Department of Organic Chemistry, School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia in Katowice, 4 Jagiellońska Str., 41-200 Sosnowiec, Poland.
Department of Solid State Physics, Institute of Physics, University of Silesia, 4 Uniwersytecka Str., 40-007 Katowice, Poland.
Molecules. 2017 Nov 1;22(11):1876. doi: 10.3390/molecules22111876.
Betulin derivatives containing a 1,2,3-triazole ring possess a wide spectrum of biological activities, including antiviral, anticancer, and antibacterial activity. A series of novel triazoles were prepared by the 1,3-dipolar cycloaddition reaction between the alkyne derivatives of betulin and organic azides. The chemical structures of the obtained compounds were defined by ¹H and C NMR, IR, and high-resolution mass spectrometry (HR-MS) analysis. The target triazoles were screened for their antiviral activity against DNA and RNA viruses. The cytotoxic activity of the obtained compounds - and - was determined using five human cancer cell lines (T47D, MCF-7, SNB-19, Colo-829, and C-32) by a WST-1 assay. The bistriazole displayed a promising IC value (0.05 μM) against the human ductal carcinoma T47D (500-fold higher potency than cisplatin). The microdilution method was applied for an evaluation of the antimicrobial activity of all of the compounds. The triazole containing a 3'-deoxythymidine-5'-yl moiety exhibited antibacterial activity against two gram-negative bacteria vz. and (minimal inhibitory concentration (MIC) range of 0.95-1.95 μM).
含 1,2,3-三唑环的白桦脂衍生物具有广泛的生物活性，包括抗病毒、抗癌和抗菌活性。通过白桦脂烷衍生物与有机叠氮化物的 1,3-偶极环加成反应，制备了一系列新型三唑。通过 ¹H 和 C NMR、IR 和高分辨率质谱 (HR-MS) 分析确定了所得化合物的化学结构。对目标三唑进行了针对 DNA 和 RNA 病毒的抗病毒活性筛选。通过 WST-1 测定法，使用五种人癌细胞系 (T47D、MCF-7、SNB-19、Colo-829 和 C-32) 测定了所得化合物 - 和 - 的细胞毒性。双三唑 对人导管腺癌 T47D 显示出有希望的 IC 值（0.05 μM）（比顺铂高 500 倍）。采用微量稀释法评价所有化合物的抗菌活性。含有 3'-去氧胸苷-5'-基的三唑对两种革兰氏阴性菌 vz. 和 （最小抑菌浓度 (MIC) 范围为 0.95-1.95 μM）具有抗菌活性。
