3-(phenylthio)butan-2-ol | 67210-37-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(phenylthio)butan-2-ol
• 英文别名: 3-Phenylthio-2-butanol；3-(Phenylthio)-2-butanol；3-phenylsulfanylbutan-2-ol
• CAS: 67210-37-1
• 化学式: C₁₀H₁₄OS
• 分子量: 182.287
• InChiKey: ZPNZKTJWTXMMEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(phenylthio)butan-2-ol 在 4,5-二氰基咪唑 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 bis[3-(phenylthio)butan-2-yl] N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  Synthesis and evaluation of sulfonylethyl-containing phosphotriesters of 3′-azido-3′-deoxythymidine as anticancer prodrugs

  摘要：

  A series of bis(sulfonylethyl) and mono(sulfonylethyl) phenyl phosphotriesters of zidovudine (3'-azido-3'-deoxythymidine, AZT) were synthesized as potential anticancer prodrugs that liberate AZT monophosphate via nonenzymatic beta-elimination mechanism. Stability studies demonstrated that all the synthesized prodrugs spontaneously liberate AZT monophosphate with half-lives in the range of 0.07-278.8 h under model physiological conditions in 0.1 M phosphate buffer at pH 7.4 and 37 degrees C. Analogous to aldophosphamide, the elimination rates were accelerated in the presence of reconstituted human plasma under the same conditions. Among the compounds, 3, 4, 8, and 10 were comparable or superior to AZT against five established human cancerous cell lines in vitro. Moreover, the selected compounds were equally sensitive to both the wild-type osteosarcoma 143B and the thymidine kinase-deficient 143B/TK cell lines. The findings are consistent with that these compounds deliver AZT monophosphate intracellularly. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.09.046
• 作为产物：
  描述：

  1,2-二甲基环氧乙烷 、 sodium thiophenolate 以 甲醇 为溶剂， 以73%的产率得到3-(phenylthio)butan-2-ol
  参考文献：
  名称：

  Synthesis and evaluation of sulfonylethyl-containing phosphotriesters of 3′-azido-3′-deoxythymidine as anticancer prodrugs

  摘要：

  A series of bis(sulfonylethyl) and mono(sulfonylethyl) phenyl phosphotriesters of zidovudine (3'-azido-3'-deoxythymidine, AZT) were synthesized as potential anticancer prodrugs that liberate AZT monophosphate via nonenzymatic beta-elimination mechanism. Stability studies demonstrated that all the synthesized prodrugs spontaneously liberate AZT monophosphate with half-lives in the range of 0.07-278.8 h under model physiological conditions in 0.1 M phosphate buffer at pH 7.4 and 37 degrees C. Analogous to aldophosphamide, the elimination rates were accelerated in the presence of reconstituted human plasma under the same conditions. Among the compounds, 3, 4, 8, and 10 were comparable or superior to AZT against five established human cancerous cell lines in vitro. Moreover, the selected compounds were equally sensitive to both the wild-type osteosarcoma 143B and the thymidine kinase-deficient 143B/TK cell lines. The findings are consistent with that these compounds deliver AZT monophosphate intracellularly. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.09.046

文献信息

• General method for the synthesis of high enantiomeric purity chiral epoxides
  作者：William H. Pirkle、Peter L. Rinaldi

  DOI：10.1021/jo00414a001

  日期：1978.9
• Eastgate, Martin D.; Fox, David J.; Morley, Thomas J., Synthesis, 2002, # 14, p. 2124 - 2128
  作者：Eastgate, Martin D.、Fox, David J.、Morley, Thomas J.、Warren, Stuart

  DOI：——

  日期：——
• Titanium Containing Complex and Condensation Reaction Catalysts, Methods for Preparing the Catalysts, and Compositions Containing the Catalysts
  申请人：Brandstadt Kurt

  公开号：US20140213690A1

  公开（公告）日：2014-07-31

  A composition is capable of curing via condensation reaction. The composition uses a new condensation reaction catalyst. The new condensation reaction catalyst is used to replace conventional tin catalysts. The composition can react to form a gum, gel, rubber, or resin.
• US9371422B2
  申请人：——

  公开号：US9371422B2

  公开（公告）日：2016-06-21
• Synthesis and evaluation of sulfonylethyl-containing phosphotriesters of 3′-azido-3′-deoxythymidine as anticancer prodrugs
  作者：Jiang Wang、Yi-Jun Wang、Zhe-Sheng Chen、Chul-Hoon Kwon

  DOI：10.1016/j.bmc.2014.09.046

  日期：2014.11

  A series of bis(sulfonylethyl) and mono(sulfonylethyl) phenyl phosphotriesters of zidovudine (3'-azido-3'-deoxythymidine, AZT) were synthesized as potential anticancer prodrugs that liberate AZT monophosphate via nonenzymatic beta-elimination mechanism. Stability studies demonstrated that all the synthesized prodrugs spontaneously liberate AZT monophosphate with half-lives in the range of 0.07-278.8 h under model physiological conditions in 0.1 M phosphate buffer at pH 7.4 and 37 degrees C. Analogous to aldophosphamide, the elimination rates were accelerated in the presence of reconstituted human plasma under the same conditions. Among the compounds, 3, 4, 8, and 10 were comparable or superior to AZT against five established human cancerous cell lines in vitro. Moreover, the selected compounds were equally sensitive to both the wild-type osteosarcoma 143B and the thymidine kinase-deficient 143B/TK cell lines. The findings are consistent with that these compounds deliver AZT monophosphate intracellularly. (C) 2014 Elsevier Ltd. All rights reserved.