3-hydroxy-4-methoxy-2-(piperidin-1-ylmethyl)benzaldehyde | 1064288-42-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-hydroxy-4-methoxy-2-(piperidin-1-ylmethyl)benzaldehyde
• CAS: 1064288-42-1
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: CQPLJVCGQRUNGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-乙酰基吡啶 、 3-hydroxy-4-methoxy-2-(piperidin-1-ylmethyl)benzaldehyde 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以65%的产率得到(E)-3-[3-hydroxy-4-methoxy-2-(piperidin-1-ylmethyl)phenyl]-1-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：

  哌啶 、 异香兰素 、 聚合甲醛 以 乙醇 、 水 为溶剂， 以82%的产率得到3-hydroxy-4-methoxy-2-(piperidin-1-ylmethyl)benzaldehyde
  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