[(3S,4R,5R)-4,5-dihydroxy-6-oxo-3-[(4-phenylphenyl)methoxy]cyclohexen-1-yl]methyl acetate | 1415025-93-2

• 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: [(3S,4R,5R)-4,5-dihydroxy-6-oxo-3-[(4-phenylphenyl)methoxy]cyclohexen-1-yl]methyl acetate
• CAS: 1415025-93-2
• 化学式: C₂₂H₂₂O₆
• 分子量: 382.413
• InChiKey: WBXWICRZQFIZRY-BVSLBCMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-溴甲基联苯 在 2,4,6-三甲基吡啶 、 pyridinium dichromate 、 水 、 sodium hydride 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 生成 [(3S,4R,5R)-4,5-dihydroxy-6-oxo-3-[(4-phenylphenyl)methoxy]cyclohexen-1-yl]methyl acetate
  参考文献：
  名称：

  Synthesis of chiral hydroxylated enones as potential anti-tumor agents

  摘要：

  A series of chiral hydroxylated enones were synthesized as COTC ether analogues to investigate the structural features required for optimal and selective anti-tumor activity. The cytotoxicity of the seven COTC ether analogues against WRL-68 normal and HepG2, HL-60 cancer cell lines were measured. C-4 ether analogues with an aliphatic chain substituent were found to be more favorable than their aromatic counterparts. Inversion of the configuration at C-4 in 5e to give 5f only resulted in reduced selectivity towards cancer cells. These results show that 4-O-pentyl-gabosine D (5e) has optimum selectivity and cytotoxicity towards two cancer cell lines. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.026

文献信息

• Synthesis of chiral hydroxylated enones as potential anti-tumor agents
  作者：Tony K.M. Shing、Ho T. Wu、H.F. Kwok、Clara B.S. Lau

  DOI：10.1016/j.bmcl.2012.10.026

  日期：2012.12

  A series of chiral hydroxylated enones were synthesized as COTC ether analogues to investigate the structural features required for optimal and selective anti-tumor activity. The cytotoxicity of the seven COTC ether analogues against WRL-68 normal and HepG2, HL-60 cancer cell lines were measured. C-4 ether analogues with an aliphatic chain substituent were found to be more favorable than their aromatic counterparts. Inversion of the configuration at C-4 in 5e to give 5f only resulted in reduced selectivity towards cancer cells. These results show that 4-O-pentyl-gabosine D (5e) has optimum selectivity and cytotoxicity towards two cancer cell lines. (c) 2012 Elsevier Ltd. All rights reserved.