1,3-di(β-D-galactopyranosyldithiomethyl)benzene | 1438416-29-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-di(β-D-galactopyranosyldithiomethyl)benzene
• 英文别名: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[[3-[[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]disulfanyl]methyl]phenyl]methyldisulfanyl]oxane-3,4,5-triol
• CAS: 1438416-29-5
• 化学式: C₂₀H₃₀O₁₀S₄
• 分子量: 558.716
• InChiKey: RANXBKQGNYWKHN-IBPYFQLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  282
• 氢给体数：
  8
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  1,3-di-{[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)dithio]methyl}benzene 在 lithium hydroxide monohydrate 作用下， 以 甲醇 为溶剂， 以95 mg的产率得到1,3-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

文献信息

• 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.