phenyl (R)-2,5,7,8-tetramethyl-2-((3'E,7'E)-4',8',12'-trimethyltrideca-3',7',11'-trienyl)chroman-6-yl iminodicarbonate | 1208120-95-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: phenyl (R)-2,5,7,8-tetramethyl-2-((3'E,7'E)-4',8',12'-trimethyltrideca-3',7',11'-trienyl)chroman-6-yl iminodicarbonate
• 英文别名: [(2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-3,4-dihydrochromen-6-yl] N-phenoxycarbonylcarbamate
• CAS: 1208120-95-9
• 化学式: C₃₇H₄₉NO₅
• 分子量: 587.8
• InChiKey: UZNAPDDKUSQART-HFYOCIDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  α-生育三烯醇 、 异氰酸基甲酸苯酯 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以60%的产率得到phenyl (R)-2,5,7,8-tetramethyl-2-((3'E,7'E)-4',8',12'-trimethyltrideca-3',7',11'-trienyl)chroman-6-yl iminodicarbonate
  参考文献：
  名称：

  Design and preliminary structure–activity relationship of redox-silent semisynthetic tocotrienol analogues as inhibitors for breast cancer proliferation and invasion

  摘要：

  Vitamin E (VE) is a generic term that represents a family of compounds composed of various tocopherol and tocotrienol isoforms. Tocotrienols display potent anti-angiogenic and antiproliferative activities. Redox-silent tocotrienol analogues also display potent anticancer activity. The ultimate objective of this study was to develop semisynthetically C-6-modified redox-silent tocotrienol analogues with enhanced antiproliferative and anti-invasive activities as compared to their parent compound. Examples of these are carbamate and ether analogues of alpha-, gamma-, and delta-tocotrienols (1-3). Various aliphatic, olefinic, and aromatic substituents were used. Steric limitation, electrostatic, hydrogen bond donor (HBD) and hydrogen bond acceptor (HBA) properties were varied at this position and the biological activities of these derivatives were tested. Three-dimensional quantitative structure-activity relationship (3D QSAR) studies were performed using Comparative Molecular Field (CoMFA) and Comparative Molecular Similarity Indices Analyses (CoMSIA) to better understand the structural basis for biological activity and guide the future design of more potent VE analogues. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.054

文献信息

• Design and preliminary structure–activity relationship of redox-silent semisynthetic tocotrienol analogues as inhibitors for breast cancer proliferation and invasion
  作者：Ahmed Y. Elnagar、Vikram B. Wali、Paul W. Sylvester、Khalid A. El Sayed

  DOI：10.1016/j.bmc.2009.11.054

  日期：2010.1

  Vitamin E (VE) is a generic term that represents a family of compounds composed of various tocopherol and tocotrienol isoforms. Tocotrienols display potent anti-angiogenic and antiproliferative activities. Redox-silent tocotrienol analogues also display potent anticancer activity. The ultimate objective of this study was to develop semisynthetically C-6-modified redox-silent tocotrienol analogues with enhanced antiproliferative and anti-invasive activities as compared to their parent compound. Examples of these are carbamate and ether analogues of alpha-, gamma-, and delta-tocotrienols (1-3). Various aliphatic, olefinic, and aromatic substituents were used. Steric limitation, electrostatic, hydrogen bond donor (HBD) and hydrogen bond acceptor (HBA) properties were varied at this position and the biological activities of these derivatives were tested. Three-dimensional quantitative structure-activity relationship (3D QSAR) studies were performed using Comparative Molecular Field (CoMFA) and Comparative Molecular Similarity Indices Analyses (CoMSIA) to better understand the structural basis for biological activity and guide the future design of more potent VE analogues. (C) 2009 Elsevier Ltd. All rights reserved.