tert-butyl (2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)carbamate | 198990-13-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tert-butyl (2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)carbamate
• 英文别名: tert-butyl N-[2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]ethyl]carbamate
• CAS: 198990-13-5
• 化学式: C₁₇H₂₂N₂O₅S
• 分子量: 366.438
• InChiKey: FBTZPXKRWVEPFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)carbamate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以98%的产率得到5-({4-[2-aminoethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  Solid-phase synthesis of hybrid thiazolidinedione-fatty acid PPARγ ligands

  摘要：

  A library of thiazolidinedione-fatty acid hybrid molecules was designed to probe the relationship between natural and synthetic PPAR ligands. Solid-phase synthesis of the library led to the identification of several high affinity PPAR gamma ligands. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10017-8
• 作为产物：
  描述：

  N-(叔丁氧羰基)乙醇胺 在 哌啶 、 甲醇 、 偶氮二甲酸二异丙酯 、 magnesium 、 三苯基膦 、 苯甲酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 13.0h， 生成 tert-butyl (2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)carbamate
  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

• Solid-phase synthesis of hybrid thiazolidinedione-fatty acid PPARγ ligands
  作者：Nicholas C.O. Tomkinson、Andrea M. Sefler、Kelli D. Plunket、Steven G. Blanchard、Derek J. Parks、Timothy M. Willson

  DOI：10.1016/s0960-894x(97)10017-8

  日期：1997.10

  A library of thiazolidinedione-fatty acid hybrid molecules was designed to probe the relationship between natural and synthetic PPAR ligands. Solid-phase synthesis of the library led to the identification of several high affinity PPAR gamma ligands. (C) 1997 Elsevier Science Ltd.
• 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.