4-乙酰氧基-3-甲氧基苯乙酰氯 | 53283-50-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: 4-乙酰氧基-3-甲氧基苯乙酰氯
• 英文名称: 4-acetoxy-3-methoxyphenylacetyl chloride
• 英文别名: acetylhomovanilloyl chloride；[4-(2-chloro-2-oxoethyl)-2-methoxyphenyl] acetate
• CAS: 53283-50-4
• 化学式: C₁₁H₁₁ClO₄
• 分子量: 242.659
• InChiKey: ZLOZJKCYFFTCKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 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：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-乙酰氧基-3-甲氧基苯乙酰氯 在 sodium hydroxide 作用下， 以 甲醇 、 乙醚 、 苯 为溶剂， 反应 6.0h， 生成 N-Octylhomovanillamide
  参考文献：
  名称：

  香草。1.具有抗伤害感受和抗炎活性的辣椒素类似物。

  摘要：

  作为建立香草醛的结构活性关系的程序的一部分，辛辣成分辣椒素的类似物，母体结构的烷基链部分（以及衍生自高香草酸的相关化合物）发生了变化。在抗伤害感受和抗炎试验（大鼠和小鼠热板以及巴豆油刺激的小鼠耳朵）中，具有广泛变化的烷基链结构的化合物具有活性。短链化合物在上述测定中通过全身给药具有活性，但它们保留了辣椒素的高刺激性和急性毒性特征。相比之下，长链顺式不饱和物NE-19550（香草基油酰胺）和NE-28345（油基单香草酰胺）具有口服活性，刺激性较低，并且比辣椒素的急性毒性小。

  DOI：

  10.1021/jm00070a002
• 作为产物：
  描述：

  高香草酸 在 氯化亚砜 、 硫酸 作用下， 生成 4-乙酰氧基-3-甲氧基苯乙酰氯
  参考文献：
  名称：

  香草。1.具有抗伤害感受和抗炎活性的辣椒素类似物。

  摘要：

  作为建立香草醛的结构活性关系的程序的一部分，辛辣成分辣椒素的类似物，母体结构的烷基链部分（以及衍生自高香草酸的相关化合物）发生了变化。在抗伤害感受和抗炎试验（大鼠和小鼠热板以及巴豆油刺激的小鼠耳朵）中，具有广泛变化的烷基链结构的化合物具有活性。短链化合物在上述测定中通过全身给药具有活性，但它们保留了辣椒素的高刺激性和急性毒性特征。相比之下，长链顺式不饱和物NE-19550（香草基油酰胺）和NE-28345（油基单香草酰胺）具有口服活性，刺激性较低，并且比辣椒素的急性毒性小。

  DOI：

  10.1021/jm00070a002

文献信息

• Compounds and compositions having anti-inflammatory and analgesic
  申请人：The Procter & Gamble Company

  公开号：US05013759A1

  公开（公告）日：1991-05-07

  Substituted phenylacetic acid amide compounds, and pharmaceutically-acceptable salts thereof, of the formula: ##STR1## wherein X is O or S; R.sub.1 is H, OH or CH.sub.3 ; R.sub.2 is straight chain alkenyl, branched chain or cyclic hydrocarbon having from about 7 to about 24 carbon atoms; R.sub.3 is OH, OSO.sub.3.sup.-, OPO.sub.3.sup.-- or a short chain ester with from about 1 to about 6 carbon atoms.

