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  • 09월 03일 23시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

제122회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Synthesis of novel biaryl sulfate core based hepatitis C virus NS5A inhibitors using sulfur(VI) fluoride exchange reaction

2018년 8월 30일 13시 36분 18초
ORGN.P-255 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
10월 18일 (목요일) 11:00~12:30
Organic Chemistry
저자 및
Youngsu You, Byeong Moon Kim*
Division of Chemistry, Seoul National University, Korea

A chemoselective coupling reaction between an arylsulfonyl fluoride and an aryl silyl ether is known as the sulfur(VI) fluoride exchange (SuFEx) reaction. This “sulfate click reaction” is extremely efficient and provides the desired products in essentially quantitative yields.

Our laboratory recently reported the discovery of biaryl sulfate core-based HCV NS5A inhibitors, which exhibit two-digit picomolar EC50 values against HCV genotype 1b and 2a. Herein, we demonstrate the utilization of the SuFEx chemistry to modify the structures of sulfate-core part of the NS5A inhibitors for further optimization of antiviral activities against HCV. The products obtained through the SuFEx click reactions were obtained in high yields. Among the compounds prepared through the SuFEx chemistry, products with potent NS5A inhibitors had two-digit picomolar EC50 values against GT-1b and single digit nanomolar activities against GT-2a strain of HCV. In addition, the biotinylated probe targeting NS5A protein and nonsymmetrical inhibitors containing an imidazole and amide linkers at the opposite sides of the core sulfate structures were also synthesized through the use of the same synthetic methodology.


1. You, Y. S.; Kim, H. S.; Bae, I. H.; Lee S. Gi.; Jee M. H.; Keum G. C.; Jang S. K.; Kim B. M., Eur. J. Med. Chem., 2017, 125, 87.

2. Bae, I. H.; Kim, H. S.; You, Y. S.; Chough, C.; Choe, W.; Seon, M. K.; Lee, S. G.; Keum, G.; Jang, S. K.; Kim, B. M., Eur. J. Med. Chem., 2015, 101, 163.

3. Bae, I. H.; Choi, J. K.; Chough, C.; Keum, S. J.; Kim, H.; Jang, S. K.; Kim, B. M., ACS Med. Chem. Lett., 2014, 5 (3), 255.