5-<(5-bromo-1-naphthalenyl)sulfonyl>-3-methyl-2,4-thiazolidinedione | 125518-61-8

• 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>-3-methyl-2,4-thiazolidinedione
• 英文别名: 5-(5-Bromonaphthalen-1-yl)sulfonyl-3-methyl-1,3-thiazolidine-2,4-dione
• CAS: 125518-61-8
• 化学式: C₁₄H₁₀BrNO₄S₂
• 分子量: 400.274
• InChiKey: JKYVVCHDTAFRDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-bromo-1-naphthalene-sulfonyl chloride 在 正丁基锂 、 sodium hydride 作用下， 反应 3.75h， 生成 5-<(5-bromo-1-naphthalenyl)sulfonyl>-3-methyl-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
• 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
• [EN] THIAZOLIDINE DERIVATIVES FOR THE TREATMENT OF PSORIASIS<br/>[FR] DERIVES DE THIAZOLIDINE POUR LE TRAITEMENT DU PSORIASIS
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：WO1995035108A1

  公开（公告）日：1995-12-28

  (EN) 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.(FR) Nouvelle utilisation médicale de certains dérivés de thiazolidine portant spécifiquement sur le traitement d'états d'hyperprolifération des cellules épithéliales tels que le psoriasis, et consistant à administrer des thiazolidinediones ou des dérivés de la thiazolidine à substitution 5'-aryle. L'invention porte également sur les structures chimiques appropriées, sur les réactions de synthèse, sur les voies d'administration et sur les dosages.