S-(β-D-glucopyranosyl) N,N-diallyldithiocarbamate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: S-(β-D-glucopyranosyl) N,N-diallyldithiocarbamate
• 英文别名: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] N,N-bis(prop-2-enyl)carbamodithioate
• 化学式: C₁₃H₂₁NO₅S₂
• 分子量: 335.445
• InChiKey: CTZAZHHADIVOOC-ZIQFBCGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) N,N-diallyldithiocarbamate 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以56%的产率得到S-(β-D-glucopyranosyl) N,N-diallyldithiocarbamate
  参考文献：
  名称：

  Sugar-Linked Dithiocarbamates as Modulators of Metabolic and Genotoxic Properties of N-Nitroso Compounds

  摘要：

  A series of putative anticarcinogenic and antimutagenic compounds was synthesized on the basis of tetraethylthiuram disulfide (disulfiram) and its metabolite, diethyldithiocarbamate (DDTC). Diallyldithiocarbamate was synthesized in order to combine the anticarcinogenic properties of diallyl sulfide, a known inhibitor of chemical carcinogenesis from Allium species, and those of DDTC. Several sugar-linked dithiocarbamates (SDTCs) were prepared using glucose, cellobiose, and lactose as glycosyl donors and DDTC and diallyldithiocarbamate as accepters. All the S-glycoside bonds of SDTCs were very stable under physiological conditions in vitro. At low nitrosamine concentrations, glucose-DDTC inhibited microsomal nitrosamine dealkylases in vitro. In vivo these enzymes were also inhibited 4 h after ip administration of glucose-DDTC or lactose-DDTC to rats (1.7 mmol/kg); after 24 h, the values had returned to control levels. Glucose-DDTC induced the activity of glutathione-related enzymes. Concomitant treatment of rats with glucose-DDTC and N-nitrosodiethylamine (NDEA) led to a depression of the oxidative metabolism of [C-14]NDEA to (CO2)-C-14 but increased the elimination of unchanged [C-14]NDEA in the urine. Furthermore, glucose-DDTC totally inhibited the formation of DNA single-strand breaks induced by NDEA. All these effects may contribute to possible antimutagenic and anticarcinogenic actions of the dithiocarbamates investigated.

  DOI：

  10.1021/jm00045a021

文献信息

• Sugar-Linked Dithiocarbamates as Modulators of Metabolic and Genotoxic Properties of N-Nitroso Compounds
  作者：Byung-Hoon Lee、Barbara Bertram、Peter Schmezer、Norbert Frank、Manfred Wiessler

  DOI：10.1021/jm00045a021

  日期：1994.9

  A series of putative anticarcinogenic and antimutagenic compounds was synthesized on the basis of tetraethylthiuram disulfide (disulfiram) and its metabolite, diethyldithiocarbamate (DDTC). Diallyldithiocarbamate was synthesized in order to combine the anticarcinogenic properties of diallyl sulfide, a known inhibitor of chemical carcinogenesis from Allium species, and those of DDTC. Several sugar-linked dithiocarbamates (SDTCs) were prepared using glucose, cellobiose, and lactose as glycosyl donors and DDTC and diallyldithiocarbamate as accepters. All the S-glycoside bonds of SDTCs were very stable under physiological conditions in vitro. At low nitrosamine concentrations, glucose-DDTC inhibited microsomal nitrosamine dealkylases in vitro. In vivo these enzymes were also inhibited 4 h after ip administration of glucose-DDTC or lactose-DDTC to rats (1.7 mmol/kg); after 24 h, the values had returned to control levels. Glucose-DDTC induced the activity of glutathione-related enzymes. Concomitant treatment of rats with glucose-DDTC and N-nitrosodiethylamine (NDEA) led to a depression of the oxidative metabolism of [C-14]NDEA to (CO2)-C-14 but increased the elimination of unchanged [C-14]NDEA in the urine. Furthermore, glucose-DDTC totally inhibited the formation of DNA single-strand breaks induced by NDEA. All these effects may contribute to possible antimutagenic and anticarcinogenic actions of the dithiocarbamates investigated.