Głowacka Iwona E, Balzarini Jan, Wróblewski Andrzej E
Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Łódź, Poland.
Arch Pharm (Weinheim). 2014 Jul;347(7):506-14. doi: 10.1002/ardp.201300468. Epub 2014 Mar 25.
A new series of 4-substituted [(1,2,3-triazol-1-yl)acetamido]methylphosphonates as acyclic nucleotide analogs were synthesized from diethyl (2-chloroacetamido)methylphosphonate via azidation followed by 1,3-dipolar cycloaddition with selected alkynes derived from natural nucleobases or their mimetics. All compounds were tested for their antiviral activities against DNA and RNA viruses as well as for cytostatic activity or cytotoxicity. Among all tested compounds, [(1,2,3-triazol-1-yl)acetamido]methylphosphonate 6e substituted with the N(3)-Bz-benzuracil moiety showed activity against the vesicular stomatitis virus (EC50 = 45 µM) in HeLa cell cultures.
一系列新的4-取代[(1,2,3-三唑-1-基)乙酰胺基]甲基膦酸酯作为无环核苷酸类似物，由(2-氯乙酰胺基)甲基膦酸二乙酯经叠氮化反应，然后与衍生自天然核碱基或其模拟物的特定炔烃进行1,3-偶极环加成反应合成。所有化合物均针对DNA和RNA病毒进行了抗病毒活性测试，以及细胞生长抑制活性或细胞毒性测试。在所有测试化合物中，被N(3)-Bz-苯并尿嘧啶部分取代的[(1,2,3-三唑-1-基)乙酰胺基]甲基膦酸酯6e在HeLa细胞培养物中显示出对水泡性口炎病毒的活性(EC50 = 45 μM)。
