1,4-di-{[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)dithio]methyl}benzene | 1379507-87-5

• 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-glucopyranosyl)dithio]methyl}benzene
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[4-[[[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]disulfanyl]methyl]phenyl]methyldisulfanyl]oxan-2-yl]methyl acetate
• CAS: 1379507-87-5
• 化学式: C₃₆H₄₆O₁₈S₄
• 分子量: 895.014
• InChiKey: RGDWIIRWWONNGA-OPJDJTOASA-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-glucopyranosyl)dithio]methyl}benzene 在 氨 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 48.0h， 以53%的产率得到1,4-di-{[(β-D-glucopyranosyl)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
• 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-glucopyranosyl)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

• Sulfenic acid – derived glycoconjugated disulfides and sulfoxides: a biological evaluation on human red blood cells
  作者：Paola Bonaccorsi、Maria Chiara Aversa、Anna Barattucci、Teresa Papalia、Agata Torre、Francesca Trischitta、Caterina Faggio

  DOI：10.1080/17415993.2013.778259

  日期：2013.12.1

  This article examines the effects of some glycoconjugated disulfides and sulfoxides on red blood cells (RBCs). Compounds under study show sugar units connected directly or through a benzene platform, and have been obtained following synthetic pathways based on the sulfenic acid chemistry. In order to evaluate the relationship between the structural features of the thioglycoconjugates under investigation and their potential biological activity, we were interested in assessing both the cytotoxicity and hemolytic activity produced on human RBCs by overnight exposition to the thioglycoconjugates. The absence of both cytotoxic effect and hemolysis produced by the tested compounds on erythrocytes supports the rational design of hemocompatible molecules for biomedical applications.[GRAPHICS].
• 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.