2,3-dihydroxy-4-[(4-methoxyphenyl)methoxymethyl]-2,3-dihydro-1H-cyclopenta[a]anthracene-6,11-dione | 178624-66-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,3-dihydroxy-4-[(4-methoxyphenyl)methoxymethyl]-2,3-dihydro-1H-cyclopenta[a]anthracene-6,11-dione
• CAS: 178624-66-3
• 化学式: C₂₆H₂₂O₆
• 分子量: 430.457
• InChiKey: HNTHUUWFBZNWFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-dihydroxy-4-[(4-methoxyphenyl)methoxymethyl]-2,3-dihydro-1H-cyclopenta[a]anthracene-6,11-dione 在 吡啶 、 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  Cyclopent[a]anthraquinones as DNA-Intercalating Agents with Covalent Bond Formation Potential:  Synthesis and Biological Activity

  摘要：

  A series of mitomycin C (MMC) analogues, namely cyclopentanthraquinone derivatives, were synthesized via Diels-Alder cyclization of naphthoquinone with 1-vinylcyclopent-1-enes. These new compounds are planar structures, like MMC, and bear an aziridine ring and a methyl carbamate side chain. After bioreduction, they are anticipated to be capable of intercalating into double-stranded DNA and bind covalently. Structure-activity relationships were studied. Of these compounds, 2,3-aziridino-4-[[(methylamino)carbonyl]methyl]cyclopent[a]anthracene-6,11-dione (4) was shown to have inhibitory activity against several leukemic and solid tumor cell lines. Mice (BDF1) bearing Lewis lung adenocarcinoma were treated with 4 and MMC (ip, QD x 5). At a dose of 30.0 mg/kg, compound 4 was as effective as MMC (0.8 mg/kg). Compound 4 appears to be less toxic than MMC. DNA unwinding assay indicated that 4 is able to intercalate into DNA double strands and is also a topoisomerase II inhibitor.

  DOI：

  10.1021/jm950881y
• 作为产物：
  描述：

  1-(2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-2-[(4-methoxyphenyl)methoxy]ethanone 在 palladium on activated charcoal 辛烯 、 仲丁基锂 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 为溶剂， 反应 76.5h， 生成 2,3-dihydroxy-4-[(4-methoxyphenyl)methoxymethyl]-2,3-dihydro-1H-cyclopenta[a]anthracene-6,11-dione
  参考文献：
  名称：

  Cyclopent[a]anthraquinones as DNA-Intercalating Agents with Covalent Bond Formation Potential:  Synthesis and Biological Activity

  摘要：

  A series of mitomycin C (MMC) analogues, namely cyclopentanthraquinone derivatives, were synthesized via Diels-Alder cyclization of naphthoquinone with 1-vinylcyclopent-1-enes. These new compounds are planar structures, like MMC, and bear an aziridine ring and a methyl carbamate side chain. After bioreduction, they are anticipated to be capable of intercalating into double-stranded DNA and bind covalently. Structure-activity relationships were studied. Of these compounds, 2,3-aziridino-4-[[(methylamino)carbonyl]methyl]cyclopent[a]anthracene-6,11-dione (4) was shown to have inhibitory activity against several leukemic and solid tumor cell lines. Mice (BDF1) bearing Lewis lung adenocarcinoma were treated with 4 and MMC (ip, QD x 5). At a dose of 30.0 mg/kg, compound 4 was as effective as MMC (0.8 mg/kg). Compound 4 appears to be less toxic than MMC. DNA unwinding assay indicated that 4 is able to intercalate into DNA double strands and is also a topoisomerase II inhibitor.

  DOI：

  10.1021/jm950881y

文献信息

• Cyclopent[<i>a</i>]anthraquinones as DNA-Intercalating Agents with Covalent Bond Formation Potential:  Synthesis and Biological Activity
  作者：Joong Young Kim、Tsann-Long Su、Ting-Chao Chou、Bernd Koehler、Alex Scarborough、Ouathek Ouerfelli、Kyoichi A. Watanabe

  DOI：10.1021/jm950881y

  日期：1996.1.1

  A series of mitomycin C (MMC) analogues, namely cyclopentanthraquinone derivatives, were synthesized via Diels-Alder cyclization of naphthoquinone with 1-vinylcyclopent-1-enes. These new compounds are planar structures, like MMC, and bear an aziridine ring and a methyl carbamate side chain. After bioreduction, they are anticipated to be capable of intercalating into double-stranded DNA and bind covalently. Structure-activity relationships were studied. Of these compounds, 2,3-aziridino-4-[[(methylamino)carbonyl]methyl]cyclopent[a]anthracene-6,11-dione (4) was shown to have inhibitory activity against several leukemic and solid tumor cell lines. Mice (BDF1) bearing Lewis lung adenocarcinoma were treated with 4 and MMC (ip, QD x 5). At a dose of 30.0 mg/kg, compound 4 was as effective as MMC (0.8 mg/kg). Compound 4 appears to be less toxic than MMC. DNA unwinding assay indicated that 4 is able to intercalate into DNA double strands and is also a topoisomerase II inhibitor.