(E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-4-(3,4-dimethoxyphenyl)but-3-en-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-4-(3,4-dimethoxyphenyl)but-3-en-2-one
• 英文别名: [(2R,3S,4R,5S,6S)-3,4,5-triacetyloxy-6-[(E)-4-(3,4-dimethoxyphenyl)-2-oxobut-3-enyl]oxan-2-yl]methyl acetate
• 化学式: C₂₆H₃₂O₁₂
• 分子量: 536.533
• InChiKey: CQWULWJFLMNGEK-QQAJUQDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-4-(3,4-dimethoxyphenyl)but-3-en-2-one 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以73%的产率得到(3E)-1-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4-(3,4-dimethoxyphenyl)but-3-en-2-one oxime
  参考文献：
  名称：

  Synthesis of C -glycosylmethyl isoxazoles via aerobic oxidation of ketoximes catalyzed by TEMPO

  摘要：

  An efficient and high yielding synthesis of C-glycosylmethyl isoxazoles by oxidation of ketoximes in the presence of oxygen and mediated by TEMPO is described. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.03.005
• 作为产物：
  描述：

  β-半乳糖苷酶 在 四氢吡咯 、 吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 (E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-4-(3,4-dimethoxyphenyl)but-3-en-2-one
  参考文献：
  名称：

  Attachment of carbohydrates to methoxyaryl moieties leads to highly selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII

  摘要：

  The transmembrane isoforms of carbonic anhydrase (hCA IX and XII) have been shown to be linked to carcinogenesis and their inhibition to arrest primary tumor and metastases growth. In this paper, we present a new class of C-glycosides incorporating the methoxyaryl moiety, that was designed to selectively target and inhibit the extracellular domains of the cancer-relevant CA isozymes. The glycosides have been prepared by aldol reaction of glycosyl ketones with the appropriate aromatic aldehydes. We also present the inhibition profile of our new glycomimetics, against four isozymes of carbonic anhydrase comprising hCAs I and II (cytosolic, ubiquitous isozymes) and hCAs IX and XII (tumor associated isozymes). In this study, per-O-acetylated glycoside 4, 6 and deprotected compounds 7, 9, 10 and 12 were identified as potent and highly selective inhibitors of hCA IX and XII. These results confirm that attaching carbohydrate moieties to CA methoxyaryl pharmacophore improves and enhances its inhibitory activity. These CA inhibitors have developmental potential to selectively target cancer cells, leading to cell death.

  DOI：

  10.1016/j.bmc.2014.07.052

文献信息

• Attachment of carbohydrates to methoxyaryl moieties leads to highly selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII
  作者：Leonardo E. Riafrecha、Oscar M. Rodríguez、Daniela Vullo、Claudiu T. Supuran、Pedro A. Colinas

  DOI：10.1016/j.bmc.2014.07.052

  日期：2014.10

  The transmembrane isoforms of carbonic anhydrase (hCA IX and XII) have been shown to be linked to carcinogenesis and their inhibition to arrest primary tumor and metastases growth. In this paper, we present a new class of C-glycosides incorporating the methoxyaryl moiety, that was designed to selectively target and inhibit the extracellular domains of the cancer-relevant CA isozymes. The glycosides have been prepared by aldol reaction of glycosyl ketones with the appropriate aromatic aldehydes. We also present the inhibition profile of our new glycomimetics, against four isozymes of carbonic anhydrase comprising hCAs I and II (cytosolic, ubiquitous isozymes) and hCAs IX and XII (tumor associated isozymes). In this study, per-O-acetylated glycoside 4, 6 and deprotected compounds 7, 9, 10 and 12 were identified as potent and highly selective inhibitors of hCA IX and XII. These results confirm that attaching carbohydrate moieties to CA methoxyaryl pharmacophore improves and enhances its inhibitory activity. These CA inhibitors have developmental potential to selectively target cancer cells, leading to cell death.
• Synthesis of C -glycosylmethyl isoxazoles via aerobic oxidation of ketoximes catalyzed by TEMPO
  作者：Helberth Llantén、Sebastian Barata-Vallejo、Al Postigo、Pedro A. Colinas

  DOI：10.1016/j.tetlet.2017.03.005

  日期：2017.4

  An efficient and high yielding synthesis of C-glycosylmethyl isoxazoles by oxidation of ketoximes in the presence of oxygen and mediated by TEMPO is described. (C) 2017 Elsevier Ltd. All rights reserved.