4-(2-Carboxy-6-hydroxy-benzoyl)-3,5-dihydroxy-benzoic acid (3S,4R)-4-(4-hydroxy-benzyl)-pyrrolidin-3-yl ester

• 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-(2-Carboxy-6-hydroxy-benzoyl)-3,5-dihydroxy-benzoic acid (3S,4R)-4-(4-hydroxy-benzyl)-pyrrolidin-3-yl ester
• 英文别名: 2-{[2,6-dihydroxy-4-({[(3S,4R)-4-[(4-hydroxyphenyl)methyl]pyrrolidin-3-yl]oxy}carbonyl)phenyl]carbonyl}-3-hydroxybenzoic acid；2-[2,6-dihydroxy-4-[(3S,4R)-4-[(4-hydroxyphenyl)methyl]pyrrolidin-3-yl]oxycarbonylbenzoyl]-3-hydroxybenzoic acid
• 化学式: C₂₆H₂₃NO₉
• 分子量: 493.47
• InChiKey: MKPSMRQVGPTYRL-QVKFZJNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  174
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  甲醇 、 4-(2-Carboxy-6-hydroxy-benzoyl)-3,5-dihydroxy-benzoic acid (3S,4R)-4-(4-hydroxy-benzyl)-pyrrolidin-3-yl ester 在 氯化亚砜 作用下， 以52%的产率得到(+/-)-anti-3-({3,5-dihydroxy-4-[2-hydroxy-6-(methoxycarbonyl)benzoyl]benzoyl}oxy)-4-(4-hydroxybenzyl)pyrrolidine
  参考文献：
  名称：

  Potent and selective PKC inhibitory 5-membered ring analogs of balanol with replacement of the carboxamide moiety

  摘要：

  Balanol ((-)-1) is a potent protein kinase inhibitory natural product isolated from the fungus Verticillium balanoides. The lack of cellular activity and protein kinase C selectivity in balanol has prompted a search for analogs that incorporate these properties, This paper describes the synthesis and biological activity of such compounds with substitution similar to balanol, but with a single atom bridge in place of the carboxamide moiety. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00311-3
• 作为产物：
  描述：

  1-benzyl-3-[(4-phenylmethoxyphenyl)methylidene]pyrrolidine-2,4-dione 在 palladium dihydroxide 、 镍 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 正丁基锂 、 氢气 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(2-Carboxy-6-hydroxy-benzoyl)-3,5-dihydroxy-benzoic acid (3S,4R)-4-(4-hydroxy-benzyl)-pyrrolidin-3-yl ester
  参考文献：
  名称：

  Potent and selective PKC inhibitory 5-membered ring analogs of balanol with replacement of the carboxamide moiety

  摘要：

  Balanol ((-)-1) is a potent protein kinase inhibitory natural product isolated from the fungus Verticillium balanoides. The lack of cellular activity and protein kinase C selectivity in balanol has prompted a search for analogs that incorporate these properties, This paper describes the synthesis and biological activity of such compounds with substitution similar to balanol, but with a single atom bridge in place of the carboxamide moiety. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00311-3