5-[4-(1-Ethyl-cyclohexylmethoxy)-benzyl]-thiazolidine-2,4-dione | 74773-26-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[4-(1-Ethyl-cyclohexylmethoxy)-benzyl]-thiazolidine-2,4-dione
• 英文别名: 5-[[4-[(1-Ethylcyclohexyl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
• CAS: 74773-26-5
• 化学式: C₁₉H₂₅NO₃S
• 分子量: 347.478
• InChiKey: FTMCRYPADARNER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (1-ethylcyclohexyl)methanol 在 palladium on activated charcoal copper(I) oxide 、 盐酸 、 氢气 、 sodium acetate 、 sodium hydride 、 sodium nitrite 作用下， 以 甲醇 、 乙二醇甲醚 、 N,N-二甲基甲酰胺 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 17.5h， 生成 5-[4-(1-Ethyl-cyclohexylmethoxy)-benzyl]-thiazolidine-2,4-dione
  参考文献：
  名称：

  Studies on antidiabetic agents. II. Synthesis of 5-(4-(1-methylcyclohexylmethoxy)-benzyl)thiazolidine-2,4-dione (ADD-3878) and its derivatives.

  摘要：

  合成了100多种5-取代的噻唑烷-2,4-二酮类化合物，并通过遗传性肥胖和糖尿病小鼠（KK黄色小鼠）评估了它们的降血糖和降血脂活性。结构-活性关系研究表明，5-(4-羟基苄基)部分对于显著活性是必要的。在这些化合物中，5-(4-环己基甲氧基)苄基噻唑烷-2,4-二酮（47）、5-[4-(1-甲基环己基甲氧基)苄基]-噻唑烷-2,4-二酮（49，ADD-3878）和5-{4-[2-(3-吡啶基)乙氧基]苄基}噻唑烷-2,4-二酮（59）在活性和毒性方面表现出最佳特性。

  DOI：

  10.1248/cpb.30.3580

文献信息

• SOHDA, TAKASHI;MIZUNO, KATSUTOSHI;IMAMIYA, EIKO;SUGIYAMA, YASUO;FUJITATAK+, CHEM. AND PHARM. BULL., 1982, 30, N 10, 3580-3600
  作者：SOHDA, TAKASHI、MIZUNO, KATSUTOSHI、IMAMIYA, EIKO、SUGIYAMA, YASUO、FUJITATAK+

  DOI：——

  日期：——
• MODULATION OF NEUROGENESIS BY PPAR AGENTS
  申请人：Barlow Carrolee

  公开号：US20100184806A1

  公开（公告）日：2010-07-22

  The instant disclosure describes methods for treating diseases and conditions of the central and peripheral nervous system including by stimulating or increasing neurogenesis, neuroproliferation, and/or neurodifferentiation. The disclosure includes compositions and methods based on use of a peroxisome proliferator-activated receptor (PPAR) agent, optionally in combination with one or more neurogenic agents, to stimulate or increase a neurogenic response and/or to treat a nervous system disease or disorder.
• [EN] MODULATION OF NEUROGENESIS BY PPAR AGENTS<br/>[FR] MODULATION DE LA NEUROGENÈSE PAR DES AGENTS PPAR
  申请人：BRAINCELLS INC

  公开号：WO2011091033A1

  公开（公告）日：2011-07-28

  The instant disclosure describes methods for treating diseases and conditions of the central and peripheral nervous system including by stimulating or increasing neurogenesis, neuroproliferation, and/or neurodifferentiation. The disclosure includes compositions and methods based on use of a peroxisome proliferator-activated receptor (PPAR) agent, optionally in combination with one or more neurogenic agents, to stimulate or increase a neurogenic response and/or to treat a nervous system disease or disorder.
• Studies on antidiabetic agents. II. Synthesis of 5-(4-(1-methylcyclohexylmethoxy)-benzyl)thiazolidine-2,4-dione (ADD-3878) and its derivatives.
  作者：TAKASHI SOHDA、KATSUTOSHI MIZUNO、EIKO IMAMIYA、YASUO SUGIYAMA、TAKESHI FUJITA、YUTAKA KAWAMATSU

  DOI：10.1248/cpb.30.3580

  日期：——

  More than 100 5-substituted thiazolidine-2, 4-diones were prepared and their hypoglycemic and hypolipidemic activities were evaluated with genetically obese and diabetic mice, yellow KK. The structure-activity relationship study showed that the 5-(4-oxybenzyl) moiety is essential for substantial activity. Among these compounds, 5-(4-cyclohexylmethoxy) benzylthiazolidine-2, 4-dione (47), 5-[4-(1-methylcyclohexylmethoxy) benzyl]-thiazolidine-2, 4-dione (49, ADD-3878) and 5-4-[2-(3-pyridyl) ethoxy] benzyl} thiazolidine-2, 4-dione (59) exhibited the most favorable properties in terms of activity and toxicity.

  合成了100多种5-取代的噻唑烷-2,4-二酮类化合物，并通过遗传性肥胖和糖尿病小鼠（KK黄色小鼠）评估了它们的降血糖和降血脂活性。结构-活性关系研究表明，5-(4-羟基苄基)部分对于显著活性是必要的。在这些化合物中，5-(4-环己基甲氧基)苄基噻唑烷-2,4-二酮（47）、5-[4-(1-甲基环己基甲氧基)苄基]-噻唑烷-2,4-二酮（49，ADD-3878）和5-4-[2-(3-吡啶基)乙氧基]苄基}噻唑烷-2,4-二酮（59）在活性和毒性方面表现出最佳特性。