methyl 14-bromodehydroabietate | 222317-39-7

• 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: methyl 14-bromodehydroabietate
• 英文别名: methyl (1R,4aS,10aR)-8-bromo-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate
• CAS: 222317-39-7
• 化学式: C₂₁H₂₉BrO₂
• 分子量: 393.364
• InChiKey: SBHUJNUUWBYESB-DUXKGJEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 14-bromodehydroabietate 在 lithium aluminium tetrahydride 作用下， 以18%的产率得到
  参考文献：
  名称：

  Dehydroabietic acid derivatives as a novel scaffold for large-Conductance calcium-Activated K+ channel openers

  摘要：

  We found that the dehydroabietic acid structure is a new scaffold for chemical modulators of large-conductance calcium-activated K+ channels (BK channels). Structure-activity relationship (SAR) studies of the dehydroabietic acid derivatives and related non-aromatic compounds such as pimaric acid revealed the importance of the carboxyl functionality and an appropriate hydrophobic moiety of the molecules for BK channel-opening ability. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.072
• 作为产物：
  描述：

  脱氢松香酸 在 N-溴代丁二酰亚胺(NBS) 、 Montmorillonite K 10 作用下， 以 甲醇 、 乙腈 、 苯 为溶剂， 生成 methyl 14-bromodehydroabietate
  参考文献：
  名称：

  Dehydroabietic acid derivatives as a novel scaffold for large-Conductance calcium-Activated K+ channel openers

  摘要：

  We found that the dehydroabietic acid structure is a new scaffold for chemical modulators of large-conductance calcium-activated K+ channels (BK channels). Structure-activity relationship (SAR) studies of the dehydroabietic acid derivatives and related non-aromatic compounds such as pimaric acid revealed the importance of the carboxyl functionality and an appropriate hydrophobic moiety of the molecules for BK channel-opening ability. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.072

文献信息

• Design, synthesis, and characterization of BK channel openers based on oximation of abietane diterpene derivatives
  作者：Yong-Mei Cui、Eriko Yasutomi、Yuko Otani、Katsutoshi Ido、Takashi Yoshinaga、Kohei Sawada、Tomohiko Ohwada

  DOI：10.1016/j.bmc.2010.09.072

  日期：2010.12

  ether derivatives at the benzylic position of unsubstituted, dichloro, trichloro, and monobromo derivatives of the aromatic C-ring of dehydroabietic acid and podocarpic acid were synthesized and evaluated as BK channel openers in an assay system of CHO-K1 cells expressing hBKα channels. Detailed SAR analysis showed that the oximation was particularly effective in the cases of dehydroabietic acid derivatives

  合成了脱氢松香酸和罗汉果酸的芳香C环的未取代，二氯，三氯和一溴衍生物的苄基位置上的肟醚衍生物，并在表达hBKα通道的CHO-K1细胞分析系统中将其作为BK通道开放剂进行评估。详细的SAR分析表明，在脱氢松香酸衍生物的情况下，肟化作用特别有效，并且这些肟衍生物中的一些表现出比标准化合物NS1619更有效的BK通道活性。本研究为开发有效的BK通道开放剂提供了新的结构基础。
• Microporous Solids for the Selective Bromination of a Diterpene Resin Acid
  作者：M. Alexandra Esteves、Nama Narender、Bárbara Gigante、M. J. Marcelo-curto、Fernanda Alvarez

  DOI：10.1080/00397919908085767

  日期：1999.1

  The liquid-phase bromination of methyl dehydroabietate with bromine or NBS in the presence of microporous solids has been investigated The reactions were fast and easily performed and the highest yield and regioselectivity were obtained with the system bromine/montmorillonite K10.