[(2S)-2-[(2R)-3,4-dibenzyloxy-5-oxo-2H-furan-2-yl]-2-hydroxyethyl] hexadecanoate | 914771-19-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [(2S)-2-[(2R)-3,4-dibenzyloxy-5-oxo-2H-furan-2-yl]-2-hydroxyethyl] hexadecanoate
• 英文别名: [(2S)-2-hydroxy-2-[(2R)-5-oxo-3,4-bis(phenylmethoxy)-2H-furan-2-yl]ethyl] hexadecanoate
• CAS: 914771-19-0
• 化学式: C₃₆H₅₀O₇
• 分子量: 594.789
• InChiKey: IQHFHNJIULBGBL-CQTOTRCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  43
• 可旋转键数：
  24
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2S)-2-[(2R)-3,4-dibenzyloxy-5-oxo-2H-furan-2-yl]-2-hydroxyethyl] hexadecanoate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 L-抗坏血酸棕榈酸酯
  参考文献：
  名称：

  Novel 6-O-acylated vitamin C derivatives as hyaluronidase inhibitors with selectivity for bacterial lyases

  摘要：

  Previously, we identified ascorbic acid 6-O-hexadecanoate as an up to 1500 times more potent inhibitor of bacterial and bovine hyaluronidases than the parent compound, vitamin C, and determined a crystal structure of hyaluronidase from Streptococcus pneumoniae in complex with the inhibitor. As the alkanoyl chain interacts with a hydrophobic patch of the enzyme we synthesized other 6-O-acylated vitamin C derivatives bearing various lipophilic residues and investigated the inhibition of Streptococcus agalactiae strain 4755 hyaluronidase (SagHyal(4755)) and of bovine testicular hyaluronidases (BTH) in a turbidimetric assay. All compounds showed selectivity for the bacterial enzyme. Whereas vitamin C 6-O-hexanoate only weakly inhibited SagHyal(4755), the inhibition of both enzymes increased with the length of the aliphatic chain. In the case of the 6-O-octadecanoate, IC50 values of 0.9 and 39 mu M for SagHyal(4755) and BTH, respectively, were determined. Partial replacement of the aliphatic chain with a phenyl, p-phenylene or p-biphenylyl group resulted in inhibitors with activity in the lower micromolar range, too. The title compounds are among the most potent inhibitors of both enzymes known to date. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.087
• 作为产物：
  描述：

  维生素 C 在 吡啶 、 4-二甲氨基吡啶 、 potassium carbonate 、 溶剂黄146 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(2S)-2-[(2R)-3,4-dibenzyloxy-5-oxo-2H-furan-2-yl]-2-hydroxyethyl] hexadecanoate
  参考文献：
  名称：

  Novel 6-O-acylated vitamin C derivatives as hyaluronidase inhibitors with selectivity for bacterial lyases

  摘要：

  Previously, we identified ascorbic acid 6-O-hexadecanoate as an up to 1500 times more potent inhibitor of bacterial and bovine hyaluronidases than the parent compound, vitamin C, and determined a crystal structure of hyaluronidase from Streptococcus pneumoniae in complex with the inhibitor. As the alkanoyl chain interacts with a hydrophobic patch of the enzyme we synthesized other 6-O-acylated vitamin C derivatives bearing various lipophilic residues and investigated the inhibition of Streptococcus agalactiae strain 4755 hyaluronidase (SagHyal(4755)) and of bovine testicular hyaluronidases (BTH) in a turbidimetric assay. All compounds showed selectivity for the bacterial enzyme. Whereas vitamin C 6-O-hexanoate only weakly inhibited SagHyal(4755), the inhibition of both enzymes increased with the length of the aliphatic chain. In the case of the 6-O-octadecanoate, IC50 values of 0.9 and 39 mu M for SagHyal(4755) and BTH, respectively, were determined. Partial replacement of the aliphatic chain with a phenyl, p-phenylene or p-biphenylyl group resulted in inhibitors with activity in the lower micromolar range, too. The title compounds are among the most potent inhibitors of both enzymes known to date. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.087

文献信息

• ASCORBIC ACID-RELATED COMPOUND AND ANTI-PLANT-VIRUS AGENT
  申请人：Nippon Soda Co., Ltd.

  公开号：EP2902387A1

  公开（公告）日：2015-08-05

  The present invention provides a compound represented by formula (1) (wherein each of X1 and X2 independently represents -OR1, -NR2R3 or -CR4R5R6 or the like, each of R1, R2, R3, R4, R5 and R6 independently represents an unsubstituted or substituent-bearing glycosyl group or an unsubstituted or substituent-bearing C1 to C30 alkyl group or the like, and A represents an unsubstituted or substituent-bearing C1 to C30 alkyl group or the like) or a salt thereof.

  本发明提供一种由式（1）表示的化合物（其中X1和X2中的每一个独立表示-OR1、-NR2R3或-CR4R5R6等，R1、R2、R3、R4、R5和R6中的每一个独立表示未取代或取代基团的糖基或未取代或取代基团的C1至C30烷基基团等，A表示未取代或取代基团的C1至C30烷基基团等）或其盐。
• Novel 6-O-acylated vitamin C derivatives as hyaluronidase inhibitors with selectivity for bacterial lyases
  作者：Martin Spickenreither、Stephan Braun、Günther Bernhardt、Stefan Dove、Armin Buschauer

  DOI：10.1016/j.bmcl.2006.07.087

  日期：2006.10

  Previously, we identified ascorbic acid 6-O-hexadecanoate as an up to 1500 times more potent inhibitor of bacterial and bovine hyaluronidases than the parent compound, vitamin C, and determined a crystal structure of hyaluronidase from Streptococcus pneumoniae in complex with the inhibitor. As the alkanoyl chain interacts with a hydrophobic patch of the enzyme we synthesized other 6-O-acylated vitamin C derivatives bearing various lipophilic residues and investigated the inhibition of Streptococcus agalactiae strain 4755 hyaluronidase (SagHyal(4755)) and of bovine testicular hyaluronidases (BTH) in a turbidimetric assay. All compounds showed selectivity for the bacterial enzyme. Whereas vitamin C 6-O-hexanoate only weakly inhibited SagHyal(4755), the inhibition of both enzymes increased with the length of the aliphatic chain. In the case of the 6-O-octadecanoate, IC50 values of 0.9 and 39 mu M for SagHyal(4755) and BTH, respectively, were determined. Partial replacement of the aliphatic chain with a phenyl, p-phenylene or p-biphenylyl group resulted in inhibitors with activity in the lower micromolar range, too. The title compounds are among the most potent inhibitors of both enzymes known to date. (c) 2006 Elsevier Ltd. All rights reserved.