5-(Diisoprenylamino)-9-methoxy-psoralen | 49739-67-5

• 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: 5-(Diisoprenylamino)-9-methoxy-psoralen
• 英文别名: 4-[Bis(3-methylbut-2-enyl)amino]-9-methoxyfuro[3,2-g]chromen-7-one
• CAS: 49739-67-5
• 化学式: C₂₂H₂₅NO₄
• 分子量: 367.445
• InChiKey: ZKQLHNBMNGZWMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  51.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  欧前胡素 在 盐酸 、 tin 、 硝酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 3.0h， 生成 5-(Diisoprenylamino)-9-methoxy-psoralen
  参考文献：
  名称：

  Synthesis and evaluation of linear furanocoumarins as potential anti-breast and anti-prostate cancer agents

  摘要：

  A series of 22 furanocoumarin derivatives were synthesized and evaluated for cytotoxicity against breast cancer (MCF-7 and MDA-MB-231) and prostate cancer (PC-3) cell lines along with normal cell line. Several analogs were synthesized by replacing prenyl moiety with alkyl, aromatic, and heteroaromatic functionality to study the structure-activity relationship. Compounds 20 and 22 with adamantoylamino, diprenylamino and substituted benzene sulfonamide substituents showed potent antiproliferative activity in MCF-7 cell line with IC50 values of 0.48 and 0.53 A mu M, respectively. Both the compounds showed higher IC50 value in MCF-10A cell lines indicating nontoxicity in normal cell lines.

  DOI：

  10.1007/s00044-014-1312-6

文献信息

• Synthesis and evaluation of linear furanocoumarins as potential anti-breast and anti-prostate cancer agents
  作者：Siddheshwar K. Chauthe、Shivani Mahajan、Mahesh Rachamalla、Kulbhushan Tikoo、Inder P. Singh

  DOI：10.1007/s00044-014-1312-6

  日期：2015.6

  A series of 22 furanocoumarin derivatives were synthesized and evaluated for cytotoxicity against breast cancer (MCF-7 and MDA-MB-231) and prostate cancer (PC-3) cell lines along with normal cell line. Several analogs were synthesized by replacing prenyl moiety with alkyl, aromatic, and heteroaromatic functionality to study the structure-activity relationship. Compounds 20 and 22 with adamantoylamino, diprenylamino and substituted benzene sulfonamide substituents showed potent antiproliferative activity in MCF-7 cell line with IC50 values of 0.48 and 0.53 A mu M, respectively. Both the compounds showed higher IC50 value in MCF-10A cell lines indicating nontoxicity in normal cell lines.