5-(Quinoline-2-sulfonyl)-thiazolidine-2,4-dione | 173019-81-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-(Quinoline-2-sulfonyl)-thiazolidine-2,4-dione
• 英文别名: 5-quinolin-2-ylsulfonyl-1,3-thiazolidine-2,4-dione
• CAS: 173019-81-3
• 化学式: C₁₂H₈N₂O₄S₂
• 分子量: 308.339
• InChiKey: PGXJMSTWVVRTMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(Quinoline-2-sulfonyl)-thiazolidine-2,4-dione 、 1-(3-bromoprop-1-yn-1-yl)-4-chlorobenzene 在 sodium hydride 作用下， 生成 5-[3(4-Chloro-phenyl)-prop-2-ynyl]-5-(quinoline-2-sulfonyl)thiazolidine-2,4-dione
  参考文献：
  名称：

  Novel 5-(3-Aryl-2-propynyl)-5-(arylsulfonyl)thiazolidine-2,4-diones as Antihyperglycemic Agents

  摘要：

  Novel 5-(3-aryl-2-propynyl)-5-(arylsulfonyl)th and 5-(3-aryl-2-propynyl)5-(arylsulfonyl)thiazolidine-2,4-diones were prepared and evaluated as oral antihyperglycemic agents in the obese, insulin resistant db/db mouse model at 100 mg/kg and, if the analogue had sufficient potency, 20 mg/kg. The sulfonylthiazolidinediones, 2, were more potent than the corresponding sulfanylthiazolidinedione congeners, 1. With regard to substituent effects on the 3-propynyl phenyl ring (Ar') of 2,4-halogen, substitution generally resulted in the more potent analogues. Substituent effects on the phenylsulfonyl moiety (Ar) of 2 were less clear, although para-halogen substitution on Ar generally was preferable. 2-Pyridinesulfonyl derivatives (Ar = 2-pyridine in 2) also had good potency. Several compounds from series 2 were effective at lowering glucose and insulin in the obese, insulin resistant ob/ob mouse at the 50 mg/kg oral dose. Compound 20 significantly improved the glucose tolerance of obese, insulin resistant Zucker rats at the 20 mg/kg dose level and had no effect on plasma glucose or on glucose tolerance in normal rats fasted for 18 h at the 100 mg/kg level.

  DOI：

  10.1021/jm9706168
• 作为产物：
  描述：

  2-喹啉硫醇 在 sodium hydroxide 、 双氧水 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 5-(Quinoline-2-sulfonyl)-thiazolidine-2,4-dione
  参考文献：
  名称：

  Novel 5-(3-Aryl-2-propynyl)-5-(arylsulfonyl)thiazolidine-2,4-diones as Antihyperglycemic Agents

  摘要：

  Novel 5-(3-aryl-2-propynyl)-5-(arylsulfonyl)th and 5-(3-aryl-2-propynyl)5-(arylsulfonyl)thiazolidine-2,4-diones were prepared and evaluated as oral antihyperglycemic agents in the obese, insulin resistant db/db mouse model at 100 mg/kg and, if the analogue had sufficient potency, 20 mg/kg. The sulfonylthiazolidinediones, 2, were more potent than the corresponding sulfanylthiazolidinedione congeners, 1. With regard to substituent effects on the 3-propynyl phenyl ring (Ar') of 2,4-halogen, substitution generally resulted in the more potent analogues. Substituent effects on the phenylsulfonyl moiety (Ar) of 2 were less clear, although para-halogen substitution on Ar generally was preferable. 2-Pyridinesulfonyl derivatives (Ar = 2-pyridine in 2) also had good potency. Several compounds from series 2 were effective at lowering glucose and insulin in the obese, insulin resistant ob/ob mouse at the 50 mg/kg oral dose. Compound 20 significantly improved the glucose tolerance of obese, insulin resistant Zucker rats at the 20 mg/kg dose level and had no effect on plasma glucose or on glucose tolerance in normal rats fasted for 18 h at the 100 mg/kg level.

