S-hexyl hexane-1-sulfinothioate | 131904-37-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代亚磺酸酯
• 英文名称: S-hexyl hexane-1-sulfinothioate
• 英文别名: 1-hexylsulfinylsulfanylhexane
• CAS: 131904-37-5
• 化学式: C₁₂H₂₆OS₂
• 分子量: 250.47
• InChiKey: FBPVGCZBKKKGRF-UHFFFAOYSA-N

物化性质

• 沸点：
  359.7±25.0 °C(Predicted)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Largazole thiol 、 S-hexyl hexane-1-sulfinothioate 在 间氯过氧苯甲酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以75%的产率得到(5R,8S,11S)-11-((E)-4-(hexyldisulfanyl)but-1-en-1-yl)-8-isopropyl-5-methyl-10-oxa-3,17-dithia-7,14,19,20-tetraazatricyclo[14.2.1.12,5]icosa-1(18),2(20),16(19)-triene-6,9,13-trione
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of largazole derivatives: alteration of the zinc-binding domain

  摘要：

  A new series of largazole analogues in which the side chain was replaced with disulfide groups were synthesized, and their biological activities were evaluated. Compound 8 bearing an octyl moiety showed much better selectivity for HDAC1 over HDAC7 than largazole (320-fold). Structure activity relationships suggested that the length in the disulfide chain of largazole is important for the selectivity toward HDAC1 over HDAC7. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.078
• 作为产物：
  描述：

  2-氰基苯甲酸 在 potassium tert-butylate 、 碘 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 3.17h， 生成 S-hexyl hexane-1-sulfinothioate
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of largazole derivatives: alteration of the zinc-binding domain

  摘要：

  A new series of largazole analogues in which the side chain was replaced with disulfide groups were synthesized, and their biological activities were evaluated. Compound 8 bearing an octyl moiety showed much better selectivity for HDAC1 over HDAC7 than largazole (320-fold). Structure activity relationships suggested that the length in the disulfide chain of largazole is important for the selectivity toward HDAC1 over HDAC7. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.078

文献信息

• Synthesis and in vitro biological evaluation of thiosulfinate derivatives for the treatment of human multidrug-resistant breast cancer
  作者：Ariane Roseblade、Alison Ung、Mary Bebawy

  DOI：10.1038/aps.2016.170

  日期：2017.10

  Organosulfur compounds derived from Allium vegetables have long been recognized for various therapeutic effects, including anticancer activity. Allicin, one of the main biologically active components of garlic, shows promise as an anticancer agent; however, instability makes it unsuitable for clinical application. The aim of this study was to investigate the effect of stabilized allicin derivatives on human breast cancer cells in vitro. In this study, a total of 22 stabilized thiosulfinate derivatives were synthesized and screened for their in vitro antiproliferative activities against drug-sensitive (MCF-7) and multidrug-resistant (MCF-7/Dx) human adenocarcinoma breast cancer cells. Assays for cell death, apoptosis, cell cycle progression and mitochondrial bioenergetic function were performed. Seven compounds (4b, 7b, 8b, 13b, 14b, 15b and 18b) showed greater antiproliferative activity against MCF-7/Dx cells than allicin. These compounds were also selective towards multidrug-resistant (MDR) cells, a consequence attributed to collateral sensitivity. Among them, 13b exhibited the greatest anticancer activity in both MCF-7/Dx and MCF-7 cells, with IC50 values of 18.54±0.24 and 46.50±1.98 μmol/L, respectively. 13b altered cellular morphology and arrested the cell cycle at the G2/M phase. Additionally, 13b dose-dependently induced apoptosis, and inhibited cellular mitochondrial respiration in cells at rest and under stress. MDR presents a significant obstacle to the successful treatment of cancer clinically. These results demonstrate that thiosulfinate derivatives have potential as novel anticancer agents and may offer new therapeutic strategies for the treatment of chemoresistant cancers.

