119th General Meeting of the KCS

Type Poster Presentation
Area 의약화학
Room No. 포스터발표장
Time 4월 20일 (목요일) 11:00~12:30
Code MEDI.P-425
Subject Solid-Phase Synthesis of 1,3,4-Thiadiazole Derivatives via Desulfurative Cyclization of Thiosemicarbazide Intermediate
Authors 양승주, ABDILDINOVA AIZHAN, 정선화, 공영대*
동국대학교 화학과, Korea
Abstract A 1,3,4-thiadiazole library was constructed by solid-phase organic synthesis. The key step of this solid-phase synthesis involves the preparation of polymer-bound 2-amido-5-amino-1,3,4- thiadiazole resin by the cyclization of thiosemicarbazide resin using p-TsCl as the desulfurative agent, followed by the functionalization of the resin by alkylation, acylation, alkylation/acylation, and Suzuki coupling reactions. Both the alkylation and acylation reactions chemoselectively occurred at the 2-amide position of 2-amido-5-amino-1,3,4-thiadiazole resin and the 5-amine position of 2-amido-5-amino-1,3,4-thiadiazole resin, respectively. Finally, these functionalized 1,3,4-thiadiazole resins were treated with trifluoroacetic acid in dichloromethane, generating myriad of 1,3,4-thiadiazole analogs in high yields and purities. The 1,3,4-thiadiazole derivatives show a different distribution of physicochemical and biological properties compared to our previously constructed 1,3,4-oxadiazole and 1,3,4-thiadiazole libraries in a range of orally available drug properties.
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