  DOI：

  10.1021/jm9706168

文献信息

• Certain-[3-aryl-prop-2-ynyl]-5-(arylsulfonyl) thiazolidine -2,4-dione
  申请人：American Home Products Corporation

  公开号：US05574051A1

  公开（公告）日：1996-11-12

  This invention relates to novel 5-[3-aryl-prop-2-ynyl]-5-(arylsulfonyl)- thiazolidine-2,4-diones and 5-[3-aryl-prop-2-ynyl]-5-(arylsulfanyl)thiazolidine-2,4-diones characterized by the general formula (I), seen below, wherein Ar is phenyl, 2-naphthyl, alkyl substituted phenyl, alkoxy substituted phenyl, halogen substituted phenyl, 2-phenyl, substituted 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-quinolinyl, 2-pyrimidinyl, 2-benzoxazolyl, 2-benzthiazolyl, 2-benzimidazolyl, 2-furanyl, 2-benzo-[b]-furanyl, 2-thienyl, 2-benzo-[b]-thienyl; n is 0 or 2; and Ar' is phenyl, alkyl substituted phenyl, perfluoroalkyl substituted phenyl, halogen substituted phenyl, alkoxy substituted phenyl, perfluoroalkoxy substituted phenyl and alkylio substituted phenyl. ##STR1## This invention also relates to the use of the abovementioned compounds in lowering the blood glucose levels in hyperglycemic mammals and pharmaceutical compositions containing the same.

  这项发明涉及新颖的5-[3-芳基-丙-2-炔基]-5-(芳基磺酰基)-噻唑烷-2,4-二酮和5-[3-芳基-丙-2-炔基]-5-(芳基硫基)噻唑烷-2,4-二酮，其具有下面的通用式(I)所示的特征，其中Ar是苯基、2-萘基、烷基取代苯基、烷氧基取代苯基、卤素取代苯基、2-苯基、取代的2-吡啶基、3-吡啶基、4-吡啶基、2-喹啉基、2-嘧啶基、2-苯并噁唑基、2-苯并噻唑基、2-苯并咪唑基、2-呋喃基、2-苯并[ b ]-呋喃基、2-噻吩基、2-苯并[ b ]-噻吩基；n为0或2；Ar'为苯基、烷基取代苯基、全氟烷基取代苯基、卤素取代苯基、烷氧基取代苯基、全氟烷氧基取代苯基和烷氧基取代苯基。该发明还涉及上述化合物在降低高血糖哺乳动物的血糖水平以及含有这些化合物的药物组合物的用途。
• Anti-hyperglycemic agents
  申请人：American Home Products Corporation

  公开号：US05605918A1

  公开（公告）日：1997-02-25

  This invention relates to novel 5-[3-aryl-prop-2-ynyl]-5-(arylsulfonyl)thiazolidine-2,4-diones and 5-[3-aryl-prop-2-ynyl]-5-(arylsulfanyl)thiazolidine-2,4-diones characterized by the general formula (I), seen below, wherein Ar is phenyl, 2-naphthyl, alkyl substituted phenyl, alkoxy substituted phenyl, halogen substituted phenyl, 2-pyridinyl, substituted 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-quinolinyl, 2-pyrimidinyl, 2-benzoxazolyl, 2-benzthiazolyl, 2-benzimidazolyl, 2-furanyl, 2-benzo-[b]-furanyl, 2-thienyl, or 2-benzo-[b]-thienyl; n is 0 or 2; and Ar' is phenyl, alkyl substituted phenyl, perfluoroalkyl substituted phenyl, halogen substituted phenyl, alkoxy substituted phenyl, perfluoroalkoxy substituted phenyl or alkylthio substituted phenyl: ##STR1## This invention also relates to the use of the abovementioned compounds in lowering the blood glucose levels in hyperglycemic mammals and pharmaceutical compositions containing the same.

  本发明涉及新颖的5-[3-芳基-丙-2-炔基]-5-(芳基磺酰基)噻唑烷-2,4-二酮和5-[3-芳基-丙-2-炔基]-5-(芳基硫基)噻唑烷-2,4-二酮，其特征是具有下面的通式(I)，其中Ar是苯基、2-萘基、烷基取代的苯基、烷氧基取代的苯基、卤素取代的苯基、2-吡啶基、取代的2-吡啶基、3-吡啶基、4-吡啶基、2-喹啉基、2-嘧啶基、2-苯并噁唑基、2-苯并噻唑基、2-苯并咪唑基、2-呋喃基、2-苯并[b]-呋喃基、2-噻吩基或2-苯并[b]-噻吩基；n为0或2；Ar'是苯基、烷基取代的苯基、全氟烷基取代的苯基、卤素取代的苯基、烷氧基取代的苯基、全氟烷氧基取代的苯基或烷基硫基取代的苯基: ##STR1## 本发明还涉及上述化合物在降低高血糖哺乳动物的血糖水平和含有它们的制药组合物中的用途。
• THIAZOLIDINEDIONE DERIVATIVES AS ANTI-HYPERGLYCEMIC AGENTS
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0749430B1

  公开（公告）日：1999-08-25
• US5574051A
  申请人：——

  公开号：US5574051A

  公开（公告）日：1996-11-12
• US5605918A
  申请人：——

  公开号：US5605918A

  公开（公告）日：1997-02-25