肉豆蔻烯酮A | 26089-54-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 肉豆蔻烯酮A
• 英文名称: 2',4',6'-trihydroxyacetophenone 2'-O-β-D-glucopyranoside
• 英文别名: 2,4,6-trihydroxyacetophenone 2-O-β-D-glucopyranoside；2,4,6-trihydroxyacetophenone-2-O-β-D-glucopyranoside；4',6'-dihydroxy-2'-O-β-D-glucopyranosyl-acetophenone；2,4,6-trihydroxyacetophenone 2-O-β-D-glucoside；2,4,6-trihydroxyacetophenone-2-O-b-D-glucopyranoside；myrciaphenone A；1-[2,4-dihydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethanone
• CAS: 26089-54-3
• 化学式: C₁₄H₁₈O₉
• 分子量: 330.292
• InChiKey: GFKQVLKFPJGJEP-RGCYKPLRSA-N

物化性质

• 熔点：
  201–203°C
• 沸点：
  625.8±55.0 °C(Predicted)
• 密度：
  1.611±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

制备方法与用途

myrciaphenone A 是一种苯乙酮糖苷。

反应信息

• 作为产物：
  描述：

  (2-acetyl-5-benzoyloxy-3-hydroxy-phenyl)-(tetra-O-acetyl-β-D-glucopyranoside) 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以12%的产率得到肉豆蔻烯酮A
  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

• Exploring the aglycon promiscuity of a new glycosyltransferase from Pueraria lobata
  作者：Lili Sun、Dawei Chen、Ridao Chen、Kebo Xie、Jimei Liu、Lin Yang、Jungui Dai

  DOI：10.1016/j.tetlet.2016.02.088

  日期：2016.3

  Enzymatic glycosylation catalyzed by glycosyltransferases has great potential for creating bioactive glycosylated small-molecule compounds. Here, we highlight the aglycon promiscuity of a new glycosyltransferase (PlGT7) from Pueraria lobata. PlGT7 exhibited the capability to glycosylate 26 structurally diverse drug-like scaffolds and simple phenolics with UDP-glucose to form O-, S-, and N-glycosides

  由糖基转移酶催化的酶促糖基化具有产生生物活性糖基化小分子化合物的巨大潜力。在这里，我们着重介绍了葛根中一种新的糖基转移酶（PlGT7）的糖苷配基混杂。PlGT7表现出用UDP-葡萄糖糖基化26种结构多样的药物样支架和简单酚类化合物以形成O-，S-和N-糖苷的能力。还利用PlGT7的可逆性及其底物​​柔性来利用简单的糖供体产生生物活性的糖苷。这些研究表明在药物开发中酶促方法对具有生物活性的天然和非天然产物进行糖基化的巨大潜力。
• 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.