2,4-噻唑烷二酮,5-(1-萘基磺酰)- | 125540-45-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2,4-噻唑烷二酮,5-(1-萘基磺酰)-
• 英文名称: 5-[(1-naphthalenyl)sulfonyl]-2,4-thiazolidinedione
• 英文别名: 5-Naphthalen-1-ylsulfonyl-1,3-thiazolidine-2,4-dione
• CAS: 125540-45-6
• 化学式: C₁₃H₉NO₄S₂
• 分子量: 307.351
• InChiKey: XUFCYFURAWHVSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 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

• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 1-萘磺酰氯 在 正丁基锂 作用下， 生成 2,4-噻唑烷二酮,5-(1-萘基磺酰)-
  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

• Tiermodell zur Entstehung und Therapie von Diabetes Mellitus
  申请人：GSF-Forschungszentrum für Umwelt und Gesundheit GmbH

  公开号：EP0979872A1

  公开（公告）日：2000-02-16

  Die Erfindung betrifft eine rekombinante DNA, umfassend einen Promotor, der in den ß-Zellen des endokrinen Pankreas exprimierbar ist, eine Sequenz, die für ein GIP-Rezeptorprotein oder ein aktives Fragment hiervon kodiert, das befähigt ist, das Peptidhormon GIP zu binden, ohne eine Signaltransduktion zu initiieren, eine Terminationssequenz und eine Polyadenylierungssequenz, wobei die DNA bei Expression in einem geeigneten Wirt einen Diabetes-Phänotyp bewirkt sowie transgene, nicht menschliche Säugetiere, die diese rekombinante DNA enthalten.

  本发明涉及一种重组DNA，该DNA包含一个可在胰腺内分泌ß细胞中表达的启动子、一个编码GIP受体蛋白或其能够结合肽类激素GIP而不启动信号转导的活性片段的序列、一个终止序列和一个多聚腺苷酸化序列，其中所述DNA在合适的宿主中表达时会导致糖尿病表型，以及含有所述重组DNA的转基因非人类哺乳动物、不启动信号转导、终止序列和多腺苷酸化序列，其中 DNA 在合适宿主中表达时导致糖尿病表型，以及含有所述重组 DNA 的转基因非人类哺乳动物。
• PROCESSES FOR THE PREPARATION OF THIAZOLIDINEDIONE DERIVATIVES AND INTERMEDIATES
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1282619B1

  公开（公告）日：2005-06-22
• 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
• 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.