1-allyl-2-(3-(allylthio)prop-1-en-1-yl)disulfane | 928838-16-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 烯丙基硫化合物
• 英文名称: 1-allyl-2-(3-(allylthio)prop-1-en-1-yl)disulfane
• 英文别名: 4,5,9-Trithiadodeca-1,6,11-triene；1-(prop-2-enyldisulfanyl)-3-prop-2-enylsulfanylprop-1-ene
• CAS: 928838-16-8
• 化学式: C₉H₁₄S₃
• 分子量: 218.408
• InChiKey: GLTDVXBMQVCMBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-allyl-2-(3-(allylthio)prop-1-en-1-yl)disulfane 在 间氯过氧苯甲酸 作用下， 生成 (Z)-ajoene
  参考文献：
  名称：

  Ajoene, A Stable Garlic By-Product, Inhibits High Fat Diet-Induced Hepatic Steatosis and Oxidative Injury Through LKB1-Dependent AMPK Activation

  摘要：

  Hepatic steatosis, a hepatic component of metabolic syndrome, is common and may progress to steatohepatitis and cirrhosis. The liver X receptor-alpha (LXR alpha)-sterol regulatory element binding protein-1c (SREBP-1c) pathway plays a key role in hepatic steatosis. This study investigated the potential of ajoene, a stable garlic by-product, to inhibit high fat diet (HFD)-induced hepatic steatosis and the underlying mechanism. Ajoene treatment attenuated fat accumulation and induction of lipogenic genes in the liver of HFD-fed mice. Blood biochemical analyses and histopathologic examinations showed that ajoene prevented liver injury with the inhibition of oxidative stress, as evidenced by thiobarbituric acid reactive substances formation and nitrotyrosinylation. Moreover, ajoene treatment inhibited LXR alpha agonist (T0901317)-mediated SREBP-1c activation, and transactivation of the lipogenic target genes in hepatocytes. Ajoene was found to activate AMP-activated protein kinase (AMPK) via LKB1, responsible for the inhibition of p70 ribosomal S6 kinase-1 (S6K1). The ability of ajoene to repress T0901317-induced SREBP-1c expression was antagonized by inhibition of AMPK or activation of S6K1, supporting the role of these kinases in the antisteatotic effect. Our results demonstrate that ajoene has an effect of activating AMPK through LKB1 and inhibit S6K1 activity, contributing to the prevention of SREBP-1c-mediated hepatic lipogenesis via the inhibition of LXR alpha activity. Antioxid Redox Signal. 14, 187-202.

  DOI：

  10.1089/ars.2010.3190
• 作为产物：
  描述：

  propargyl thioacetate 在 偶氮二异丁腈 、 三氟乙酸酐 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.75h， 生成 1-allyl-2-(3-(allylthio)prop-1-en-1-yl)disulfane
  参考文献：
  名称：

  批量阿霍烯、(E,Z)-4,5,9-Trithiadodeca-1,6,11-三烯 9-氧化物和 (E,Z)-4,5,9-Trithiadodeca-1 的简短全合成，连续流动中的 7,11-三烯。

  摘要：

  阿霍烯 ( E,Z )-4,5,9-trithiadodeca-1,6,11-三烯 9-氧化物的简短全合成已通过六个步骤实现。此外，还描述了从简单且易于获得的起始原料开始，在温和反应条件下连续流动合成 ( E,Z )-4,5,9-trithiadodeca-1,7,11-三烯。经过炔丙基化、硫代乙酸酯自由基加成、脱保护和二硫键形成/烯丙基化四个步骤，可以以0.26 gh -1的速率获得目标产物，总产率为12%。

  DOI：

  10.1002/chem.202001598

文献信息

• Substituted ajoenes as novel anti-cancer agents
  作者：Roger Hunter、Catherine H. Kaschula、Iqbal M. Parker、Mino R. Caira、Philip Richards、Susan Travis、Francois Taute、Thozama Qwebani

