methyl (2R)-1-{[3-(benzyloxy)-6,7-dimethoxy-9-phenanthryl]methyl}-5-oxopyrrolidine-2-carboxylate | 1422707-32-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: methyl (2R)-1-{[3-(benzyloxy)-6,7-dimethoxy-9-phenanthryl]methyl}-5-oxopyrrolidine-2-carboxylate
• 英文别名: methyl (2R)-1-[(6,7-dimethoxy-3-phenylmethoxyphenanthren-9-yl)methyl]-5-oxopyrrolidine-2-carboxylate
• CAS: 1422707-32-1
• 化学式: C₃₀H₂₉NO₆
• 分子量: 499.563
• InChiKey: MGYPDYNOWARAKZ-AREMUKBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2R)-1-{[3-(benzyloxy)-6,7-dimethoxy-9-phenanthryl]methyl}-5-oxopyrrolidine-2-carboxylate 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 草酰氯 、 水 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 18.25h， 生成 (13aR)-3-(benzyloxy)-6,7-dimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline
  参考文献：
  名称：

  Stereospecific Synthesis and Biological Evaluation of Monodesmethyl Metabolites of (+)-13a-(S)-Deoxytylophorinine as Potential Antitumor Agents

  摘要：

  Three major monodesmethyl metabolites of (+)-13a-(S)-deoxytylophorinine were synthesized stereospecifically and their configurations at C-13a were determined. Biological assays revealed that one of the metabolites, 3-O-desmethyl-13a-(S)-deoxytylophorinine, had a higher cytotoxic potency than the parent compound or the positive controls doxorubicin (Adriamycin) and paclitaxel (Taxol).

  DOI：

  10.1055/s-0032-1316810
• 作为产物：
  描述：

  3-hydroxy-6,7-dimethoxy-9-phenanthrenecarboxylic acid methyl ester 在 lithium aluminium tetrahydride 、 potassium carbonate 、 sodium iodide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 丙酮 、 乙腈 为溶剂， 反应 12.5h， 生成 methyl (2R)-1-{[3-(benzyloxy)-6,7-dimethoxy-9-phenanthryl]methyl}-5-oxopyrrolidine-2-carboxylate
  参考文献：
  名称：

  Stereospecific Synthesis and Biological Evaluation of Monodesmethyl Metabolites of (+)-13a-(S)-Deoxytylophorinine as Potential Antitumor Agents

  摘要：

  Three major monodesmethyl metabolites of (+)-13a-(S)-deoxytylophorinine were synthesized stereospecifically and their configurations at C-13a were determined. Biological assays revealed that one of the metabolites, 3-O-desmethyl-13a-(S)-deoxytylophorinine, had a higher cytotoxic potency than the parent compound or the positive controls doxorubicin (Adriamycin) and paclitaxel (Taxol).

  DOI：

  10.1055/s-0032-1316810

文献信息

• Stereospecific Synthesis and Biological Evaluation of Monodesmethyl Metabolites of (+)-13a-(S)-Deoxytylophorinine as Potential Antitumor Agents
  作者：Shishan Yu、Pengfei Yu、Haining Lv、Chao Li、Jinhong Ren、Shuanggang Ma、Song Xu、Xiaoguang Chen

  DOI：10.1055/s-0032-1316810

  日期：——

  Three major monodesmethyl metabolites of (+)-13a-(S)-deoxytylophorinine were synthesized stereospecifically and their configurations at C-13a were determined. Biological assays revealed that one of the metabolites, 3-O-desmethyl-13a-(S)-deoxytylophorinine, had a higher cytotoxic potency than the parent compound or the positive controls doxorubicin (Adriamycin) and paclitaxel (Taxol).