(R)-3-(3-chlorophenyl)-2-((2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)thiazolidin-4-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-3-(3-chlorophenyl)-2-((2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)thiazolidin-4-one
• 英文别名: (2R)-3-(3-chlorophenyl)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-thiazolidin-4-one
• 化学式: C₁₄H₁₆ClNO₅S
• 分子量: 345.804
• InChiKey: ALMXKFHVHSOQAJ-QKGWFMCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-氯苯胺 、 2,5-脱水-d-甘露糖 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 (R)-3-(3-chlorophenyl)-2-((2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)thiazolidin-4-one 、 (S)-3-(3-chlorophenyl)-2-((2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)thiazolidin-4-one
  参考文献：
  名称：

  Synthesis and immunostimulating activity of C-pseudonucleosides containing N-phenyl thiazolidin-4-one

  摘要：

  Several novel C-pseudonucleosides containing N-phenyl thiazolidin-4-one were synthesized at room temperature using the unprotected sugar aldehyde as the starting material. The effects of the compounds on Con A-induced T cell proliferation were evaluated at five concentrations of 5, 10, 25, 50, and 100 mu M. Some compounds, such as 5d, 5e, 5f, and 4g could significantly increase the proliferation by 62, 63, 70, and 53 % at low concentration of 5 mu M, respectively. The structure-activity relationship indicated that the lipophilicity substituents like chloro atom, methyl, and methoxyl on the para position of N-3 phenyl at the thiazolidin-4-one ring had a detrimental impact on the T cell proliferation. The C-2 configuration and the electronic property of the lipophilicity substituents likely had slight effects on the immunostimulatory activities of such C-pseudonucleosides.

  DOI：

  10.1007/s00044-013-0560-1

文献信息

• Synthesis and immunostimulating activity of C-pseudonucleosides containing N-phenyl thiazolidin-4-one
  作者：Hua Chen、Fang Gao、Chunxiao Li、Xiaoliu Li、Na Li、Ming Meng

  DOI：10.1007/s00044-013-0560-1

  日期：2013.12

  Several novel C-pseudonucleosides containing N-phenyl thiazolidin-4-one were synthesized at room temperature using the unprotected sugar aldehyde as the starting material. The effects of the compounds on Con A-induced T cell proliferation were evaluated at five concentrations of 5, 10, 25, 50, and 100 mu M. Some compounds, such as 5d, 5e, 5f, and 4g could significantly increase the proliferation by 62, 63, 70, and 53 % at low concentration of 5 mu M, respectively. The structure-activity relationship indicated that the lipophilicity substituents like chloro atom, methyl, and methoxyl on the para position of N-3 phenyl at the thiazolidin-4-one ring had a detrimental impact on the T cell proliferation. The C-2 configuration and the electronic property of the lipophilicity substituents likely had slight effects on the immunostimulatory activities of such C-pseudonucleosides.