5-[2,4-Dioxo-thiazolidin-(5E)-ylidenemethyl]-2-methoxy-benzoic acid methyl ester | 186312-71-0

• 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: 5-[2,4-Dioxo-thiazolidin-(5E)-ylidenemethyl]-2-methoxy-benzoic acid methyl ester
• 英文别名: Methyl 5-(2,4-dioxothiazolidin-5-ylidene)methyl-2-methoxybenzoate；methyl 5-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-methoxybenzoate
• CAS: 186312-71-0
• 化学式: C₁₃H₁₁NO₅S
• 分子量: 293.3
• InChiKey: UOERQDNMYPQTSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-[2,4-Dioxo-thiazolidin-(5E)-ylidenemethyl]-2-methoxy-benzoic acid methyl ester 在 盐酸 、 氰基磷酸二乙酯 、 三乙胺 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-[2,4-Dioxo-thiazolidin-(5E)-ylidenemethyl]-2-methoxy-N-[2-(4-trifluoromethyl-phenyl)-ethyl]-benzamide
  参考文献：
  名称：

  (3-Substituted benzyl)thiazolidine-2,4-diones as structurally new antihyperglycemic agents

  摘要：

  A series of 3-[(2,4-dioxothiazolidin-5-yl)methyl]benzamide derivatives was prepared as part of a search for antidiabetic agents. A structure-activity relationship study of these compounds led to the identification of 5-[(2,4-dioxothiazolidin-5-yl)methyl] -2-methoxy-N-[[4-trifluoromethyl)phenyl]methyl]benzamide (KRP-297) as a candidate drug for the treatment of diabetes mellitus. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00039-6
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 5-甲酰基-2-甲氧基苯甲酸甲酯 在 ammonium acetate 作用下， 以 溶剂黄146 、 苯 为溶剂， 生成 5-[2,4-Dioxo-thiazolidin-(5E)-ylidenemethyl]-2-methoxy-benzoic acid methyl ester
  参考文献：
  名称：

  (3-Substituted benzyl)thiazolidine-2,4-diones as structurally new antihyperglycemic agents

  摘要：

  A series of 3-[(2,4-dioxothiazolidin-5-yl)methyl]benzamide derivatives was prepared as part of a search for antidiabetic agents. A structure-activity relationship study of these compounds led to the identification of 5-[(2,4-dioxothiazolidin-5-yl)methyl] -2-methoxy-N-[[4-trifluoromethyl)phenyl]methyl]benzamide (KRP-297) as a candidate drug for the treatment of diabetes mellitus. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00039-6

文献信息

• N-benzyldioxothiazolidylbenzamide derivatives and processes for
  申请人：Kyorin Pharameuticals Co., Ltd.

  公开号：US06001862A1

  公开（公告）日：1999-12-14

  The present invention provides novel N-benzyldioxothiazolidylbenzamide derivatives that improve the insulin resistance and have potent hypoglycemic and lipid-lowering effects and processes for preparing the same, and relates to N-benzyldioxothiazolidylbenzamide derivatives characterized by being represented by a general formula (1) ##STR1## [wherein R.sup.1 and R.sup.2 denote identically or differently hydrogen atoms, lower alkyl groups with carbon atoms of 1 to 4, lower alkoxy groups with carbon atoms of 1 to 3, lower haloalkyl groups with carbon atoms of 1 to 3, lower haloalkoxy groups with carbon atoms of 1 to 3, halogen atoms, hydroxyl groups, nitro groups, amino groups which may be substituted with lower alkyl group(s) with carbon atoms of 1 to 3 or hetero rings, or R.sup.1 and R.sup.2 link to form a methylenedioxy group, R.sup.3 denotes a lower alkoxy group with carbon atoms of 1 to 3, hydroxyl group or halogen atom, and dotted line indicates double bond or single bond in combination with solid line], and processes for preparing the same.

