(4-异氰酰基苯基)乙酸乙酯 | 827629-60-7

• 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: (4-异氰酰基苯基)乙酸乙酯
• 中文别名: （4-异氰酸根合苯基）乙酸乙酯
• 英文名称: ethyl (4-isocyanatophenyl)acetate
• 英文别名: ethyl 2-(4-isocyanatophenyl)acetate；(4-isocyanato-phenyl)-acetic acid ethyl ester
• CAS: 827629-60-7
• 化学式: C₁₁H₁₁NO₃
• mdl: MFCD09971933
• 分子量: 205.213
• InChiKey: WJCNECDZVRTPNU-UHFFFAOYSA-N

物化性质

• 沸点：
  115-118 °C(Press: 3 Torr)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2929109000

反应信息

• 作为反应物：
  描述：

  2-(2-furyl)-8-methyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine 、 (4-异氰酰基苯基)乙酸乙酯 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以82%的产率得到Ethyl 2-[4-[[4-(furan-2-yl)-11-methyl-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(12),2,4,7,9-pentaen-7-yl]carbamoylamino]phenyl]acetate
  参考文献：
  名称：

  Combined Target-Based and Ligand-Based Drug Design Approach as a Tool To Define a Novel 3D-Pharmacophore Model of Human A₃ Adenosine Receptor Antagonists:  Pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidine Derivatives as a Key Study

  摘要：

  A combined target-based and ligand-based drug design approach has been carried out to define a novel pharmacophore model of the human A(3) receptor antagonists. High throughput molecular docking and comparative molecular field analysis (CoMFA) have been used in tandem to assemble a new target based pharmacophore model. In parallel, to provide more accurate information about the putative binding site of these A(3) inhibitors, a rhodopsin-based model of the human A(3) receptor was built and a novel Y-shape binding motif has been proposed. Docking-based structure superimposition has been used to perform a quantitative study of the structure-activity relationships for binding of these pyrazolo-triazolo-pyrimidines to adenosine A(3) receptor using CoMFA. Both steric and the electrostatic contour plots obtained from the CoMFA analysis nicely fit on the hypothetical binding site obtained by molecular docking. On the basis of the combined hypothesis, we have designed, synthesized, and tested 17 new derivatives. Consistently, the predicted K-i values were very close to the experimental values.

  DOI：

  10.1021/jm049662f
• 作为产物：
  描述：

  4-氨基苯乙酸乙酯 在 硫酸 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 (4-异氰酰基苯基)乙酸乙酯
  参考文献：
  名称：

  Organosilicon synthesis of isocyanates: III. Synthesis of aliphatic, carbocyclic, aromatic, and alkylaromatic isocyanatocatboxylic acid esters

  摘要：

  A series of aminoacid esters was prepared by treating the aminoacid suspensions in ethanol with thionyl chloride. Best conversion of aminoacid esters to corresponding isocyanates was achieved in the case of aromatic and carbocyclic aminoesters by phosgeneation of their N-silyl derivatives, and in the case of aliphatic and alkylaromatic aminoesters by phosgeneation of O-silyl or N,O-bissilylurethanes on their basis. In the last case additional step of esterification of the by-products isocyanatoalkylcarboxylic acid chlorides is reqired after phosgeneation. Unusual generation of cynnamates and intramolecular N -> O-migration of trimethylsilyl group in the solutions of silylated alkylaromatic beta-aminoacid esters were found.

  DOI：

  10.1134/s1070363206070115

文献信息

• Quinolines useful in treating cardiovascular disease
  申请人：Collini D. Michael

  公开号：US20050131014A1

  公开（公告）日：2005-06-16

  This invention provides compounds of formula I that are useful in the treatment or inhibition of LXR mediated diseases.

