4,8-dimethyl-7-[(3-methyl-2-buten-1-yl)oxy]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-[(3-methyl-2-buten-1-yl)oxy]coumarin
• 英文别名: 4,8-dimethyl-7-[(3-methylbut-2-en-1-yl)oxy]-2H-chromen-2-one；4,8-dimethyl-7-(3-methylbut-2-enoxy)chromen-2-one
• 化学式: C₁₆H₁₈O₃
• mdl: MFCD04213510
• 分子量: 258.317
• InChiKey: CFFXIVLRWQIMSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二氟甲烷亚磺酸钠 、 4,8-dimethyl-7-[(3-methyl-2-buten-1-yl)oxy]coumarin 在 溶剂红 43 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以55%的产率得到3-difluoromethyl-4,8-dimethyl-7-(3-methylbut-2-en-1-yl)oxy-2H-chromen-2-one
  参考文献：
  名称：

  Visible-Light- and Oxygen-Promoted Direct Csp²-H Radical Difluoromethylation of Coumarins and Antifungal Activities

  摘要：

  An efficient general method using a clean and transition-metal-free photochemical strategy for the direct Csp(2)-H radical difluoromethylation of coumarins with HCF2SO2Na was developed. The visible-light-promoted strategy proceeds with 5 mol % Eosin Y under mild reaction conditions and showed excellent functional group compatibility. The control experiments illustrated that O(2)(center dot- )participated in this process and plays an important role in the reactions. Moreover, the representative products exhibited excellent antifungal activities in vitro. It was noted that the EC50 value of compound 3a was determined to be as low as 1.5463 mu g/mL against Rhizoctorzia solani, which was better than Boscalid (EC50 = 2.9767 mu g/mL).

  DOI：

  10.1021/acs.orglett.8b02965
• 作为产物：
  描述：

  7-羟基-4,8-二甲基香豆素 、 1-溴-3-甲基-2-丁烯 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 14.0h， 以17%的产率得到4,8-dimethyl-7-[(3-methyl-2-buten-1-yl)oxy]coumarin
  参考文献：
  名称：

  Phototoxicity of 7-oxycoumarins with keratinocytes in culture

  摘要：

  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.

  DOI：

  10.1016/j.bioorg.2019.103014

文献信息

• 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.
• Visible-Light- and Oxygen-Promoted Direct Csp²-H Radical Difluoromethylation of Coumarins and Antifungal Activities
  作者：Peng Dai、Xiang Yu、Peng Teng、Wei-Hua Zhang、Chao Deng

  DOI：10.1021/acs.orglett.8b02965

  日期：2018.11.2

  An efficient general method using a clean and transition-metal-free photochemical strategy for the direct Csp(2)-H radical difluoromethylation of coumarins with HCF2SO2Na was developed. The visible-light-promoted strategy proceeds with 5 mol % Eosin Y under mild reaction conditions and showed excellent functional group compatibility. The control experiments illustrated that O(2)(center dot- )participated in this process and plays an important role in the reactions. Moreover, the representative products exhibited excellent antifungal activities in vitro. It was noted that the EC50 value of compound 3a was determined to be as low as 1.5463 mu g/mL against Rhizoctorzia solani, which was better than Boscalid (EC50 = 2.9767 mu g/mL).