7-(4-methoxybenzyloxy)-8-{[phenethyl-(4-methoxybenzyl)amino]methyl}-2-methylchromone | 912353-07-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 7-(4-methoxybenzyloxy)-8-{[phenethyl-(4-methoxybenzyl)amino]methyl}-2-methylchromone
• 英文别名: 7-[(4-Methoxyphenyl)methoxy]-8-[[(4-methoxyphenyl)methyl-(2-phenylethyl)amino]methyl]-2-methylchromen-4-one
• CAS: 912353-07-2
• 化学式: C₃₅H₃₅NO₅
• 分子量: 549.667
• InChiKey: HPEKNVRQNXOXAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-(4-methoxybenzyloxy)-8-{[phenethyl-(4-methoxybenzyl)amino]methyl}-2-methylchromone 在 氢氧化钾 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 7-hydroxy-8-[[(4-methoxyphenyl)methyl-(2-phenylethyl)amino]methyl]-2-(2-thiophen-2-ylethenyl)chromen-4-one
  参考文献：
  名称：

  Synthesis and anticancer activity of lavendustin A derivatives containing arylethenylchromone substituents

  摘要：

  2-Styrylchromones, which are relatively scarce in nature, have been reported to possess potent cytotoxicities on KB cell line. Lavendustin A, a metabolite of Streptomyces griseolavendus, has been shown to inhibit a growth of A431 cell line. Accordingly, a series of compounds 3a-g having structural features of styrylehromones and lavendustin A were synthesized and evaluated for cytotoxicity using SRB assay on four tumor cell lines. Compounds 3a-g were synthesized by the condensation of 2-methylchromone derivative 7 with several aromatic aldehydes. Among synthesized, compound 3e showed the significant cytotoxic activity on HCT-15 cell line with IC50 values of 7.17 mu g/ml indicating that lavendustin A derivatives containing 2-arylethenylchromone ring have a potential in anti-tumor application. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.04.008
• 作为产物：
  描述：

  7-(4-methoxybenzyloxy)-2-methyl-8-formylchromone 在 sodium tetrahydroborate 、 sodium hydride 、 sodium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 7-(4-methoxybenzyloxy)-8-{[phenethyl-(4-methoxybenzyl)amino]methyl}-2-methylchromone
  参考文献：
  名称：

  Synthesis and anticancer activity of lavendustin A derivatives containing arylethenylchromone substituents

  摘要：

  2-Styrylchromones, which are relatively scarce in nature, have been reported to possess potent cytotoxicities on KB cell line. Lavendustin A, a metabolite of Streptomyces griseolavendus, has been shown to inhibit a growth of A431 cell line. Accordingly, a series of compounds 3a-g having structural features of styrylehromones and lavendustin A were synthesized and evaluated for cytotoxicity using SRB assay on four tumor cell lines. Compounds 3a-g were synthesized by the condensation of 2-methylchromone derivative 7 with several aromatic aldehydes. Among synthesized, compound 3e showed the significant cytotoxic activity on HCT-15 cell line with IC50 values of 7.17 mu g/ml indicating that lavendustin A derivatives containing 2-arylethenylchromone ring have a potential in anti-tumor application. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.04.008

文献信息

• Synthesis and anticancer activity of lavendustin A derivatives containing arylethenylchromone substituents
  作者：Ki Yong Lee、Dong Hyuk Nam、Chang Sang Moon、Seon Hee Seo、Jae Yeol Lee、Yong Sup Lee

  DOI：10.1016/j.ejmech.2006.04.008

  日期：2006.8

  2-Styrylchromones, which are relatively scarce in nature, have been reported to possess potent cytotoxicities on KB cell line. Lavendustin A, a metabolite of Streptomyces griseolavendus, has been shown to inhibit a growth of A431 cell line. Accordingly, a series of compounds 3a-g having structural features of styrylehromones and lavendustin A were synthesized and evaluated for cytotoxicity using SRB assay on four tumor cell lines. Compounds 3a-g were synthesized by the condensation of 2-methylchromone derivative 7 with several aromatic aldehydes. Among synthesized, compound 3e showed the significant cytotoxic activity on HCT-15 cell line with IC50 values of 7.17 mu g/ml indicating that lavendustin A derivatives containing 2-arylethenylchromone ring have a potential in anti-tumor application. (c) 2006 Elsevier SAS. All rights reserved.