7-(4-methoxybenzyloxy)-8-[(phenethylamino)methyl]-2-methylchromone | 912353-08-3

• 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-[(phenethylamino)methyl]-2-methylchromone
• 英文别名: 7-(4-methoxybenzyloxy)-2-methyl-8-((phenethylamino)methyl)-4H-chromen-4-one；7-[(4-Methoxyphenyl)methoxy]-2-methyl-8-[(2-phenylethylamino)methyl]chromen-4-one
• CAS: 912353-08-3
• 化学式: C₂₇H₂₇NO₄
• 分子量: 429.516
• InChiKey: JTWRJKGZBKWHOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-(4-methoxybenzyloxy)-8-[(phenethylamino)methyl]-2-methylchromone 在 氢氧化钾 、 sodium hydride 、 三氟乙酸 、 sodium iodide 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 7-hydroxy-8-[[(4-methoxyphenyl)methyl-(2-phenylethyl)amino]methyl]-2-(2-pyridin-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-hydroxy-8-formyl-2-methylchromone 在 sodium tetrahydroborate 、 potassium carbonate 、 sodium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 7-(4-methoxybenzyloxy)-8-[(phenethylamino)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 chromone-based analogs of lavendustin A
  作者：Dong Hyuk Nam、Ki Yong Lee、Chang Sang Moon、Yong Sup Lee

  DOI：10.1016/j.ejmech.2010.06.030

  日期：2010.9

  Lavendustin A and hormothamnione were reported to exhibit cytotoxic effects on tumor cell lines. In the present studies, a series of chromone-based lavendustin analogs were synthesized as a simplified hybrid of hormothamnione and lavendustin A by the reductive-amination of formyl-chromone 5 with various amines followed by aminoalkylation. Most compounds synthesized showed significantly improved potencies

  据报道，薰衣草素A和hormothamnione对肿瘤细胞系表现出细胞毒性作用。在本研究中，通过用各种胺对氨基甲酰基色酮5进行还原胺化反应，然后进行氨基烷基化反应，合成了一系列基于色酮的拉文达斯汀类似物，作为Hormothamnione和拉文达斯汀A的简化混合物。与标准化合物3相比，大多数合成的化合物对大多数测试的癌细胞系显示出显着改善的效力，表明苯乙烯基的去除增强了癌细胞的生长抑制活性。化合物4h和4k对GI 50表现出最强的抑制活性 对于A-549和HCT-15细胞，其值在6.01-9.92μg/ ml的范围内。
• 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.