112177-79-4Relevant academic research and scientific papers
Novel Synthesis of Agaritine, a 4-Hydrazinobenzyl-Alcohol Derivative Occuring in Agaricaceae
Datta, Subir,Hoesch, Lienhard
, p. 1261 - 1267 (1987)
The 4-hydrazinobenzyl alcohol (3) was prepared (58percent) by diisobutylaluminiumhydride reduction of methyl 4-hydrazinobenzoate (4), whereas LiAlH4 of LiBH4 reduction of 4 proceeded further to yield (via intermediate 3) (4-tolylhydrazine (5).The alcohol 3 was stable under O2-free conditions and exhibited no tendency to eliminate H2O, neither thermally nor with H+ catalysis.Oxidation of 3 with SeO2 yielded 4-(hydroxymethyl)benzenediazonium ion (8), identified by its azo coupling product 9 with 2-naphthol.Condensation of 3 with 1-benzyl 5-hydrogen N-(benzyloxycarbonyl)-L-glutamate (1) in presence of dicyclohexylcarbodiimide afforded 82percent of N2-(benzyloxycarbonyl)-L-glutamic acid 1-(benzyl-ester) 5-(2-hydrazide) (11) which upon controlled hydrogenolysis (quinoline-sulfur-poisoned Pd/C catalyst) gave 82percent of L-glutamic acid 5-(2-hydrazide) (1), i.e. agaritine, a metabolite of Agaricus bisporus.Without poisoning of the catalyst, hydrogenolysis of (11) yielded L-glutamic acid 5-2-(4-tolyl)hydrazide) (12).
An azobenzene-based heteromeric prodrug for hypoxia-activated chemotherapy by regulating subcellular localization
Li, Shiying,Jiang, Xueyan,Zheng, Rongrong,Zuo, Shengjia,Zhao, Linping,Fan, Guiling,Fan, Jinghao,Liao, Yonghua,Yu, Xiyong,Cheng, Hong
, p. 7983 - 7986 (2018)
An azobenzene-based heteromeric prodrug (hNDP) was prepared for targeted chemotherapy against hypoxic tumor. hNDP could divert the parent drug from nucleus to cytoplasm with lower toxicity, while the azoreduction of hNDP in hypoxia would activate the drug with a robust anti-tumor effect by initiating the apoptosis-related biochemical cascades.
