N-(2-{4-[2,4-dioxo(1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)-5-(1,2-dithiolan-3-yl)-N-methylpentanamide | 292615-76-0

• 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)-N-methylpentanamide
• 英文别名: N-[2-[4-[(2,4-Dioxo-5-thiazolidinyl)methyl]phenoxy]ethyl]-N-methyl-1,2-dithiolane-3-pentanamide；N-[2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]ethyl]-5-(dithiolan-3-yl)-N-methylpentanamide
• CAS: 292615-76-0
• 化学式: C₂₁H₂₈N₂O₄S₃
• 分子量: 468.662
• InChiKey: DPKRZECBZUCROC-UHFFFAOYSA-N

物化性质

• 沸点：
  681.1±35.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(2-{4-[2,4-dioxo(1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)-5-(1,2-dithiolan-3-yl)-N-methylpentanamide 在 吡啶 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 9.0h， 生成 4-({8-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)(methyl)amino]-3-mercapto-8-oxooctyl}thio)-4-oxobutanoic acid
  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
• 作为产物：
  描述：

  tert-butyl (2-{4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy}ethyl)methylcarbamate 在 盐酸 、 甲醇 、 magnesium 、 氯甲酸异丙酯 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 为溶剂， 反应 5.67h， 生成 N-(2-{4-[2,4-dioxo(1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)-5-(1,2-dithiolan-3-yl)-N-methylpentanamide
  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。
• 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.