(E)-S-[3-(prop-1-ylthio)propen-1-yl] ethanethioate | 1080588-20-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: (E)-S-[3-(prop-1-ylthio)propen-1-yl] ethanethioate
• 英文别名: (E)-S-1-(4-thiahept-1-enyl) ethanethioate；(E)-S-1-(4-thiahept-1-enyl)ethanethioate；S-[(E)-3-propylsulfanylprop-1-enyl] ethanethioate
• CAS: 1080588-20-0
• 化学式: C₈H₁₄OS₂
• 分子量: 190.331
• InChiKey: LQXVEHZQAZGLPD-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  propyl 2-propynyl sulfide 、 硫代乙酸 在 1,1'-偶氮(氰基环己烷) 作用下， 以 甲苯 为溶剂， 生成 (Z)-S-[3-(prop-1-ylthio)propen-1-yl] ethanethioate 、 (E)-S-[3-(prop-1-ylthio)propen-1-yl] ethanethioate
  参考文献：
  名称：

  结构活性研究Ajoene类似物在WHCO1食管癌细胞中的抗增殖活性

  摘要：

  大蒜碎物中发现的大蒜素重排产生的有机硫化合物阿霍烯可以通过诱导G 2 / M细胞周期停滞和凋亡来抑制肿瘤细胞的增殖。我们报告了一个简明的四步合成法的应用（Hunter等，2008 [1]），该合成法允许使用末端烯丙基被取代的阿霍恩类似物。经过测试的十二种此类衍生物的文库对WHCO1食道癌细胞的抗增殖活性，已鉴定出一种衍生物，该衍生物含有对-甲氧基苄基（PMB）取代的端基，其活性是Z-阿Z烯的十二倍，IC 50为50为2.1μM（Kaschula等，2011 [2]）。结构活性研究涉及该铅的亚砜和乙烯基二硫化物基团的修饰，发现该二硫化物是负责抑制WHCO1细胞生长，通过caspase-3激活诱导G 2 / M细胞周期停滞和凋亡的阿霍烯药效团，并且乙烯基基团将抗扩散活性进一步提高了八倍。铅与半胱氨酸在回流的THF中的反应作为基于硫醇/二硫键交换的阿霍内作用机理的模型反应的模型反应表明，二硫化乙烯基的烯丙基硫是交换中硫醇攻击的位点。

  DOI：

  10.1016/j.ejmech.2012.01.058

文献信息

• Organosulfur Compounds, a Method of Making Organosulfur Compounds and their Use for Inhibiting the Growth of Tumour Cells
  申请人：Kaschula Catherine Hart

  公开号：US20110190368A1

  公开（公告）日：2011-08-04

  Organosulfur compounds of the general formula (2) are described, wherein R 1 and R 2 are linear or branched C1-C5 alkyl; linear or branched C1-C5 alkenyl with the proviso that R 1 is not prop-1-enyl (allyl); substituted linear or branched C1-C5 alkenyl or substituted linear or branched C1-C5 alkyl, in which the substituents are selected from OR 3 , NR 4 R 5 , COOR 6 , CON—R 7 R 8 , in which R 3 is selected from H, COR 9 , para-methoxybenzyl and trialkylsilyl, in which R 9 is alkyl or substituted alkyl; R 4 N and R 5 are alkyl or R 4 and R 5 together form a phthalimido group; R 6 is alkyl or substituted alkyl; and R 7 and R 8 are alkyl or substituted alkyl; substituted or unsubstituted aromatic specifically where R 1 and R 2 are benzyl, para-methoxybenzyl and/or ortho,para-methoxybenzyl and substituted or unsubstituted heteroaromatic. The compounds can be used for inhibiting the growth of tumour cells and for treating cancer. A pharmaceutical composition and a method of preparing the compounds are also described.

