{2,6-di-tert-butyl-4-[1-(3,5-di-tert-butyl-4-hydroxyphenylsulfanyl)-1-methylethylsulfanyl]phenoxy}acetic acid ethyl ester | 216168-57-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: {2,6-di-tert-butyl-4-[1-(3,5-di-tert-butyl-4-hydroxyphenylsulfanyl)-1-methylethylsulfanyl]phenoxy}acetic acid ethyl ester
• 英文别名: {2,6-di-tert-butyl-4-[1-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-1-methyl-ethylsulfanyl]-phenoxy}-acetic acid ethyl ester；ethyl 2-[2,6-ditert-butyl-4-[2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylpropan-2-ylsulfanyl]phenoxy]acetate
• CAS: 216168-57-9
• 化学式: C₃₅H₅₄O₄S₂
• 分子量: 602.943
• InChiKey: MRABESNKOUOIGU-UHFFFAOYSA-N

物化性质

• 沸点：
  618.3±55.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  {2,6-di-tert-butyl-4-[1-(3,5-di-tert-butyl-4-hydroxyphenylsulfanyl)-1-methylethylsulfanyl]phenoxy}acetic acid ethyl ester 在 4-二甲氨基吡啶 、 lithium hydroxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (2S)-2-[[2-[2,6-ditert-butyl-4-[2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylpropan-2-ylsulfanyl]phenoxy]acetyl]amino]pentanedioic acid
  参考文献：
  名称：

  Discovery of Novel Phenolic Antioxidants as Inhibitors of Vascular Cell Adhesion Molecule-1 Expression for Use in Chronic Inflammatory Diseases

  摘要：

  Vascular cell adhesion molecule-1 (VCAM-1) mediates recruitment of leukocytes to endothelial cells and is implicated in many inflammatory conditions. Since part of the signal transduction pathway that regulates the activation of VCAM-1 expression is redox-sensitive, compounds with antioxidant properties may have inhibitory effects on VCAM-1 expression. Novel phenolic compounds have been designed and synthesized starting from probucol (1). Many of these compounds demonstrated potent inhibitory effects on cytokine-induced VCAM-1 expression and displayed potent antioxidant effects in. vitro. Some of these derivatives (4o, 4p, 4w, and 4x) inhibited lipopolysaccharide (LPS)-induced secretion of pro-inflammatory cytokines such as tumor necrosis factor-alpha (TNF-alpha), interleukin-1beta (IL-1beta), and IL-6 from human peripheral blood mononuclear cells (hPBMCs) in a concentration-dependent manner in vitro and showed antiinflammatory effects in an animal model. Compounds 4ad and 4ae are currently in clinical trials for the treatment of rheumatoid arthritis (RA) and prevention of chronic organ transplant rejection, respectively.

  DOI：

  10.1021/jm049685u
• 作为产物：
  描述：

  普罗布考 、 碘代醋酸乙酯 在 aluminum oxide 、 potassium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 {2,6-di-tert-butyl-4-[1-(3,5-di-tert-butyl-4-hydroxyphenylsulfanyl)-1-methylethylsulfanyl]phenoxy}acetic acid ethyl ester
  参考文献：
  名称：

  [EN] PHENOLIC ANTIOXIDANTS FOR THE TREATMENT OF DISORDERS INCLUDING ARTHRITIS, ASTHMA AND CORONARY ARTERY DISEASE
  [FR] ANTIOXYDANTS PHÉNOLIQUES POUR LE TRAITEMENT DE TROUBLES INCLUANT L'ARTHRITE, L'ASTHME ET LES TROUBLES DES ARTÈRES CORONAIRES

  摘要：

  公开号：

  WO2005112914A3

文献信息

• Process for preparation of probucol derivatives and polymorphic forms thereof
  申请人：Strange L. Matthew

  公开号：US20060025481A1

  公开（公告）日：2006-02-02

  A process is described for the preparation of polymorphic forms of water-soluble derivatives of probucol compounds. The process generally includes reacting a probucol compound with a solution of alkali metal oxide, reacting the salt mixture with a solution of an alkyl or aryl halo-substituted carboxylate, hydrolyzing the resulting compound; and separating a crystalline, polymorphic form of the compound from the hydrolyzing mixture. Polymorphic forms of the probucol compounds are also described.

  描述了一种制备水溶性衍生物的多晶形式的过程。该过程通常包括将probucol化合物与碱金属氧化物溶液反应，将盐混合物与烷基或芳基卤代羧酸酯溶液反应，水解生成的化合物；并从水解混合物中分离出化合物的结晶多晶形式。还描述了probucol化合物的多晶形式。
• Compounds and methods of treating transplant rejection
  申请人：——

  公开号：US20030153536A1

  公开（公告）日：2003-08-14

  The use of compounds of the formula 1 and pharmaceutically acceptable salts thereof, alone or in combination for the treatment of transplant rejection, wherein the substituents are defined in the application.

  使用公式1的化合物和药学上可接受的盐，单独或组合使用于移植排斥的治疗中，其中取代基在申请中有所定义。
• Phenolic antioxidants for the treatment of disorders including arthritis, asthma and coronary artery disease
  申请人：Meng Q. Charles

  公开号：US20060020038A1

  公开（公告）日：2006-01-26

  The invention relates to compounds, pharmaceutical compositions comprising the compounds, and methods of using the compounds, wherein the compounds are of the following Formulas: or a pharmaceutically acceptable salt, ester or prodrug thereof, wherein the substituents are defined in the application. The invention further provides methods of treatment of inflammatory disorders by administering the compounds.

  本发明涉及化合物、包含该化合物的药物组成物以及使用该化合物的方法，其中该化合物的结构式为：或其药学上可接受的盐、酯或前药，其中取代基在申请中有定义。本发明进一步提供通过给予该化合物治疗炎症性疾病的方法。
• Process of Preparing Esters and Ethers of Probucol and Derivatives Thereof
  申请人：Sikorski A. James

  公开号：US20080009642A1

  公开（公告）日：2008-01-10

  A probucol or a probucol derivative can be efficiently converted to a monoester or monoether of probucol by reacting the free hydroxyl-containing probucol or a derivative thereof (by which is meant a probucol compound with at least one substituent that is different from that on the parent probucol molecule but which maintains the two free hydroxyl groups) with a Grignard reagent or a lithium reagent that produces a magnesium bromide or lithium salt of probucol or the probucol derivative. The probucol compound anion anion is then reacted with an ester or ether forming compound.
• US7271274B2
  申请人：——

  公开号：US7271274B2

  公开（公告）日：2007-09-18