1-[2-hydroxy-4-(5-tetrahydro-1H-1-pyrrolylpentyloxy)phenyl]-1-ethanone | 850152-93-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[2-hydroxy-4-(5-tetrahydro-1H-1-pyrrolylpentyloxy)phenyl]-1-ethanone
• 英文别名: 1-(2-hydroxy-4-((5-(pyrrolidin-1-yl)pentyl)oxy)phenyl)ethan-1-one；1-[2-Hydroxy-4-(5-pyrrolidin-1-ylpentoxy)phenyl]ethanone；1-[2-hydroxy-4-(5-pyrrolidin-1-ylpentoxy)phenyl]ethanone
• CAS: 850152-93-1
• 化学式: C₁₇H₂₅NO₃
• 分子量: 291.39
• InChiKey: HNTQVZIEPURAGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[2-hydroxy-4-(5-tetrahydro-1H-1-pyrrolylpentyloxy)phenyl]-1-ethanone 在 盐酸 、 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 96.0h， 生成 2-(4-methoxyphenyl)-7-[(5-tetrahydro-1H-1-pyrrolylpentyl)oxy]-4-chromanone
  参考文献：
  名称：

  Homopterocarpanes as bridged triarylethylene analogues: synthesis and antagonistic effects in human MCF-7 breast cancer cells

  摘要：

  A series of new compounds structurally derived from 6a,12a-dihydro-6H,7H-[1]-benzopyran-[4,3-b]-benzopyran (homopterocarpane) was efficiently synthesized by reduction of the corresponding pyrilium salts obtained by treatment of selected flavanones and aldehydes with anhydrous HClO4. Cytotoxic effects on the human breast cancer cell line MCF-7 and antiestrogenic activity (only for compounds which resulted more active than tamoxifen (TAM)) on MCF-7 cells stimulated by 17beta-estradiol were evaluated. In vivo antiestrogenic activity and the relative binding affinity were also assessed. Some of the new compounds (4c, 4h, 4i and 4l) showed a biological activity in the micromolar range, and were more potent than TAM taken as the reference.

  DOI：

  10.1016/j.farmac.2004.09.006
• 作为产物：
  描述：

  1-溴-5-氯戊烷 在 potassium carbonate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 34.0h， 生成 1-[2-hydroxy-4-(5-tetrahydro-1H-1-pyrrolylpentyloxy)phenyl]-1-ethanone
  参考文献：
  名称：

  Homopterocarpanes as bridged triarylethylene analogues: synthesis and antagonistic effects in human MCF-7 breast cancer cells

  摘要：

  A series of new compounds structurally derived from 6a,12a-dihydro-6H,7H-[1]-benzopyran-[4,3-b]-benzopyran (homopterocarpane) was efficiently synthesized by reduction of the corresponding pyrilium salts obtained by treatment of selected flavanones and aldehydes with anhydrous HClO4. Cytotoxic effects on the human breast cancer cell line MCF-7 and antiestrogenic activity (only for compounds which resulted more active than tamoxifen (TAM)) on MCF-7 cells stimulated by 17beta-estradiol were evaluated. In vivo antiestrogenic activity and the relative binding affinity were also assessed. Some of the new compounds (4c, 4h, 4i and 4l) showed a biological activity in the micromolar range, and were more potent than TAM taken as the reference.

  DOI：

  10.1016/j.farmac.2004.09.006

文献信息

• Design, synthesis and biological evaluation of 2-acetyl-5- O -(amino-alkyl)phenol derivatives as multifunctional agents for the treatment of Alzheimer’s disease
  作者：Zhipei Sang、Keren Wang、Huifang Wang、Huijuan Wang、Qianwen Ma、Xue Han、Mengyao Ye、Lintao Yu、Wenmin Liu

  DOI：10.1016/j.bmcl.2017.09.057

  日期：2017.11

  A series of 2-acetyl-5-O-(amino-alkyl)phenol derivatives was designed, synthesized and evaluated as multi-function inhibitors for the treatment of Alzheimer’s disease (AD). The results revealed that compound TM-3 indicated selective AChE inhibitory potency (eeAChE, IC50 = 0.69 μM, selective index (SI) = 32.7). Both kinetic analysis of AChE inhibition and molecular modeling study suggested that TM-3

  设计，合成和评估了一系列2-乙酰基-5- O-（氨基-烷基）苯酚衍生物作为多功能抑制剂，用于治疗阿尔茨海默氏病（AD）。结果表明，化合物TM-3具有选择性的AChE抑制能力（ee AChE，IC 50  = 0.69μM，选择性指数（SI）= 32.7）。AChE抑制的动力学分析和分子建模研究均表明TM-3可以同时结合AChE的催化活性位点和外围阴离子位点。和TM-3也是一个高度选择性的MAO-B抑制剂（IC 50  = 6.8微米）。此外，TM-3可以作为抗氧化剂（ORAC值为1.5 eq）和神经保护剂，以及选择性金属螯合剂。更有趣的是，化合物TM-3可以在体外穿过血脑屏障（BBB），并遵守Lipinski的5原则。因此，化合物TM-3是一种有前途的多靶点活性分子，为针对AD的药物发现过程中进一步的先导优化提供了一个有吸引力的起点。
• Homopterocarpanes as bridged triarylethylene analogues: synthesis and antagonistic effects in human MCF-7 breast cancer cells
  作者：Angela Rampa、Alessandra Bisi、Federica Belluti、Silvia Gobbi、Lorna Piazzi、Piero Valenti、Antonella Zampiron、Anna Caputo、Katia Varani、Pier Andrea Borea、Maria Carrara

  DOI：10.1016/j.farmac.2004.09.006

  日期：2005.2

  A series of new compounds structurally derived from 6a,12a-dihydro-6H,7H-[1]-benzopyran-[4,3-b]-benzopyran (homopterocarpane) was efficiently synthesized by reduction of the corresponding pyrilium salts obtained by treatment of selected flavanones and aldehydes with anhydrous HClO4. Cytotoxic effects on the human breast cancer cell line MCF-7 and antiestrogenic activity (only for compounds which resulted more active than tamoxifen (TAM)) on MCF-7 cells stimulated by 17beta-estradiol were evaluated. In vivo antiestrogenic activity and the relative binding affinity were also assessed. Some of the new compounds (4c, 4h, 4i and 4l) showed a biological activity in the micromolar range, and were more potent than TAM taken as the reference.