tert-butyl (2-{4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy}ethyl)methylcarbamate | 905990-90-1

• 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-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy}ethyl)methylcarbamate
• 英文别名: (Z)-5-[4-[2-[Boc-(methyl)amino]ethoxy]benzylidene]thiazolidine-2,4-dione；tert-butyl N-[2-[4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]ethyl]-N-methylcarbamate
• CAS: 905990-90-1
• 化学式: C₁₈H₂₂N₂O₅S
• 分子量: 378.449
• InChiKey: JSHFTMXOQZNRSO-KAMYIIQDSA-N

物化性质

• 熔点：
  157.2-160 °C(Solv: water (7732-18-5))
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-(N-Boc-N-甲基氨基)乙醇 在 哌啶 、 偶氮二甲酸二异丙酯 、 三苯基膦 、 苯甲酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 9.0h， 生成 tert-butyl (2-{4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy}ethyl)methylcarbamate
  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

• [EN] DESIGN AND SYNTHESIS OF OPTIMIZED LIGANDS FOR PPAR<br/>[FR] CONCEPTION ET SYNTHESE DE LIGANDS OPTIMISE POUR PPAR
  申请人：BETHESDA PHARMACEUTICALS INC

  公开号：WO2005009437A1

  公开（公告）日：2005-02-03

  This invention provides new chemical entities useful for treating a variety of clinical disorders including those that areinfluenced by the activity of peroxisome proliferator activated receptors (PPAR). The structures of the compounds and methods to design, make and use the compounds are provided. Compounds and methods for administering therapeutic compositions comprising the compounds in cases of the disease psoriasis are provided. An exemplary compound having the formula compound is 5­adamantan-2-yl-pentanoic acid 2-[4-(2,4-dioxo-thiazolidin-5-yl-methyl)-phenoxy]-ethyl}-methyl-amide is provided.

  这项发明提供了新的化学实体，可用于治疗各种临床疾病，包括那些受过氧化物酶体增殖物激活受体（PPAR）活性影响的疾病。提供了这些化合物的结构以及设计、制造和使用这些化合物的方法。提供了在牛皮癣病例中使用这些化合物的治疗组合物的化合物和方法。提供了一个具有以下结构的示例化合物：5-金刚烷基-2-基戊酸2-[4-(2,4-二氧-噻唑啉-5-基-甲基)-苯氧基]-乙基}-甲基酰胺。
• 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.