2-(6-(4-methoxyphenylamino)pyridin-2-ylamino)ethanol | 1312310-35-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(6-(4-methoxyphenylamino)pyridin-2-ylamino)ethanol
• 英文别名: VUT-MK396；2-(6-(4-methoxyphenylamino)pyridin-2-ylamino)ethan-1-ol；2-[[6-(4-methoxyanilino)pyridin-2-yl]amino]ethanol
• CAS: 1312310-35-2
• 化学式: C₁₄H₁₇N₃O₂
• 分子量: 259.308
• InChiKey: RXAVFGDRWOFIDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  66.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,6-二氯吡啶 在 palladium diacetate 、 potassium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 反应 72.5h， 生成 2-(6-(4-methoxyphenylamino)pyridin-2-ylamino)ethanol
  参考文献：
  名称：

  Metal assisted synthesis of mono and diamino substituted pyridines

  摘要：

  A microwave assisted Buchwald-Hartwig amination protocol is reported for a series of dihalopyridine precursors. Using this procedure, selective substitution of one halogen by aryl or alkylamines is possible in very short time, usually 30 min. Mild base (K(2)CO(3)) can be used successfully, which broadens the substrate scope. The second halogen can then be substituted using alkylamines under nucleophilic substitution condition or via a Suzuki-Miyaura cross-coupling reaction. The target compounds are potential inducers of cardiomyogenesis as innovative approach in regenerative medicine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.060

文献信息

• SUBSTITUTED PYRIDINES AND PYRIMIDINES
  申请人：Mihovilovic Marko

  公开号：US20120294835A1

  公开（公告）日：2012-11-22

  Provided is a compound of formula (I), and/or salt thereof, wherein the radicals have various meanings, a process for producing cardiomyocyte-like cells from mammalian cells by culturing mammalian cells in the presence of the compound of formula (I), the pharmaceutical use of compounds of formula (I) for producing cardiomyocyte-like cells from omnipotent, pluripotent, or lineage committed mammalian cells, and the use of thus produced cardiomyocyte-like cells for treating disorders associated with impaired function of the heart.

  提供的是式（I）的化合物和/或其盐， 其中基团具有各种含义，一种从哺乳动物细胞中培养类心肌细胞的方法，通过在存在式（I）的化合物的情况下培养哺乳动物细胞，化合物式（I）用于从全能、多能或已分化的哺乳动物细胞中产生类心肌细胞的药用途，以及用于治疗与心脏功能受损有关的疾病的由此产生的类心肌细胞。
• VUT-MK142 : a new cardiomyogenic small molecule promoting the differentiation of pre-cardiac mesoderm into cardiomyocytes
  作者：Moumita Koley、Agnes K. Mike、Philipp Heher、Xaver Koenig、Michael Schön、Michael Schnürch、Karlheinz Hilber、Georg Weitzer、Marko D. Mihovilovic

  DOI：10.1039/c3md00101f

  日期：——

  Intra-cardiac cell transplantation is a new therapy after myocardial infarction. Its success, however, is impeded by the limited capacity of donor cells to differentiate into functional cardiomyocytes in the heart. A strategy to overcome this problem is the induction of cardiomyogenic function in cells prior to transplantation. Among other approaches, recently, synthetic small molecules were identified, which promote differentiation of stem cells of various origins into cardiac-like cells or cardiomyocytes. The aim of this study was to develop and characterise new promising cardiomyogenic synthetic low-molecular weight compounds. Therefore, the structure of the known cardiomyogenic molecule cardiogenol C was selectively modified, and the effects of the resulting compounds were tested on various cell types. From this study, VUT-MK142 was identified as the most promising candidate with respect to cardiomyogenic activity. Treatment using this novel agent induced the strongest up-regulation of expression of the cardiac marker ANF in both P19 embryonic carcinoma cells and C2C12 skeletal myoblasts. The activity of VUT-MK142 on this marker superseded CgC; moreover, the novel compound significantly up-regulated the expression of other cardiac markers, and promoted the development of beating cardiomyocytes from cardiovascular progenitor cells. We conclude that VUT-MK142 is a potent new cardiomyogenic synthetic agent promoting the differentiation of pre-cardiac mesoderm into cardiomyocytes, which may be useful to differentiate stem cells into cardiomyocytes for cardiac repair. Additionally, an efficient synthesis of VUT-MK142 is reported taking advantage of continuous flow techniques superior to classical batch reactions both in yield and reaction time.

  心内细胞移植是一种心肌梗死后的新疗法。然而，由于供体细胞在心脏中分化为功能性心肌细胞的能力有限，其成功受到阻碍。克服这一问题的一种策略是在移植前诱导细胞的心肌功能。最近，研究者们发现了一些合成小分子，可以促进不同来源的干细胞向心脏样细胞或心肌细胞的分化。本研究的目的是开发并表征新的有前景的心肌合成低分子化合物。因此，选择性地修改了已知心肌合成分子心肌生素C的结构，并对所得化合物在各种细胞类型上的影响进行了测试。研究中，VUT-MK142被确定为在心肌活性方面最有前途的候选者。使用这种新型药剂的处理在P19胚胎癌细胞和C2C12骨骼肌前体细胞中诱导了心脏标志物ANF表达的最强上调。VUT-MK142对该标志物的活性超越了CgC；此外，这种新化合物显著上调了其他心脏标志物的表达，并促进了心血管祖细胞向节律性心肌细胞的发展。我们得出结论，VUT-MK142是一种有效的新型心肌合成合成剂，促进前心中胚层向心肌细胞的分化，这可能对将干细胞分化为心肌细胞以进行心脏修复是有用的。此外，报告了VUT-MK142的高效合成，利用连续流动技术，相对于经典的批量反应在产量和反应时间上具有优势。
• Substituted pyridines and pyrimidines
  申请人：Mihovilovic Marko

  公开号：US08986994B2

  公开（公告）日：2015-03-24

  Provided are compounds of formula (I) and/or salts thereof, of the class of substituted pyridines and pyrimidines, useful for inducing cardiomyogenesis, a process for producing cardiomyocyte-like cells from mammalian cells by culturing mammalian cells in the presence of the compound of formula (I), the pharmaceutical use of compounds of formula (I) for producing cardiomyocyte-like cells from omnipotent, pluripotent, or lineage committed mammalian cells, and the use of thus produced cardiomyocyte-like cells for treating disorders associated with impaired function of the heart.

  提供了式（I）的化合物和/或其盐，属于取代吡啶和嘧啶类，可用于诱导心肌发生作用。通过在化合物（I）的存在下培养哺乳动物细胞，从而从哺乳动物细胞中产生类心肌细胞的过程，化合物（I）的制药用途用于从全能、多能或分化系承诺的哺乳动物细胞中产生类心肌细胞，以及用于治疗与心脏功能受损有关的疾病所产生的类心肌细胞。
• [EN] SUBSTITUTED PYRIDINES AND PYRIMIDINES FOR THE PRODUCTION OF CARDIOMYOCYTE - LIKE CELLS<br/>[FR] PYRIDINES ET PYRIMIDINES SUBSTITUÉES
  申请人：UNIV WIEN TECH

  公开号：WO2011079343A3

  公开（公告）日：2011-10-13
• SUBSTITUTED PYRIDINES AND PYRIMIDINES FOR THE PRODUCTION OF CARDIOMYOCYTE-LIKE CELLS
  申请人：Technische Universität Wien

  公开号：EP2519501A2

  公开（公告）日：2012-11-07