N-[3-(4,4-diethoxybutylcarbamoyl)-propyl]-4-(7-oxo-7H-furo[3,2-g]chromen-4-yloxy)-butyramide | 746677-10-1

• 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: N-[3-(4,4-diethoxybutylcarbamoyl)-propyl]-4-(7-oxo-7H-furo[3,2-g]chromen-4-yloxy)-butyramide
• CAS: 746677-10-1
• 化学式: C₂₇H₃₆N₂O₈
• 分子量: 516.591
• InChiKey: OOIGPABGOGNZFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  37.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  129.24
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-(溴甲基)丙烯酸 、 N-[3-(4,4-diethoxybutylcarbamoyl)-propyl]-4-(7-oxo-7H-furo[3,2-g]chromen-4-yloxy)-butyramide 在 盐酸 、 溶剂黄146 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙二醇甲醚 、 水 为溶剂， 反应 21.0h， 以61%的产率得到N-[3-(4-methylidene-5-oxooxolan-2-yl)propyl]-4-[4-(7-oxofuro[3,2-g]chromen-4-yl)oxybutanoylamino]butanamide
  参考文献：
  名称：

  Synthesis and photocytotoxic activity of new α-methylene-γ-butyrolactone-psoralen heterodimers

  摘要：

  The synthesis of a new alpha-methylene-gamma-butyrolactone-psoralen heterodimer 2 is reported. its photoantiproliferative activity and skin phototoxicity were compared with that of 5-methoxypsoralen (5-MOP) and another heterodimer 1. Both derivatives show a significant phototoxicity toward malignant cell lines including melanoma cells A375 compared to their intrinsic cytotoxicity, in the dark. Both compounds were found to be nonphototoxic on mice skin and therefore could be active potential drugs in photochemotherapy. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.019
• 作为产物：
  描述：

  4-(7-Oxo-7H-furo[3,2-g]chromen-4-yloxy)-butyric acid 2,2,2-trichloro-ethyl ester 在 4-二甲氨基吡啶 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 锌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 21.5h， 生成 N-[3-(4,4-diethoxybutylcarbamoyl)-propyl]-4-(7-oxo-7H-furo[3,2-g]chromen-4-yloxy)-butyramide
  参考文献：
  名称：

  Synthesis and photocytotoxic activity of new α-methylene-γ-butyrolactone-psoralen heterodimers

  摘要：

  The synthesis of a new alpha-methylene-gamma-butyrolactone-psoralen heterodimer 2 is reported. its photoantiproliferative activity and skin phototoxicity were compared with that of 5-methoxypsoralen (5-MOP) and another heterodimer 1. Both derivatives show a significant phototoxicity toward malignant cell lines including melanoma cells A375 compared to their intrinsic cytotoxicity, in the dark. Both compounds were found to be nonphototoxic on mice skin and therefore could be active potential drugs in photochemotherapy. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.019