  本发明提供了一种新型的N-苄基二氧噻唑基苯甲酰胺衍生物，可以改善胰岛素抵抗，并具有强效的降血糖和降脂作用，以及制备该化合物的方法。本发明涉及一般式（1）所表示的以N-苄基二氧噻唑基苯甲酰胺衍生物为特征的化合物。其中，R1和R2表示相同或不同的氢原子、碳原子数为1到4的低碳基、碳原子数为1到3的低碳氧基、碳原子数为1到3的低卤代烷基、碳原子数为1到3的低卤代氧基、卤素原子、羟基、硝基、氨基，其可以被碳原子数为1到3的低碳基或杂环取代，或者R1和R2连接形成亚甲二氧基基团；R3表示碳原子数为1到3的低碳氧基、羟基或卤素原子；虚线表示与实线结合形成双键或单键。同时还提供了制备该化合物的方法。
• N-benzyldioxothiazolidylbenzamide derivatives and process for producing
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：US06030990A1

  公开（公告）日：2000-02-29

  The present invention provides novel N-benzyldioxothiazolidylbenzamide derivatives that improve the insulin resistance and have potent hypoglycemic and lipid-lowering effects and processes for preparing the same, and relates to N-benzyldioxothiazolidylbenzamide derivatives characterized by being represented by a general formula (1) ##STR1## wherein R.sup.1 and R.sup.2 denote identically or differently hydrogen atoms, lower alkyl groups with carbon atoms of 1 to 4, lower alkoxy groups with carbon atoms of 1 to 3, lower haloalkyl groups with carbon atoms of 1 to 3, lower haloalkoxy groups with carbon atoms of 1 to 3, halogen atoms, hydroxyl groups, nitro groups, amino groups which may be substituted with lower alkyl group(s) with carbon atoms of 1 to 3 or hetero rings, or R.sup.1 and R.sup.2 link to form a methylenedioxy group, R.sup.3 denotes a lower alkoxy group with carbon atoms of 1 to 3, hydroxyl group or halogen atom, and dotted line indicates double bond or single bond in combination with solid line, and processes for preparing the same.

  本发明提供了一种新型的N-苯甲酰基二氧噻唑基苯甲酰胺衍生物，其改善胰岛素抵抗，并具有强效的降血糖和降脂作用，以及制备该衍生物的过程。该N-苯甲酰基二氧噻唑基苯甲酰胺衍生物的特征在于其由一般式（1）所表示，其中R1和R2表示相同或不同的氢原子，具有1到4个碳原子的低碳基，具有1到3个碳原子的低烷氧基，具有1到3个碳原子的低卤代烷基，具有1到3个碳原子的低卤代烷氧基，卤素原子，羟基，硝基，氨基，可以用具有1到3个碳原子的低碳基或杂环取代的氨基，或R1和R2连接形成亚甲二氧基基团，R3表示具有1到3个碳原子的低烷氧基，羟基或卤素原子，虚线表示与实线相结合的双键或单键，以及制备该衍生物的过程。
• (3-Substituted benzyl)thiazolidine-2,4-diones as structurally new antihyperglycemic agents
  作者：Masahiro Nomura、Susumu Kinoshita、Hiroya Satoh、Toshio Maeda、Koji Murakami、Masaki Tsunoda、Hiroyuki Miyachi、Katsuya Awano

  DOI：10.1016/s0960-894x(99)00039-6

  日期：1999.2

  A series of 3-[(2,4-dioxothiazolidin-5-yl)methyl]benzamide derivatives was prepared as part of a search for antidiabetic agents. A structure-activity relationship study of these compounds led to the identification of 5-[(2,4-dioxothiazolidin-5-yl)methyl] -2-methoxy-N-[[4-trifluoromethyl)phenyl]methyl]benzamide (KRP-297) as a candidate drug for the treatment of diabetes mellitus. (C) 1999 Elsevier Science Ltd. All rights reserved.