  本文描述了通式（2）的有机硫化合物，其中R1和R2是线性或支链的C1-C5烷基；线性或支链的C1-C5烯基，其中R1不是丙烯基；取代的线性或支链的C1-C5烯基或取代的线性或支链的C1-C5烷基，其中取代基从OR3，NR4R5，COOR6，CON—R7R8中选择，其中R3从H，COR9，对甲氧基苄基和三烷基硅烷中选择，其中R9是烷基或取代烷基；R4N和R5是烷基或R4和R5组成邻二甲酰亚胺基团；R6是烷基或取代烷基；R7和R8是烷基或取代烷基；取代或未取代的芳香族，特别是当R1和R2为苄基，对甲氧基苄基和/或邻，对-甲氧基苄基和取代或未取代的杂环芳香族时。这些化合物可用于抑制肿瘤细胞生长和治疗癌症。还描述了一种制备这些化合物的制药组合物和方法。
• [EN] ORGANOSULFUR COMPOUNDS, A METHOD OF MAKING ORGANOSULFUR COMPOUNDS AND THEIR USE FOR INHIBITING THE GROWTH OF TUMOUR CELLS<br/>[FR] COMPOSÉS D'ORGANOSOUFRE, PROCÉDÉ DE FABRICATION DE COMPOSÉS D'ORGANOSOUFRE ET LEUR UTILISATION POUR INHIBER LA CROISSANCE DE CELLULES TUMORALES
  申请人：UNIV CAPE TOWN

  公开号：WO2010016011A1

  公开（公告）日：2010-02-11

  Organosulfur compounds of the general formula (2) are described, wherein R1 and R2 are linear or branched C1- C5 alkyl; linear or branched C1- C5 alkenyl with the proviso that R1 is not prop-1-enyl (allyl); substituted linear or branched C1- C5 alkenyl or substituted linear or branched C1- C5 alkyl, in which the substituents are selected from OR3, NR4R5, COOR6, CONR7R8, in which R3 is selected from H, COR9, para- methoxybenzyl and trialkylsilyl, in which R9 is alkyl or substituted alkyl; R4 and R5 are alkyl or R4 and R5 together form a phthalimido group; R6 is alkyl or substituted alkyl; and R7 and R8 are alkyl or substituted alkyl; substituted or unsubstituted aromatic specifically where R1 and R2 are benzyl, para-methoxybenzyl and/or ortho,para- methoxybenzyl and substituted or unsubstituted heteroaromatic. The compounds can be used for inhibiting the growth of tumour cells and for treating cancer. A pharmaceutical composition and a method of preparing the compounds are also described.

  本文描述了一般式（2）的有机硫化合物，其中R1和R2为线性或支链烷基C1-C5；线性或支链烯基C1-C5，但R1不是丙烯基（烯丙基）；取代的线性或支链烯基或取代的线性或支链烷基，其中取代基被选择为OR3，NR4R5，COOR6，CONR7R8，其中R3被选择为H，COR9，对甲氧基苄基和三烷基硅基，其中R9是烷基或取代烷基；R4和R5是烷基或R4和R5共同形成邻二甲酰亚胺基团；R6是烷基或取代烷基；R7和R8是烷基或取代烷基；取代或未取代的芳香族，特别是当R1和R2为苄基，对甲氧基苄基和/或邻、对-甲氧基苄基和取代或未取代的杂环芳香族时。这些化合物可用于抑制肿瘤细胞的生长和治疗癌症。还描述了一种制备这些化合物的药物组合物和方法。
• 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.
• New Excursions Into the Synthesis and Medicinal Chemistry of the Disulfide Bond
  作者：Roger Hunter*、Catherine Kaschula、Nashia Stellenboom、Jonathan Cotton、M. Iqbal Parker

  DOI：10.1080/10426507.2012.736107

  日期：2013.11.1

  The presentation discusses two themes of current interest in my research group in conjunction with a garlic mimics program. The first involves a new one-pot methodology for preparing unsymmetrical disulfides in high yield using 1-chlorobenzotriazole (BtCl) as oxidant, which can be applied to a range of functional types. The second part of the lecture will discuss the synthesis of derivatives of the garlic-derived natural product ajoene, in conjunction with an anti-cancer screening program. The synthesis has been used to prepare a fluorescently tagged derivative of the natural product that has been used to investigate localization and mode of action within the cancer cell using confocal laser scanning microscopy.
• US8524781B2
  申请人：——

  公开号：US8524781B2

  公开（公告）日：2013-09-03