5-[[4-(2-甲基-2-苯基丙氧基)苯基]甲基]-1,3-噻唑烷-2,4-二酮 | 74772-68-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-[[4-(2-甲基-2-苯基丙氧基)苯基]甲基]-1,3-噻唑烷-2,4-二酮
• 英文名称: 5-<4-(2-methyl-2-phenylpropoxy)benzyl>thiazolidine-2,4-dione
• 英文别名: 5-<4-(2-methyl-2-phenylpropoxy)benzyl>thiazolidin-2,4-dione；5-[4-(2-methyl-2-phenylpropyloxy)-benzyl]thiazolidine-2,4-dione；5-[4-(2-methyl-2-phenylpropoxy)benzyl]thiazolidine-2,4-dione；5-(4-(2-Methyl-2-phenylpropoxy)benzyl)thiazolidine-2,4-dione；5-[[4-(2-methyl-2-phenylpropoxy)phenyl]methyl]-1,3-thiazolidine-2,4-dione
• CAS: 74772-68-2
• 化学式: C₂₀H₂₁NO₃S
• 分子量: 355.458
• InChiKey: FZKKPKRWTSYXLF-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  547.9±33.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[[4-(2-甲基-2-苯基丙氧基)苯基]甲基]-1,3-噻唑烷-2,4-二酮 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3-methyl-5-<4-(2-methyl-2-phenylpropoxy)benzyl>thiazolidin-2,4-dione
  参考文献：
  名称：

  Studies on antidiabetic agents. I. Synthesis of 5-(4-(2-methyl-2-phenylpropoxy)-benzyl)thiazolidine-2,4-dione (AL-321) and related compounds.

  摘要：

  一系列含有4-(2-甲基-2-苯基丙氧基)苄基结构的化合物被制备出来，并在遗传性肥胖和糖尿病小鼠KK黄色中评估了它们的降血糖和降血脂活性。在这些化合物中，5-[4-(2-甲基-2-苯基丙氧基)苄基]噻唑烷-2,4-二酮（化合物18，AL-321）显示出比或相当于乙基2-氯-3-[4-(2-甲基-2-苯基丙氧基)苯基]丙酸酯（化合物1a）更高的降血糖和降血脂活性。酸性噻唑烷-2,4-二酮环似乎对这些活性至关重要。

  DOI：

  10.1248/cpb.30.3563
• 作为产物：
  描述：

  2-溴-3-[4-(2-甲基-2-苯基丙氧基)苯基]丙腈 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 5-[[4-(2-甲基-2-苯基丙氧基)苯基]甲基]-1,3-噻唑烷-2,4-二酮
  参考文献：
  名称：

  Studies on antidiabetic agents. I. Synthesis of 5-(4-(2-methyl-2-phenylpropoxy)-benzyl)thiazolidine-2,4-dione (AL-321) and related compounds.

  摘要：

  一系列含有4-(2-甲基-2-苯基丙氧基)苄基结构的化合物被制备出来，并在遗传性肥胖和糖尿病小鼠KK黄色中评估了它们的降血糖和降血脂活性。在这些化合物中，5-[4-(2-甲基-2-苯基丙氧基)苄基]噻唑烷-2,4-二酮（化合物18，AL-321）显示出比或相当于乙基2-氯-3-[4-(2-甲基-2-苯基丙氧基)苯基]丙酸酯（化合物1a）更高的降血糖和降血脂活性。酸性噻唑烷-2,4-二酮环似乎对这些活性至关重要。

  DOI：

  10.1248/cpb.30.3563

文献信息

• 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。
• Thiazolidine derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04438141A1

  公开（公告）日：1984-03-20

  Thiazolidine derivatives of the general formula: ##STR1## [wherein R.sup.1 is alkyl, cycloalkyl, phenylalkyl, phenyl, a five- or six-membered heterocyclic group including one or two hetero-atoms selected from the group consisting of nitrogen, oxygen and sulfur or a group of the formula ##STR2## (where R.sup.3 and R.sup.4 are the same or different and each is lower alkyl or R.sup.3 and R.sup.4 are combined to each other either directly or as interrupted by a hetero-atom selected from the group consisting of nitrogen, oxygen and sulfur to form a five- or six-membered ring); R.sup.2 means a bond or a lower alkylene group; L.sup.1 and L.sup.2 are the same or different and each is lower alkyl or L.sup.1 and L.sup.2 are combined to form an alkylene group, provided that when R.sup.1 is other than alkyl, L.sup.1 and L.sup.2 may further be hydrogen, respectively] are novel compounds and useful as, for example, remedies for diabetes, hyperlipemia and so on of mammals including human beings.

