4,8-dimethyl-7-(octyloxy)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: 4,8-dimethyl-7-(octyloxy)coumarin
• 英文别名: 4,8-Dimethyl-7-octoxychromen-2-one
• 化学式: C₁₉H₂₆O₃
• 分子量: 302.414
• InChiKey: IKVMYQMOCQKAES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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-羟基-4,8-二甲基香豆素 、 1-溴辛烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 16.08h， 以94%的产率得到4,8-dimethyl-7-(octyloxy)coumarin
  参考文献：
  名称：

  合成香豆素对胰腺癌抗衰老细胞毒性的评价

  摘要：

  合成了一系列功能化的香豆素，并评估了其抑制胰腺癌细胞对饥饿的抗性的能力。使用优先细胞毒性试验评估了这种形式的细胞毒性，称为“抗紧缩”活性，该试验比较了在营养缺乏和营养丰富的条件下的细胞存活率。17种化合物中的6种对PANC-1的抗紧缩活性较弱。化合物34对PANC-1，MIA PaCa-2和Capan-1癌细胞具有活性。所有测试的化合物均为先前报道的天然产物铅的简化结构类似物。其中六个化合物，包括34个包含官能化的三唑，作为天然产物安吉林的侧链的新型潜在生物等位线。总体而言，发现类似物相对于相应的天然产物具有较低的抗紧缩活性。

  DOI：

  10.1016/j.bmcl.2016.01.054

文献信息

• Evaluation of synthetic coumarins for antiausterity cytotoxicity against pancreatic cancers
  作者：Conner M. Farley、Dya Fita Dibwe、Jun-ya Ueda、Eric A. Hall、Suresh Awale、Jakob Magolan

  DOI：10.1016/j.bmcl.2016.01.054

  日期：2016.3

  A series of functionalized coumarins were synthesized and evaluated for their capacity to inhibit the resistance to starvation of pancreatic cancer cells. This form of cytotoxicity, termed ‘antiausterity’ activity, was evaluated using a preferential cytotoxicity assay that compared cell survival in nutrient poor and nutrient rich conditions. Six of the seventeen compounds showed weak antiausterity

  合成了一系列功能化的香豆素，并评估了其抑制胰腺癌细胞对饥饿的抗性的能力。使用优先细胞毒性试验评估了这种形式的细胞毒性，称为“抗紧缩”活性，该试验比较了在营养缺乏和营养丰富的条件下的细胞存活率。17种化合物中的6种对PANC-1的抗紧缩活性较弱。化合物34对PANC-1，MIA PaCa-2和Capan-1癌细胞具有活性。所有测试的化合物均为先前报道的天然产物铅的简化结构类似物。其中六个化合物，包括34个包含官能化的三唑，作为天然产物安吉林的侧链的新型潜在生物等位线。总体而言，发现类似物相对于相应的天然产物具有较低的抗紧缩活性。
• Phototoxicity of 7-oxycoumarins with keratinocytes in culture
  作者：Christophe Guillon、Yi-Hua Jan、Diane E. Heck、Thomas M. Mariano、Robert D. Rapp、Michele Jetter、Keith Kardos、Marilyn Whittemore、Eric Akyea、Ivan Jabin、Jeffrey D. Laskin、Ned D. Heindel

  DOI：10.1016/j.bioorg.2019.103014

  日期：2019.8

  Seventy-one 7-oxycoumarins, 66 synthesized and 5 commercially sourced, were tested for their ability to inhibit growth in murine PAM212 keratinocytes. Forty-nine compounds from the library demonstrated light-induced lethality. None was toxic in the absence of UVA light. Structure-activity correlations indicate that the ability of the compounds to inhibit cell growth was dependent not only on their physiochemical characteristics, but also on their ability to absorb UVA light. Relative lipophilicity was an important factor as was electron density in the pyrone ring. Coumarins with electron withdrawing moieties - cyan and fluoro at C-3 - were considerably less active while those with bromines or iodine at that location displayed enhanced activity. Coumarins that were found to inhibit keratinocyte growth were also tested for photo-induced DNA plasmid nicking. A concentration-dependent alteration in migration on neutral gels caused by nicking was observed.