1-[2-hydroxy-4-(3-methylbut-2-enyloxy)-3-(morpholinomethyl)phenyl]ethanone | 1064288-37-4

• 英文名称: 1-[2-hydroxy-4-(3-methylbut-2-enyloxy)-3-(morpholinomethyl)phenyl]ethanone
• CAS: 1064288-37-4
• 化学式: C₁₈H₂₅NO₄
• 分子量: 319.401
• InChiKey: RXHWZVPQIFDSNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.0
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-甲基噻吩醛 、 1-[2-hydroxy-4-(3-methylbut-2-enyloxy)-3-(morpholinomethyl)phenyl]ethanone 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以82%的产率得到(E)-1-[2-hydroxy-4-(3-methylbut-2-enyloxy)-3-(morpholinomethyl)phenyl]-3-(3-methylthiophen-2-yl)prop-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
• 作为产物：
  描述：

  吗啉 、 聚合甲醛 、 1-[2-羟基-4-(3-甲基-2-丁烯氧基)-苯基]-乙酮 以 乙醇 、 水 为溶剂， 以86%的产率得到1-[2-hydroxy-4-(3-methylbut-2-enyloxy)-3-(morpholinomethyl)phenyl]ethanone
  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