4-O-(2-chloro-4-fluorobenzyl)sinapic acid ethyl ester | 881855-04-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-O-(2-chloro-4-fluorobenzyl)sinapic acid ethyl ester
• CAS: 881855-04-5
• 化学式: C₂₀H₂₀ClFO₅
• 分子量: 394.827
• InChiKey: BHJAHZKPJBXHLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-O-(2-chloro-4-fluorobenzyl)sinapic acid ethyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以45%的产率得到4-O-(2-chloro-4-fluorobenzyl)sinapic alcohol
  参考文献：
  名称：

  Design, synthesis, and SAR analysis of cytotoxic sinapyl alcohol derivatives

  摘要：

  Five series totalling 51 of sinapyl alcohol derivatives were designed and synthesized. Their cytotoxicity analyses were performed oil six human tumor cell lines Such as PC-3. CNE, KB, A549, BEL-7404, and HeLa. Certain sinapyl alcohol derivatives showed significant cytotoxic activities. Compound 14d exhibited especially potent cytotoxicity against the BEL-7404 cell line with an IC50 value of 0.7 mu M, which showed more cytotoxic activity than the positive control, cisplatin. The structure-cytotoxicity relationships were discussed and the CoMFA analysis was performed using the cytotoxic data against HeLa cells as a template. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.056
• 作为产物：
  描述：

  3,4,5-三甲氧基苄醇 在 六甲基磷酰三胺 、 sodium hydride 、 potassium carbonate 、 苯硫酚 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 、 苯 为溶剂， 生成 4-O-(2-chloro-4-fluorobenzyl)sinapic acid ethyl ester
  参考文献：
  名称：

  Design, synthesis, and SAR analysis of cytotoxic sinapyl alcohol derivatives

  摘要：

  Five series totalling 51 of sinapyl alcohol derivatives were designed and synthesized. Their cytotoxicity analyses were performed oil six human tumor cell lines Such as PC-3. CNE, KB, A549, BEL-7404, and HeLa. Certain sinapyl alcohol derivatives showed significant cytotoxic activities. Compound 14d exhibited especially potent cytotoxicity against the BEL-7404 cell line with an IC50 value of 0.7 mu M, which showed more cytotoxic activity than the positive control, cisplatin. The structure-cytotoxicity relationships were discussed and the CoMFA analysis was performed using the cytotoxic data against HeLa cells as a template. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.056