S-丙基丙烷-1-硫代亚磺酸盐 | 1948-52-3

• 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
• 中文名称: S-丙基丙烷-1-硫代亚磺酸盐
• 英文名称: propyl propylthiosulfinate
• 英文别名: 1-propanesulfinothioic acid S-propyl ester；S-propyl propane-1-sulfinothioate；n-propyl propane-1-sulfinothioate；propyl propane thiosulfinate；propyl propanethiosulfinate；dipropyl thiosulfinate；1-Propanesulfinothioic acid, S-propyl ester；1-propylsulfinylsulfanylpropane
• CAS: 1948-52-3
• 化学式: C₆H₁₄OS₂
• 分子量: 166.309
• InChiKey: XPRZAEWSYWTDSQ-UHFFFAOYSA-N

物化性质

• 溶解度：
  20 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  5
• 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：

  S-丙基丙烷-1-硫代亚磺酸盐 以 水 、 苯 为溶剂， 反应 36.0h， 以9.6%的产率得到propyl 1-(propylsulfinyl)propyl disulfide
  参考文献：
  名称：

  Allium Chemistry:  Synthesis of 1-[Alk(en)ylsulfinyl]propyl Alk(en)yl Disulfides (Cepaenes), Antithrombotic Flavorants from Homogenates of Onion (Allium cepa)

  摘要：

  A series of 1-[alk(en)ylsulfinyl]propyl alk(en)yl disulfides (alpha-sulfinyl disulfides) of structure RS(O)CHEtSSR', R, R' = Me, (E,Z)-MeCH=CH, n-Pr, and CH2=CHCH2, termed cepaenes, have been synthesized by a variety of routes including oxidation of 1-[alk(en)ylthio]propyl alk(en)yl disulfides, RSCHEtSSR', termed deoxycepaenes. The cepaenes are identical to compounds isolated from homogenates of onion (Allium cepa) and to compounds identified in these homogenates by liquid chromatography/mass spectrometry, while the deoxycepaenes are identical to compounds found in Allium distilled oils and in other materials: The antithrombotic activities for several cepaenes are reported.

  DOI：

  10.1021/jf9705126
• 作为产物：
  描述：

  二丙基二硫 在 甲酸 、 双氧水 作用下， 以 水 为溶剂， 生成 S-丙基丙烷-1-硫代亚磺酸盐
  参考文献：
  名称：

  基于原位甲硫氨酸 γ-裂解酶的硫代亚磺酸盐生成系统与合成硫代亚磺酸盐的抗念珠菌活性

  摘要：

  白色念珠菌和非白色念珠菌 念珠菌属是人类粘膜感染、血流感染和深部真菌病的常见原因。念珠菌属耐药性的出现。为了将抗真菌药物应用于实践，需要寻找新的抗真菌药物。本研究揭示了合成二烷（烯）基硫代亚磺酸盐与基于酶促原位甲硫氨酸γ-裂解酶的硫代亚磺酸盐生成系统（TGS）的抗真菌潜力。首次通过 1H NMR 光谱研究了 TGS 反应的动力学，即蛋氨酸 γ-裂合酶催化的 S-烷（烯）基-L-半胱氨酸亚砜的 β-消除，揭示了快速的转化率和高效生产抗念珠菌二烷基（烯）基硫代亚磺酸盐。通过体外测定研究了该系统与合成硫代亚磺酸盐的抗念珠菌潜力。 TGS 被证明比单一物质（MIC 范围 0.69-3.31 μg/mL）更有效（MIC 范围 0.36-1.1 μg/mL）。测试的制剂与市售抗真菌药氟康唑、两性霉素 B 和 5-氟胞嘧啶具有相加作用，显示分数抑制系数指数在 0.5–2 μg/mL 范围内。 TGS 可

  DOI：

  10.3390/ph16121695

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。
• Natural product inspired allicin analogs as novel anti-cancer agents
  作者：Ishani Bhaumik、Kunal Pal、Utsab Debnath、Parimal Karmakar、Kuladip Jana、Anup Kumar Misra

