ethyl 3-[4-(methoxymethoxy)phenyl]-2-methylthiopropionate | 197299-04-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 3-[4-(methoxymethoxy)phenyl]-2-methylthiopropionate
• 英文别名: Ethyl 3-[4-(methoxymethoxy)phenyl]-2-methylsulfanylpropanoate
• CAS: 197299-04-0
• 化学式: C₁₄H₂₀O₄S
• 分子量: 284.376
• InChiKey: BQBDHLGTRRMDAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-[4-(methoxymethoxy)phenyl]-2-methylthiopropionate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以99%的产率得到ethyl 3-(4-hydroxyphenyl)-2-(methylthio)propionate
  参考文献：
  名称：

  Synthesis and biological activity of novel α-substituted β-phenylpropionic acids having pyridin-2-ylphenyl moiety as antihyperglycemic agents

  摘要：

  We previously reported the identification of novel oximes having 5-benzyl-2,4-thiazolidinedione with anti hyperglycemic activity. We now report the synthesis and biological activity of a novel series of oximes and amides having alpha-substituted-beta-phenylpropionic acids. In this series, we obtained potent PPARalpha/gamma dual agonist (S)-9d, with which activation of PPARalpha and PPARgamma was considerably more potent than that of the reference compounds GW9578 22 and rosiglitazone 3, respectively. This means (S)-9d is of the strongest class of PPARalpha/gamma dual agonists. In the course of this study, we also obtained 8h, which indicated potent plasma glucose lowering effect in spite of weak PPARalpha/gamma agonistic activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.048
• 作为产物：
  描述：

  3-(4-羟基苯基)乳酸乙酯 在 18-冠醚-6 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 23.0h， 生成 ethyl 3-[4-(methoxymethoxy)phenyl]-2-methylthiopropionate
  参考文献：
  名称：

  Synthesis and biological activity of novel α-substituted β-phenylpropionic acids having pyridin-2-ylphenyl moiety as antihyperglycemic agents

  摘要：

  We previously reported the identification of novel oximes having 5-benzyl-2,4-thiazolidinedione with anti hyperglycemic activity. We now report the synthesis and biological activity of a novel series of oximes and amides having alpha-substituted-beta-phenylpropionic acids. In this series, we obtained potent PPARalpha/gamma dual agonist (S)-9d, with which activation of PPARalpha and PPARgamma was considerably more potent than that of the reference compounds GW9578 22 and rosiglitazone 3, respectively. This means (S)-9d is of the strongest class of PPARalpha/gamma dual agonists. In the course of this study, we also obtained 8h, which indicated potent plasma glucose lowering effect in spite of weak PPARalpha/gamma agonistic activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.048

文献信息

• PHENYLALKYLCARBOXYLIC ACID DERIVATIVES
  申请人：Sankyo Company, Limited

  公开号：EP0916651A1

  公开（公告）日：1999-05-19

  Phenylalkylcarboxylic acid derivatives of the general formula: wherein R1 represents an alkyl group and the like, R2 represents an alkylene group, R3 represents a hydrogen atom and the like, X represents a substituted or unsubstituted aryl group and the like, Y represents an oxygen atom and the like, Z represents an alkylene group and the like, and W represents an alkyl group and the like), the pharmacologically acceptable salts thereof or the pharmacologically acceptable esters thereof are useful as therapeutic or preventive agents for hyperglycemia and the like.

  通式如下的苯基烷基羧酸衍生物 其中 R1 代表烷基等，R2 代表亚烷基等，R3 代表氢原子等，X 代表取代或未取代的芳基等，Y 代表氧原子等，Z 代表亚烷基等，W 代表烷基等）、 其药理学上可接受的盐类或其药理学上可接受的酯类可用作高血糖等的治疗或预防剂。
• US6103907A
  申请人：——

  公开号：US6103907A

  公开（公告）日：2000-08-15
• Synthesis and biological activity of novel α-substituted β-phenylpropionic acids having pyridin-2-ylphenyl moiety as antihyperglycemic agents
  作者：Makoto Takamura、Mitsuya Sakurai、Eriko Yamada、Sachie Fujita、Makoto Yachi、Toshiyuki Takagi、Aya Isobe、Yuka Hagisawa、Toshihiko Fujiwara、Hiroaki Yanagisawa

  DOI：10.1016/j.bmc.2004.01.048

  日期：2004.5

  We previously reported the identification of novel oximes having 5-benzyl-2,4-thiazolidinedione with anti hyperglycemic activity. We now report the synthesis and biological activity of a novel series of oximes and amides having alpha-substituted-beta-phenylpropionic acids. In this series, we obtained potent PPARalpha/gamma dual agonist (S)-9d, with which activation of PPARalpha and PPARgamma was considerably more potent than that of the reference compounds GW9578 22 and rosiglitazone 3, respectively. This means (S)-9d is of the strongest class of PPARalpha/gamma dual agonists. In the course of this study, we also obtained 8h, which indicated potent plasma glucose lowering effect in spite of weak PPARalpha/gamma agonistic activity. (C) 2004 Elsevier Ltd. All rights reserved.