tert-butyl (2-(4-formylphenoxy)ethyl)(methyl)carbamate | 198990-10-2

• 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-formylphenoxy)ethyl)(methyl)carbamate
• 英文别名: 4-[2-[Boc-(methyl)amino]ethoxy]benzaldehyde；tert-butyl N-[2-(4-formylphenoxy)ethyl]-N-methylcarbamate
• CAS: 198990-10-2
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: IIOQOPHSNFKBGN-UHFFFAOYSA-N

物化性质

• 熔点：
  63.5-65.6 °C
• 沸点：
  406.8±28.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2-(4-formylphenoxy)ethyl)(methyl)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)-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 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 tert-butyl (2-(4-formylphenoxy)ethyl)(methyl)carbamate
  参考文献：
  名称：

  [EN] IMIDAZO [2, 1-F] [1, 2, 4] TRIAZIN-4-AMINE DERIVATIVES AS TLR7 AGONIST
  [FR] DÉRIVÉS D'IMIDAZO[2,1-F] [1, 2, 4] TRIAZIN-4-AMINE UTILISÉS EN TANT QU'AGONISTES DE TLR7

  摘要：

  披露的是一种咪唑[2,1-f][1,2,4]三嗪-4-胺衍生物或其立体异构体，或其药用可接受盐，用作TLR7激动剂，以及包含该化合物的药物组合物。还披露了一种使用咪唑[2,1-f][1,2,4]三嗪-4-胺衍生物或其立体异构体，或其药用可接受盐作为TLR7激动剂来治疗癌症的方法。

  公开号：

  WO2020160711A1

文献信息

• Trifluoromethyl ketone analogs as selective cPLA2 inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US06255496B1

  公开（公告）日：2001-07-03

  Selective inhibitors of the cPLA2 enzymes are provided which are of use in controlling a wide variety of inflammatory diseases. The inhibitors of the present invention have the general formula

  选择性抑制cPLA2酶的抑制剂，可用于控制多种炎症性疾病。本发明提供的抑制剂具有以下通用公式
• [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。
• Design, synthesis, and biological evaluation of 5‐aminotetrahydroquinoline‐based LSD1 inhibitors acting on Asp375
  作者：Jiangkun Yan、Yanting Gu、Yixiang Sun、Ziheng Zhang、Xiangyu Zhang、Xinran Wang、Tianxiao Wu、Dongmei Zhao、Maosheng Cheng

  DOI：10.1002/ardp.202100102

  日期：2021.8

  histone demethylase 1 (LSD1) is associated with different cancer types, and LSD1 inhibitory activity seems to have high therapeutic potential in cancer treatment. Here, we report the design, synthesis, and biochemical evaluation of novel 5-aminotetrahydroquinoline-based LSD1 inhibitors. Among them, compounds A6, A8, B1–B5, and C4 showed preferable inhibitory effects on LSD1, with IC50 = 0.19–0.82 µM

  赖氨酸特异性组蛋白去甲基化酶 1 (LSD1) 的异常表达与不同的癌症类型有关，LSD1 抑制活性似乎在癌症治疗中具有很高的治疗潜力。在这里，我们报告了基于 5-氨基四氢喹啉的新型 LSD1 抑制剂的设计、合成和生化评估。其中，化合物A6、A8、B1 - B5和C4对LSD1显示出较好的抑制作用，IC 50 = 0.19–0.82 µM。选择了几种有效的化合物来评估它们对 LSD1 高表达的 A549 细胞和 MCF-7 细胞的抗增殖活性。通过分子对接揭示了化合物的潜在结合模式，以合理化化合物对 LSD1 的效力。我们的数据认识到，5-氨基四氢喹啉支架可作为开发用于癌症治疗的有效 LSD1 抑制剂的起点。
• 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 optimized ligands for ppar
  申请人：Avery A. Mitchell

  公开号：US20070099969A1

  公开（公告）日：2007-05-03

  This invention provides new chemical entities useful for treating a variety of clinical disorders including those that are influenced 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.