(2-Acetyl-4-methyl-phenyl)-acetic acid | 90149-73-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-Acetyl-4-methyl-phenyl)-acetic acid
• 英文别名: 2-(2-Acetyl-4-methylphenyl)acetic acid
• CAS: 90149-73-8
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: RSJOZYWKHZRYHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-Acetyl-4-methyl-phenyl)-acetic acid 在 乙醇 、 硫酸 、 氧气 、 sodium 作用下， 反应 72.0h， 生成 2-hydroxy-6-methylnaphthoquinone
  参考文献：
  名称：

  .beta.-Lapachone: synthesis of derivatives and activities in tumor models

  摘要：

  In order to find a 3,4-dihydro-2H-naphtho[1,2-b]pyran-5,6-dione more potent than the naturally occurring 2,2-dimethyl derivative [beta-lapachone (10a)], we synthesized a series of analogous compounds with modifications at position 2 of the pyran ring or at positions 8 and 9 of the benzene ring. Of the compounds tested in vitro for inhibition of RNA-dependent DNA polymerase and in mice infected with Rauscher leukemia, all retained good enzyme activity. Inhibition of the reverse transcriptase activity of the 2,2-substituted derivatives 10b-e was as strong as 10a. However, only the 2-methyl-2-phenyl derivative 10e proved to be about as potent as the 2,2-dimethyl reference compound 10a in prolonging the mean survival time of mice with Rauscher leukemia virus induced leukemia.

  DOI：

  10.1021/jm00374a010

文献信息

• .beta.-Lapachone: synthesis of derivatives and activities in tumor models
  作者：Karl Schaffner-Sabba、Karl H. Schmidt-Ruppin、Walter Wehrli、Alfred R. Schuerch、Jan W. F. Wasley

  DOI：10.1021/jm00374a010

  日期：1984.8

  In order to find a 3,4-dihydro-2H-naphtho[1,2-b]pyran-5,6-dione more potent than the naturally occurring 2,2-dimethyl derivative [beta-lapachone (10a)], we synthesized a series of analogous compounds with modifications at position 2 of the pyran ring or at positions 8 and 9 of the benzene ring. Of the compounds tested in vitro for inhibition of RNA-dependent DNA polymerase and in mice infected with Rauscher leukemia, all retained good enzyme activity. Inhibition of the reverse transcriptase activity of the 2,2-substituted derivatives 10b-e was as strong as 10a. However, only the 2-methyl-2-phenyl derivative 10e proved to be about as potent as the 2,2-dimethyl reference compound 10a in prolonging the mean survival time of mice with Rauscher leukemia virus induced leukemia.