  本发明提供了式I化合物的用途，它们在治疗或抑制LXR介导的疾病中是有用的。
• 6,7-asymmetrically disubstituted quinoxalinecarboxylic acid derivatives, addition salts thereof, and processes for the preparation of both
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：US06348461B1

  公开（公告）日：2002-02-19

  The present invention provides 6,7-asymmetrically disubstituted quinoxalinecarboxylic acid compounds and their addition salts, and processes for preparing them, which have antagonism against excitatory amino acid receptors, in particular, an AMPA receptor. The 6,7-asymmetrically disubstituted quinoxalinecarboxylic acid compounds and their addition salts of the present invention are represented by formula (1) wherein Q, R, R1 and R2 are as described in the specification.

  本发明提供了6,7-不对称二取代喹喔啉羧酸化合物及其加合盐，以及制备它们的方法，这些化合物对兴奋性氨基酸受体，特别是AMPA受体具有拮抗作用。本发明的6,7-不对称二取代喹喔啉羧酸化合物及其加合盐由下式表示（1式），其中Q、R、R1和R2如规范中所述。
• NAMPT INHIBITORS
  申请人：Curtin Michael L.

  公开号：US20120122924A1

  公开（公告）日：2012-05-17

  Disclosed are compounds which inhibit the activity of NAMPT, compositions containing the compounds and methods of treating diseases during which NAMPT is expressed.

  揭示了抑制NAMPT活性的化合物，包含这些化合物的组合物以及治疗NAMPT表达疾病的方法。
• Discovery and Preclinical Development of Antigiardiasis Fumagillol Derivatives
  作者：Janak Padia、Liudmila Kulakova、Andrey Galkin、Osnat Herzberg

  DOI：10.1128/aac.00582-20

  日期：2020.9.21

  Giardiasis, caused by the intestinal parasite Giardia lamblia , is a severe diarrheal disease, endemic in poverty-stricken regions of the world, and also a common infection in developed countries. The available therapeutic options are associated with adverse effects, and G. lamblia resistance to the standard-of-care drugs is spreading. Fumagillin, an antimicrosporidiosis drug, is a therapeutic agent with potential for the treatment of giardiasis. However, it exhibits considerable, albeit reversible, toxicity when used to treat immunocompromised microsporidiosis patients.

  贾第虫病，由肠寄生虫引起 贾第虫引起的 贾第虫病是一种严重的腹泻疾病，在世界贫困地区流行，在发达国家也是一种常见的感染。现有的治疗方案都会产生不良反应，而 兰姆利亚革兰氏菌 对标准治疗药物的抗药性正在蔓延。福马吉林（Fumagillin）是一种抗孢子虫病药物，是一种有潜力治疗贾第虫病的药物。然而，在用于治疗免疫力低下的微孢子虫病患者时，它表现出相当大的毒性，尽管这种毒性是可逆的。
• Design and synthesis of novel 7-heterocycle-6-trifluoromethyl-3-oxoquinoxaline-2-carboxylic acids bearing a substituted phenyl group as superior AMPA receptor antagonists with good physicochemical properties
  作者：Yasuo Takano、Futoshi Shiga、Jun Asano、Wataru Hori、Kazunori Fukuchi、Tsuyoshi Anraku、Takashi Uno

  DOI：10.1016/j.bmc.2005.08.060

  日期：2006.2

  We describe the design, synthesis, and physicochemical and biological properties of a novel series of 7-heterocycle-6-trifluoromethyl-3-oxoquinoxaline-2-carboxylic acids bearing a substituted phenyl group joined through a urethane or urea linkage to the heterocycle at the 7 position. Introduction of the trifluoromethyl group at the 6 position conferred good biological activity, including neuroprotective effects, as well as good physicochemical properties. In terms of alpha-amino-3-hydroxy-5-methylisoxazole propionate receptor (AMPA-R) affinity, a urea linkage was equivalent to a urethane linkage and a pyrrole ring at the 7 position reduced affinity in comparison with an imidazole ring. Among this series, compound 14h (KRP-199), which has a 4-carboxyphenyl group joined through a urethane linkage to a 7-imidazolyl heterocycle, was found to possess high potency and selectivity for the AMPA-R in vitro and to exhibit good neuroprotective effects in vivo. Furthermore, the compound showed good physicochemical properties, including stability to light and good solubility in aqueous solutions. (c) 2005 Elsevier Ltd. All rights reserved.