title: Solid-Phase Parallel Synthesis of N-Substituted-2-aminothiazolo[4,5-b]pyrazine Derivatives via Tandem Reaction of Isothiocyanate Terminated Resin with o-Bromo-2-Aminopyrazines.
abstract: A novel solid-phase synthesis methodology of N-substituted-2-aminothiazolo[4,5-b]pyrazine derivatives was developed. The key step in this synthesis strategy is the tandem reaction of isothiocyanate terminated resin 2 with o-bromo-2-aminopyrazine, affording cyclized 2-aminothiazolo[4,5-b]pyrazine resin 4. To increase the diversity of our library, Suzuki coupling reaction was performed at the position C6. Further functionalization of 2-aminothiazolo[4,5-b]pyrazine core skeleton with various electrophiles such as alkyl halides, acyl chlorides, and sulfonyl chlorides and cleavage from the resin with TFA in DCM generated N-alkyl-, N-acyl-, and N-sulfonyl-2-aminothiazolo[4,5-b]pyrazine derivatives. The physicochemical properties and the polar surface areas of synthesized compounds were evaluated.
authors: Innovative Drug Library Research Center, Department of Chemistry, College of Science, Dongguk University , 26, 3-ga, Pil-dong, Jung-gu, Seoul 04620, Korea.
authors: Aizhan
authors: A
authors: Abdildinova
authors: Innovative Drug Library Research Center, Department of Chemistry, College of Science, Dongguk University , 26, 3-ga, Pil-dong, Jung-gu, Seoul 04620, Korea.
authors: Seung-Ju
authors: SJ
authors: Yang
authors: Innovative Drug Library Research Center, Department of Chemistry, College of Science, Dongguk University , 26, 3-ga, Pil-dong, Jung-gu, Seoul 04620, Korea.
authors: Young-Dae
authors: YD
authors: Gong
mesh_terms: D003500:Cyclization; D017879:Isothiocyanates / Q000737:chemistry*; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D011719:Pyrazines / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D060327:Solid-Phase Synthesis Techniques / Q000379:methods*; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D017879:Isothiocyanates; D011719:Pyrazines; D013844:Thiazoles; C079424:2-aminopyrazine
keywords: BOMBA resin; solid-phase; tandem reaction; thiazolo[4,5-b]pyrazine