5-allyl-3-[(4-(2-hydroxyethyl)piperidin-1-yl)methyl]benzene-1,2-diol

• 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: 5-allyl-3-[(4-(2-hydroxyethyl)piperidin-1-yl)methyl]benzene-1,2-diol
• 英文别名: 3-[[4-(2-Hydroxyethyl)piperidin-1-yl]methyl]-5-prop-2-enylbenzene-1,2-diol；3-[[4-(2-hydroxyethyl)piperidin-1-yl]methyl]-5-prop-2-enylbenzene-1,2-diol
• 化学式: C₁₇H₂₅NO₃
• 分子量: 291.39
• InChiKey: URSJTJKHWKBVDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  63.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-哌啶乙醇 、 聚合甲醛 、 4-烯丙基儿茶酚 以 甲醇 为溶剂， 反应 0.5h， 生成 5-allyl-3-[(4-(2-hydroxyethyl)piperidin-1-yl)methyl]benzene-1,2-diol
  参考文献：
  名称：

  Synthetic modification of hydroxychavicol by Mannich reaction and alkyne–azide cycloaddition derivatives depicting cytotoxic potential

  摘要：

  Here we report the design, synthesis and lead optimization of hydroxychavicol (1) a high yielding metabolite ubiquitously present in the Piper betel leaves with the significant cytotoxic activity. This is the first report to describe the synthetic strategies of two distinct series of hydroxychavicol by Mannich reaction (2-10) and alkyne-azide cycloaddition (11-20). Furthermore, all the synthesized derivatives along with parent compound were evaluated for their in-vitro cytotoxic and antiproliferative potential in several distinct cancers cell lines. Among all, the Mannich reaction derived molecules 6, 8 and 10 displayed more potent cytotoxic activities with IC50 value in a range from 3 to 9 mu M, which were 7-10 fold more potent than 1 against five human cancer cell lines viz. HL-60, Mia PaCa-2, MCF-7, HEP G2 and SK-N-SH. Our results describe an efficient synthetic approach used to evaluate the structure activity relationship of 1 and its derivative in search of potential new anticancer agents. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.12.047

文献信息

• Synthetic modification of hydroxychavicol by Mannich reaction and alkyne–azide cycloaddition derivatives depicting cytotoxic potential
  作者：Sunil Kumar、Anoop S. Pathania、Naresh K. Satti、Parbhu Dutt、Neha Sharma、Fayaz A. Mallik、Asif Ali

  DOI：10.1016/j.ejmech.2014.12.047

  日期：2015.3

  Here we report the design, synthesis and lead optimization of hydroxychavicol (1) a high yielding metabolite ubiquitously present in the Piper betel leaves with the significant cytotoxic activity. This is the first report to describe the synthetic strategies of two distinct series of hydroxychavicol by Mannich reaction (2-10) and alkyne-azide cycloaddition (11-20). Furthermore, all the synthesized derivatives along with parent compound were evaluated for their in-vitro cytotoxic and antiproliferative potential in several distinct cancers cell lines. Among all, the Mannich reaction derived molecules 6, 8 and 10 displayed more potent cytotoxic activities with IC50 value in a range from 3 to 9 mu M, which were 7-10 fold more potent than 1 against five human cancer cell lines viz. HL-60, Mia PaCa-2, MCF-7, HEP G2 and SK-N-SH. Our results describe an efficient synthetic approach used to evaluate the structure activity relationship of 1 and its derivative in search of potential new anticancer agents. (C) 2014 Elsevier Masson SAS. All rights reserved.