5-<(6-hydroxy-2-naphthalenyl)thio>-2,4-thiazolidinedione | 125518-74-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-<(6-hydroxy-2-naphthalenyl)thio>-2,4-thiazolidinedione
• 英文别名: 5-[(6-hydroxy-2-naphthalenyl)thio]-2,4-thiazolidinedione；5-[(6-Hydroxyl-2-naphthalenyl)thio]-2,4-thiazolidinedione；5-(6-hydroxynaphthalen-2-yl)sulfanyl-1,3-thiazolidine-2,4-dione
• CAS: 125518-74-3
• 化学式: C₁₃H₉NO₃S₂
• 分子量: 291.351
• InChiKey: NVHFRSHAUQAENH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 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：
  117
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  carbonic acid 6-[(2,4-dioxo-5-thiazolidinyl)thio]-2-naphthalenyl ethyl ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 5-<(6-hydroxy-2-naphthalenyl)thio>-2,4-thiazolidinedione
  参考文献：
  名称：

  5-[(1- and 2-naphthalenyl) sulfonyl]-2,4-thiazolidinediones and

  摘要：

  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。

  公开号：

  US04997948A1

文献信息

• Thiazolidine derivatives for the treatment of psoriasis
  申请人：Regents of the University of California

  公开号：US05594015A1

  公开（公告）日：1997-01-14

  A new medical use for certain thiazolidine derivatives is disclosed. Specifically, treatment of hyperproliferative epithelial cell conditions, such as psoriasis, by administration of thiazolidinediones or 5'-aryl substituted thiazolidine derivatives is described. Appropriate chemical structures, synthetic reactions, formulations, routes of administration and dosages are included.

  本文披露了某些噻唑烷衍生物的新医疗用途。具体来说，描述了通过给予噻唑烷二酮或5'-芳基取代的噻唑烷衍生物治疗过度增生的上皮细胞病症，如牛皮癣。包括适当的化学结构、合成反应、制剂、给药途径和剂量。
• Synthesis and antihyperglycemic activity of novel 5-(naphthalenylsulfonyl)-2,4-thiazolidinediones
  作者：Arie Zask、Ivo Jirkovsky、James W. Nowicki、Michael L. McCaleb

  DOI：10.1021/jm00167a022

  日期：1990.5

  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.
• THIAZOLIDINE DERIVATIVES FOR THE TREATMENT OF PSORIASIS
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：EP0804193A1

  公开（公告）日：1997-11-05
• EP0804193A4
  申请人：——

  公开号：EP0804193A4

  公开（公告）日：2002-03-27
• US4997948A
  申请人：——

  公开号：US4997948A

  公开（公告）日：1991-03-05