5-(2-naphthalenylsulfinyl)-2,4-thiazolidinedione | 125518-53-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(2-naphthalenylsulfinyl)-2,4-thiazolidinedione
• 英文别名: 5-Naphthalen-2-ylsulfinyl-1,3-thiazolidine-2,4-dione
• CAS: 125518-53-8；125518-54-9
• 化学式: C₁₃H₉NO₃S₂
• 分子量: 291.351
• InChiKey: FLVMECNYQDKWKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：
  108
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  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

文献信息

• 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
• PHARMACEUTICAL COMPOSITION OF NATEGLINIDE AND ANOTHER ANTIDIABETIC AGENT
  申请人：Novartis AG

  公开号：EP1218015A2

  公开（公告）日：2002-07-03
• DIPEPTIDYL PEPTIDASE INHIBITORS FOR TREATING DIABETES
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1942898A1

  公开（公告）日：2008-07-16
• US5594015A
  申请人：——

  公开号：US5594015A

  公开（公告）日：1997-01-14