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

中文名称
——
中文别名
——
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
3-(phenylthio)butan-2-ol化学式
CAS
67210-37-1
化学式
C10H14OS
mdl
——
分子量
182.287
InChiKey
ZPNZKTJWTXMMEW-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

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-ol4,5-二氰基咪唑三乙胺 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
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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
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同类化合物

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