Harkala Karna Ji, Eppakayala Laxminarayana, Maringanti Thirumala Chary
Department of Physics and Chemistry, Mahatma Gandhi Institute of Technology, Chaitanya Bharathi, Gandipet, Hyderabad, 500075, India.
Department of Chemistry, College of Engineering, Jawaharlal Nehru Technological University, Hyderabad, Nachupally, Karimnagar, 505501, India.
Org Med Chem Lett. 2014 Dec;4(1):14. doi: 10.1186/s13588-014-0014-x. Epub 2014 Dec 2.
Benzimidazoles and triazoles are useful structures for research and development of new pharmaceutical molecules and have received much attention in the last decade because of their highly potent medicinal activities.
A simple and efficient synthesis of triazole was carried out by treatment of 2-(4-azidophenyl)-1H-benzo[d]imidazole (6) with different types of terminal alkynes in t-BuOH/H2O, sodium ascorbate, and Zn(OTf)2, screened for cytotoxicity assay and achieved good results. A series of new benzimidazole-linked 1,2,3-triazole (8a-i) congeners were synthesized through cyclization of terminal alkynes and azide. These synthesized congeners 8a-i were evaluated for their cytotoxicity against five human cancer cell lines. These benzimidazole-linked 1,2,3-triazole derivatives have shown promising activity with IC50 values ranging from 0.1 to 43 μM. Among them, the compounds (8a, 8b, 8c, and 8e) showed comparable cytotoxicity with adriamycin control drug.
In conclusion, we have developed a simple, convenient, and an efficient convergent approach for the synthesis of benzimidazole-linked 1,2,3-triazole congeners as agents. Graphical Abstract Synthesis of 1,2,3-triazole derivatives.
苯并咪唑和三唑是新型药物分子研发中有用的结构，在过去十年中因其高效的药用活性而备受关注。
通过在叔丁醇/水、抗坏血酸钠和三氟甲磺酸锌存在下，用不同类型的末端炔烃处理2-(4-叠氮基苯基)-1H-苯并[d]咪唑(6)，进行了一种简单高效的三唑合成方法，并对其进行细胞毒性测定筛选，取得了良好结果。通过末端炔烃与叠氮化物的环化反应合成了一系列新的苯并咪唑连接的1,2,3-三唑(8a-i)同系物。对这些合成的同系物8a-i针对五种人类癌细胞系的细胞毒性进行了评估。这些苯并咪唑连接的1,2,3-三唑衍生物表现出有前景的活性，IC50值范围为0.1至43μM。其中，化合物(8a、8b、8c和8e)与阿霉素对照药物表现出相当的细胞毒性。
总之，我们开发了一种简单、方便且高效的收敛方法来合成作为药剂的苯并咪唑连接的1,2,3-三唑同系物。图形摘要1,2,3-三唑衍生物的合成。
