Ethyl 6-Hydroxy-4-methylbenzo[4,3-b]pyridine-3-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: Ethyl 6-Hydroxy-4-methylbenzo[4,3-b]pyridine-3-carboxylate
• 英文别名: ethyl 6-hydroxy-4-methyl-[1]benzofuro[2,3-b]pyridine-3-carboxylate
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: IZDXENCAHQKCPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  烟酸乙酯 在 copper(l) iodide 、 高氯酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 Ethyl 6-Hydroxy-4-methylbenzo[4,3-b]pyridine-3-carboxylate
  参考文献：
  名称：

  Synthesis and first biological evaluation of 1-aza-9-oxafluorenes as novel lead structures for the development of small-sized cytostatics

  摘要：

  A first series of novel 1-aza-9-oxafluorenes has been prepared from 3-carbonyl substituted 1,4-dihydropyridines and p-benzoquinone as small-sized cytostatics. Biological evaluation has been carried out in various cancer cell-lines. First structure-activity relationships proved the 4-phenyl substituent to be more favorable than the 4-methyl substituent. Cytostatic properties are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00769-7

文献信息

• Evaluation of the First Cytostatically Active 1-Aza-9-oxafluorenes as Novel Selective CDK1 Inhibitors with P-Glycoprotein Modulating Properties
  作者：Kristin Brachwitz、Burkhardt Voigt、Laurent Meijer、Olivier Lozach、Christoph Schächtele、Josef Molnár、Andreas Hilgeroth

  DOI：10.1021/jm021090g

  日期：2003.2.1

  The first series of synthetic 1-aza-9-oxafluorenes with cytostatic activities in the micromolar range was evaluated as cyclin-dependent kinase (CDK1) inhibitors. Activity was found to be selective in comparison to the inhibition of other kinases within the CDK family. Compounds were shown to inhibit the membrane-efflux pump P-glycoprotein responsible for multidrug resistance in cancer cells. First structure-activity relationships are discussed.