2-acetyl-3,5-dimethoxy-6-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)phenyl 3-chlorobenzoate | 916888-58-9

• 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: 2-acetyl-3,5-dimethoxy-6-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)phenyl 3-chlorobenzoate
• CAS: 916888-58-9
• 化学式: C₂₃H₂₄ClNO₅
• 分子量: 429.9
• InChiKey: ICIPVKSRKWPTIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-acetyl-3,5-dimethoxy-6-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)phenyl 3-chlorobenzoate 在 sodium hydride 、 硫酸 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以45%的产率得到2-(3-chlorophenyl)-5,7-dimethoxy-8-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-4H-benzopyran-4-one
  参考文献：
  名称：

  Bioactivity of glycogen phosphorylase inhibitors that bind to the purine nucleoside site

  摘要：

  The bioactivity in hepatocytes of glycogen phosphorylase inhibitors that bind to the active site, the allosteric activator site and the indole carboxamide site has been described. However, the pharmacological potential of the purine nucleoside inhibitor site has remained unexplored. We report the chemical synthesis and bioactivity in hepatocytes of four new olefin derivatives of flavopiridol (1-4) that bind to the purine site. Flavopiridol and 1-4 counteracted the activation of phosphorylase in hepatocytes caused by AICAR (5-aminoimidazole-4-carboxamide 1-beta-D-ribofuranoside), which is metabolised to an AMP analogue. Unlike an indole carboxamide inhibitor, the analogues I and 4 suppressed the basal rate of glycogenolysis in hepatocytes by allosteric inhibition rather than by inactivation of phosphorylase, and accordingly caused negligible stimulation of glycogen synthesis. However, they counteracted the stimulation of glycogenolysis by dibutyryl cAMP by both allosteric inhibition and inactivation of phosphorylase. Cumulatively, the results show key differences between purine site and indole carboxamide site inhibitors in terms of (i) relative roles of dephosphorylation of phosphorylase-a as compared with allosteric inhibition, (ii) counteraction of the efficacy of the inhibitors on glycogenolysis by dibutyryl-cAMP and (iii) stimulation of glycogen synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.060
• 作为产物：
  描述：

  3,5-Dimethoxy-2-(1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenol 在 吡啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 2-acetyl-3,5-dimethoxy-6-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)phenyl 3-chlorobenzoate
  参考文献：
  名称：

  Structure–activity relationship studies of flavopiridol analogues

  摘要：

  Cyclin dependent kinases (CDKs) along with the complementary cyclins form key regulatory checkpoint controls on the cell cycle. Flavopiridol is a synthetic flavone that shows potent and selective cyclin-dependent kinase inhibitory activity. In this paper, we report modifications of the 3-hydroxy-1-methylpiperidinyl (D ring) of flavopiridol and their effect on CDK inhibitory activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00156-6