N-(2-{4-[2,4-dioxo(1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)-5-(1,2-dithiolan-3-yl) pentanamide | 292615-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: N-(2-{4-[2,4-dioxo(1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)-5-(1,2-dithiolan-3-yl) pentanamide
• 英文别名: N-[2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]ethyl]-5-(dithiolan-3-yl)pentanamide
• CAS: 292615-75-9
• 化学式: C₂₀H₂₆N₂O₄S₃
• 分子量: 454.635
• InChiKey: VDWFJOXRKJFJMP-UHFFFAOYSA-N

物化性质

• 沸点：
  722.0±40.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：5mg/mL； DMSO：5mg/mL； DMSO:PBS(pH 7.2)(1:5)：0.15 mg/ml；乙醇：3mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  160
• 氢给体数：
  2
• 氢受体数：
  7

安全信息

• 储存条件：
  -20℃

反应信息

• 作为产物：
  描述：

  tert-butyl [2-(4-formylphenoxy)ethyl]carbamate 在 哌啶 、 盐酸 、 甲醇 、 magnesium 、 氯甲酸异丙酯 、 三乙胺 、 苯甲酸 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 11.67h， 生成 N-(2-{4-[2,4-dioxo(1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)-5-(1,2-dithiolan-3-yl) pentanamide
  参考文献：
  名称：

  Design and Synthesis of the First Generation of Dithiolane Thiazolidinedione- and Phenylacetic Acid-Based PPARγ Agonists

  摘要：

  A series of novel derivatives of potent antioxidant vitamin, alpha-lipoic acid, and related analogues were designed, synthesized, and evaluated for their PPAR gamma agonist activities. Compounds 9a and the water soluble analogue 11e were found to be potent PPAR gamma agonists. Compound 9a appeared to have a significant role in improving insulin sensitivity and reducing triglyceride levels in fa/fa rats as well as inhibited proliferation of a variety of normal and neoplastic cultured human cell types. These novel compounds may prove efficacious not only in the treatment of Type 2 diabetes, but also atherosclerosis, prevention of vascular restenosis, and inflammatory skin diseases.

  DOI：

  10.1021/jm0510880

文献信息

• 1,2-dithiolane derivatives
  申请人：University of Mississippi

  公开号：US06353011B1

  公开（公告）日：2002-03-05

  This invention provides new thiazolindinedione derivatives and new arylacetic acid derivatives. These compounds are useful for the treatment of cardiovascular diseases, certain endocrine diseases, certain inflammatory diseases, certain neoplastic (malignant) and non-malignant proliferative diseases, certain neuro-psychiatric disorders, certain viral diseases, and diseases associated with these viral infections as discussed herein.

  这项发明提供了新的噻唑烷二酮衍生物和新的芳基乙酸衍生物。这些化合物对治疗心血管疾病、某些内分泌疾病、某些炎症性疾病、某些恶性和非恶性增殖性疾病、某些神经精神障碍、某些病毒性疾病以及与这些病毒感染相关的疾病是有用的。
• PROPHYLACTIC AGENT AND/OR THERAPEUTIC AGENT FOR CATARACT, MEDICINAL COMPOSITION FOR PREVENTING AND/OR TREATING CATARACT, USE OF PPAR ACTIVATOR FOR PRODUCING SAME, AND EYEDROPS
  申请人：University of Fukui

  公开号：EP3733203A1

  公开（公告）日：2020-11-04

  Provided are agents for prevention and therapeutic treatment of cataract that act by a different mechanism from conventional agents, and use of a PPAR activator for production of such agents. An agent for prevention and/or therapeutic treatment of cataract, containing a PPAR activator as an active ingredient, is used.

  本发明提供了预防和治疗白内障的药剂，其作用机理与传统药剂不同，还提供了使用 PPAR 激活剂生产此类药剂的方法。一种用于预防和/或治疗白内障的药剂含有 PPAR 激活剂作为活性成分。
• Design and Synthesis of the First Generation of Dithiolane Thiazolidinedione- and Phenylacetic Acid-Based PPARγ Agonists
  作者：Amar G. Chittiboyina、Meenakshi S. Venkatraman、Cassia S. Mizuno、Prashant V. Desai、Akshay Patny、Stephen C. Benson、Christopher I. Ho、Theodore W. Kurtz、Harrihar A. Pershadsingh、Mitchell A. Avery

  DOI：10.1021/jm0510880

  日期：2006.7.1

  A series of novel derivatives of potent antioxidant vitamin, alpha-lipoic acid, and related analogues were designed, synthesized, and evaluated for their PPAR gamma agonist activities. Compounds 9a and the water soluble analogue 11e were found to be potent PPAR gamma agonists. Compound 9a appeared to have a significant role in improving insulin sensitivity and reducing triglyceride levels in fa/fa rats as well as inhibited proliferation of a variety of normal and neoplastic cultured human cell types. These novel compounds may prove efficacious not only in the treatment of Type 2 diabetes, but also atherosclerosis, prevention of vascular restenosis, and inflammatory skin diseases.