alpha,alpha’-对二甲苯基二甲烷硫代磺酸酯 | 3948-46-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: alpha,alpha’-对二甲苯基二甲烷硫代磺酸酯
• 中文别名: α，α'-对二甲苯基双甲硫代磺酸盐
• 英文名称: 1,4-bis(methanesulfonylthiomethyl)benzene
• 英文别名: α,α'-Bis-methansulfonylthio-p-xylol；1,4-bis(methylsulfonylsulfanylmethyl)benzene
• CAS: 3948-46-7
• 化学式: C₁₀H₁₄O₄S₄
• 分子量: 326.483
• InChiKey: FJJMUASPEZRNQI-UHFFFAOYSA-N

物化性质

• 熔点：
  180-182°C
• 沸点：
  594.2±43.0 °C(Predicted)
• 密度：
  1.450±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（略微加热）、乙酸乙酯（略微加热）

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  2,3,4,6-四-O-乙酰基-1-硫代-BETA-D-吡喃半乳糖 、 alpha,alpha’-对二甲苯基二甲烷硫代磺酸酯 在 lithium hydroxide monohydrate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成 1,4-di(β-D-galactopyranosyldithiomethyl)benzene
  参考文献：
  名称：

  Aromatic glycosyl disulfide derivatives: Evaluation of their inhibitory activities against Trypanosoma cruzi

  摘要：

  Aromatic oligovalent glycosyl disulfides and some diglycosyl disulfides were tested against three different Trypanosoma cruzi strains. Di-(beta-D-galactopyranosyl-dithiomethylene) benzenes 2b and 4b proved to be the most active derivatives against all three strains of cell culture-derived trypomastigotes with IC50 values ranging from 4 to 11 mu M at 37 degrees C. The inhibitory activities were maintained, although somewhat lowered, at a temperature of 4 degrees C as well. Three further derivatives displayed similar activities against at least one of the three strains. Low cytotoxicities of the active compounds, tested on confluent HeLa, Vero and peritoneal macrophage cell cultures, resulted in significantly higher selectivity indices (SI) than that of the reference drug benznidazole. Remarkably, several molecules of the tested panel strongly inhibited the parasite release from T. cruzi infected HeLa cell cultures suggesting an effect against the intracellular development of T. cruzi amastigotes as well. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.030
• 作为产物：
  描述：

  1,4-二(溴甲基)苯 、 硫甲磺酸钠 以 乙醇 为溶剂， 生成 alpha,alpha’-对二甲苯基二甲烷硫代磺酸酯
  参考文献：
  名称：

  Studies on Antitumor Substances. III. Syntheses of Bis(methanesulphonylthio)alkanes

  摘要：

  合成了二甲烷磺酰硫烷及其类似化合物，方法是通过相应的硫代磺酸钠与适当的二溴化物反应，以测试其与美乐安的抗肿瘤活性比较。研究发现，这些化合物中的一些显著抑制了由厄尔希腹水癌细胞产生的实体肿瘤的生长。

  DOI：

  10.1248/cpb.12.1271

文献信息

• Bivalent O -glycoside mimetics with S /disulfide/ Se substitutions and aromatic core: Synthesis, molecular modeling and inhibitory activity on biomedically relevant lectins in assays of increasing physiological relevance
  作者：Herbert Kaltner、Tamás Szabó、Krisztina Fehér、Sabine André、Sára Balla、Joachim C. Manning、László Szilágyi、Hans-Joachim Gabius

  DOI：10.1016/j.bmc.2017.04.011

  日期：2017.6

  cellular glycans by lectins for diverse aspects of pathophysiology is a strong incentive for considering development of bioactive and non-hydrolyzable glycoside derivatives, for example by introducing S/Se atoms and the disulfide group instead of oxygen into the glycosidic linkage. We report the synthesis of 12 bivalent thio-, disulfido- and selenoglycosides attached to benzene/naphthalene cores. They

  凝集素对病理生理学各个方面的识别对细胞聚糖的重要性正在显着提高，以考虑开发具有生物活性和不可水解的糖苷衍生物，例如通过在糖苷键中引入S / Se原子和二硫基而不是氧。我们报告了12个二价硫代，二硫键和硒代糖苷的合成，苯/萘核心。他们提出了半乳糖（用于阻断植物毒素）或乳糖（粘附/生长调节半乳糖凝素的规范配体）。建模显示出不受约束的灵活性和头组之间的距离太小，无法在同一凝集素中桥接两个位点。首先使用表面呈递的糖蛋白通过固相分析检测抑制活性，相对于游离同源糖，每糖单位的相对活性提高了近10倍。还观察到凝集素与人癌细胞表面结合的抑制活性。为了在组织环境中表征这种能力，将在存在抑制剂的情况下对凝集素结合的监测扩展到了三种鼠类器官的模型部分。事实证明该方法非常适合确定糖化合物的相对活性水平，以阻止毒素和不同人半乳糖凝集素在切片中不同部位与天然糖缀合物的结合。关于两种萘基二硫化物和硒化物的最有效抑制结果
• Studies on Antitumor Substances. III. Syntheses of Bis(methanesulphonylthio)alkanes
  作者：Seigoro Hayashi、Hiroshi Ueki、Seiko Harano、Junko Komiya、Susumu Iyama、Kazunobu Harano、Katsuaki Miyata、Kunihiro Niigata、Yoshiro Yonemura

  DOI：10.1248/cpb.12.1271

  日期：——

  Dimethanesulphonylthioalkanes and analogous compounds were synthesized by the reaction of corresponding sodium thiosulphonate and appropriate dibromide to test the carcinostatic activity compaed with Myleran. It was found that some of these compounds inhibited pronouncedly the growth of the solid tumor produced by Ehrlich ascites carcinoma cells.

  合成了二甲烷磺酰硫烷及其类似化合物，方法是通过相应的硫代磺酸钠与适当的二溴化物反应，以测试其与美乐安的抗肿瘤活性比较。研究发现，这些化合物中的一些显著抑制了由厄尔希腹水癌细胞产生的实体肿瘤的生长。
• Aromatic glycosyl disulfide derivatives: Evaluation of their inhibitory activities against Trypanosoma cruzi
  作者：Bessy Gutiérrez、Christian Muñoz、Luis Osorio、Krisztina Fehér、Tünde-Zita Illyés、Zsuzsa Papp、Ambati Ashok Kumar、Katalin E. Kövér、Hernán Sagua、Jorge E. Araya、Patricio Morales、László Szilágyi、Jorge González

  DOI：10.1016/j.bmcl.2013.04.030

  日期：2013.6

  Aromatic oligovalent glycosyl disulfides and some diglycosyl disulfides were tested against three different Trypanosoma cruzi strains. Di-(beta-D-galactopyranosyl-dithiomethylene) benzenes 2b and 4b proved to be the most active derivatives against all three strains of cell culture-derived trypomastigotes with IC50 values ranging from 4 to 11 mu M at 37 degrees C. The inhibitory activities were maintained, although somewhat lowered, at a temperature of 4 degrees C as well. Three further derivatives displayed similar activities against at least one of the three strains. Low cytotoxicities of the active compounds, tested on confluent HeLa, Vero and peritoneal macrophage cell cultures, resulted in significantly higher selectivity indices (SI) than that of the reference drug benznidazole. Remarkably, several molecules of the tested panel strongly inhibited the parasite release from T. cruzi infected HeLa cell cultures suggesting an effect against the intracellular development of T. cruzi amastigotes as well. (C) 2013 Elsevier Ltd. All rights reserved.