13-(1-acetoxy-1-methylethyl)-7-oxopodocarpe-8,11,13-triene-15-carboxylic acid methyl ester | 53655-46-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 13-(1-acetoxy-1-methylethyl)-7-oxopodocarpe-8,11,13-triene-15-carboxylic acid methyl ester
• 英文别名: methyl 7-keto-15-acetoxydehydroabietate；methyl 13-(1-acetoxy-1-methylethyl)-7-oxopodocarpe-8,11,13-trien-15-oate；15-acetoxy-7-oxo-abieta-8,11,13-trien-18-oic acid methyl ester；15-Acetoxy-7-oxo-abieta-8,11,13-trien-18-saeure-methylester；methyl (1R,4aS,10aR)-7-(2-acetyloxypropan-2-yl)-1,4a-dimethyl-9-oxo-3,4,10,10a-tetrahydro-2H-phenanthrene-1-carboxylate
• CAS: 53655-46-2
• 化学式: C₂₃H₃₀O₅
• 分子量: 386.488
• InChiKey: CFDCDPLGCRQYIE-UEVCKROQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  13-(1-acetoxy-1-methylethyl)-7-oxopodocarpe-8,11,13-triene-15-carboxylic acid methyl ester 在 palladium on activated charcoal 作用下， 生成 methyl 7-keto-15(16)-dehydrodehydroabietate
  参考文献：
  名称：

  1, 2, 3, 4, 4a, 9, 10, 10a- octahydro-9-hydroxy-1-hydroxymethyl-7-isopropenyl-1, 4a-dimethylphenanthrene

  摘要：

  公开号：

  US02750365A1
• 作为产物：
  描述：

  脱氢松香酸 在 chromium(VI) oxide 、 硫酸 、 溶剂黄146 作用下， 反应 27.5h， 生成 13-(1-acetoxy-1-methylethyl)-7-oxopodocarpe-8,11,13-triene-15-carboxylic acid methyl ester
  参考文献：
  名称：

  Design, synthesis, and BK channel-opening activity of hexahydrodibenzazepinone derivatives

  摘要：

  In order to explore new scaffolds for large-conductance Ca2+ -activated K+ channel (BK channel) openers, we carried out molecular design and synthesis on the basis of the following two concepts: (1) introduction of a heteroatom into the dehydroabietic acid (BK channel opener) skeleton would allow easier introduction of substituents. (2) Because of the fourfold symmetrical structure of BK channels, dimeric compounds in which two pharmacophores are linked through a tether are expected to have a greater binding probability to the channels, resulting in increased channel-opening activity. Herein, we explore the usefulness of the hexahydrodibenzazepinone structure as a new scaffold for BK channel openers. The synthesized monomer compounds of hexahydrodibenzazepinone derivatives, which can be derived from dehydroabietic acid, were subjected to electrophysiological patch-clamp studies, followed by Magnus contraction-relaxation assay using rabbit urinary bladder smooth muscle strips to assess overall activities. Dimeric compounds were designed by linking the monomeric hexahydrodibenzazepinone derivatives through a diacetylenebenzene tether, and their channel-opening activities were evaluated by electrophysiological methods. Finally, we concluded that the critical structure for BK channel-opening activity is the hexahydrodibenzazepin one monomer substituted with a phenyl-bearing alkynyl substituent on the lactam amide. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.042

文献信息

• Preparation of Potential Anti-inflammatory Agents from Dehydroabietic Acid
  作者：Wen-Shyong Li、James D. McChesney

  DOI：10.1002/jps.2600810711

  日期：1992.7

  ehydroabietate (29), 16-nor-16-carboxydehydroabietic acid (30), 16-nor-16-carboxydehydroabietinol (31), 7-keto-16-nor-16-carboxydehydroabietic acid (32), methyl 7-hydroxy-16-nor-16-carboxydehydroabietate (33), and 7-hydroxy-16-nor-16-carboxydehydroabietic acid (34) were prepared from dehydroabietic acid. Only 22 and 32 had weak anti-inflammatory activity.

  16-nor-16-羧基脱氢松香酸甲酯（22），16-nor-16-羧基脱氢松香醇乙酸酯（23），7-酮16-nor-16-nor-16-羧基脱氢松香酸甲酯（29），16-nor-16-羧基脱氢松香酸（30） ），16-nor-16-羧基脱氢松香醇（31），7-酮-16-nor-16-羧基脱氢松香酸（32），7-羟基-16-nor-16-羧基脱氢松香酸甲酯（33）和7-羟基-由脱氢松香酸制备16-nor-16-羧基脱氢松香酸（34）。只有22和32的抗炎活性较弱。
• Synthesis and structural characterisation of ring B oxidised derivatives of dehydroabietic acid
  作者：Silvia M. C. S. Monteiro、Armando J. D. Silvestre、Artur M. S. Silva、Jose′ A. S. Cavaleiro、Vitor Fe′lix、Michael G. B. Drew

  DOI：10.1039/b103737b

  日期：——

  The synthesis and structural characterisation of some new derivatives of dehydroabietic acid, oxidised in the 6 and 7 positions of ring B, are described. Other known derivatives were exhaustively characterised for the first time and the previous NMR assignments for three compounds are corrected.

  描述了一些新的脱氢松香酸衍生物的合成和结构表征，这些衍生物在环B的6和7位被氧化。首次对其他已知衍生物进行了详尽的表征，并更正了先前对三种化合物的NMR指认。
• GIGANTE, BARBARA;MARCELO-CURTO, M. JOAO;LOBO, ANA M.;PRABHAKAR, SUNDARESA+, J. NATUR. PROD., 52,(1989) N, C. 85-94
  作者：GIGANTE, BARBARA、MARCELO-CURTO, M. JOAO、LOBO, ANA M.、PRABHAKAR, SUNDARESA+

  DOI：——

  日期：——
• GUPTA, K. K.;TANEJA, S. C.;DHAR, K. L., INDIAN J. CHEM. B , 28,(1989) N, C. 136-140
  作者：GUPTA, K. K.、TANEJA, S. C.、DHAR, K. L.

  DOI：——

  日期：——
• 1, 2, 3, 4, 4a, 9, 10, 10a- octahydro-9-hydroxy-1-hydroxymethyl-7-isopropenyl-1, 4a-dimethylphenanthrene
  申请人：HERCULES POWDER CO LTD

  公开号：US02750365A1

  公开（公告）日：1956-06-12