1464-99-9Relevant academic research and scientific papers
Zn(OTf)2-catalyzed, microwave-promoted synthesis of 2-substituted 5-methyloxazoles from propargylic amides
Safrygin, Alexander,Dar'in, Dmitry,Lukin, Alexei,Bakholdina, Anna,Sapegin, Alexander,Krasavin, Mikhail
supporting information, p. 777 - 779 (2019/02/13)
The versatile conversion of propargylic amides to the respective 2-substituted 5-methyloxazoles was efficiently catalyzed by Zn(OTf)2 (5 mol%) under microwave irradiation in toluene. The method was applicable to a wide range of aliphatic, aroma
Glycosyl triazoles as novel insect β-N-acetylhexosaminidase OfHex1 inhibitors: Design, synthesis, molecular docking and MD simulations
Dong, Lili,Shen, Shengqiang,Chen, Wei,Lu, Huizhe,Xu, Dongdong,Jin, Shuhui,Yang, Qing,Zhang, Jianjun
, p. 2315 - 2322 (2018/12/11)
The insect enzyme GH20 β-N-acetyl-D-hexosaminidase OfHex1 represents an important chitinolytic enzyme found in the agricultural pest Ostrinia furnacalis (Guenée) and inhibition of this enzyme has been considered a promising strategy for the development of eco-friendly pesticides. In this article, based on the structure of the catalytic domains of OfHex1, a series of novel glycosyl triazoles were designed and synthesized via Cu-catalyzed azide-alkyne [3+2] cycloaddition reaction. To investigate the potency and selectivity of these glycosyl triazoles, the inhibition activities towards OfHex1 and HsHexB (human β-N-acetylhexosaminidase B) were studied. Particularly compound 17c (OfHex1, Ki = 28.68 μM; HsHexB, Ki > 100 μM) exhibited a suitable activity and selectivity against OfHex1. Furthermore, the possible inhibitory mechanisms of 17c with OfHex1 were studied using molecular docking and MD simulations. The structure-activity relationship results as well as the formed binding patterns may provide promising insights into the further development of novel OfHex1 inhibitors.
Palladium-Catalyzed Cascade Difluoroalkylation/Cyclization of N-Propargylamides: Synthesis of Oxazoles and Oxazolines
Ma, Jun-Wei,Wang, Qiang,Wang, Xin-Gang,Liang, Yong-Min
, p. 13296 - 13307 (2018/11/02)
A palladium-catalyzed process to construct oxazoles and oxazolines with broad functional-group tolerance has been developed, and the method introduces difluoromethyl groups into heterocycles in a one-pot fashion. This system uses a carbonyl oxygen as the acceptor for the addition of a vinylpalladium intermediate to achieve the cyclization. Oxazoline derivatives are generated as the Z-isomer with high stereoselectivity. Additionally, we validated the tentative mechanism of this reaction.
Cu(I)-catalyzed synthesis of dihydropyrimidin-4-ones toward the preparation of β- And β3-amino acid analogues
Rajagopal, Basker,Chen, Ying-Yu,Chen, Chun-Chi,Liu, Xuan-Yu,Wang, Huei-Ren,Lin, Po-Chiao
supporting information, p. 1254 - 1264 (2014/03/21)
A copper(I)-catalyzed synthesis of substituted dihydropyrimidin-4-ones from propargyl amides via the formation of ketenimine intermediate has been successfully developed; the synthesis afforded good isolated yields (80-95%). The mild reaction conditions at room temperature allow the reaction to proceed to completion in a few hours without altering the stereochemistry. Further, by involving a variety of reactive nucleophiles, the obtained substituted dihydropyrimidin-4-ones were elegantly transformed into the corresponding β- and β3-amino acid analogues.
