6-[2-(3,4-dimethoxybenzoyl)-1,3-thiazol-4-yl]-3,4-dihydro-1H-quinolin-2-one | 145737-92-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-[2-(3,4-dimethoxybenzoyl)-1,3-thiazol-4-yl]-3,4-dihydro-1H-quinolin-2-one
• CAS: 145737-92-4
• 化学式: C₂₁H₁₈N₂O₄S
• 分子量: 394.451
• InChiKey: GXJUSZGBRXHIAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-[2-(3,4-dimethoxybenzoyl)-1,3-thiazol-4-yl]-3,4-dihydro-1H-quinolin-2-one 在 sodium tetrahydroborate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 1.0h， 以52.5%的产率得到6-[2-[(3,4-dimethoxyphenyl)-hydroxymethyl]-1,3-thiazol-4-yl]-3,4-dihydro-1H-quinolin-2-one
  参考文献：
  名称：

  Novel Thiazole Derivatives as Inhibitors of Superoxide Production by Human Neutrophils: Synthesis and Structure-Activity Relationships

  摘要：

  Neutrophils have an important role in the self-defense systems of organisms through the production of superoxide. On the other hand, it has been proposed that abnormal amounts of superoxide produced by neutrophils are a serious factor in tissue injury. A series of novel thiazole derivatives was prepared and evaluated inhibitory effect on superoxide production by human neutrophils in vitro. Among these compounds, 6-[2-(3,4-diethoxyphenyl)thiazol-4-yl]-pyridine-2-carboxylic acid (OPC-6535) was selected as one of the most promising compounds. The synthesis and structure-activity relationships of these compounds are reported herein.

  DOI：

  10.1021/jm00002a017
• 作为产物：
  描述：

  3,4-二甲氧基苯乙腈 在 chromium(VI) oxide 、 盐酸 、 硫代乙酰胺 作用下， 以 乙醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 6-[2-(3,4-dimethoxybenzoyl)-1,3-thiazol-4-yl]-3,4-dihydro-1H-quinolin-2-one
  参考文献：
  名称：

  Novel Thiazole Derivatives as Inhibitors of Superoxide Production by Human Neutrophils: Synthesis and Structure-Activity Relationships

  摘要：

  Neutrophils have an important role in the self-defense systems of organisms through the production of superoxide. On the other hand, it has been proposed that abnormal amounts of superoxide produced by neutrophils are a serious factor in tissue injury. A series of novel thiazole derivatives was prepared and evaluated inhibitory effect on superoxide production by human neutrophils in vitro. Among these compounds, 6-[2-(3,4-diethoxyphenyl)thiazol-4-yl]-pyridine-2-carboxylic acid (OPC-6535) was selected as one of the most promising compounds. The synthesis and structure-activity relationships of these compounds are reported herein.

  DOI：

  10.1021/jm00002a017

文献信息

• ACTIVE OXYGEN INHIBITOR
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0513387A1

  公开（公告）日：1992-11-19

  An active oxygen inhibitor which contains an azole derivative represented by general formula (1) or a salt thereof as the active ingredient, wherein R¹ represents phenyl which may be substituted by 1 to 3 lower alkoxy groups or by a lower alkyleneoxy group, etc.; R² represents hydrogen, phenyl, halogen, lower alkoxycarbonyl, lower alkyl, lower aminoalkyl which may be substituted by lower alkyl, dihydrocarbostyrilyl, etc.; R³ represents the group (α), wherein R4B represents hydroxy, carboxy, lower alkenyl or lower alkyl, and m represents 0, 1 or 2; and X represents sulfur or oxygen.

  R²代表氢、苯基、卤素、低级烷氧基羰基、低级烷基、可被低级烷基取代的低级氨基烷基、二氢羧基等；R³代表基团（α），其中 R4B 代表羟基、羧基、低级烯基或低级烷基，m 代表 0、1 或 2；X 代表硫或氧。
• Azole derivatives and their use as superoxide radical inhibitors
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP1130017A2

  公开（公告）日：2001-09-05

  A superoxide radical inhibitor containing, as an effective ingredient, an azole derivative represented by the general formula (1), [wherein R1 represents a phenyl group which may have 1-3 lower alkoxy groups as substituent(s) on the phenyl ring, a phenyl group having a lower alkylenedioxy group, or the like; R2 represents a hydrogen atom, a phenyl group, a halogen atom, a lower alkoxycarbonyl group, a lower alkyl group, an amino-lower alkyl group which may have a lower alkyl group as a substituent, a dihydrocarbostyril group, or the like; R3 represents a group of the formula, (R4B represents a hydroxyl group, a carboxy group, a lower alkenyl group or a lower alkyl group. m represents 0, 1 or 2); X represents a sulfur atom : ] or a salt thereof.

  一种超氧自由基抑制剂，其有效成分含有通式(1)代表的唑衍生物、 [其中 R1 代表苯基，苯基环上可以有 1-3 个低级烷氧基作为取代基，苯基上可以有低级烷基二氧基等；R2 代表氢原子、苯基、卤素原子、低级烷氧基羰基、低级烷基、氨基低级烷基，氨基低级烷基上可以有低级烷基作为取代基，二氢羰基等；R3 代表式中的一个基团、 (R4B 代表羟基、羧基、低级烯基或低级烷基，m 代表 0、1 或 2）； X 代表硫原子： ]或其盐。
• Azole derivatives as superoxide radical inhibitor
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0934937B1

  公开（公告）日：2002-02-27
• US5643932A
  申请人：——

  公开号：US5643932A

  公开（公告）日：1997-07-01
• US5677319A
  申请人：——

  公开号：US5677319A

  公开（公告）日：1997-10-14