  通式为：##STR1## 的噻唑烷衍生物 [其中 R.sup.1 是烷基、环烷基、苯基烷基、苯基、含有一个或两个氮、氧和硫中的选自一组杂原子的五元或六元杂环基或式子 ##STR2## 的基团（其中 R.sup.3 和 R.sup.4 相同或不同，且每个都是低级烷基或 R.sup.3 和 R.sup.4 相互结合，直接或通过选自氮、氧和硫组成的杂原子的五元或六元环形成一个环）; R.sup.2 表示键或低级烷基烷基; L.sup.1 和 L.sup.2 相同或不同，每个都是低级烷基或 L.sup.1 和 L.sup.2 相互结合形成一个烷基烷基，但当 R.sup.1 不是烷基时，L.sup.1 和 L.sup.2 可以进一步是氢] 是新的化合物，可用作哺乳动物，包括人类的糖尿病、高脂血症等药物。
• Thiazolidine derivatives, preparing same and pharmaceutical compositions comprising same
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0008203A1

  公开（公告）日：1980-02-20

  Thiazolidine derivations of the general formula: wherein R1 is alkyl, cycloalkyl, phenylalkyl, phenyl, a five-or six-membered heterocyclic group including one or two hetero-atoms selected from nitrogen, oxygen and sulphur or a group of the formula (where R3 and R4 are the same or different and each is lower alkyl or R3 and R4 are combined with each other either directly or interrupted by a hetero-atom selected from nitrogen, oxygen and sulphur to form a five- or six-membered ring); R2 means a bond or a lower alkylene group; L1 and L2 are the same or different and each is lower alkyl or L' and L2 are combined to form an alkylene group, provided that, when R' is other than alkyl, L' and L2 may be further hydrogen, are novel compounds and useful as, for example remedies for diabetes, hyperlipemia and so on of the mammals including human beings.

  通式如下的噻唑烷衍生物 其中 R1 是烷基、环烷基、苯基烷基、苯基、包括一个或两个选自氮、氧和硫的杂原子的五或六元杂环基团或通式如下的基团 (其中 R3 和 R4 相同或不同，且各自为低级烷基，或 R3 和 R4 直接相互结合，或由选自氮、氧和硫的杂原子间断，形成五元或六元环）；R2 指键或低级亚烷基；L1 和 L2 相同或不同，且各自为低级烷基，或 L' 和 L2 结合形成亚烷基，但当 R' 不是烷基时，L' 和 L2 可进一步为氢、 是新型化合物，可用于治疗包括人类在内的哺乳动物的糖尿病、高脂血症等。
• REMEDIES FOR DIABETES
  申请人：Fujimoto Brothers Co., Ltd.

  公开号：EP1179343A1

  公开（公告）日：2002-02-13

  This invention relates to therapeutic agents for diabetes comprising a 2-(N-cyanoimino)thiazolidine-4-one derivatives represented by formula I or a solvate or a pharmaceutically acceptable salt thereof as an active ingredient: wherein ring A represents a benzene ring, a condensed ring, or a heterocyclic ring, each of which may be substituted by one or more substituents selected from a straight or branched C1-C4 alkyl group, a haloalkyl group, a halogen atom or -OR5, R1 represents a single bond, an oxygen atom, a sulfur atom, a methyne group, a straight. or branched C1 - C4 alkylene or alkenylene group optionally substituted by a phenyl group, R6-X, X-R6, X-R6-X, R6-X-R6, -C(=O)-NR7- or -NR7-C(=O)-, R2 and R3 are the same or different and each represents a hydrogen atom, a C1 - C4 alkyl group, -OR8 or a halogen atom, R4 represents a hydrogen atom or a C1 - C4 alkyl group, R5 represents a hydrogen atom or a C1 - C4 alkyl group, R6 represents a straight or branched C1 - C4 alkylene or alkenylene group, R7 represents a hydrogen atom or a C1 - C4 alkyl group, R8 represents a hydrogen atom, a C1 - C4 alkyl group or an aralkyl group, X represents an oxygen atom or a sulfur atom, the configuration of the exocyclic methylene group at 5-position of the thiazolidine ring includes both E- and Z-configuration.

  本发明涉及由式 I 所代表的 2-(N-氰基亚胺)噻唑烷-4-酮衍生物或其溶液或药学上可接受的盐作为活性成分的糖尿病治疗剂： 其中环 A 代表苯环、缩合环或杂环，每个环可被一个或多个选自直链或支链 C1-C4 烷基、卤代烷基、卤素原子或 -OR5 的取代基取代、 R1 代表单键、氧原子、硫原子、甲基、任选被苯基取代的直链或支链 C1-C4 烯基或烯基、R6-X、X-R6、X-R6-X、R6-X-R6、-C(＝O)-NR7-或-NR7-C(＝O)-、 R2 和 R3 相同或不同，各自代表氢原子、C1-C4 烷基、-OR8 或卤素原子、 R4 代表氢原子或 C1 - C4 烷基、 R5 代表氢原子或 C1 - C4 烷基、 R6 代表直链或支链 C1 - C4 烯基或烯基、 R7 代表氢原子或 C1 - C4 烷基、 R8 代表氢原子、C1 - C4 烷基或芳烷基、 X 代表氧原子或硫原子、 噻唑烷环 5 位的外环亚甲基的构型包括 E- 和 Z- 构型。
• Methods and pharmaceutical compositions for inhibiting tumour cell growth
  申请人：DANA-FARBER CANCER INSTITUTE

  公开号：EP1410799A1

  公开（公告）日：2004-04-21

  Methods for inhibiting proliferation of a PPARγ-responsive hyperproliferative cell using PPARγ agonists are described. Pharmaceutical compositions as well as method for diagnosing and treating a PPARγ-responsive hyperproliferative cell are also described.

  描述了使用 PPARγ 激动剂抑制 PPARγ 反应性高增殖细胞增殖的方法。还描述了药物组合物以及诊断和治疗 PPARγ 反应性高增殖细胞的方法。