  DOI：10.1016/j.bmcl.2008.08.056

  日期：2008.10

  A new synthesis of the ajoene pharmacophore core is presented involving the regioselective radical addition of a thiyl radical to a terminal alkyne as the key step. The synthesis allows structural variation of the two end groups on sulfur, and a range of novel derivatives varying the R(1) group (sulfoxide end) has been prepared and tested against CT-1 transformed. broblast cells for anti-cancer activity. The results indicate comparable or even improved activity compared to the parent natural product ajoene isomers. This opens up the way to systematically studying the biology of the ajoene core. (c) 2008 Elsevier Ltd. All rights reserved.
• Short Total Synthesis of Ajoene, ( <i>E</i> , <i>Z</i> )‐4,5,9‐Trithiadodeca‐1,6,11‐triene 9‐oxide, in Batch and ( <i>E</i> , <i>Z</i> )‐4,5,9‐Trithiadodeca‐1,7,11‐triene in Continuous Flow
  作者：Marina Yamamoto Raynbird、Filipa Silva、Harry Smallman、Shaista S. Khokhar、Daniel Neef、Gareth J. S. Evans、Thomas Wirth

  DOI：10.1002/chem.202001598

  日期：2020.7.8

  A short total synthesis of ajoene, (E,Z )‐4,5,9‐trithiadodeca‐1,6,11‐triene 9‐oxide, has been achieved over six steps. In addition, a continuous flow synthesis under mild reaction conditions to (E,Z )‐4,5,9‐trithiadodeca‐1,7,11‐triene is described starting from simple and easily accessible starting materials. Over four steps including propargylation, radical addition of thioacetate, deprotection, and

  阿霍烯 ( E,Z )-4,5,9-trithiadodeca-1,6,11-三烯 9-氧化物的简短全合成已通过六个步骤实现。此外，还描述了从简单且易于获得的起始原料开始，在温和反应条件下连续流动合成 ( E,Z )-4,5,9-trithiadodeca-1,7,11-三烯。经过炔丙基化、硫代乙酸酯自由基加成、脱保护和二硫键形成/烯丙基化四个步骤，可以以0.26 gh -1的速率获得目标产物，总产率为12%。
• Ajoene, A Stable Garlic By-Product, Inhibits High Fat Diet-Induced Hepatic Steatosis and Oxidative Injury Through LKB1-Dependent AMPK Activation
  作者：Chang Yeob Han、Sung Hwan Ki、Young Woo Kim、Kyoung Noh、Da Yeon Lee、Bomi Kang、Jae-Ha Ryu、Raok Jeon、Eun Hyun Kim、Se Jin Hwang、Sang Geon Kim

  DOI：10.1089/ars.2010.3190

  日期：2011.1.15

  Hepatic steatosis, a hepatic component of metabolic syndrome, is common and may progress to steatohepatitis and cirrhosis. The liver X receptor-alpha (LXR alpha)-sterol regulatory element binding protein-1c (SREBP-1c) pathway plays a key role in hepatic steatosis. This study investigated the potential of ajoene, a stable garlic by-product, to inhibit high fat diet (HFD)-induced hepatic steatosis and the underlying mechanism. Ajoene treatment attenuated fat accumulation and induction of lipogenic genes in the liver of HFD-fed mice. Blood biochemical analyses and histopathologic examinations showed that ajoene prevented liver injury with the inhibition of oxidative stress, as evidenced by thiobarbituric acid reactive substances formation and nitrotyrosinylation. Moreover, ajoene treatment inhibited LXR alpha agonist (T0901317)-mediated SREBP-1c activation, and transactivation of the lipogenic target genes in hepatocytes. Ajoene was found to activate AMP-activated protein kinase (AMPK) via LKB1, responsible for the inhibition of p70 ribosomal S6 kinase-1 (S6K1). The ability of ajoene to repress T0901317-induced SREBP-1c expression was antagonized by inhibition of AMPK or activation of S6K1, supporting the role of these kinases in the antisteatotic effect. Our results demonstrate that ajoene has an effect of activating AMPK through LKB1 and inhibit S6K1 activity, contributing to the prevention of SREBP-1c-mediated hepatic lipogenesis via the inhibition of LXR alpha activity. Antioxid Redox Signal. 14, 187-202.