(-)-(6aR,11aR)-2,3,9-trimethoxypterocarpan | 56782-49-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: (-)-(6aR,11aR)-2,3,9-trimethoxypterocarpan
• 英文别名: (-)-2,3,9-trimethoxypterocarpan；Sparticarpin monomethyl ether；(6aR,11aR)-2,3,9-trimethoxy-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene
• CAS: 56782-49-1
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: XCRBPIBUMBLGCZ-UGSOOPFHSA-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：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (+/-)-2,3,9-Trimethoxy-6,6a-dihydro-11aH-benzofuro<3,2-c><1>benzopyran 在 Daicel CHIRALPAKIA Semi-Prep column 作用下， 以 正己烷 、 异丙醇 为溶剂， 以48.6 mg的产率得到(+)-2,3,9-trimethoxypterocarpan
  参考文献：
  名称：

  Antitumor Potential of the Isoflavonoids (+)- and (−)-2,3,9-Trimethoxypterocarpan: Mechanism-of-Action Studies

  摘要：

  Synthetically derived samples of (+)-(6aS,11aS)-2,3,9-trimethoxypterocarpan [(+)-1] and its enantiomer [(-)-1], both of which are examples of naturally occurring isoflavonoids, were evaluated, together with the corresponding racemate, as cytotoxic agents against the HL-60, HCT-116, OVCAR-8, and SF-295 tumor cell lines. As a result it was established that compound (+)-1 was particularly active with OVCAR-8 cells being the most sensitive and responding in a dose-dependent manner. A study of cell viability and drug-induced morphological changes revealed the compound causes cell death through a mechanism characteristic of apoptosis. Finally, a computational study of the interactions of compound (+)-1 and (S)-monastrol, an established, synthetically derived, potent, and cell-permeant inhibitor of mitosis, with the kinesin-type protein Eg5 revealed that both bind to this receptor in a similar manner. Significantly, compound (+)-1 binds with greater affinity, an effect attributed to the presence of the associated methoxy groups.

  DOI：

  10.1021/acsmedchemlett.0c00097

文献信息

• [EN] METHOD FOR PRODUCING PTEROCARPANS, CYTOMODULATING COMPOSITION CONTAINING PTEROCARPANS, AND USE OF PTEROCARPANS<br/>[FR] PROCÉDÉ DE PRODUCTION DE PTÉROCARPANES, COMPOSITION CYTOMODULATRICE COMPRENANT DES PTÉROCARPANES, ET UTILISATION DE PTÉROCARPANES<br/>[PT] PROCESSO DE PRODUÇÃO DE PTEROCARPANOS, COMPOSIÇÃO CITOMODULADORA COMPREENDO PTEROCARPANOS, E USO DE PTEROCARPANOS
  申请人：UNIV FED DO CEARA UFC

  公开号：WO2013000054A1

  公开（公告）日：2013-01-03

  A presente invenção proporciona um processo de produção de pterocarpanos, uma composição compreendendo pterocarpanos e o uso de pterocarpans na preparação de composições farmacêuticas. Os compostos da presente invenção são particularmente úteis para a citomodulação, como aquela utilizada no tratamento de tumores.
• Antitumor Potential of the Isoflavonoids (+)- and (−)-2,3,9-Trimethoxypterocarpan: Mechanism-of-Action Studies
  作者：Kaio Farias、Roner F. da Costa、Assuero S. Meira、Jairo Diniz-Filho、Eveline M. Bezerra、Valder N. Freire、Prue Guest、Maryam Nikahd、Xinghua Ma、Michael G. Gardiner、Martin G. Banwell、Maria da C. F. de Oliveira、Manoel O. de Moraes、Claudia do Ó Pessoa

  DOI：10.1021/acsmedchemlett.0c00097

  日期：2020.6.11

  Synthetically derived samples of (+)-(6aS,11aS)-2,3,9-trimethoxypterocarpan [(+)-1] and its enantiomer [(-)-1], both of which are examples of naturally occurring isoflavonoids, were evaluated, together with the corresponding racemate, as cytotoxic agents against the HL-60, HCT-116, OVCAR-8, and SF-295 tumor cell lines. As a result it was established that compound (+)-1 was particularly active with OVCAR-8 cells being the most sensitive and responding in a dose-dependent manner. A study of cell viability and drug-induced morphological changes revealed the compound causes cell death through a mechanism characteristic of apoptosis. Finally, a computational study of the interactions of compound (+)-1 and (S)-monastrol, an established, synthetically derived, potent, and cell-permeant inhibitor of mitosis, with the kinesin-type protein Eg5 revealed that both bind to this receptor in a similar manner. Significantly, compound (+)-1 binds with greater affinity, an effect attributed to the presence of the associated methoxy groups.