N-(6-acetyl-1,3-benzodioxol-5-yl)anthracene-1-carboxamide | 1177265-98-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N-(6-acetyl-1,3-benzodioxol-5-yl)anthracene-1-carboxamide
• CAS: 1177265-98-3
• 化学式: C₂₄H₁₇NO₄
• 分子量: 383.403
• InChiKey: GCJRRVOYARKMJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(6-acetyl-1,3-benzodioxol-5-yl)anthracene-1-carboxamide 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以48%的产率得到2-(1-anthracenyl)-6,7-methylenedioxyquinolin-4-one
  参考文献：
  名称：

  Design and Synthesis of 2-(3-Benzo[b]thienyl)-6,7-methylenedioxyquinolin-4-one Analogues as Potent Antitumor Agents that Inhibit Tubulin Assembly

  摘要：

  As part of our continuing investigation of azo-flavonoid derivatives as potential anticancer drug candidates, a series of 2-aryl-6,7-methylenedioxyquinolin-4-one analogues was designed and synthesized. The design combined structural features of 2-(2-fluorophenyl)-6,7-methylenedioxyquinolin-4-one (CHM-1), a previously discovered compound with potent in vivo antitumor activity, and 2-arylquinolin-4-ones, identified by CoMFA models, The newly synthesized analogues were evaluated for cytotoxicity against seven human cancer cell lines, and structure-activity relationship (SAR) correlations were established. Analogues 1, 37, and 39 showed potent cytotoxicity against different cancer cell lines. Compound I demonstrated selective cytotoxicity against Hep 3B (hepatoma) cells. Compound 37 was cytotoxic against HL-60 (leukemia), HCT-116 (colon cancer), Hep 3B (hepatoma), and SK-MEL-5 (melanoma) cells. Compound 39 exhibited broad cytotoxicity against all seven cancer cell lines, with IC50 values between 0.07and 0.19 mu M. Results from mechanism of action studies revealed that these new quinolone derivatives function as antitubulin agents.

  DOI：

  10.1021/jm900456w
• 作为产物：
  描述：

  anthroic acid chloride 、 2'-氨基-4',5'-亚甲二氧基苯乙酮 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 N-(6-acetyl-1,3-benzodioxol-5-yl)anthracene-1-carboxamide
  参考文献：
  名称：

  Design and Synthesis of 2-(3-Benzo[b]thienyl)-6,7-methylenedioxyquinolin-4-one Analogues as Potent Antitumor Agents that Inhibit Tubulin Assembly

  摘要：

  As part of our continuing investigation of azo-flavonoid derivatives as potential anticancer drug candidates, a series of 2-aryl-6,7-methylenedioxyquinolin-4-one analogues was designed and synthesized. The design combined structural features of 2-(2-fluorophenyl)-6,7-methylenedioxyquinolin-4-one (CHM-1), a previously discovered compound with potent in vivo antitumor activity, and 2-arylquinolin-4-ones, identified by CoMFA models, The newly synthesized analogues were evaluated for cytotoxicity against seven human cancer cell lines, and structure-activity relationship (SAR) correlations were established. Analogues 1, 37, and 39 showed potent cytotoxicity against different cancer cell lines. Compound I demonstrated selective cytotoxicity against Hep 3B (hepatoma) cells. Compound 37 was cytotoxic against HL-60 (leukemia), HCT-116 (colon cancer), Hep 3B (hepatoma), and SK-MEL-5 (melanoma) cells. Compound 39 exhibited broad cytotoxicity against all seven cancer cell lines, with IC50 values between 0.07and 0.19 mu M. Results from mechanism of action studies revealed that these new quinolone derivatives function as antitubulin agents.

  DOI：

  10.1021/jm900456w

文献信息

• Design and Synthesis of 2-(3-Benzo[<i>b</i>]thienyl)-6,7-methylenedioxyquinolin-4-one Analogues as Potent Antitumor Agents that Inhibit Tubulin Assembly
  作者：Yu-Hsun Chang、Mei-Hua Hsu、Sheng-Hung Wang、Li-Jiau Huang、Keduo Qian、Susan L. Morris-Natschke、Ernest Hamel、Sheng-Chu Kuo、Kuo-Hsiung Lee

  DOI：10.1021/jm900456w

  日期：2009.8.13

  As part of our continuing investigation of azo-flavonoid derivatives as potential anticancer drug candidates, a series of 2-aryl-6,7-methylenedioxyquinolin-4-one analogues was designed and synthesized. The design combined structural features of 2-(2-fluorophenyl)-6,7-methylenedioxyquinolin-4-one (CHM-1), a previously discovered compound with potent in vivo antitumor activity, and 2-arylquinolin-4-ones, identified by CoMFA models, The newly synthesized analogues were evaluated for cytotoxicity against seven human cancer cell lines, and structure-activity relationship (SAR) correlations were established. Analogues 1, 37, and 39 showed potent cytotoxicity against different cancer cell lines. Compound I demonstrated selective cytotoxicity against Hep 3B (hepatoma) cells. Compound 37 was cytotoxic against HL-60 (leukemia), HCT-116 (colon cancer), Hep 3B (hepatoma), and SK-MEL-5 (melanoma) cells. Compound 39 exhibited broad cytotoxicity against all seven cancer cell lines, with IC50 values between 0.07and 0.19 mu M. Results from mechanism of action studies revealed that these new quinolone derivatives function as antitubulin agents.