10.1021/acscombsci.7b00174.s001
Ji-Eun Ha
Ji-Eun
Ha
Seung-Ju Yang
Seung-Ju
Yang
Young-Dae Gong
Young-Dae
Gong
Construction of 1,3,4-Oxadiazole and 1,3,4-Thiadiazole
Library with a High Level of Skeletal Diversity Based on Branching
Diversity-Oriented Synthesis on Solid-Phase Supports
American Chemical Society
2018
3 D-space
dehydrative cyclizations
diversity-oriented synthesis
DOS
oxadiazole
thiadiazole
drug-like properties
solid-supported resin
column chromatography
Branching Diversity-Oriented Synthesis
core skeleton resins
physicochemical properties
High Level
thiosemicarbazide resin
Skeletal Diversity
2018-01-08 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Construction_of_1_3_4-Oxadiazole_and_1_3_4-Thiadiazole_Library_with_a_High_Level_of_Skeletal_Diversity_Based_on_Branching_Diversity-Oriented_Synthesis_on_Solid-Phase_Supports/5817702
An
efficient solid-phase synthetic route for the construction of
1,3,4-oxadiazole and 1,3,4-thiadiazole libraries based on branching
diversity-oriented synthesis (DOS) has been developed in this study.
The core skeleton resins, 1,3,4-oxadiazole and 1,3,4-thiadiazole,
were obtained through desulfurative and dehydrative cyclizations of
thiosemicarbazide resin, respectively. Various functional groups have
been introduced to the core skeleton resins, such as aryl, amine,
amide, urea, thiourea, and an amino acid. Most of the libraries were
purified by simple trituration without extraction or column chromatography
after cleavage of the products from the solid-supported resin. As
a result, we obtained high yields of pure 1,3,4-oxadiazole and 1,3,4-thiadiazole
derivatives (total numbers = 128). Finally, we confirmed the drug-like
properties of our library by calculation of physicochemical properties,
displays of the skeletal diversities of the library in 3D-space, and
occupation of a broad range of areas by their functional groups.