5-(喹啉-2-硫烷基)-噻唑烷-2,4-二酮 | 1027590-08-4

• 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
• 中文名称: 5-(喹啉-2-硫烷基)-噻唑烷-2,4-二酮
• 英文名称: 5-(quinoline-2-sulfanyl)-thiazolidine-2,4-dione
• 英文别名: 5-Quinolin-2-ylsulfanyl-1,3-thiazolidine-2,4-dione
• CAS: 1027590-08-4
• 化学式: C₁₂H₈N₂O₂S₂
• 分子量: 276.34
• InChiKey: PDGIJSQJXQZRRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 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：
  110
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(喹啉-2-硫烷基)-噻唑烷-2,4-二酮 、 1-(3-bromoprop-1-yn-1-yl)-4-chlorobenzene 在 sodium hydride 作用下， 生成 5-[3-(4-Chlorophenyl)-prop-2-ynyl]-5-(quinoline-2-sulfanyl)-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：

  5-溴噻唑烷-2,4-二酮 、 2-喹啉硫醇 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 5-(喹啉-2-硫烷基)-噻唑烷-2,4-二酮
  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

• THIAZOLIDINEDIONE DERIVATIVES AS ANTI-HYPERGLYCEMIC AGENTS
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0749430A1

  公开（公告）日：1996-12-27
• 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
• [EN] THIAZOLIDINEDIONE DERIVATIVES AS ANTI-HYPERGLYCEMIC AGENTS<br/>[FR] DERIVES DE THIAZOLIDINEDIONE UTILISES COMME AGENTS ANTI-HYPERGLYCEMIQUES
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：WO1995024400A1

  公开（公告）日：1995-09-14

  (EN) 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 general formula (I), 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, 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 alkylthio substituted phenyl. 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.(FR) L'invention concerne de nouvelles 5-[3-aryl-prop-2-ynyl]-5-(arylsulfonyl)-thiazolidine-2,4-diones et 5-[3-aryl-prop-2-ynyl]-5-(arylsulfanyl)thiazolidine-2,4-diones caractérisées par la formule générale (I), où Ar représente phényle, 2-naphtyle, phényle substitué par alkyle, phényle substitué par alcoxy, phényle substitué par halogène, 2-pyridinyle, 2-pyridinyle substitué, 3-pyridinyle, 4-pyridinyle, 2-quinolinyle, 2-pyrimidinyle, 2-benzoxazolyle, 2-benzthiazolyle, 2-benzimidazolyle, 2-furanyle, 2-benzo-[b]-furanyle, 2-thiényle, 2-benzo-[b]-thiényle; n est égal à 0 ou 2; et Ar' représente phényle, phényle substitué par alkyle, phényle substitué par perfluoroalkyle, phényle substitué par halogène, phényle substitué par alcoxy, phényle substitué par perfluoroalcoxy et phényle substitué par alkylthio. L'invention concerne également l'utilisation des composés mentionnés ci-dessus pour abaisser les taux de glycémie chez les mammifères hyperglycémiques, et les compositions pharmaceutiques contenant ces composés.