methyl 12-bromo-7-oxodehydrodeisopropylabietate | 18492-70-1

• 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 12-bromo-7-oxodehydrodeisopropylabietate
• 英文别名: (1R,4aS,10aR)-methyl 6-bromo-1,2,3,4,4a,9,10,10aoctahydro-7-isopropyl-1,4a-dimethyl-9-oxophenanthrene-1-carboxylate；methyl (1R,4aS,10aR)-6-bromo-1,4a-dimethyl-9-oxo-7-propan-2-yl-3,4,10,10a-tetrahydro-2H-phenanthrene-1-carboxylate
• CAS: 18492-70-1
• 化学式: C₂₁H₂₇BrO₃
• 分子量: 407.348
• InChiKey: OYAKFDBFYSBGBP-HMXCVIKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 12-bromo-7-oxodehydrodeisopropylabietate 在 potassium tert-butylate 、 盐酸 作用下， 以 二甲基亚砜 、 水 为溶剂， 反应 0.67h， 以15%的产率得到(1R,4aS,10aR)-6-bromo-1,2,3,4,4a,9,10,10a-octahydro-7-isopropyl-1,4a-dimethyl-9-oxophenanthrene-1-carboxylic acid
  参考文献：
  名称：

  基于己二烯二萜衍生物肟化的BK通道开放剂的设计，合成和表征

  摘要：

  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。

  DOI：

  10.1016/j.bmc.2010.09.072
• 作为产物：
  描述：

  脱氢枞酸甲酯 在 chromium(VI) oxide 、 N-溴代丁二酰亚胺(NBS) 作用下， 生成 methyl 12-bromo-7-oxodehydrodeisopropylabietate
  参考文献：
  名称：

  Synthesis and metal ion binding activity of methyl 12-amino-13-nitro-7-oxo dehydrodeisopropylabietate derivatives

  摘要：

  Starting from dehydrobaietic acid with the analogous structure of carnosic acid, the intermediate methyl 12-bromo-13-nitro-7-oxo dehydrodeisopropylabietate was synthesized through methylation, bromination, carbonylation, and nitration. Subsequently, the coupling of methyl 12-bromo-13-nitro-7-oxo dehydrodeisopropylabietate with aliphatic or aromatic primary amine by Ullmann condensation reaction produced a series of methyl 12-imino-13-nitro-7-oxo dehydrodeisopropylabietate derivatives. In order to probe their antioxidant effects through metal ion chelation mechanism, the metal ion binding abilities on Cu2+ and Fe2+ of these compounds were studied using fluorescence quenching method. The results indicated that each compound showed obvious chelation activity with the binding constants (K (A)) of the 10(2) L mol(-1) order of magnitude, which implied its potential pharmacology application as antioxidant by the inhibition of Feton reaction through chelation with Cu2+ and Fe2+.

  DOI：

  10.1007/s00044-011-9766-2

文献信息

• 7-肟醚酰胺脱氢枞酸化合物及其合成方法
  申请人：上海大学

  公开号：CN105175278B

  公开（公告）日：2017-06-23

  本发明涉及一种7‑肟醚酰胺脱氢枞酸化合物及其合成方法。该化合物的结构式为：其中，R1为 H、Br；R2为C1~C6直链或支链或环状烷基、芳香系取代基、杂环系取代基；本发明涉及一类高效、简洁的7‑肟醚酰胺脱氢枞酸衍生物的制备方法。该化合物及其药学可接受的盐、水合物、溶剂化物、晶体形式、非对映异构体、前药或混合物等，特别用于治疗与大电导钙激活钾离子通道相关的病症。
• The synthesis and BK channel-opening activity of N- acylaminoalkyloxime derivatives of dehydroabietic acid
  作者：Yong-Mei Cui、Xin-Lan Liu、Wen-Ming Zhang、Hai-Xia Lin、Tomohiko Ohwada、Katsutoshi Ido、Kohei Sawada

  DOI：10.1016/j.bmcl.2015.12.038

  日期：2016.1

  A series of N-acylaminoalkyloxime derivatives of dehydroabietic acid were synthesized and evaluated for BK channel-opening activities in an assay system of CHO-K1 cells expressing hBK alpha channels. The structure-activity relationship study revealed that a non-covalent interaction between the S atom of the 2-thiophene and the carbonyl O atom may contribute to conformation restriction for interaction with the ion channel. This research could guide the design and synthesis of novel abietane-based BK channel opener. (C) 2015 Elsevier Ltd. All rights reserved.