1750-81-8Relevant academic research and scientific papers
A KHSO4 mediated facile synthesis of 2-amino-1,3,4-oxadiazole derivatives
Gan, Zongjie,Han, Lei,Hu, Xiangnan,Long, Binyu,Tang, Qiang,Tian, Binghua,Wang, Chenyu,Wang, Zifan,Wu, Yue,Yu, Yu
supporting information, (2021/08/18)
A novel, efficient and mild KHSO4 mediated synthesis for 2-amino-1,3,4-oxadiazoles has been established via the cyclodesulfurization of benzoylhydrazine and isothiocyanate derivatives in one pot. The reactions proceeded smoothly at room tempera
Synthesis of 2-Amino-1,3,4-oxadiazoles through Elemental Sulfur Promoted Cyclization of Hydrazides with Isocyanides
Bao, Wenhu,Chen, Chuang,Yi, Niannian,Jiang, Jun,Zeng, Zebing,Deng, Wei,Peng, Zhihong,Xiang, Jiannan
, p. 1611 - 1618 (2017/10/06)
A novel sulfur-promoted cyclization of hydrazides and isonitriles to produce 1,3,4-oxadiazole has been developed. The method is operationally simple and compatible with a wide scope of substrates and various 2-amino- 1,3,4-oxadiazoles are efficiently obtained in good yields.
Oxadiazoles in medicinal chemistry
Bostr?m, Jonas,Hogner, Anders,Llinàs, Antonio,Wellner, Eric,Plowright, Alleyn T.
, p. 1817 - 1830 (2012/05/05)
Oxadiazoles are five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom, and they exist in different regioisomeric forms. Oxadiazoles are frequently occurring motifs in druglike molecules, and they are often used with the intention of being bioisosteric replacements for ester and amide functionalities. The current study presents a systematic comparison of 1,2,4- and 1,3,4-oxadiazole matched pairs in the AstraZeneca compound collection. In virtually all cases, the 1,3,4-oxadiazole isomer shows an order of magnitude lower lipophilicity (log D), as compared to its isomeric partner. Significant differences are also observed with respect to metabolic stability, hERG inhibition, and aqueous solubil ity, favoring the 1,3,4-oxadiazole isomers. The difference in profile between the 1,2,4 and 1,3,4 regioisomers can be rationalized by their intrinsically different charge distributions (e.g., dipole moments). To facilitate the use of these heteroaromatic rings, novel synthetic routes for ready access of a broad spectrum of 1,3,4-oxadiazoles, under mild conditions, are described.
