4-[3-[(4-methoxyphenyl)methoxy]prop-1-en-2-yl]-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxole | 178624-63-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[3-[(4-methoxyphenyl)methoxy]prop-1-en-2-yl]-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxole
• CAS: 178624-63-0
• 化学式: C₁₉H₂₄O₄
• 分子量: 316.397
• InChiKey: IWMKCKZULYIMTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[3-[(4-methoxyphenyl)methoxy]prop-1-en-2-yl]-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxole 在 palladium on activated charcoal 吡啶 、 辛烯 、 水 、 4-甲基苯磺酸吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 100.5h， 生成 [(2R,3S)-4-(methylcarbamoyloxymethyl)-3-methylsulfonyloxy-6,11-dioxo-2,3-dihydro-1H-cyclopenta[a]anthracen-2-yl] methanesulfonate
  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：

  2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxole-6-carbaldehyde 在 正丁基锂 、 仲丁基锂 、 二甲基亚砜 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 6.17h， 生成 4-[3-[(4-methoxyphenyl)methoxy]prop-1-en-2-yl]-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxole
  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