(2S)-2-(4-chlorophenyl)-3-[5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose-5-C-yl]thiazolidin-4-one | 1097199-88-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-2-(4-chlorophenyl)-3-[5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose-5-C-yl]thiazolidin-4-one
• 英文别名: (2S)-3-[[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl]-2-(4-chlorophenyl)-1,3-thiazolidin-4-one
• CAS: 1097199-88-6
• 化学式: C₁₇H₂₀ClNO₅S
• 分子量: 385.869
• InChiKey: USEHTJMPTQAKJT-MBEZOWKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  93.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-amino-5-deoxy-1,2-O-isopropylidene-a-D-xylofuranose 、 4-氯苯甲醛 、 巯基乙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 为溶剂， 反应 1.17h， 以39.4%的产率得到(2S)-2-(4-chlorophenyl)-3-[5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose-5-C-yl]thiazolidin-4-one
  参考文献：
  名称：

  Synthesis and biological activity of novel thiazolidin-4-ones with a carbohydrate moiety

  摘要：

  Some novel 2-aryl-3-[5-deoxy-1,2-O-isopropylidene-alpha-D-Xylofuranose-5-C-yl] thiazolidin-4-ones were synthesized by the three-component condensation of an amino sugar 1, an aromatic alclehyde 2, and mercaptoacetic acid 3 in the presence of DCC and DMAP at room temperature. Two diastereoisomers 4 and 5 were afforded as the main products in totally isolated yields of 25.4-70%. The reaction was carried out with almost no observed stereoselectivity except in the case of 2c, which showed a moderate stereoselectivity. The structures of the new compounds were determined by NMR spectroscopy and mass spectrometry (MS), and the configuration of the newly generated chiral carbon (C-2) in the thiazolidin-4-one ring was tentatively assigned based on the X-ray crystallographic structure of 5d and the comparison of their corresponding NMR signals. The antitumor (human cervical cancer cells) activity and the inhibition against the glycosidases (alpha-glucosidase, beta-glucosidase, (alpha-amylase) have been evaluated for the new compounds, some of which exhibited antitumor activity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.09.004

文献信息

• Synthesis and biological activity of novel thiazolidin-4-ones with a carbohydrate moiety
  作者：Hua Chen、Lingling Jiao、Zaihong Guo、Xiaoliu Li、Cuilan Ba、Jinchao Zhang

  DOI：10.1016/j.carres.2008.09.004

  日期：2008.12

  Some novel 2-aryl-3-[5-deoxy-1,2-O-isopropylidene-alpha-D-Xylofuranose-5-C-yl] thiazolidin-4-ones were synthesized by the three-component condensation of an amino sugar 1, an aromatic alclehyde 2, and mercaptoacetic acid 3 in the presence of DCC and DMAP at room temperature. Two diastereoisomers 4 and 5 were afforded as the main products in totally isolated yields of 25.4-70%. The reaction was carried out with almost no observed stereoselectivity except in the case of 2c, which showed a moderate stereoselectivity. The structures of the new compounds were determined by NMR spectroscopy and mass spectrometry (MS), and the configuration of the newly generated chiral carbon (C-2) in the thiazolidin-4-one ring was tentatively assigned based on the X-ray crystallographic structure of 5d and the comparison of their corresponding NMR signals. The antitumor (human cervical cancer cells) activity and the inhibition against the glycosidases (alpha-glucosidase, beta-glucosidase, (alpha-amylase) have been evaluated for the new compounds, some of which exhibited antitumor activity. (C) 2008 Elsevier Ltd. All rights reserved.