1-(4-hydroxytetrahydro-2H-pyran-4-yl)-2-(m-tolyl)ethane-1,2-dione | 1435770-46-9

• 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: 1-(4-hydroxytetrahydro-2H-pyran-4-yl)-2-(m-tolyl)ethane-1,2-dione
• 英文别名: 1-(4-Hydroxyoxan-4-yl)-2-(3-methylphenyl)ethane-1,2-dione；1-(4-hydroxyoxan-4-yl)-2-(3-methylphenyl)ethane-1,2-dione
• CAS: 1435770-46-9
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: PKVPXEZAKAVOPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-hydroxytetrahydro-2H-pyran-4-yl)-2-(m-tolyl)ethane-1,2-dione 在 dipotassium peroxodisulfate 、 ammonium acetate 、 copper(II) acetate monohydrate 作用下， 以 水 、 溶剂黄146 为溶剂， 生成 US10865384, Example 4a
  参考文献：
  名称：

  Tri-substituted imidazole analogues of SB203580 as inducers for cardiomyogenesis of human embryonic stem cells

  摘要：

  The p38 alpha mitogen-activated protein kinase (MAPK) inhibitor SB203580 had been reported to enhance the cardiomyogenesis of human embryonic stem cells (hESCs). To investigate if tri-substituted imidazole analogues of SB203580 are equally effective inducers for cardiomyogenesis of hESCs, and if there is a correlation between p38 alpha MAPK inhibition and cardiomyogenesis, we designed and synthesized a series of novel tri-substituted imidazoles with a range of p38 alpha MAPK inhibitory activities. Our studies demonstrated that suitably designed analogues of SB203580 can also be inducers of cardiomyogenesis in hESCs and that cell growth is affected by changes in the imidazole structures. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.103
• 作为产物：
  描述：

  4-(m-tolylethynyl)tetrahydro-2H-pyran-4-ol 在 potassium permanganate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以64%的产率得到1-(4-hydroxytetrahydro-2H-pyran-4-yl)-2-(m-tolyl)ethane-1,2-dione
  参考文献：
  名称：

  Tri-substituted imidazole analogues of SB203580 as inducers for cardiomyogenesis of human embryonic stem cells

  摘要：

  The p38 alpha mitogen-activated protein kinase (MAPK) inhibitor SB203580 had been reported to enhance the cardiomyogenesis of human embryonic stem cells (hESCs). To investigate if tri-substituted imidazole analogues of SB203580 are equally effective inducers for cardiomyogenesis of hESCs, and if there is a correlation between p38 alpha MAPK inhibition and cardiomyogenesis, we designed and synthesized a series of novel tri-substituted imidazoles with a range of p38 alpha MAPK inhibitory activities. Our studies demonstrated that suitably designed analogues of SB203580 can also be inducers of cardiomyogenesis in hESCs and that cell growth is affected by changes in the imidazole structures. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.103

文献信息

• 2,4,5-tri-substituted azole-based casein kinase 1 inhibitors as inducers for cardiomyogenesis
  申请人：AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH

  公开号：US10865384B2

  公开（公告）日：2020-12-15

  This invention relates to a method for inducing or enhancing the differentiation of pluripotent stem cells into cardiomyocyte via casein kinase 1 inhibition said method comprising culturing the stem cells in the presence of a medium comprising a casein kinase 1 inhibitor of the formula (I) or (II) or a stereoisomer, tautomer, or a salt thereof wherein R1, R2 and R3 independently from another represent hydrogen, optionally substituted alkyl, alkenyl, alkynyl, heterocyclyl, heteroaryl or aryl; X represents NR4, O or S; and R4 represents hydrogen, optionally substituted alkyl, alkenyl, alkynyl, heterocyclyl, heteroaryl or aryl. The method can be used in the late phase of stem cell differentiation and in the compounds of formula (I) or (II) in combination with other small molecules can lead to especially high differentiation of stem cells into cardiomyocytes. The invention further relates to novel compounds which can be used in the method of the invention and kits for stem cell differentiation.

  本发明涉及一种通过抑制酪蛋白激酶1诱导或增强多能干细胞向心肌细胞分化的方法，所述方法包括在含有式(I)或(II)的酪蛋白激酶1抑制剂或其立体异构体、同系物或盐的培养基存在下培养干细胞，其中R1、R2和R3独立地代表氢、任选取代的烷基、烯基、炔基、杂环基、杂芳基或芳基；X 代表 NR4、O 或 S；R4 代表氢、任选取代的烷基、烯基、炔基、杂环基、杂芳基或芳基。该方法可用于干细胞分化的后期阶段，式（I）或（II）化合物与其他小分子结合使用，可使干细胞分化为心肌细胞的程度特别高。本发明进一步涉及可用于本发明方法和干细胞分化试剂盒的新型化合物。
• 2,4,5-TRI-SUBSTITUTED AZOLE-BASED CASEIN KINASE 1 INHIBITORS AS INDUCERS FOR CARDIOMYOGENESIS
  申请人：Agency for Science, Technology and Research

  公开号：EP3102207B1

  公开（公告）日：2022-05-11
• Tri-substituted imidazole analogues of SB203580 as inducers for cardiomyogenesis of human embryonic stem cells
  作者：Joo-Leng Low、Gerrit Jürjens、Jayasree Seayad、Jasmine Seow、Sherwin Ting、Filip Laco、Shaul Reuveny、Steve Oh、Christina L.L. Chai

  DOI：10.1016/j.bmcl.2013.03.103

  日期：2013.6

  The p38 alpha mitogen-activated protein kinase (MAPK) inhibitor SB203580 had been reported to enhance the cardiomyogenesis of human embryonic stem cells (hESCs). To investigate if tri-substituted imidazole analogues of SB203580 are equally effective inducers for cardiomyogenesis of hESCs, and if there is a correlation between p38 alpha MAPK inhibition and cardiomyogenesis, we designed and synthesized a series of novel tri-substituted imidazoles with a range of p38 alpha MAPK inhibitory activities. Our studies demonstrated that suitably designed analogues of SB203580 can also be inducers of cardiomyogenesis in hESCs and that cell growth is affected by changes in the imidazole structures. (C) 2013 Elsevier Ltd. All rights reserved.