1-methylpiperidin-4-yl (4-(methylsulfinyl)butyl)carbamodithioate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-methylpiperidin-4-yl (4-(methylsulfinyl)butyl)carbamodithioate
• 英文别名: (1-methylpiperidin-4-yl) N-(4-methylsulfinylbutyl)carbamodithioate
• 化学式: C₁₂H₂₄N₂OS₃
• 分子量: 308.533
• InChiKey: LLVLFRDNRZSECR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-甲基-4-巯基哌啶 、 莱菔硫烷 以 四氢呋喃 为溶剂， 反应 2.0h， 以39%的产率得到1-methylpiperidin-4-yl (4-(methylsulfinyl)butyl)carbamodithioate
  参考文献：
  名称：

  Discovery of a crystalline sulforaphane analog with good solid-state stability and engagement of the Nrf2 pathway in vitro and in vivo

  摘要：

  The antioxidant natural product sulforaphane (SFN) is an oil with poor aqueous and thermal stability. Recent work with SFN has sought to optimize methods of formulation for oral and topical administration. Herein we report the design of new analogs of SFN with the goal of improving stability and drug-like properties. Lead compounds were selected based on potency in a cellular screen and physicochemical properties. Among these, 12 had good aqueous solubility, permeability and long-term solid-state stability at 23 degrees C. Compound 12 also displayed comparable or better efficacy in cellular assays relative to SFN and had in vivo activity in a mouse cigarette smoke challenge model of acute oxidative stress.

  DOI：

  10.1016/j.bmc.2018.12.026

文献信息

• Discovery of a crystalline sulforaphane analog with good solid-state stability and engagement of the Nrf2 pathway in vitro and in vivo
  作者：Jeffrey Boehm、Roderick Davis、Claudia E. Murar、Tindy Li、Brent McCleland、Shuping Dong、Hongxing Yan、Jeffrey Kerns、Christopher J. Moody、Anthony J. Wilson、Alan P. Graves、Mary Mentzer、Hongwei Qi、John Yonchuk、Jen-Pyng Kou、Joseph Foley、Yolanda Sanchez、Patricia L. Podolin、Brian Bolognese、Catherine Booth-Genthe、Marc Galop、Lawrence Wolfe、Robin Carr、James F. Callahan

  DOI：10.1016/j.bmc.2018.12.026

  日期：2019.2

  The antioxidant natural product sulforaphane (SFN) is an oil with poor aqueous and thermal stability. Recent work with SFN has sought to optimize methods of formulation for oral and topical administration. Herein we report the design of new analogs of SFN with the goal of improving stability and drug-like properties. Lead compounds were selected based on potency in a cellular screen and physicochemical properties. Among these, 12 had good aqueous solubility, permeability and long-term solid-state stability at 23 degrees C. Compound 12 also displayed comparable or better efficacy in cellular assays relative to SFN and had in vivo activity in a mouse cigarette smoke challenge model of acute oxidative stress.