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  • 09월 04일 17시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

제114회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Privileged Substructure-Based Diversity-Oriented Synthesis Pathway for Diverse Pyrimidine-Embedded Polyheterocycles

2014년 9월 1일 17시 00분 01초
ORGN.O-1 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
금 10시 : 00분
유기화학 - Oral Presentation for Young Organic Chemists
저자 및
김희준, 박승범*
서울대학교 화학부, Korea
Facile fabrication of a structurally diverse small-molecule library plays a crucial role in drug discovery and chemical biology. In particular, the unbiased collection of small molecules has become an inevitable resource because it can provide a unique opportunity for the identification of novel chemical entities from phenotype-based screening, which is the leading approach for the development of first-in-class drugs. Diversity-oriented synthesis (DOS) plays an indispensable role to access the unexplored molecular frameworks with maximum structural and stereo-chemical diversity. Along with this endeavor, we proposed a privileged substructure-based DOS (pDOS) for the efficient generation of distinct polyheterocyclic core skeletons embedded with privileged substructures. Pyrimidine has been extensively explored in synthetic and medicinal chemistry owing to its unique mimicking of nucleosides and hydrogen bonding ability with nucleic acids in biological systems. We developed a new pDOS strategy with pyrimidine as the privileged substructure. Five core skeletons were synthesized by silver- or iodine-mediated cascade cyclization with various amines under different reaction conditions. The resulting discrete scaffolds consist of unique pyrimidine-embedded polyheterocycles fused with distinct sizes and orientation. This pDOS strategy allows the fabrication of unique polyheterocycles along with a wide spatial coverage around pyrimidine as the privileged substructure that ensures high potential for molecular interactions with biopolymers in a selective and specific manner.