Han, Chaebin Choi, Sun Yu, Jinha 2024-01-19T09:30:29Z 2024-01-19T09:30:29Z 2023-08-02 2023-06 0040-4020 https://pubs.kist.re.kr/handle/201004/113628 Urea-functionalized nucleobases and nucleosides have emerged as versatile compounds with potential applications in a wide range of fields. Conventionally, the synthesis of urea involves the reaction of isocyanates with nucleobases and nucleosides. In contrast, this study presents a novel and efficient one pot method for the synthesis of urea-substituted nucleobases and nucleosides without the use of isocyanates. The reaction was carried out in the presence of DMAP and TBPP, resulting in moderate to good yields of various urea-substituted nucleobases and nucleosides. Notably, N6-(N-threonyl-carbonyl) adenosine was also synthesized using this method. Furthermore, the synthesized compounds with adenine scaffold were evaluated for their binding affinity to adenosine receptors, but none of them exhibited binding, indicating a need for further modifications. These findings hold great promise for the facile synthesis of urea-functionalized nucleobases and nucleosides with potential applications in various fields. & COPY; 2023 Published by Elsevier Ltd. English Pergamon Press Ltd. DMAP and TBPP-mediated synthesis of urea-substituted nucleobases and nucleosides Article 10.1016/j.tet.2023.133472 1 Tetrahedron, v.140 Tetrahedron 140 N scie scopus 001027541700001 2-s2.0-85160323013 Chemistry, Organic Chemistry Article DERIVATIVES ANALOGS CANCER Urea Nucleoside Adenine DMAP TBPP