(E)-3-[3-hydroxy-4-methoxy-2-(morpholinomethyl)phenyl]-1-p-tolylprop-2-en-1-one | 1064288-31-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-[3-hydroxy-4-methoxy-2-(morpholinomethyl)phenyl]-1-p-tolylprop-2-en-1-one
• 英文别名: (E)-3-[3-hydroxy-4-methoxy-2-(morpholin-4-ylmethyl)phenyl]-1-(4-methylphenyl)prop-2-en-1-one
• CAS: 1064288-31-8
• 化学式: C₂₂H₂₅NO₄
• 分子量: 367.445
• InChiKey: BULBNMFBNXNKJA-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-hydroxy-4-methoxy-2-(morpholinomethyl)benzaldehyde 、 对甲基苯乙酮 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以83%的产率得到(E)-3-[3-hydroxy-4-methoxy-2-(morpholinomethyl)phenyl]-1-p-tolylprop-2-en-1-one
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of Mannich bases of heterocyclic chalcone analogs as cytotoxic agents

  摘要：

  The chalcone skeleton (1,3-diphenyl-2-propen-1-one) is a unique template that is associated with various biological activities. We synthesized Mannich bases of heterocyclic chalcones (9-47) using a one-step Claisen-Schmidt condensation of heterocyclic aldehydes with Mannich bases of acetophenones, and tested the target compounds for cytotoxicity against three human cancer cell lines (prostate, PC-3; breast, MCF-7; nasopharynx, KB) and a multi-drug resistant subline (KB-VIN). Out of the 39 chalcones synthesized, 31 compounds showed potent activity against at least one cell line with IC50 values ranging from 0.03 to 3.80 mu g/mL. Structure-activity relationships (SAR) are also discussed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.018