  取代苯乙酸酰胺化合物及其药用盐，化学式如下：##STR1## 其中X为O或S；R.sub.1为H、OH或CH.sub.3；R.sub.2为直链烯烃、支链或环烃，碳原子数约为7至24个；R.sub.3为OH、OSO.sub.3.sup.-、OPO.sub.3.sup.--或具有约1至6个碳原子的短链酯。
• Penicillin derivatives
  申请人：Beecham Group Limited

  公开号：US04308259A1

  公开（公告）日：1981-12-29

  A penicillin of formula (I) or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof: ##STR1## wherein R is C.sub.1-6 alkyl; an optionally substituted 5-membered heterocyclic ring containing one or two heteroatoms selected from oxygen, sulphur and nitrogen; phenyl; mono-substituted phenyl where the substituent is halogen, hydroxy, C.sub.1-6 alkoxy, nitro, amino, C.sub.1-6 alkyl, or C.sub.1-6 haloalkyl, C.sub.1-6 alkylcarbonyloxy, or C.sub.1-6 alkyl sulphonylamino; or di-substituted phenyl where the substituents are selected from hydroxy, halogen, methoxy, acetoxy and amino; and X represents a group of formula: ##STR2## wherein R.sup.1 represents C.sub.1 to C.sub.6 alkyl, or C.sub.1 to C.sub.6 alkoxy. Their preparation and use is described.

  一种化学式（I）的青霉素或其药用可接受盐或体内水解酯：其中R为C.sub.1-6烷基；一种可选择含有氧、硫和氮中的一个或两个杂原子的可选取代的5-成员杂环环；苯基；单取代苯基，其中取代基为卤素、羟基、C.sub.1-6烷氧基、硝基、氨基、C.sub.1-6烷基或C.sub.1-6卤代烷基、C.sub.1-6烷基羰氧基或C.sub.1-6烷基磺酰氨基；或二取代苯基，其中取代基可选择为羟基、卤素、甲氧基、乙酰氧基和氨基；X代表化学式的一个基团：其中R.sup.1代表C.sub.1到C.sub.6烷基或C.sub.1到C.sub.6烷氧基。它们的制备和用途已经描述。
• Analogs of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 1. The aromatic "A-region"
  作者：Christopher S. J. Walpole、Roger Wrigglesworth、Stuart Bevan、Elizabeth A. Campbell、Andy Dray、Iain F. James、Martin N. Perkins、Derek J. Reid、Janet Winter

  DOI：10.1021/jm00068a014

  日期：1993.8

  A series of analogues of capsaicin, the pungent principle of chilli peppers, was synthesized and tested in assays for capsaicin-like agonism in vitro. The results of these assays were compared with activities in an acute nociceptive model and a correlation was observed which established that the results of these in vitro assays were predictive of analgesia. Using a modular approach the structure-activity profile of specific regions of capsaicin congeners was established using an in vitro assay measuring Ca-45(2+) uptake into neonatal rat dorsal root ganglia neurones. Substituted benzylnonanamides 2a-z and N-octyl-substituted phenylacetamides 4a-v were made to test the requirements for activity in the aromatic ''A-region'' of the molecule. Compounds with the natural substitution pattern (2b and 4c) and the corresponding catechols (2i and 4g) were the most potent, although the catechols were less potent in vivo. Other substitution patterns have reduced activity. These results have established stringent structural requirements for capsaicin-like activity in this part of the molecule.
• Analogs of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 3. The hydrophobic side-chain "C-region"
  作者：Christopher S. J. Walpole、Roger Wrigglesworth、Stuart Bevan、Elizabeth A. Campbell、Andy Dray、Iain F. James、Kay J. Masdin、Martin N. Perkins、Janet Winter

  DOI：10.1021/jm00068a016

  日期：1993.8

  Structural variants of the hydrophobic side chain (''C region'') of the capsaicin molecule have been incorporated into a series of vanillylamides and vanillylthioureas. These compounds have been tested in an in vitro assay for agonism (Ca-45(2+) influx into dorsal root ganglia neurones), previously shown to be predictive of analgesic activity. The results of this study have established the requirement for a hydrophobic substituent of limited size (molar refractivity, MR, <55) in order to obtain high potency. Combination of the information gained here about the ''C-region'' of the capsaicin molecule with the studies described in the preceding two papers provides a rational basis for the design of compounds of increased potency.
• Penicillin derivatives, process for their preparation and pharmaceutical composition comprising them
  申请人：BEECHAM GROUP PLC

  公开号：EP0015690B1

  公开（公告）日：1983-04-06