  DOI：10.1016/j.bioorg.2019.01.057

  日期：2019.5

  nontoxic to the normal cells. Based on the LD50 values and selectivity index (SI), compound 3h (S-p-methoxybenzyl (p-methoxyphenyl)methanesulfinothioate) was considered as most promising anticancer agent amongst the above three compounds. Further bio-chemical studies confirmed that compound 3h promotes ROS generation, changes in mitochondrial permeability transition and induced caspase mediated DNA

  以高收率合成了大蒜中存在的一系列大蒜素的新类似物（S-烯丙基丙-2-烯-1-磺基硫代乙酸盐）。针对不同的乳腺癌细胞（MDA-MB-468和MCF-7）和非癌细胞（WI38）评估了合成的23种化合物。四种化合物（3f，3h，3m和3u）对癌细胞具有明显的细胞毒性，而对正常细胞无毒性。基于LD 50值和选择性指数（SI），化合物3h（Sp-甲氧基苄基（对甲氧基苯基）甲亚磺酸硫酯）被认为是上述三种化合物中最有希望的抗癌剂。进一步的生化研究证实，化合物3h促进ROS的产生，线粒体通透性转变的变化并诱导caspase介导的DNA损伤和凋亡。
• First insights into the mode of action of a “lachrymatory factor synthase” – Implications for the mechanism of lachrymator formation in Petiveria alliacea, Allium cepa and Nectaroscordum species
  作者：Quan He、Roman Kubec、Abhijit P. Jadhav、Rabi A. Musah

  DOI：10.1016/j.phytochem.2011.07.013

  日期：2011.11

  alliacea L. (Phytolaccaceae) to yield the P. alliacea lachrymator (phenylmethanethial S-oxide) showed the protein to be a dehydrogenase. It functions by abstracting hydride from sulfenic acids of appropriate structure to form their corresponding sulfines. Successful hydride abstraction is dependent upon the presence of a benzyl group on the sulfur to stabilize the intermediate formed on abstraction of hydride

  一项酶与 Petiveria alliacea L.（Phytolaccaceae）中的蒜氨酸酶产生的次磺酸反应以产生 P. alliacea lachrymator（苯甲硫基 S-氧化物）的研究表明该蛋白质是一种脱氢酶。它的作用是从适当结构的次磺酸中提取氢化物以形成相应的亚磺酸。成功的氢化物提取取决于硫上苄基的存在，以稳定提取氢化物时形成的中间体。这种脱氢酶活性与在洋葱中发现的催泪因子合酶 (LFS) 的活性形成对比，后者催化 1-丙烯亚磺酸重排为 (Z)-丙硫醇 S-氧化物，即洋葱催泪剂。根据其催化的反应类型，洋葱 LFS 应归类为异构酶，并称为“
• Direct Bis-Alkyl Thiolation for Indoles with Sulfinothioates under Pummerer-Type Conditions
  作者：Peng Qi、Fang Sun、Ning Chen、Hongguang Du

  DOI：10.1021/acs.joc.1c02502

  日期：2022.1.21

  applications. This approach enabled double C–H thiolation at the C2 and C3 of the indole in one pot. The mechanism studies suggested the thiolation was realized through the sulfoxonium salt rather than sulfenyl carboxylate.

  描述了在 Pummerer 型条件下吲哚与硫代硫酸盐的无碱双烷基硫醇化反应。用 2,2,2-三氟乙酸酐活化的硫代硫酸盐被证明是一种适用于广泛应用的有效硫醇化试剂。这种方法能够在一锅中在吲哚的 C2 和 C3 上进行双 C-H 硫醇化。机理研究表明，硫醇化是通过氧化鎓盐而不是亚磺基羧酸盐实现的。
• Selective Oxidation of Sulfides in Flow Chemistry
  作者：Filipa Silva、Alastair Baker、James Stansall、Weronika Michalska、Mehkman S. Yusubov、Michael Graz、Robert Saunders、Gareth J. S. Evans、Thomas Wirth

  DOI：10.1002/ejoc.201800339

  日期：2018.5.15

  A packed bed reactor with oxone has been employed for selective oxidations of sulfur compounds. Various sulfides containing different functional groups are efficiently oxidized to the corresponding sulfoxides without formation of sulfones or other side products.

  带有 oxone 的填充床反应器已被用于硫化合物的选择性氧化。含有不同官能团的各种硫化物被有效地氧化成相应的亚砜，而不会形成砜或其他副产物。

表征谱图