9-(2-propen-1-yloxy)-7H-furo[3,2-g][1]benzopyran-7-one | 62188-89-0

• 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-(2-propen-1-yloxy)-7H-furo[3,2-g][1]benzopyran-7-one
• 英文别名: 9-(allyloxy)-7H-furo[3,2-g]chromen-7-one；8-Allyloxypsoralen；9-prop-2-enoxyfuro[3,2-g]chromen-7-one
• CAS: 62188-89-0
• 化学式: C₁₄H₁₀O₄
• 分子量: 242.231
• InChiKey: NSKDBUBAOLSDRF-UHFFFAOYSA-N

物化性质

• 熔点：
  75 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  429.1±45.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-(2-propen-1-yloxy)-7H-furo[3,2-g][1]benzopyran-7-one 在 N,N-二乙基苯胺 作用下， 反应 1.0h， 生成 4-Allyl-9-hydroxy-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：
• 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-(2-propen-1-yloxy)-7H-furo[3,2-g][1]benzopyran-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。
• Design, Synthesis and Preliminary Evaluation of Novel Imperatorin Derivatives as Vasorelaxant Agents
  作者：Na Li、Jianyu He、Yingzhuan Zhan、Nan Zhou、Jie Zhang

  DOI：10.2174/157340611794072715

  日期：2011.1.1

  A series of novel imperatorin derivatives were synthesized from commercially available xanthotoxin. The in vitro pharmacological evaluation indicated that all of the compounds possessed potent vasodilatory activity. Among them, compounds (5b), (5d) and (5e) exhibited higher vasdilatory activity (with EC50 values of 0.68 μM, 0.59 μM and 0.49 μM, respectively) than imperatorin (EC50 = 1.12 μM). The program Volsurf was used to predict the derivatives' ADME relevant descriptors. The results suggested that these novel compounds had a potential interest for the development of novel and potent vasorelaxant agents.

  研究人员从市售的黄腐毒素中合成了一系列新型黄腐素衍生物。体外药理评估表明，所有化合物都具有强效的血管扩张活性。其中，化合物(5b)、(5d)和(5e)的血管舒张活性（EC50 值分别为 0.68 μM、0.59 μM 和 0.49 μM）高于黄藤素（EC50 = 1.12 μM）。研究人员使用 Volsurf 程序预测了衍生物的 ADME 相关描述符。结果表明，这些新型化合物具有开发新型强效血管舒张剂的潜在兴趣。
• 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.
• EL-KHRISY, E. A. M.;ABDEL-HAFEZ, O. M.;NOFAL, Z. M.;NASSAR, M. I.;ABU-MUS+, EGYPT. J. CHEM., 30,(1987) N, C. 387-394
  作者：EL-KHRISY, E. A. M.、ABDEL-HAFEZ, O. M.、NOFAL, Z. M.、NASSAR, M. I.、ABU-MUS+

  DOI：——

  日期：——
• BANERJEE, S. K.;GUPTA, B. D.;SINGH, K., J. CHEM. SOC. CHEM. COMMUN., 1982, N 14, 815-816
  作者：BANERJEE, S. K.、GUPTA, B. D.、SINGH, K.

  DOI：——

  日期：——