benzylidine-2-methoxy-5,6-benzoacetophenone | 4487-15-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: benzylidine-2-methoxy-5,6-benzoacetophenone
• 英文别名: 1-(2-methoxy-naphthalen-1-yl)-3-phenyl-propenone；1-(2-methoxy-[1]naphthyl)-3-phenyl-propenone；1-(2-Methoxy-[1]naphthyl)-3-phenyl-propenon；1-Cinnamoyl-naphthol-(2)-methylaether；Styryl-(2-methoxy-naphthyl-(1))-keton；2-Methoxy-1-cinnamoyl-naphthalin；1-Cinnamoyl-2-methoxy-naphthalene；1-(2-methoxynaphthalen-1-yl)-3-phenylprop-2-en-1-one
• CAS: 4487-15-4
• 化学式: C₂₀H₁₆O₂
• 分子量: 288.346
• InChiKey: JZZBWIKGCLNJCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzylidine-2-methoxy-5,6-benzoacetophenone 在 sodium ethanolate 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 54.0h， 生成 ethyl 2-[[6-(2-methoxynaphthalen-1-yl)-4-phenyl-4,5-dihydropyrimidin-2-yl]sulfanyl]acetate
  参考文献：
  名称：

  Amine; Nassar; El-Hashash, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 4, p. 388 - 391

  摘要：

  DOI：
• 作为产物：
  描述：

  1-乙酰基-2-萘酚 在 caesium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 36.5h， 生成 benzylidine-2-methoxy-5,6-benzoacetophenone
  参考文献：
  名称：

  Synthesis, biological evaluation, and molecular modelling of new naphthalene-chalcone derivatives as potential anticancer agents on MCF-7 breast cancer cells by targeting tubulin colchicine binding site

  摘要：

  A series of naphthalene-chalcone derivatives (3a-3t) were prepared and evaluated as tubulin polymerisation inhibitor for the treatment of breast cancer. All compounds were evaluated for their antiproliferative activity against MCF-7 cell line. The most of compounds displayed potent antiproliferative activity. Among them, compound 3a displayed the most potent antiproliferative activity with an IC50 value of 1.42 +/- 0.15 mu M, as compared to cisplatin (IC50 = 15.24 +/- 1.27 mu M). Additionally, the promising compound 3a demonstrated relatively lower cytotoxicity on normal cell line (HEK293) compared to tumour cell line. Furthermore, compound 3a was found to induce significant cell cycle arrest at the G(2)/M phase and cell apoptosis. Compound 3a displayed potent tubulin polymerisation inhibitory activity with an IC50 value of 8.4 mu M, which was slightly more active than the reference compound colchicine (IC50=10.6 mu M). Molecular docking analysis suggested that 3a interact and bind at the colchicine binding site of the tubulin.

  DOI：

  10.1080/14756366.2019.1690479

文献信息

• Fries; Schimmelschmidt, Chemische Berichte, 1925, vol. 58, p. 2844
  作者：Fries、Schimmelschmidt

  DOI：——

  日期：——
• Belton; Nowlan; Wheeler, Scientific Proceedings of the Royal Dublin Society, 1949, vol. 25, p. 19,28
  作者：Belton、Nowlan、Wheeler

  DOI：——

  日期：——
• Hutchins et al., Journal of the Chemical Society, 1938, p. 1882,1884
  作者：Hutchins et al.

  DOI：——

  日期：——
• STUDIES IN THE PERINAPHTHENE¹ SERIES. IV². SOME ATTEMPTS TO SYNTHESIZE 9-PHENYL-PERINAPHTHANONE-7
  作者：C. F. KOELSCH、J. A. ANTHES

  DOI：10.1021/jo01204a009

  日期：1941.7
• El-Hashash,M.A.; Essawy,A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1979, vol. 17, p. 454 - 457
  作者：El-Hashash,M.A.、Essawy,A.

  DOI：——

  日期：——