8-allyl-7-(1,1-dimethylallyloxy)coumarin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 8-allyl-7-(1,1-dimethylallyloxy)coumarin
• 英文别名: 8-Allyl-7-(1,1-dimethyl-allyloxy)-chromen-2-one；7-(2-methylbut-3-en-2-yloxy)-8-prop-2-enylchromen-2-one
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: NRWXKUNIMMFBEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  7-allyloxycoumarin 在 Lindlar catalyst 喹啉 、 氢气 、 potassium carbonate 作用下， 以 对二甲苯 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 8-allyl-7-(1,1-dimethylallyloxy)coumarin
  参考文献：
  名称：

  一类新型的类固醇5α-还原酶抑制剂：伞形酮衍生物的合成和评估。

  摘要：

  制备了一系列伞形酮衍生物，并在细胞培养系统中评估了它们的5α-还原酶1型抑制活性。我们的研究确定了一系列新的有效5α-还原酶1型抑制剂，并为进一步开发与5α-还原酶1型产生DHT相关的人类内分泌疾病提供了基础。初步的结构活性关系被描述为阐明基本的结构要求。

  DOI：

  10.1016/s0960-894x(01)00429-2

文献信息

• A novel class of inhibitors for steroid 5α-Reductase: synthesis and evaluation of umbelliferone derivatives
  作者：Gao-jun Fan、Woongchon Mar、Man Ki Park、Eun Wook Choi、Kinam Kim、Sanghee Kim

  DOI：10.1016/s0960-894x(01)00429-2

  日期：2001.9

  A series of umbelliferone derivatives was prepared and their 5alpha-reductase type 1 inhibitory activities were evaluated in cell culture systems. Our studies have identified a new series of potent 5alpha-reductase type 1 inhibitors and provided the basis for further development for the treatment of human endocrine disorders associated with overproduction of DHT by 5alpha-reductase type 1. The preliminary

  制备了一系列伞形酮衍生物，并在细胞培养系统中评估了它们的5α-还原酶1型抑制活性。我们的研究确定了一系列新的有效5α-还原酶1型抑制剂，并为进一步开发与5α-还原酶1型产生DHT相关的人类内分泌疾病提供了基础。初步的结构活性关系被描述为阐明基本的结构要求。
• Synthesis and anthelmintic activity of osthol analogs against Dactylogyrus intermedius in goldfish
  作者：Guang-Lu Liu、Bing Hao、Shao-Peng Liu、Gao-Xue Wang

  DOI：10.1016/j.ejmech.2012.06.009

  日期：2012.8

  In an attempt to develop novel anthelmintic agents, our previously isolated osthol was used as lead structures for further optimization. In our research, a series of coumarin analogs, prepared from 7-hydroxy coumarin or 7-hydroxy-4-methyl coumarin, have been evaluated for their anthelmintic activities. In all of the compounds, 6 and 7 were first synthesized, and their structures were identified based on NMR and MS values. Among the candidates, 8-allyl-7-allyloxycoumarin showed better anthelmintic activity than other compounds against Dactylogyrus infestation with EC50 value of 1.81 mg/L The quantitative structure-activity relationship (QSAR) of 16 osthol analogs with anthelmintic activity expressed as pEC(50) and toxicity to goldfish expressed pLC(50), such results can offer useful theoretical references for future experimental works. (C) 2012 Elsevier Masson SAS. All rights reserved.