(3b,25R)-3-hydroxyfurosta-5,20(22)-dien-26-yl 4-Methylbenzenesulfonate | 991-62-8

• 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: (3b,25R)-3-hydroxyfurosta-5,20(22)-dien-26-yl 4-Methylbenzenesulfonate
• 英文别名: 26-pseudodiosgenyl 4-methylbenzenesulfonate；26-O-p-tosylpseudodiosgenin；(25R)-26-(toluene-4-sulfonyloxy)-furosta-5,20(22)-dien-3β-ol；O²⁶-(toluene-4-sulfonyl)-pseudodiosgenin
• CAS: 991-62-8
• 化学式: C₃₄H₄₈O₅S
• 分子量: 568.818
• InChiKey: UIAHDNXEPLYKAA-DFTRIAHPSA-N

物化性质

• 熔点：
  140-142 °C
• 沸点：
  686.6±55.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.34
• 重原子数：
  40.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3b,25R)-3-hydroxyfurosta-5,20(22)-dien-26-yl 4-Methylbenzenesulfonate 在 叠氮化钾 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 (25R)-20,26-azanediyl-22-ethoxy-(20αH,22βH)-furost-5-en-3β-ol
  参考文献：
  名称：

  Synthesis and transformations of a heptacyclic triazoline derived from pseudodiosgenin

  摘要：

  DOI：

  10.1021/jo01280a065
• 作为产物：
  描述：

  薯蓣皂素 在 吡啶 、 乙酸酐 、 乙酰氯 作用下， 以 对二甲苯 为溶剂， 反应 24.0h， 生成 (3b,25R)-3-hydroxyfurosta-5,20(22)-dien-26-yl 4-Methylbenzenesulfonate
  参考文献：
  名称：

  Synthesis and cytotoxic effect of pseudodiosgenyl saponins with thio-ring F

  摘要：

  Both the sugar moieties and aglycons of steroid saponins play important roles for their bioactivities. In order to test the biological contribution of the glycosyl residue and search new saponins with notable anticancer activity, mono- and di-saccharide pseudodiosgenyl saponins 22-28 together with two pseudodiosgenyl conjugates 29 and 30 were conveniently synthesized, all of which were based on the aglycon 7 bearing the thio-ring F. The cytotoxicity on human cancer cells (MCF-7, HepG-2, A549) for all of the synthesized compounds 7 and 22-30 was evaluated by MTT method. The thio-aglycon 7 when conjugated with sugars exhibited potent cytotoxicity, and the introduction of D-glucosamine into aglycon 7 led to the most potent compound 28. Furthermore, DAPI staining, AV/PI staining, AO-relocation, AO-uptake and LysoTracker Red-uptake assays demonstrated that the cell death caused by neosaponin 28 was at least partially through apoptosis involving lysosomal membrane permeabilization. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.055

文献信息

• Convergent synthesis and cytotoxic activities of 26-thio- and selenodioscin
  作者：Pengwei Chen、Peng Wang、Ni Song、Ming Li

  DOI：10.1016/j.steroids.2013.05.018

  日期：2013.9

  Convergent block syntheses of 26-thio- and selenodioscin have been achieved by developing the highly stereoselective 1,2-trans glycosylations of chacotriosyl imidate without recourse to neighboring group assistance. Both thiodioscin and selenodioscin possess cytotoxic activities similar to dioscin, a natural spirostanol glycoside. (C) 2013 Elsevier Inc. All rights reserved.
• Synthesis and evaluation of in vitro anticancer activity of novel solasodine derivatives
  作者：Xiao Ming Zha、Fei Ran Zhang、Jia Qi Shan、Yi Hua Zhang、Jun O. Liu、Hong Bin Sun

  DOI：10.1016/j.cclet.2010.04.020

  日期：2010.9

  Solasodine 11 is a steroidal alkaloid with various biological activities. Herein, 8 novel solasodine derivatives were synthesized and their effect on prostate cancer cell proliferation was assessed in vitro. Significant improvement in antiproliferative activity was achieved among some of the synthetic analogs. In particular, 19 exhibited the most potent inhibitory effect against the proliferation of PC-3 cell line (IC(50) = 3.91 mu mol/L). (C) 2010 Jun O. Liu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.