9-benzyloxy-7H-furo[3,2-g]chromen-7-one | 42207-40-9

• 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: 9-benzyloxy-7H-furo[3,2-g]chromen-7-one
• 英文别名: 9-(phenylmethoxy)-7H-furo[3,2-g][1]benzopyran-7-one；8-benzyloxypsoralen；9-benzyloxy-furo[3,2-g]chromen-7-one；9-Benzyloxy-furo[3,2-g]chromen-7-on；9-Phenylmethoxyfuro[3,2-g]chromen-7-one
• CAS: 42207-40-9
• 化学式: C₁₈H₁₂O₄
• 分子量: 292.291
• InChiKey: QGAJGPMGOOQAQU-UHFFFAOYSA-N

物化性质

• 熔点：
  120-122 °C(Solv: acetonitrile (75-05-8); water (7732-18-5))
• 沸点：
  507.6±50.0 °C(Predicted)
• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  欧前胡素 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 2.0h， 生成 9-benzyloxy-7H-furo[3,2-g]chromen-7-one
  参考文献：
  名称：

  Loutfy; Khatibie, Pharmazie, 1983, vol. 38, # 2, p. 137 - 138

  摘要：

  DOI：

文献信息

• A simple one-step synthesis of phenyl ethers from phenyl acetates
  作者：Sunil K. Banerjee、Bishan D. Gupta、Kuber Singh

  DOI：10.1039/c39820000815

  日期：——

  Phenyl acetates when refluxed with alkyl halides in acetone solution in the presence of a crown ether and anhydrous potassium carbonate undergo alkylation yielding phenyl ethers.

  在冠醚和无水碳酸钾的存在下，乙酸苯酯与烷基卤在丙酮溶液中回流时，进行烷基化，生成苯基醚。
• Synthesis of Imperatorin Analogs and Their Evaluation as Acetylcholinesterase and Butyrylcholinesterase Inhibitors
  作者：Sebastian Granica、Anna K. Kiss、Małgorzata Jarończyk、Jan K. Maurin、Aleksander P. Mazurek、Zbigniew Czarnocki

  DOI：10.1002/ardp.201300259

  日期：2013.11

  In this study, we synthesized several imperatorin analogs using imperatorin and xanthotoxin as substrates. The anti‐cholinesterase activities of all compounds were evaluated in in vitro experiments according to the modified Ellman's method. For each synthesized compound, IC50 values for both enzymes were established. Galantamine hydrobromide was used as a positive control in the enzymatic experiments

  在这项研究中，我们使用欧前胡素和黄花素作为底物合成了几种欧前胡素类似物。根据改良的 Ellman 方法在体外实验中评估所有化合物的抗胆碱酯酶活性。对于每种合成的化合物，确定了两种酶的 IC50 值。加兰他敏氢溴酸盐用作酶促实验中的阳性对照。所有活性化合物均显示出对丁酰胆碱酯酶 (BuChE) 而非乙酰胆碱酯酶的选择性。最活跃的是 8-(3-甲基丁氧基)-补骨脂素和 8-己氧基补骨脂素，BuChE 的 IC50 值分别约为 16.5 和 16.4 µM。我们的研究结果可能被视为基于天然呋喃香豆素结构寻找潜在抗阿尔茨海默病药物的开始。
• 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.
• Caporale; Antonello, Farmaco, Edizione Scientifica, 1958, vol. 13, p. 363,366
  作者：Caporale、Antonello

  DOI：——

  日期：——
• Deng, Xian-Qing; Wei, Cheng-Xi; Song, Ming-Xia, Arzneimittel-Forschung/Drug Research, 2010, vol. 60, # 10, p. 587 - 592
  作者：Deng, Xian-Qing、Wei, Cheng-Xi、Song, Ming-Xia、Quan, Zhe-Shan

  DOI：——

  日期：——