1-[3-hydroxy-4-(morpholinomethyl)phenyl]ethanone | 1064288-39-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[3-hydroxy-4-(morpholinomethyl)phenyl]ethanone
• 英文别名: 1-[3-Hydroxy-4-(4-morpholinylmethyl)phenyl]ethanone；1-[3-hydroxy-4-(morpholin-4-ylmethyl)phenyl]ethanone
• CAS: 1064288-39-6
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: HKTOLFBGWPAMMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-吡啶甲醛 、 1-[3-hydroxy-4-(morpholinomethyl)phenyl]ethanone 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以59%的产率得到(E)-1-[3-hydroxy-4-(morpholin-4-ylmethyl)phenyl]-3-pyridin-3-ylprop-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 、 3-羟基苯乙酮 以 乙醇 、 水 为溶剂， 以37%的产率得到1-[3-hydroxy-4-(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