7-(benzyloxy)-3-bromo-2-ethyl-8-methyl-4H-chromen-4-one | 1362586-55-7

• 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-(benzyloxy)-3-bromo-2-ethyl-8-methyl-4H-chromen-4-one
• 英文别名: 3-Bromo-2-ethyl-8-methyl-7-phenylmethoxychromen-4-one
• CAS: 1362586-55-7
• 化学式: C₁₉H₁₇BrO₃
• 分子量: 373.246
• InChiKey: TUVAFPJQAQWENI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(2-hydroxy-4-(methoxymethoxy)-3-methylphenyl)ethanone 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 26.75h， 生成 7-(benzyloxy)-3-bromo-2-ethyl-8-methyl-4H-chromen-4-one
  参考文献：
  名称：

  Antitumor agents 292. Design, synthesis and pharmacological study of S- and O-substituted 7-mercapto- or hydroxy-coumarins and chromones as potent cytotoxic agents

  摘要：

  Thirty-five S- and O-substituted 7-mercaptocoumarin (9-23) and 7-hydroxy- or 7-mercapto-chromone (24-43) analogs were designed, synthesized and evaluated in vitro against four human tumor cell lines [KB (nasopharyngeal), KB-vin (vincristine-resistant subline), A549 (lung) and DU145 (prostate)] with paclitaxel as the positive control. Many of the synthesized compounds exhibited potent cytotoxic activity. Among them, compounds 10 and 18 showed broad spectrum activity with GI(50) values ranging from 0.92 to 2.11 mu M and 2.06-14.07 mu M, respectively. However, 33, a 3-brominated compound, displayed significant and selective inhibition against MDR KB-vin with a GI(50) of 5.84 mu M. Regardless of the size of the 7-alkoxy group, 2-alpha-bromoethyl-8-bromomethyl compounds (40-43) exhibited increased cytotoxicity compared with 2-ethyl-8-bromomethyl compounds (36-39). Moreover, in a preliminary pharmacological study, 10 not only remarkably increased cellular apoptosis in a concentration-dependent manner, but also clearly induced A549 cell cycle arrest at the G2/M phase. Thus, these coumarin derivatives merit investigation as novel potential antitumor agents with further structural modification to produce an optimal lead compound and elucidate the detailed pharmacological mechanism(s). (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.12.025

文献信息

• Antitumor agents 292. Design, synthesis and pharmacological study of S- and O-substituted 7-mercapto- or hydroxy-coumarins and chromones as potent cytotoxic agents
  作者：Ying Chen、Hong-Rui Liu、Hong-Shan Liu、Ming Cheng、Peng Xia、Keduo Qian、Pei-Chi Wu、Chin-Yu Lai、Yi Xia、Zheng-Yu Yang、Susan L. Morris-Natschke、Kuo-Hsiung Lee

  DOI：10.1016/j.ejmech.2011.12.025

  日期：2012.3

  Thirty-five S- and O-substituted 7-mercaptocoumarin (9-23) and 7-hydroxy- or 7-mercapto-chromone (24-43) analogs were designed, synthesized and evaluated in vitro against four human tumor cell lines [KB (nasopharyngeal), KB-vin (vincristine-resistant subline), A549 (lung) and DU145 (prostate)] with paclitaxel as the positive control. Many of the synthesized compounds exhibited potent cytotoxic activity. Among them, compounds 10 and 18 showed broad spectrum activity with GI(50) values ranging from 0.92 to 2.11 mu M and 2.06-14.07 mu M, respectively. However, 33, a 3-brominated compound, displayed significant and selective inhibition against MDR KB-vin with a GI(50) of 5.84 mu M. Regardless of the size of the 7-alkoxy group, 2-alpha-bromoethyl-8-bromomethyl compounds (40-43) exhibited increased cytotoxicity compared with 2-ethyl-8-bromomethyl compounds (36-39). Moreover, in a preliminary pharmacological study, 10 not only remarkably increased cellular apoptosis in a concentration-dependent manner, but also clearly induced A549 cell cycle arrest at the G2/M phase. Thus, these coumarin derivatives merit investigation as novel potential antitumor agents with further structural modification to produce an optimal lead compound and elucidate the detailed pharmacological mechanism(s). (C) 2011 Elsevier Masson SAS. All rights reserved.