Chemistry - A European Journal p. 8214 - 8220 (2021)
Update date:2022-08-03
Topics:
Ma, Fei
Li, Jie
Zhang, Shuning
Gu, Yuang
Tan, Tingting
Chen, Wanting
Wang, Shuyue
Ma, Peixiang
Xu, Hongtao
Yang, Guang
Lerner, Richard A.
DNA-encoded combinatorial chemical library (DEL) technology, an approach that combines the power of genetics and chemistry, has emerged as an invaluable tool in drug discovery. Skeletal diversity plays a fundamental importance in DEL applications, and relies heavily on novel DNA-compatible chemical reactions. We report herein a phylogenic chemical transformation strategy using DNA-conjugated benzoyl hydrazine as a common versatile precursor in azole chemical expansion of DELs. DNA-compatible reactions deriving from the common benzoyl hydrazine precursor showed excellent functional group tolerance with exceptional efficiency in the synthesis of various azoles, including oxadiazoles, thiadiazoles, and triazoles, under mild reaction conditions. The phylogenic chemical transformation strategy provides DELs a facile way to expand into various unique chemical spaces with privileged scaffolds and pharmacophores.
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