peroxisomicine A1 | 110270-61-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: peroxisomicine A1
• 英文别名: (3S)-3,8,9-trihydroxy-3-methyl-7-[(2S)-2,5,10-trihydroxy-2-methyl-4-oxo-1,3-dihydroanthracen-9-yl]-2,4-dihydroanthracen-1-one
• CAS: 110270-61-6
• 化学式: C₃₀H₂₆O₈
• 分子量: 514.532
• InChiKey: FBPZAGOTWAVQJH-KYJUHHDHSA-N

物化性质

• 沸点：
  776.2±60.0 °C(Predicted)
• 密度：
  1.539±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  38
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  156
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 peroxisomicine A1 以 乙醇 为溶剂， 反应 0.75h， 生成 (6S,2'S)-1,6,2',5'-Tetrahydroxy-9,10'-dimethoxy-6,2'-dimethyl-6,7,2',3'-tetrahydro-5H,1'H-[2,9']bianthracenyl-8,4'-dione
  参考文献：
  名称：

  The absolute configuration of peroxisomicines A1 and A2

  摘要：

  Peroxisomicine A1 is a potentially antineoplastic compound isolated from the seeds of Karwinskia parvifolia. It is considered as a useful chemotype for the preparation of topoisomerase II targeted anticancer cells. Stereochemically, it is characterized by the presence of two stereocenters and a rotationally hindered and thus likewise stereogenic biaryl axis. In this contribution, the absolute configuration of peroxisomicine A1 and its epimer, peroxisomicine A2, was established by means of a five-step degradative procedure giving the respective R- and S-configured methyl 2-(2'-methyl-5'-oxotetrahydrofuryl)acetates. The configuration of the degradation product was obtained by means of optical rotation, H-1 NMR analysis using a chiral displacement reagent, and by experimental and quantum chemical circular dichroism (CD) investigations. Based on the results obtained here and considering our previous work on the relative configuration at centers versus axis of these compounds, peroxisomicine A1 resulted to be the P,3S,3'S-isomer and peroxisomicine A2 the P,3R,3'S-isomer. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.123

文献信息

• The absolute configuration of peroxisomicines A1 and A2
  作者：Alejandro Pérez、Rosalba Ramírez-Durón、Alfredo Piñeyro-López、Noemí Waksman、Matthias Reichert、Gerhard Bringmann

  DOI：10.1016/j.tet.2004.06.123

  日期：2004.9

  Peroxisomicine A1 is a potentially antineoplastic compound isolated from the seeds of Karwinskia parvifolia. It is considered as a useful chemotype for the preparation of topoisomerase II targeted anticancer cells. Stereochemically, it is characterized by the presence of two stereocenters and a rotationally hindered and thus likewise stereogenic biaryl axis. In this contribution, the absolute configuration of peroxisomicine A1 and its epimer, peroxisomicine A2, was established by means of a five-step degradative procedure giving the respective R- and S-configured methyl 2-(2'-methyl-5'-oxotetrahydrofuryl)acetates. The configuration of the degradation product was obtained by means of optical rotation, H-1 NMR analysis using a chiral displacement reagent, and by experimental and quantum chemical circular dichroism (CD) investigations. Based on the results obtained here and considering our previous work on the relative configuration at centers versus axis of these compounds, peroxisomicine A1 resulted to be the P,3S,3'S-isomer and peroxisomicine A2 the P,3R,3'S-isomer. (C) 2004 Elsevier Ltd. All rights reserved.