2-(4-methylcyclohex-3-enyl)propan-2-yl 2-(2,3-dihydroxypropylthio)acetate

• 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: 2-(4-methylcyclohex-3-enyl)propan-2-yl 2-(2,3-dihydroxypropylthio)acetate
• 英文别名: 2-(4-Methylcyclohex-3-en-1-yl)propan-2-yl 2-(2,3-dihydroxypropylsulfanyl)acetate；2-(4-methylcyclohex-3-en-1-yl)propan-2-yl 2-(2,3-dihydroxypropylsulfanyl)acetate
• 化学式: C₁₅H₂₆O₄S
• 分子量: 302.435
• InChiKey: RVDWSMMLQWPSQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  92.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  松油醇 在 吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 19.0h， 生成 2-(4-methylcyclohex-3-enyl)propan-2-yl 2-(2,3-dihydroxypropylthio)acetate
  参考文献：
  名称：

  Discovery of a novel series of α-terpineol derivatives as promising anti-asthmatic agents: Their design, synthesis, and biological evaluation

  摘要：

  A series of novel alpha-terpineol derivatives were designed and synthesized through structural derivatization of the tertiary hydroxyl moiety or reduction of the double bond. Of the resulting compounds, eight compounds enhanced relaxation of airway smooth muscle (ASM) compared to the alpha-terpineol precursor, and four compounds (4a, 4d, 4e, and 4i)were superior or comparable to aminophylline at a concentration of 0.75 mmol/L. Assays for 3'-5'-Cyclic adenosine monophpsphate (cAMP) activation revealed that some representative alpha-terpineol derivatives in this series were capable of upregulating the level of cAMP in ASM cells. Further in vivo investigation using the asthmatic rat model, illustrated that treatment with the compounds 4a and 4e resulted in significantly lowered lung resistance (RL) and enhanced dynamic lung compliance (Cldyn), two important parameters for lung fuction. Moreover, treatment with 4e down regulated the levels of both IL-4 and IL-17. Due to its several favorable physiological functions, including ASM relaxation activity, cAMP activation capability, and in vivo anti-asthmatic efficacy, 4e is a promising remedy for bronchial asthma, meriting extensive development. (C) 2017 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2017.07.068

文献信息

• Discovery of a novel series of α-terpineol derivatives as promising anti-asthmatic agents: Their design, synthesis, and biological evaluation
  作者：Wanping Zhu、Xia Liu、Yuji Wang、Yeling Tong、Yongzhou Hu

  DOI：10.1016/j.ejmech.2017.07.068

  日期：2018.1

  A series of novel alpha-terpineol derivatives were designed and synthesized through structural derivatization of the tertiary hydroxyl moiety or reduction of the double bond. Of the resulting compounds, eight compounds enhanced relaxation of airway smooth muscle (ASM) compared to the alpha-terpineol precursor, and four compounds (4a, 4d, 4e, and 4i)were superior or comparable to aminophylline at a concentration of 0.75 mmol/L. Assays for 3'-5'-Cyclic adenosine monophpsphate (cAMP) activation revealed that some representative alpha-terpineol derivatives in this series were capable of upregulating the level of cAMP in ASM cells. Further in vivo investigation using the asthmatic rat model, illustrated that treatment with the compounds 4a and 4e resulted in significantly lowered lung resistance (RL) and enhanced dynamic lung compliance (Cldyn), two important parameters for lung fuction. Moreover, treatment with 4e down regulated the levels of both IL-4 and IL-17. Due to its several favorable physiological functions, including ASM relaxation activity, cAMP activation capability, and in vivo anti-asthmatic efficacy, 4e is a promising remedy for bronchial asthma, meriting extensive development. (C) 2017 Published by Elsevier Masson SAS.