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Synthesis and antiproliferative activity of new hybrids bearing neocryptolepine, acridine and α-aminophosphonate scaffolds
Journal of the Iranian Chemical Society ( IF 2.2 ) Pub Date : 2020-01-21 , DOI: 10.1007/s13738-019-01849-2
Abdullah A. S. Ahmed , Hanem M. Awad , Ibrahim El-Tantawy El-Sayed , Ahmed A. El Gokha

Synthesis of novel α-aminophosphonate hybrids 8a–f was accomplished by the reaction of 11-phenoxy-4-formylneocryptolepine 3, aminoalkylamino acridines 6a–f and diphenyl phosphite 7 in the presence of lithium perchlorate as Lewis acid catalyst in methanol. The starting aldehyde 3 was obtained by reaction of 11-chloroneocryptolpine 1 with 4-hydroxybenzaldehyde 2 in the presence of potassium carbonate in DMF, whereas 9-aminoalkylamino acridines 6a–f were synthesized by reaction of 9-chloroacridine 4 with appropriate diamines 5a–f. The structure of all synthesized hybrids was confirmed by spectroscopic methods and showed spectra in consistence with the expected structures. The antiproliferative activity of all synthesized hybrids was evaluated against HCT-116, MCF-7, HepG2 and A549 human cancer cell lines. The screened results proved that most of the reported compounds are potent, especially hybrid 8a, which displayed the highest activity against MCF-7, HepG2 and A549 cancer cell lines with IC50 8.2, 23.1 and 19.4 µM, respectively. This activity is significantly higher than the standard drug doxorubicin. Moreover, hybrid 8f showed most potent activity against HCT-116 cancer cell line with IC50 2.4 µM higher than the reference drug doxorubicin (IC50:10.90 µM).

中文翻译:

带有新隐油菜籽,a啶和α-氨基膦酸酯支架的新杂种的合成及其抗增殖活性

新型α-氨基膦酸酯杂化物8a-f的合成是在高氯酸锂作为路易斯酸催化剂在甲醇中的条件下,使11-苯氧基-4-甲酰基新隐油菜籽油3,氨基烷基氨基a啶6a-f和亚磷酸二苯酯7反应完成的。在碳酸钾存在下,DMF中11-氯代新隐油菜碱1与4-羟基苯甲醛2反应得到起始醛3,而9-氯代ac啶4与适当的二胺5a-f反应合成9-氨基烷基氨基a啶6a -f。。所有合成的杂种的结构通过光谱学方法确认,并显示与预期结构一致的光谱。评估了所有合成杂种对HCT-116,MCF-7,HepG2和A549人癌细胞系的抗增殖活性。筛选结果证明,大多数报道的化合物都是有效的,尤其是杂种8a,其对MCF-7,HepG2和A549癌细胞的活性最高,分别为IC 50 8.2、23.1和19.4 µM。该活性明显高于标准药物阿霉素。此外,杂种8f对HCT-116癌细胞系表现出最有效的活性,IC 50比参考药物阿霉素(IC 50)高2.4 µM。50:10.90 µM)。
更新日期:2020-01-21
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