8-Chloro-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione | 90149-82-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 8-Chloro-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione
• 英文别名: 8-Chloro-2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione
• CAS: 90149-82-9
• 化学式: C₁₅H₁₃ClO₃
• 分子量: 276.719
• InChiKey: JFEKENRBJBRARS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2-Acetyl-4-chloro-phenyl)-acetic acid ethyl ester 在 氢氧化钾 、 乙醇 、 硫酸 、 氧气 、 sodium 、 potassium iodide 作用下， 反应 16.25h， 生成 8-Chloro-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione
  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.