5-[(2-Naphthalenyl)thio]-2,4-thiazolidinedione | 125518-72-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-[(2-Naphthalenyl)thio]-2,4-thiazolidinedione
• 英文别名: 5-Naphthalen-2-ylsulfanyl-1,3-thiazolidine-2,4-dione
• CAS: 125518-72-1
• 化学式: C₁₃H₉NO₂S₂
• 分子量: 275.352
• InChiKey: ZHCHOIFRLFSHKK-UHFFFAOYSA-N

物化性质

• 沸点：
  536.7±43.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  96.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[(2-Naphthalenyl)thio]-2,4-thiazolidinedione 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以52%的产率得到5-(2-naphthalenylsulfinyl)-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：

  5-溴噻唑烷-2,4-二酮 、 2-萘硫醇 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 5-[(2-Naphthalenyl)thio]-2,4-thiazolidinedione
  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

• 5-[(1- and 2-naphthalenyl) sulfonyl]-2,4-thiazolidinediones and
  申请人：American Home Products

  公开号：US04997948A1

  公开（公告）日：1991-03-05

  Disclosed herein are 1- or 2-thio, thiomethylene, and sulfonylnaphthalene derivatives of formulas I and II ##STR1## or a pharmaceutically acceptable catonic salt thereof, wherein n is 0 or 1 R.sub.5 is hydrogen, bromo, chloro, trifluoromethyl or difluoroethyl; R.sub.6 is hydrogen, hydroxy, methoxy or ethoxy; and R.sub.7 is hydrogen or R.sub.7 and R.sub.6 are both methyl or ethyl carbonate, provided that, when S(O).sub.2 is in the 2 position of the naphthalene ring, R.sub.5, R.sub.6 and R.sub.7 are each hydrogen. The disclosed compounds possess blood-glucose lowering actions and are useful in the treatment of diabetes mellitus.

  本文披露了公式I和II的1-或2-硫、硫亚甲基和磺酰基萘衍生物，或其药用可接受的阳离子盐，其中n为0或1，R.sub.5为氢、溴、氯、三氟甲基或二氟乙基；R.sub.6为氢、羟基、甲氧基或乙氧基；R.sub.7为氢或R.sub.7和R.sub.6都是甲基或乙基碳酸酯，但当S(O).sub.2在萘环的2位置时，R.sub.5、R.sub.6和R.sub.7都是氢。所披露的化合物具有降低血糖作用，并可用于治疗糖尿病。
• J. Med. Chem. 1990, 33, 1418-1423
  作者：

  DOI：——

  日期：——
• 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
• US4997948A
  申请人：——

  公开号：US4997948A

  公开（公告）日：1991-03-05
• US5068342A
  申请人：——

  公开号：US5068342A

  公开（公告）日：1991-11-26