Glycosides of N-hydroxy-N-arylamine derivatives. Part 1. Synthesis and mutagenicity of O-glucosides of N-Hydroxy-N-arylamines and their acetohydroxamic acids
Glycosides of N-hydroxy-N-arylamine derivatives. Part 1. Synthesis and mutagenicity of O-glucosides of N-Hydroxy-N-arylamines and their acetohydroxamic acids
复制标题
N-羟基-N-芳胺衍生物的苷。
DOI：
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发表时间：
1985
期刊：
影响因子：
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通讯作者：
T. Uematsu
中科院分区：
文献类型：
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作者：
T. Yoshioka;T. Uematsu
N-乙酰基-N-芳基氨基 β-D-吡喃葡萄糖苷 (7a-d) 是通过原酸酯糖基化方法通过 N-芳基氨基 β-D-吡喃葡萄糖苷 (6a-d) 合成的，并且分子中具有 N-O-C-1 键的 N-乙酰酰胺通过化学、酶促和光谱分析进行了表征。在使用鼠伤寒沙门氏菌 TA100 菌株（有或没有豚鼠肝脏的各种细胞内部分）进行的突变测定中，这些糖苷（7a-d）本身不具有诱变性，但在线粒体后上清液（S9）或微粒体部分（Ms）存在的情况下表现出诱变活性，除了糖苷（7a）之外。在糖苷 (7b-d) 中，氯原子较少的化合物比具有多个氯的化合物更能有效地诱导突变。在可溶性上清液级分(S10.5)存在的情况下没有观察到诱变活性。糖苷 (7b-d) 的致突变性似乎是由于微粒体脱乙酰酶水解形成相应的 N-脱乙酰化合物 (6b-d)。讨论了糖苷 (7b-d) 的代谢激活途径。
N-Acetyl-N-arylamino β-D-glucopyranosides (7a–d) were synthesized by the orthoester glycosylation method via N-arylamino β-D-glucopyranosides (6a–d), and the N-acetyl amides, having an N–O–C-1 linkage in their molecules, were characterized by chemical, enzymatic, and spectral analyses. In the mutation assay using Salmonella typhimurium TA100 strain with or without various intracellular fractions of guinea pig liver, these glucosides (7a–d) were non-mutagenic per se, but showed mutagenic activity in the presence of the post-mitochondrial supernatant (S9) or the microsomal fraction (Ms), except for the glucoside (7a). Of the glucosides (7b–d), the compounds having fewer chlorine atoms were more effective in inducing mutations than were those having multiple chlorines. No mutagenic activity was observed in the presence of the soluble supernatant fraction (S10.5). The mutagenicity of the glucosides (7b–d) seemed to be due to the corresponding N-deacetylated compounds (6b–d) formed through hydrolysis by a microsomal deacetylase(s). The pathway of the metabolic activation of the glucosides (7b–d) is discussed.