Teleb Mohamed A Mohamed, Kamel Monica G, Mikhail Madonna S, Hassaneen Hamdi M, Erian Ayman W, Helmy Mirna T
Department of Chemistry, Faculty of Science, Cairo University, Giza, 12613, Egypt.
BMC Chem. 2025 Jul 8;19(1):204. doi: 10.1186/s13065-025-01557-4.
Stirring of 2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)acetonitrile 1 with thiophene-2-carbaldehyde 2 in absolute ethanol in the presence of hydrochloric acid yielded 2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)-3-(thiophen-2-yl)acrylonitrile hydrochloride 3. Refluxing of arylidene 3 with α-ketohydrazonoyl halides 4-7 in the presence of triethylamine in chloroform afforded dihydropyrrolo[2,1-a]isoquinolines 11-14. Claisen-Schmidt condensation of 11 with aryl aldehydes 15a-f or pyrazole aldehydes 17a-d in ethanol in the presence of sodium hydroxide solution produced chalcones 16a-f and 18a-d. Refluxing of chalcone 16f with hydrazine hydrate in ethanol afforded pyrazoline 19 which gave N-phenylcarbothioamide derivative 20 on stirring with phenyl isothiocyanate in dry ether. Also, refluxing of 19 with acetic anhydride or formic acid afforded acetyl-pyrazoline derivative 21 or formyl-pyrazoline derivative 22, respectively. Antitumor activity for some new synthesized compounds showed that compounds 16b and 16d had anticancer activities. Antimicrobial activities for the newly synthesized compounds revealed the most potent compounds 16c, 18b and 18d against E. coli, compounds 16b, 18b and 18d against B. mycoides, and compounds 16b, 16c and 18b against C. albicans. Moreover, compound 18b had the lowest MIC values against E. coli and B. mycoides, with MIC values of 40 and 60 µg/ml, respectively.
在盐酸存在下，将2-(6,7-二甲氧基-3,4-二氢异喹啉-1-基)乙腈1与噻吩-2-甲醛2在无水乙醇中搅拌，得到2-(6,7-二甲氧基-3,4-二氢异喹啉-1-基)-3-(噻吩-2-基)丙烯腈盐酸盐3。在三乙胺存在下，将亚芳基3与α-酮腙酰卤4 - 7在氯仿中回流，得到二氢吡咯并[2,1 - a]异喹啉11 - 14。在氢氧化钠溶液存在下，将11与芳醛15a - f或吡唑醛17a - d在乙醇中进行克莱森 - 施密特缩合反应，生成查耳酮16a - f和18a - d。在乙醇中，将查耳酮16f与水合肼回流得到吡唑啉19，在干燥乙醚中与异硫氰酸苯酯搅拌时，吡唑啉19生成N - 苯基硫代甲酰胺衍生物20。此外，将19与乙酸酐或甲酸回流，分别得到乙酰基吡唑啉衍生物21或甲酰基吡唑啉衍生物22。对一些新合成化合物的抗肿瘤活性研究表明，化合物16b和16d具有抗癌活性。对新合成化合物的抗菌活性研究表明，化合物16c、18b和18d对大肠杆菌最有效，化合物16b、18b和18d对蕈状芽孢杆菌最有效，化合物16b、16c和18b对白色念珠菌最有效。此外，化合物18b对大肠杆菌和蕈状芽孢杆菌的最低抑菌浓度值最低，分别为40和60μg/ml。
