bis(methylthiomethyl) disulfide | 85544-38-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 有机二硫化物
• 英文名称: bis(methylthiomethyl) disulfide
• 英文别名: 2,4,5,7-tetrathiaoctane；bis-methylsulfanylmethyl-disulfane；Bis-(methylmercapto-methyl)-disulfid；Disulfide, bis((methylthio)methyl)；methylsulfanyl-(methylsulfanylmethyldisulfanyl)methane
• CAS: 85544-38-3
• 化学式: C₄H₁₀S₄
• 分子量: 186.387
• InChiKey: QLDCJQYUNZUCHD-UHFFFAOYSA-N

物化性质

• 保留指数：
  1476

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  8
• 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：
  101
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis(methylthiomethyl) disulfide 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 以62%的产率得到2,4,5,7-tetrathiooctane 2-oxide
  参考文献：
  名称：

  Simple Total Syntheses of Biologically Active Pentathiadecane Natural Products, 2,4,5,7,9-Pentathiadecane 2,2,9,9-Tetraoxide (Dysoxysulfone), from Dysoxylum richii, and 2,3,5,7,9-Pentathiadecane 9,9-Dioxide, the Misidentified Lenthionine Precursor SE-3 from Shiitake Mushroom (Lentinus edodes)

  摘要：

  Brief total syntheses are reported for 2,4,5,7,9-pentathiadecane 2,2,9,9-tetraoxide (dysoxysulfone, 1), from the Fijian tree Dysoxylum richii, 2,3,5,7,9-pentathiadecane 9,9-dioxide (8), from shiitake mushroom (Lentinus edodes),and 2,4,5,7-tetrathiaoctane 2,2-dioxide (2a) from Tulbaghia violacea, starting from 1,2,4-trithiolane (4) for 1, 1,2,4,6-tetrathiepane (5) for 8, and 2,4,5,7-tetrathiaoctane (9) for 2a and employing regiospecific oxidation of intermediate penta- or tetrasulfides using KMnO4 along with Zn(OAc)(2) or FeCl3 to prevent product degradation by the base produced during oxidation.

  DOI：

  10.1021/jo00088a001
• 作为产物：
  描述：

  氯甲基甲硫醚 在 lithium sulfide 、 sulfur 、 cetyl trimethyl ammonium bromide 作用下， 以 氯仿 、 水 为溶剂， 反应 11.0h， 以48%的产率得到bis(methylthiomethyl) disulfide
  参考文献：
  名称：

  Hase, T. A.; Peraekylae, H., Synthetic Communications, 1982, vol. 12, # 12, p. 947 - 950

  摘要：

  DOI：

文献信息

• Novel Disulfides with Antitumour Efficacy and Specificity
  作者：Rebecca Griffiths、W. Wei-Lynn Wong、Stephen P. Fletcher、Linda Z. Penn、Richard F. Langler

  DOI：10.1071/ch03105

  日期：——

  Some disulfides have previously been shown to possess antifungal and/or antileukaemic activity. Importantly, this cytotoxicity can be selective. We have previously shown that a subset of these compounds does not block the proliferative potential of normal, non-transformed cells. Based on these results and proposed mechanisms of action, a new set of structurally modified organosulfur compounds, including α-substituted disulfides and a thiosulfonate ester, have been prepared and evaluated for their potential as antileukaemic agents. Compounds were screened for antiproliferative activity against a panel of human cells derived from acute lymphocytic and acute myelogenous leukaemia, as well as non-transformed cells. We have identified five new disulfides and a thiosulfonate that can trigger tumour cells to undergo cell death by an apoptotic mechanism in a sensitive and specific manner.

  一些二硫化物先前已被证明具有抗真菌和/或抗白血病活性。重要的是，这种细胞毒性具有选择性。我们之前已经证明，这些化合物中的一个子集不会阻碍正常、非转化细胞的增殖潜力。根据这些结果和提出的作用机制，我们制备了一组新的结构修饰型有机硫化合物，包括α-取代二硫化物和硫代磺酸酯，并对其作为抗白血病药物的潜力进行了评估。我们对来自急性淋巴细胞白血病和急性髓性白血病以及非转化细胞的一系列人类细胞进行了化合物抗增殖活性筛选。我们发现了五种新的二硫化物和一种硫代磺酸盐，它们能以敏感而特异的方式引发肿瘤细胞通过凋亡机制死亡。
• Sulfur containing compounds
  申请人：——

  公开号：US20030220524A1

  公开（公告）日：2003-11-27

  This invention is directed to novel and known stufur containing compounds and pharmaceutically acceptable salts thereof that have utility as antifungals and as antiproliferative agents against mammalian cells, in particular cancer cells and most particularly leukemia-derived cells. The invention provides a method for synthesizing certain of the sulfur containing compounds that is more efficient than previously known methods.

  这项发明涉及新颖且已知的含有硫的化合物以及具有抗真菌活性和作为哺乳动物细胞，特别是癌细胞，尤其是白血病来源细胞的抗增殖剂的药用可接受盐。发明提供了一种合成某些含硫化合物的方法，该方法比先前已知的方法更有效。
• The S2 Oxygen Atoms Are Essential for the Pronounced Fungitoxicity of the Sulfur-Rich Natural Product, Dysoxysulfone
  作者：Sharon A. Bewick、Stephen Duffy、Stephen P. Fletcher、Richard F. Langler、Heather G. Morrison、Erin M. O'Brien、Charles Ross、Vanessa C. Stephenson

  DOI：10.1071/ch03253

  日期：——

  Synthesis and antifungal testing of 2,4,5,7,9-pentathiadecane 9,9-dioxide has established that the absence of oxygen atoms on S2 significantly attenuates fungitoxicity in accord with our earlier proposal. Attempts to convert that compound into dysoxysulfone led to the discovery of a novel oxidative conversion of unsymmetrical γ-sulfonyl disulfides into the corresponding symmetrical γ-sulfonyl disulfides.

  2,4,5,7,9-五硫杂十烷 9,9-二氧化物的合成和抗真菌测试表明，S2 上氧原子的缺失会显著降低真菌毒性，这与我们之前的提议不谋而合。在尝试将该化合物转化为二异砜的过程中，我们发现了一种将非对称γ-砜基二硫化物氧化转化为相应的对称γ-砜基二硫化物的新方法。
• Weissflog, Eckhard, Phosphorus and Sulfur and the Related Elements, 1983, vol. 15, p. 27 - 32
  作者：Weissflog, Eckhard

  DOI：——

  日期：——
• Synthesis of Di(methylthiomethyl) Polysulfides
  作者：Mario R. Altamura、Torsten Hasselstrom、Louis Long

  DOI：10.1021/jo01044a504

  日期：1963.9