研究，从而导致开发出一种小分子，其对KDM2A / 7A的选择性是其他KDM的75倍以上，并且在低摩尔浓度。