三氮烯吲唑和三氮烯吡唑的合成及其抗增殖活性：一项比较研究。

Synthesis and antiproliferative activity of triazenoindazoles and triazenopyrazoles: a comparative study.

作者信息

Daidone Giuseppe, Raffa Demetrio, Maggio Benedetta, Valeria Raimondi Maria, Plescia Fabiana, Schillaci Domenico

机构信息

Dipartimento di Chimica e Tecnologie Farmaceutiche, Università degli Studi di Palermo, via Archirafi 32, 90123 Palermo, Italy.

出版信息

Eur J Med Chem. 2004 Mar;39(3):219-24. doi: 10.1016/j.ejmech.2003.11.012.

DOI:10.1016/j.ejmech.2003.11.012

PMID:15051169

Abstract

Several triazenoindazoles and triazenopyrazoles were prepared transforming the appropriate aminoindazoles and aminopyrazoles in the corresponding diazonium salts which were reacted with dimethylamine, diethylamine and pyrrolidine. All the triazenes were tested for their antiproliferative activity against K562, HL60, L1210 and MCF7 cell lines. The biological data showed that the benzocondensation plays a positive role on the antiproliferative activity. The (1)H-NMR spectra showed that the rotational barrier around the N(2)-N(3) bond in the triazene group can be influenced both by the position of this group in the indazole nucleus and by the substitution pattern in the benzene moiety.

摘要

通过将相应的氨基吲唑和氨基吡唑转化为相应的重氮盐，并使其与二甲胺、二乙胺和吡咯烷反应，制备了几种三氮烯并吲唑和三氮烯并吡唑。测试了所有三氮烯对K562、HL60、L1210和MCF7细胞系的抗增殖活性。生物学数据表明，苯并缩合对抗增殖活性起积极作用。(1)H-NMR光谱表明，三氮烯基团中N(2)-N(3)键周围的旋转势垒既受该基团在吲唑核中的位置影响，也受苯部分的取代模式影响。