3-(4-hydroxyphenyl)-2',4',6'-trihydroxypropyl 2'-O-β-D-glucopyranoside | 1133352-85-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-hydroxyphenyl)-2',4',6'-trihydroxypropyl 2'-O-β-D-glucopyranoside
• 英文别名: (2S,3R,4S,5S,6R)-2-(3,5-dihydroxy-2-(3-(4-hydroxyphenyl)propyl)phenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol；(2S,3R,4S,5S,6R)-2-[3,5-dihydroxy-2-[3-(4-hydroxyphenyl)propyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1133352-85-8
• 化学式: C₂₁H₂₆O₉
• 分子量: 422.432
• InChiKey: XVEIZRPEUQSVDV-YMQHIKHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  160
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxyphenyl)-2',4',6'-trihydroxypropyl 2'-O-β-D-glucopyranoside 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 2-(3-(4-hydroxyphenyl)propyl)benzene-1,3,5-triol
  参考文献：
  名称：

  Synthesis and biological evaluation of phloridzin analogs as human concentrative nucleoside transporter 3 (hCNT3) inhibitors

  摘要：

  Nucleoside transporter inhibitors have potential therapeutic applications as anticancer, antiviral, cardio-protective and neuroprotective agents. Although quite a few potent inhibitors of the equilibrative nucleoside transporters are known, largely missing are the concentrative nucleoside transporter inhibitors. Phloridzin (3, K-i = 16.00 mu M) is a known moderate inhibitor of the concentrative nucleoside transporters. We have synthesized and evaluated analogs of phloridzin at the hCNT3 nucleoside transporter. Within the series of synthesized analogs compound 16 (K-i = 2.88 mu M), possessing a ribofuranose sugar unit instead of a glucopyranose as present in phloridzin, exhibited the highest binding affinity at the hCNT3 transporter. Phloridzin and compound 16 have also been shown to be selective for the hCNT3 transporter as compared with the hENT1 transporter. Compound 16 can serve as a new lead which after further modi. cations could yield selective and potent hCNT3 inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.112
• 作为产物：
  描述：

  phloridizin 在 三乙基硅烷 、 三氟乙酸 作用下， 反应 3.0h， 生成 3-(4-hydroxyphenyl)-2',4',6'-trihydroxypropyl 2'-O-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and biological evaluation of phloridzin analogs as human concentrative nucleoside transporter 3 (hCNT3) inhibitors

  摘要：

  Nucleoside transporter inhibitors have potential therapeutic applications as anticancer, antiviral, cardio-protective and neuroprotective agents. Although quite a few potent inhibitors of the equilibrative nucleoside transporters are known, largely missing are the concentrative nucleoside transporter inhibitors. Phloridzin (3, K-i = 16.00 mu M) is a known moderate inhibitor of the concentrative nucleoside transporters. We have synthesized and evaluated analogs of phloridzin at the hCNT3 nucleoside transporter. Within the series of synthesized analogs compound 16 (K-i = 2.88 mu M), possessing a ribofuranose sugar unit instead of a glucopyranose as present in phloridzin, exhibited the highest binding affinity at the hCNT3 transporter. Phloridzin and compound 16 have also been shown to be selective for the hCNT3 transporter as compared with the hENT1 transporter. Compound 16 can serve as a new lead which after further modi. cations could yield selective and potent hCNT3 inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.112

文献信息

• Synthesis and biological evaluation of phloridzin analogs as human concentrative nucleoside transporter 3 (hCNT3) inhibitors
  作者：Amol Gupte、John K. Buolamwini

  DOI：10.1016/j.bmcl.2008.11.112

  日期：2009.2

  Nucleoside transporter inhibitors have potential therapeutic applications as anticancer, antiviral, cardio-protective and neuroprotective agents. Although quite a few potent inhibitors of the equilibrative nucleoside transporters are known, largely missing are the concentrative nucleoside transporter inhibitors. Phloridzin (3, K-i = 16.00 mu M) is a known moderate inhibitor of the concentrative nucleoside transporters. We have synthesized and evaluated analogs of phloridzin at the hCNT3 nucleoside transporter. Within the series of synthesized analogs compound 16 (K-i = 2.88 mu M), possessing a ribofuranose sugar unit instead of a glucopyranose as present in phloridzin, exhibited the highest binding affinity at the hCNT3 transporter. Phloridzin and compound 16 have also been shown to be selective for the hCNT3 transporter as compared with the hENT1 transporter. Compound 16 can serve as a new lead which after further modi. cations could yield selective and potent hCNT3 inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.