(+/-)-trans-3-(4-hydroxybenzamido)-4-({4-[2-hydroxy-6-(hydroxycarbonyl)benzoyl]-3,5-dihydroxybenzoyl}oxy)pyrrolidine

• 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: (+/-)-trans-3-(4-hydroxybenzamido)-4-({4-[2-hydroxy-6-(hydroxycarbonyl)benzoyl]-3,5-dihydroxybenzoyl}oxy)pyrrolidine
• 英文别名: 2-{[2,6-dihydroxy-4-({[(3R,4R)-4-[(4-hydroxybenzene)amido]pyrrolidin-3-yl]oxy}carbonyl)phenyl]carbonyl}-3-hydroxybenzoic acid；2-[2,6-dihydroxy-4-[(3R,4R)-4-[(4-hydroxybenzoyl)amino]pyrrolidin-3-yl]oxycarbonylbenzoyl]-3-hydroxybenzoic acid
• 化学式: C₂₆H₂₂N₂O₁₀
• 分子量: 522.468
• InChiKey: YIZRPXUMLQCIMQ-OXQOHEQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  203
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  氯甲酸甲酯 、 (+/-)-trans-3-(4-hydroxybenzamido)-4-({4-[2-hydroxy-6-(hydroxycarbonyl)benzoyl]-3,5-dihydroxybenzoyl}oxy)pyrrolidine 在 吡啶 作用下， 以9%的产率得到(3R,4R)-3-[4-(2-Carboxy-6-hydroxy-benzoyl)-3,5-dihydroxy-benzoyloxy]-4-(4-hydroxy-benzoylamino)-pyrrolidine-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and Protein Kinase C Inhibitory Activities of Balanol Analogs with Replacement of the Perhydroazepine Moiety

  摘要：

  Balanol is a potent protein kinase C (PKC) inhibitor that is structurally composed of a benzophenone diacid, a 4-hydroxybenzamide, and a perhydroazepine ring. A number of balanol analogs in which the perhydroazepine moiety is replaced have been synthesized and their biological activities evaluated against both PKC and cAMP-dependent kinase (PKA). The results suggested that the activity and the isozyme/kinase selectivity of these compounds are largely related to the conformation about this nonaromatic structural element of the molecules.

  DOI：

  10.1021/jm960497g
• 作为产物：
  描述：

  在 palladium dihydroxide 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 生成 (+/-)-trans-3-(4-hydroxybenzamido)-4-({4-[2-hydroxy-6-(hydroxycarbonyl)benzoyl]-3,5-dihydroxybenzoyl}oxy)pyrrolidine
  参考文献：
  名称：

  Synthesis and Protein Kinase C Inhibitory Activities of Balanol Analogs with Replacement of the Perhydroazepine Moiety

  摘要：

  Balanol is a potent protein kinase C (PKC) inhibitor that is structurally composed of a benzophenone diacid, a 4-hydroxybenzamide, and a perhydroazepine ring. A number of balanol analogs in which the perhydroazepine moiety is replaced have been synthesized and their biological activities evaluated against both PKC and cAMP-dependent kinase (PKA). The results suggested that the activity and the isozyme/kinase selectivity of these compounds are largely related to the conformation about this nonaromatic structural element of the molecules.

  DOI：

  10.1021/jm960497g

文献信息

• Labeled pkg-1-alpha-binding compounds and their use in imaging and quantifying pain
  申请人：THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK

  公开号：US20160243266A1

  公开（公告）日：2016-08-25

  The present invention relates to the use of compounds that selectively bind to activated protein kinase G 1 alpha for imaging the anatomic basis for chronic pain. Such imaging may also be used to objectively quantify chronic pain.
• Synthesis and Protein Kinase C Inhibitory Activities of Balanol Analogs with Replacement of the Perhydroazepine Moiety
  作者：Yen-Shi Lai、José S. Mendoza、G. Erik Jagdmann、David S. Menaldino、Christopher K. Biggers、Julia M. Heerding、Joseph W. Wilson、Steven E. Hall、Jack B. Jiang、William P. Janzen、Lawrence M. Ballas

  DOI：10.1021/jm960497g

  日期：1997.1.1

  Balanol is a potent protein kinase C (PKC) inhibitor that is structurally composed of a benzophenone diacid, a 4-hydroxybenzamide, and a perhydroazepine ring. A number of balanol analogs in which the perhydroazepine moiety is replaced have been synthesized and their biological activities evaluated against both PKC and cAMP-dependent kinase (PKA). The results suggested that the activity and the isozyme/kinase selectivity of these compounds are largely related to the conformation about this nonaromatic structural element of the molecules.