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A convenient synthesis, reactions and biological evaluation of novel pyrazolo[3,4- b ]selenolo[3,2- e ]pyrazine heterocycles as potential anticancer and antimicrobial agents
Medicinal Chemistry Research ( IF 2.6 ) Pub Date : 2020-09-22 , DOI: 10.1007/s00044-020-02635-z
Remon M. Zaki , Mokhtar A. Abdul-Malik , Saber H. Saber , Shaban M. Radwan , Adel M. Kamal El-Dean

A novel series of 5-amino-6-substituted-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]selenolo[3,2-e]pyrazines (3a–e) was synthesized by the reaction of the chloro pyrazolo[3,4-b]pyrazine carbonitrile 1 with selenium element in the presence of sodium borohydride and ethanol, followed by the reaction with α-halo alkylating agents to produce the selanyl-alkylated derivatives 2a–e. The latter compounds underwent Thorpe-Ziegler cyclization upon heating with ethanolic sodium ethoxide solution to afford the target selenolopyrazolopyrazine compounds. The 5-amino-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]selenolo[3,2-e]pyrazine-6-carboxamide (3b) was used as a versatile precursor for synthesis of new heterocyclic fused to the pyrazoloselenolopyrazine moiety namely: pyrimidine and imidazopyrimidine. Assignment of the chemical structures for the newly synthesized compounds was confirmed on the bases of elemental and spectral techniques including FT-IR, 1H NMR, 13C NMR, and mass spectra. Furthermore, certain compounds were screened for their antimicrobial activity which revealed remarkable activities against various pathogenic strains of bacteria and fungi. Alternatively, some of these compounds exhibited promising anticancer action against some colon and breast cancer cells.



中文翻译:

新型吡唑并[3,4-b]硒代[3,2-e]吡嗪杂环化合物作为潜在的抗癌和抗菌药物的便捷合成,反应和生物学评价

新型的5-氨基-6-取代-3-甲基-1-苯基-1H-吡唑并[3,4- b ]硒并[3,2- e ]吡嗪(3a–e)的反应是合成的。在硼氢化钠和乙醇的存在下,用硒元素引发的氯吡唑并[3,4-b]吡嗪腈1和硒元素,然后与α-卤代烷基化剂反应生成硒代烷基化衍生物2a-e。后者的化合物在乙醇乙醇钠溶液中加热后进行Thorpe-Ziegler环化反应,得到目标硒代吡唑并吡咯并吡嗪化合物。5-氨基-3-甲基-1-苯基-1 H-吡唑并[3,4- b ]硒代[3,2-e ]吡嗪-6-羧酰胺(3b)用作合成与吡唑并硒代吡喃并吡嗪部分嘧啶和咪唑并嘧啶的新杂环的通用前体。在包括FT-IR,1 H NMR,13 C NMR和质谱在内的元素和光谱技术的基础上,确认了新合成化合物的化学结构分配。此外,筛选了某些化合物的抗微生物活性,这些化合物显示出对细菌和真菌的各种致病菌株的显着活性。或者,这些化合物中的一些对某些结肠和乳腺癌细胞表现出有希望的抗癌作用。

更新日期:2020-10-07
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