(1R,4aS,E)-6-bromo-7-isopropyl-1,4a-dimethyl-9-(2-(thiophene-3-carboxamido)ethoxyimino)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid

• 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: (1R,4aS,E)-6-bromo-7-isopropyl-1,4a-dimethyl-9-(2-(thiophene-3-carboxamido)ethoxyimino)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
• 英文别名: (1R,4aS,9E,10aR)-6-bromo-1,4a-dimethyl-7-propan-2-yl-9-[2-(thiophene-3-carbonylamino)ethoxyimino]-3,4,10,10a-tetrahydro-2H-phenanthrene-1-carboxylic acid
• 化学式: C₂₇H₃₃BrN₂O₄S
• 分子量: 561.54
• InChiKey: JGYMVGDMUIQVOM-QWGYIVJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (1R,4aS,E)-methyl 6-bromo-7-isopropyl-1,4a-dimethyl-9-(2-(thiophene-3-carboxamido)ethoxyimino)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以63%的产率得到(1R,4aS,E)-6-bromo-7-isopropyl-1,4a-dimethyl-9-(2-(thiophene-3-carboxamido)ethoxyimino)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid
  参考文献：
  名称：

  The synthesis and BK channel-opening activity of N- acylaminoalkyloxime derivatives of dehydroabietic acid

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2015.12.038

文献信息

• 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.