Miao, Shi-Xing; Wan, Lin-Xi; He, Zhen-Xiang; Zhou, Xian-Li; Li, Xiaohuan; Gao, Feng published their research in Journal of Natural Products in 2021. The article was titled 《Pd-Catalyzed Direct Diversification of Natural Anti-Alzheimer’s Disease Drug: Synthesis and Biological Evaluation of N-Aryl Huperzine A Analogues》.SDS of cas: 2398-37-0 The article contains the following contents:
The first systematic direct diversification of a complex natural product by metal-catalyzed N-H functionalization was carried out. A new series of N-(hetero)aryl analogs I (Ar = Ph, 2-naphthyl, 4-methylpyridin-2-yl, etc.) of the natural anti-Alzheimer’s disease drug huperzine A (HPA) was prepared via palladium-catalyzed Buchwald-Hartwig cross-coupling reactions of HPA with various aryl bromides ArBr in good yields. Most of the N-aryl-huperzine A (N-aryl-HPA) analogs showed good acetylcholinesterase (AChE) inhibitory activity in in vitro experiments Three arylated huperzine A analogs I (Ar = 4-FC6H4, 4-methoxy-2,6-dimethylphenyl, 5-methoxypyridin-2-yl) exhibited stronger anti-AChE activity than HPA. The 5-methoxy-2-pyridyl analog I (Ar = 5-methoxypyridin-2-yl) displayed the most potent AChE inhibition activity, with an IC50 value of 1.5μM, which was 7.6-fold more active than HPA. Compound I (Ar = 5-methoxypyridin-2-yl) also exhibited better neuroprotective activity for H2O2-induced damage in SH-SY5Y cells than HPA. Structure-activity relationship anal. suggested that the electron d. of the installed aromatic ring or heteroaromatic ring played a significant role in inducing the AChE inhibition activity. Overall, compound I (Ar = 5-methoxypyridin-2-yl) showed the advantages of easy synthesis, high potency and selectivity, and improved neuroprotection, making it a potential huperzine-type lead compound for Alzheimer’s disease drug development. In the experimental materials used by the author, we found 1-Bromo-3-methoxybenzene(cas: 2398-37-0SDS of cas: 2398-37-0)
1-Bromo-3-methoxybenzene(cas: 2398-37-0) is a compound useful in organic synthesis and other chemical processes. It is an intermediate used for pharmaceuticals, perfumes and agrochemicals.SDS of cas: 2398-37-0
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem