[(3-ethoxyphenyl)sulfanyl]acetic acid | 85352-13-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [(3-ethoxyphenyl)sulfanyl]acetic acid
• 英文别名: 2-(3-Ethoxyphenyl)sulfanylacetic acid
• CAS: 85352-13-2
• 化学式: C₁₀H₁₂O₃S
• 分子量: 212.269
• InChiKey: SWNOLXWHQDPSAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(3-ethoxyphenyl)sulfanyl]acetic acid 在 盐酸 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 8-{[(3-ethoxyphenyl)sulfanyl]methyl}caffeine
  参考文献：
  名称：

  Inhibition of monoamine oxidase by 8-phenoxymethylcaffeine derivatives

  摘要：

  A recent study has reported that a series of 8-benzyloxycaffeines are potent and reversible inhibitors of both human monoamine oxidase (MAO) isoforms, MAO-A and -B. In an attempt to discover additional caffeine derivatives with potent MAO inhibitory activities, and to contribute to the known structure-activity relationships of MAO inhibition by caffeine derived compounds, the present study investigates the MAO inhibitory potencies of series of 8-phenoxymethylcaffeine and 8-[(phenylsulfanyl)methyl]caffeine derivatives. The results document that the 8-phenoxymethylcaffeine derivatives act as potent reversible inhibitors of MAO-B, with IC50 values ranging from 0.148 to 5.78 mu M. In contrast, the 8-[(phenylsulfanyl) methyl] caffeine derivatives were found to be weak inhibitors of MAO-B, with IC50 values ranging from 4.05 to 124 mu M. Neither the 8-phenoxymethylcaffeine nor the 8-[(phenylsulfanyl) methyl] caffeine derivatives exhibited high binding affinities for MAO-A. While less potent than the 8-benzyloxycaffeines as MAO-B inhibitors, this study concludes that 8-phenoxymethylcaffeines may act as useful leads for the design of MAO-B selective inhibitors. Such compounds may find application in the therapy of neurodegenerative disorders such as Parkinson's disease. Using molecular docking experiments, this study also proposes possible binding orientations of selected caffeine derivatives in the active sites of MAO-A and -B. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.048
• 作为产物：
  描述：

  3-乙氧基苯硫酚 、 sodium monochloroacetic acid 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 以85%的产率得到[(3-ethoxyphenyl)sulfanyl]acetic acid
  参考文献：
  名称：

  Inhibition of monoamine oxidase by 8-phenoxymethylcaffeine derivatives

  摘要：

  A recent study has reported that a series of 8-benzyloxycaffeines are potent and reversible inhibitors of both human monoamine oxidase (MAO) isoforms, MAO-A and -B. In an attempt to discover additional caffeine derivatives with potent MAO inhibitory activities, and to contribute to the known structure-activity relationships of MAO inhibition by caffeine derived compounds, the present study investigates the MAO inhibitory potencies of series of 8-phenoxymethylcaffeine and 8-[(phenylsulfanyl)methyl]caffeine derivatives. The results document that the 8-phenoxymethylcaffeine derivatives act as potent reversible inhibitors of MAO-B, with IC50 values ranging from 0.148 to 5.78 mu M. In contrast, the 8-[(phenylsulfanyl) methyl] caffeine derivatives were found to be weak inhibitors of MAO-B, with IC50 values ranging from 4.05 to 124 mu M. Neither the 8-phenoxymethylcaffeine nor the 8-[(phenylsulfanyl) methyl] caffeine derivatives exhibited high binding affinities for MAO-A. While less potent than the 8-benzyloxycaffeines as MAO-B inhibitors, this study concludes that 8-phenoxymethylcaffeines may act as useful leads for the design of MAO-B selective inhibitors. Such compounds may find application in the therapy of neurodegenerative disorders such as Parkinson's disease. Using molecular docking experiments, this study also proposes possible binding orientations of selected caffeine derivatives in the active sites of MAO-A and -B. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.048

文献信息

• Verfahren zur Herstellung von S-Aryl-thioglycolsäuren
  申请人：BAYER AG

  公开号：EP0067352A1

  公开（公告）日：1982-12-22

  Verfahren zur Herstellung von S-Arylthioglycolsäuren der Formel in der A einen Benzolring bezeichnet, der durch 1,2,3,4 oder 5 Substituenten aus der Reihe Halogen, Nitro, Hydroxy, Mercapto, Trifluormethyl, Alkyl, Aryl, Alkoxy, Aryloxy, Acylami. no, Alkylamino, Arylamino, Alkylmercapto, Arylmercapto, Cyan, Carboxy, Alkylcarbonyl, Arylcarbonyl, Alkoxycarbonyl, Aryloxycarbonyl oder gegebenenfalls substituiertes Aminocarbonyl substituiert sein kann oder für einen gegebenenfalls 1 oder 2 der vorstehend genannten Substituenten tragenden Benzolring, an den ein carbocyclischer oder heterocyclischer aromatischer Ring angegliedert ist, steht, dadurch gekennzeichnet, daß man Aryl-diazonium-salze der Formel in der A die zu Formel (I) angegebene Bedeutung hat und X den Rest einer zur Salzbildung mit dem Diazoniumkation befähigten Säure bezeichnet, im wäßrig sauren Medium mit Thioglycolsäure in Gegenwart von Cu(I)- oder Cu(II)-salzen umsetzt und man das Reaktionsgemisch auf Verbindungen der Formel (I) bzw. deren Salze hin aufarbeitet.

  一种制备式 S-芳基硫代乙醇酸的工艺 其中 A 表示被卤素、硝基、羟基、巯基、三氟甲基、烷基、芳基、烷氧基、芳氧基、酰氨基、芳酰胺、烷基巯基、芳基巯基、氰基、羧基、烷基巯基、芳基巯基、氰基、烷基酰胺、芳酰胺、烷基巯基、芳基巯基、氰基等系列中的 1、2、3、4 或 5 个取代基取代的苯环。否、烷基氨基、芳基氨基、烷基巯基、芳基巯基、氰基、羧基、烷基羰基、芳基羰基、烷氧基羰基、芳氧基羰基或任选取代的氨基羰基，或代表任选带有 1 或 2 个上述取代基并连接有碳环或杂环芳香环的苯环，其特征在于，如下式的芳基重氮盐 在 Cu(I) 或 Cu(II) 盐存在下，在水性酸性介质中与硫代乙醇酸反应，反应混合物经加工得到式 (I) 的化合物或其盐。
• US4461911A
  申请人：——

  公开号：US4461911A

  公开（公告）日：1984-07-24
• Inhibition of monoamine oxidase by 8-phenoxymethylcaffeine derivatives
  作者：Thokozile Okaecwe、Abraham J. Swanepoel、Anél Petzer、Jacobus J. Bergh、Jacobus P. Petzer

  DOI：10.1016/j.bmc.2012.05.048

  日期：2012.7

  A recent study has reported that a series of 8-benzyloxycaffeines are potent and reversible inhibitors of both human monoamine oxidase (MAO) isoforms, MAO-A and -B. In an attempt to discover additional caffeine derivatives with potent MAO inhibitory activities, and to contribute to the known structure-activity relationships of MAO inhibition by caffeine derived compounds, the present study investigates the MAO inhibitory potencies of series of 8-phenoxymethylcaffeine and 8-[(phenylsulfanyl)methyl]caffeine derivatives. The results document that the 8-phenoxymethylcaffeine derivatives act as potent reversible inhibitors of MAO-B, with IC50 values ranging from 0.148 to 5.78 mu M. In contrast, the 8-[(phenylsulfanyl) methyl] caffeine derivatives were found to be weak inhibitors of MAO-B, with IC50 values ranging from 4.05 to 124 mu M. Neither the 8-phenoxymethylcaffeine nor the 8-[(phenylsulfanyl) methyl] caffeine derivatives exhibited high binding affinities for MAO-A. While less potent than the 8-benzyloxycaffeines as MAO-B inhibitors, this study concludes that 8-phenoxymethylcaffeines may act as useful leads for the design of MAO-B selective inhibitors. Such compounds may find application in the therapy of neurodegenerative disorders such as Parkinson's disease. Using molecular docking experiments, this study also proposes possible binding orientations of selected caffeine derivatives in the active sites of MAO-A and -B. (C) 2012 Elsevier Ltd. All rights reserved.