  葱属蔬菜衍生出的有机硫化合物因其多种治疗效果而被长期认可，其中包括抗癌活性。大蒜的主要生物活性成分之一——蒜素，有望作为抗癌剂；然而，其不稳定性使其不适合临床应用。本研究旨在探究稳定化的蒜素衍生物对人类乳腺癌细胞的体外效应。本研究中，共合成了22种稳定化的硫氧化物衍生物，并对其针对药物敏感型（MCF-7）和多药耐药型（MCF-7/Dx）人类乳腺癌腺癌细胞的体外抗增殖活性进行了筛选。进行了细胞死亡、凋亡、细胞周期进程和线粒体生物能学功能的检测。七种化合物（4b、7b、8b、13b、14b、15b和18b）对MCF-7/Dx细胞的抗增殖活性高于蒜素。这些化合物对多药耐药（MDR）细胞也具有选择性，这一结果归因于附属敏感性。其中，13b在MCF-7/Dx和MCF-7细胞中显示出最大的抗癌活性，IC50值分别为18.54±0.24和46.50±1.98 μmol/L。13b改变了细胞形态，并将细胞周期阻滞在G2/M期。此外，13b剂量依赖性地诱导凋亡，并抑制静息和应激状态下细胞的线粒体呼吸。MDR在临床上成功治疗癌症方面构成了重大障碍。这些结果表明，硫氧化物衍生物具有作为新型抗癌剂的潜力，并为治疗化学耐药性癌症提供了新的治疗策略。
• Allicin and derivates are cysteine protease inhibitors with antiparasitic activity
  作者：Thilo Waag、Christoph Gelhaus、Jennifer Rath、August Stich、Matthias Leippe、Tanja Schirmeister

  DOI：10.1016/j.bmcl.2010.07.062

  日期：2010.9

  Allicin and derivatives thereof inhibit the CAC1 cysteine proteases falcipain 2, rhodesain, cathepsin B and L in the low micromolar range. The structure–activity relationship revealed that only derivatives with primary carbon atom in vicinity to the thiosulfinate sulfur atom attacked by the active-site Cys residue are active against the target enzymes. Some compounds also show potent antiparasitic

  大蒜素及其衍生物在低微摩尔范围内抑制CAC1半胱氨酸蛋白酶falcipain 2，rhodesain，cathepsin B和L。结构-活性关系表明，只有在活性位点Cys残基攻击的硫代亚硫酸盐硫原子附近具有伯碳原子的衍生物才对目标酶具有活性。一些化合物还显示出对恶性疟原虫和布鲁氏锥虫的有效抗寄生虫活性。
• Biodegradable Polymers with Sulfenamide Bonds for Drug Delivery Applications
  申请人：Bowden Ned B.

  公开号：US20140099506A1

  公开（公告）日：2014-04-10

  The present invention provides polysulfenamides and methods of making same.

  本发明提供了聚硫胺酰胺及其制备方法。
• New Class of Biodegradable Polymers Formed from Reactions of an Inorganic Functional Group
  作者：Jun Yoo、Denison J. Kuruvilla、Sheetal R. D’Mello、Aliasger K. Salem、Ned B. Bowden

  DOI：10.1021/ma300190b

  日期：2012.3.13

  Although numerous small molecules have been synthesized with sulfenamide bonds (R2N-SR), this is the first report of the synthesis of polysulfenamides. These polymers are readily synthesized at room temperature using secondary diamines and dithiosuccinimides. The dithiosuccinimides were readily synthesized in one step by the reaction of dithiols such as HS(CH2)(6)SH with N-chlorosuccinimide. The resulting dithiosuccinimides were either recrystallized or readily purified by chromatography on silica gel and required no special handling. The conversions of polymerization ranged from 95 to 98%, and the molecular weights of the polymer reached as high as 6300 g mol(-1). The sulfenamide bond was very stable in organic solvents, and no degradation was observed under atmospheric conditions in C6D6 for 30 days. In contrast, the sulfenamide bond readily decomposed in less than 12 h in D2O. Polysulfenamides were fabricated into micrometer-sized particles loaded with dye and endocytosed into JAWSII immature dendritic and HEK293 cells. Polysulfenamides represent a new class of polymers that are readily synthesized, stable in aprotic solvents, and readily degrade in water.
• MUSHRUSH, GEORGE W.;PELLENBARG, ROBERT E.;HAZLETT, ROBERT N.;HARDY, DENNI+, FUEL SCI. AND TECHNOL. INT., 9,(1991) N, C. 549-565
  作者：MUSHRUSH, GEORGE W.、PELLENBARG, ROBERT E.、HAZLETT, ROBERT N.、HARDY, DENNI+

  DOI：——

  日期：——