1,4-di-{[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)dithio]methyl}benzene | 1379507-89-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-di-{[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)dithio]methyl}benzene
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[[4-[[[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]disulfanyl]methyl]phenyl]methyldisulfanyl]oxan-2-yl]methyl acetate
• CAS: 1379507-89-7
• 化学式: C₃₆H₄₆O₁₈S₄
• 分子量: 895.014
• InChiKey: RGDWIIRWWONNGA-BPHOTFDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  58
• 可旋转键数：
  26
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  330
• 氢给体数：
  0
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  1,4-di-{[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)dithio]methyl}benzene 在 氨 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 48.0h， 以50%的产率得到1,4-di(β-D-galactopyranosyldithiomethyl)benzene
  参考文献：
  名称：

  Synthesis and biological evaluation of a new class of glycoconjugated disulfides that exhibit potential anticancer properties

  摘要：

  A synthetic strategy, based on the in situ generation of sulfenic acids and their thermolysis in the presence of thiols, was developed for obtaining a collection of polyvalent disulfides in which a benzene scaffold accommodates two or three flexible arms connecting saccharide moieties. Targeting carbohydrate metabolism or carbohydrate-binding proteins may constitute important approaches in the discovery process of new therapeutic anticancer agents. Therefore, a preliminary screening to ascertain the cytostatic/cytotoxic potential of this new class of enantiopure glycoconjugated disulfides has been conducted. Among them, products with two disulfide arms, harbouring galactose rings, induced high levels of apoptosis on U937 histiocytic lymphoma cells, but lower levels of cell death on peripheral blood mononuclear cells from healthy donors. Further experiments indicated that apoptosis induced by these glycoconjugated bis(disulfides) in U937 cells corresponds to the Bcl-2-sensitive, intrinsic form of apoptotic cell death. The bioinvestigation was extended to a panel of human cancer cell lines with different levels of malignancy and resistance to chemotherapeutic agents. Compounds under study proved to induce detectable levels of cell death towards all the tested cancer cell lines. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.070
• 作为产物：
  描述：

  1,4-苯二甲硫醇 在 苄基三甲基氢氧化铵 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 1.83h， 生成 1,4-di-{[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)dithio]methyl}benzene
  参考文献：
  名称：

  Synthesis and biological evaluation of a new class of glycoconjugated disulfides that exhibit potential anticancer properties

  摘要：

  A synthetic strategy, based on the in situ generation of sulfenic acids and their thermolysis in the presence of thiols, was developed for obtaining a collection of polyvalent disulfides in which a benzene scaffold accommodates two or three flexible arms connecting saccharide moieties. Targeting carbohydrate metabolism or carbohydrate-binding proteins may constitute important approaches in the discovery process of new therapeutic anticancer agents. Therefore, a preliminary screening to ascertain the cytostatic/cytotoxic potential of this new class of enantiopure glycoconjugated disulfides has been conducted. Among them, products with two disulfide arms, harbouring galactose rings, induced high levels of apoptosis on U937 histiocytic lymphoma cells, but lower levels of cell death on peripheral blood mononuclear cells from healthy donors. Further experiments indicated that apoptosis induced by these glycoconjugated bis(disulfides) in U937 cells corresponds to the Bcl-2-sensitive, intrinsic form of apoptotic cell death. The bioinvestigation was extended to a panel of human cancer cell lines with different levels of malignancy and resistance to chemotherapeutic agents. Compounds under study proved to induce detectable levels of cell death towards all the tested cancer cell lines. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.070

文献信息

• Synthesis and biological evaluation of a new class of glycoconjugated disulfides that exhibit potential anticancer properties
  作者：Paola Bonaccorsi、Francesca Marino-Merlo、Anna Barattucci、Gianluca Battaglia、Emanuela Papaianni、Teresa Papalia、Maria C. Aversa、Antonio Mastino

  DOI：10.1016/j.bmc.2012.03.070

  日期：2012.5

  A synthetic strategy, based on the in situ generation of sulfenic acids and their thermolysis in the presence of thiols, was developed for obtaining a collection of polyvalent disulfides in which a benzene scaffold accommodates two or three flexible arms connecting saccharide moieties. Targeting carbohydrate metabolism or carbohydrate-binding proteins may constitute important approaches in the discovery process of new therapeutic anticancer agents. Therefore, a preliminary screening to ascertain the cytostatic/cytotoxic potential of this new class of enantiopure glycoconjugated disulfides has been conducted. Among them, products with two disulfide arms, harbouring galactose rings, induced high levels of apoptosis on U937 histiocytic lymphoma cells, but lower levels of cell death on peripheral blood mononuclear cells from healthy donors. Further experiments indicated that apoptosis induced by these glycoconjugated bis(disulfides) in U937 cells corresponds to the Bcl-2-sensitive, intrinsic form of apoptotic cell death. The bioinvestigation was extended to a panel of human cancer cell lines with different levels of malignancy and resistance to chemotherapeutic agents. Compounds under study proved to induce detectable levels of cell death towards all the tested cancer cell lines. (C) 2012 Elsevier Ltd. All rights reserved.
• 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.