4-C-(2-benzyloxyethyl)-5-O-tetradecanoyl-2,3-dideoxy-D-glycero-pentono-1,4-lactone | 688329-92-2

• 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: 4-C-(2-benzyloxyethyl)-5-O-tetradecanoyl-2,3-dideoxy-D-glycero-pentono-1,4-lactone
• CAS: 688329-92-2
• 化学式: C₂₈H₄₄O₅
• 分子量: 460.654
• InChiKey: WWNVKBVECGPWKI-MUUNZHRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.91
• 重原子数：
  33.0
• 可旋转键数：
  19.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-C-(2-benzyloxyethyl)-5-O-tetradecanoyl-2,3-dideoxy-D-glycero-pentono-1,4-lactone 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以92%的产率得到Tetradecanoic acid (R)-2-(2-hydroxy-ethyl)-5-oxo-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Conformationally constrained diacylglycerol (DAG) analogs: 4-C-hydroxyethyl-5-O-acyl-2,3-dideoxy-D-glyceropentono-1,4-lactone analogs as protein kinase C (PKC) ligands

  摘要：

  The (R)-DAG-lactones (5 and 7E/Z) are conformationally constrained diacylglycerol (DAG) analogs with high potency as protein kinase C (PKC) ligands. Here, we have prepared and characterized their one-carbon lengthened analogs (6 and 8E/Z). The target compounds were synthesized from 1,2-O-isopropylidene D-xylose through a key intermediate, 4-C-hydroxyethyl-2,3-dideoxy-D-glyceropentono-1,4-lactone (13); they were evaluated as competitive ligands to displace bound [H-3]phorbol 12,13-dibutyrate (PDBU) from a recombinant single isozyme (PKC-alpha). The binding affinities of the synthesized compounds were K-i = 2.623 muM for 6, K-i = 1.080 muM for 8Z and K-i = 0.92 muM for 8E, which were ca. 27, 90, and 70 times less potent than the corresponding parent compounds (5, 7Z and 7E). Molecular modeling indicated that the reduced binding affinity of the representative 3-alkylidene lactone 8Z, as compared to 7Z, may be explained by its poor fit in the sn-1 binding mode as well as by its entropic loss due to the relatively flexible hydroxyethyl group. (C) 2003 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.10.006
• 作为产物：
  描述：

  6-O-benzyl-4-C-tert-butyldimethylsilyloxymethyl-2,3-dideoxy-D-threo-hexono-1,4-lactone 在 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 6.5h， 生成 4-C-(2-benzyloxyethyl)-5-O-tetradecanoyl-2,3-dideoxy-D-glycero-pentono-1,4-lactone
  参考文献：
  名称：

  Conformationally constrained diacylglycerol (DAG) analogs: 4-C-hydroxyethyl-5-O-acyl-2,3-dideoxy-D-glyceropentono-1,4-lactone analogs as protein kinase C (PKC) ligands

  摘要：

  The (R)-DAG-lactones (5 and 7E/Z) are conformationally constrained diacylglycerol (DAG) analogs with high potency as protein kinase C (PKC) ligands. Here, we have prepared and characterized their one-carbon lengthened analogs (6 and 8E/Z). The target compounds were synthesized from 1,2-O-isopropylidene D-xylose through a key intermediate, 4-C-hydroxyethyl-2,3-dideoxy-D-glyceropentono-1,4-lactone (13); they were evaluated as competitive ligands to displace bound [H-3]phorbol 12,13-dibutyrate (PDBU) from a recombinant single isozyme (PKC-alpha). The binding affinities of the synthesized compounds were K-i = 2.623 muM for 6, K-i = 1.080 muM for 8Z and K-i = 0.92 muM for 8E, which were ca. 27, 90, and 70 times less potent than the corresponding parent compounds (5, 7Z and 7E). Molecular modeling indicated that the reduced binding affinity of the representative 3-alkylidene lactone 8Z, as compared to 7Z, may be explained by its poor fit in the sn-1 binding mode as well as by its entropic loss due to the relatively flexible hydroxyethyl group. (C) 2003 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.10.006