5-<(5-bromo-1-naphthalenyl)sulfonyl>-2,4-thiazolidinedione | 125518-60-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-<(5-bromo-1-naphthalenyl)sulfonyl>-2,4-thiazolidinedione
• 英文别名: 5-[(5-bromo-1-naphthalenyl)sulfonyl]-2,4-thiazolidinedione；5-(5-bromonaphthalen-1-yl)sulfonyl-1,3-thiazolidine-2,4-dione
• CAS: 125518-60-7
• 化学式: C₁₃H₈BrNO₄S₂
• 分子量: 386.247
• InChiKey: NHGDNRXYCKECLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 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：
  114
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-<(5-bromo-1-naphthalenyl)sulfonyl>-2,4-thiazolidinedione 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以59%的产率得到5-<(5-bromo-1-naphthalenyl)sulfonyl>-3,5-dimethyl-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：

  2,4-噻唑烷二酮 、 5-bromo-1-naphthalene-sulfonyl chloride 在 正丁基锂 作用下， 生成 5-<(5-bromo-1-naphthalenyl)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

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。
• 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
• US5594015A
  申请人：——

  公开号：US5594015A

  公开（公告）日：1997-01-14
• US5824694A
  申请人：——

  公开号：US5824694A

  公开（公告）日：1998-10-20