5-(4-fluorophenylsulfanyl)-thiazolidine-2,4-dione | 125518-79-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-(4-fluorophenylsulfanyl)-thiazolidine-2,4-dione
• 英文别名: 5-(4-Fluorophenyl-sulfanyl)-thiazolidine-2,4-dione；5-(4-fluorophenyl)sulfanyl-1,3-thiazolidine-2,4-dione
• CAS: 125518-79-8
• 化学式: C₉H₆FNO₂S₂
• 分子量: 243.283
• InChiKey: VBYXAYZVDCWXLU-UHFFFAOYSA-N

物化性质

• 熔点：
  99-100 °C
• 沸点：
  445.5±40.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  96.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(4-fluorophenylsulfanyl)-thiazolidine-2,4-dione 在 双氧水 、 sodium hydride 作用下， 以 溶剂黄146 为溶剂， 反应 6.5h， 生成 5-<<4-<(1-methylcyclohexyl)methoxy>phenyl>sulfonyl>-2,4-thiazolidinedione
  参考文献：
  名称：

  Synthesis and antihyperglycemic activity of novel 5-(naphthalenylsulfonyl)-2,4-thiazolidinediones

  摘要：

  A series of 5-(naphthalenylsulfonyl)-2,4-thiazolidinediones were synthesized and evaluated for antihyperglycemic activity in an insulin-resistant, genetically diabetic db/db mouse model of non-insulin-dependent diabetes mellitus (NIDDM). The sulfones could be synthesized by a novel, selective C-5 sulfonylation of dilithio-2,4-thiazolidinedione with appropriate sulfonyl chlorides. Within this series, naphthalene was found to be superior to other groups for eliciting antihyperglycemic activity, including the p-alkoxyphenyl group found in ciglitazone, a prototypical agent for this activity. Attachment of the 5-sulfonyl-2,4-thiazolidinedione moiety to the 2-naphthalene position led to optimum activity. Other linkers between the naphthalene and 2,4-thiazolidinedione rings, such as thio, methylene, oxy, and sulfinyl led to decreased antihyperglycemic activity. The best analogue, 5-(2-naphthalenylsulfonyl)-2,4-thiazolidinedione (AY-31,637) was equipotent to ciglitazone in two animal models of NIDDM.

  DOI：

  10.1021/jm00167a022
• 作为产物：
  描述：

  对氟苯硫酚 、 5-溴噻唑烷-2,4-二酮 在 sodium carbonate 作用下， 以 水 为溶剂， 反应 16.0h， 以75%的产率得到5-(4-fluorophenylsulfanyl)-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

• Method of using 5-(arysulfonyl)-, 5-(arylsulfanyl)-and 5-(arylsulfanyl)thiazolidine-2,4-diones for inhibition of farnesyl-protein transferase
  申请人：American Cyanamid Company

  公开号：US20030144301A1

  公开（公告）日：2003-07-31

  This invention relates to a method of using novel 5-(arylsulfonyl)-, 5-(arylsulfinyl)- and 5-(arylsulfanyl)thiazolidine-2,4-diones of Formula (1), wherein Ar, Ar′, R 6 , m and n are as defined in the specification as inhibitors of Ras FPTase, and may be used as an alternative to, or in conjunction with, traditional cancer therapy for treating ras- oncogene-dependent tumors, such as cancers of the pancreas, colon, bladder, and thyroid. 1

  这项发明涉及使用新型5-(芳基磺酰基)-、5-(芳基亚砜基)-和5-(芳基硫基)噻唑烷-2,4-二酮的方法，其化学式如下(1)，其中Ar、Ar′、R6、m和n如规范中定义的作为Ras FPTase的抑制剂，并可作为传统癌症治疗的替代方案或与之结合，用于治疗Ras-致癌基因依赖性肿瘤，如胰腺癌、结肠癌、膀胱癌和甲状腺癌。
• 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。
• 5-(arylsulfonyl)-,5-(arylsulfinyl), and 5-(arylsulfanyl)-thiazolidine-2,4-diones useful for inhibition of farnesyl-protein transferase
  申请人：American Cyanamid Company

  公开号：US20030149063A1

  公开（公告）日：2003-08-07

  This invention relates to a method of using novel 5-(arylsulfonyl)-,5- (arylsulfinyl), and 5-(arylsulfanyl)-thiazolidine-2,4-diones of Formula (I), wherein Ar, Ar′, R 6 , m and n are as defined in the specification as inhibitors of Ras FPTase, and may be used as an alternative to, or in conjunction with, traditional cancer therapy for treating ras- oncogene-dependent tumors, such as cancers of the pancreas, colon, bladder, and thyroid. 1

  本发明涉及一种使用新型5-(芳基磺酰基)-、5-(芳基亚磺酰基)和5-(芳基硫基)-噻唑烷-2,4-二酮（式（I）中的Ar、Ar'、R6、m和n如规范中定义）作为Ras FPTase抑制剂的方法，可用作替代传统癌症治疗或与之结合治疗ras-oncogene依赖性肿瘤，例如胰腺癌、结肠癌、膀胱癌和甲状腺癌。
• 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