(1S,2R,5S,6R,7R,9R,11S,12S,15R,16S)-5-(furan-2-ylmethylsulfanyl)-6-hydroxy-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-3-one | 1325214-17-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (1S,2R,5S,6R,7R,9R,11S,12S,15R,16S)-5-(furan-2-ylmethylsulfanyl)-6-hydroxy-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-3-one
• CAS: 1325214-17-2
• 化学式: C₃₃H₄₄O₇S
• 分子量: 584.774
• InChiKey: AFNVTCVNYORPLU-XSFKRGTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  糠基硫醇 、 醉茄素 A 在 三乙胺 作用下， 以 甲醇 为溶剂， 以84%的产率得到(1S,2R,5S,6R,7R,9R,11S,12S,15R,16S)-5-(furan-2-ylmethylsulfanyl)-6-hydroxy-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-3-one
  参考文献：
  名称：

  Ring A structural modified derivatives of withaferin A and the evaluation of their cytotoxic potential

  摘要：

  Regio-/stereoselective Michael addition to ring A of withaferin-A was performed using an optimized reaction procedure to synthesise a library of 2,3-dihydro,3-beta-substituted withaferin-A derivatives. The analogues thus obtained were evaluated for in vitro cytotoxicity against various human cancer cell lines. 3-Azido analogue exhibited 35-fold increase (IC(50) = 0.02-1.9 mu M) in cytotoxicity against almost the entire cell lines tested when compared to the parent molecule. However, further modifications of 3-azido analogue with various alkynes under Husigen's cycloaddition conditions generated a variety of triazole derivatives with reduced cytotoxicity. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.05.012

文献信息

• Ring A structural modified derivatives of withaferin A and the evaluation of their cytotoxic potential
  作者：Syed Khalid Yousuf、Rabiya Majeed、Mudassier Ahmad、Payare lal Sangwan、Basant Purnima、A.K. Saxsena、K.A. Suri、Debaraj Mukherjee、Subhash Chandra Taneja

  DOI：10.1016/j.steroids.2011.05.012

  日期：2011.9

  Regio-/stereoselective Michael addition to ring A of withaferin-A was performed using an optimized reaction procedure to synthesise a library of 2,3-dihydro,3-beta-substituted withaferin-A derivatives. The analogues thus obtained were evaluated for in vitro cytotoxicity against various human cancer cell lines. 3-Azido analogue exhibited 35-fold increase (IC(50) = 0.02-1.9 mu M) in cytotoxicity against almost the entire cell lines tested when compared to the parent molecule. However, further modifications of 3-azido analogue with various alkynes under Husigen's cycloaddition conditions generated a variety of triazole derivatives with reduced cytotoxicity. (C) 2011 Elsevier Inc. All rights reserved.