53121-35-0Relevant academic research and scientific papers
Discovery of novel ketamine-inspired derivatives as a protective agent against renal ischemic/reperfusion injury in Wistar rats
Zhang, Yin,Zhu, Li
, (2022/05/23)
Renal ischemia-reperfusion (I/R) injury is a limiting factor for the success of renal grafts and is deemed greatly responsible for the mortality. A novel series of ketamine-inspired compounds was synthesized and subjected to NF-?B transcriptional inhibitory activity in LPS-stimulated RAW264.7 cells, where entire set of compounds showed mild-to-moderate significant NF-?B transcriptional inhibitory activity (IC50 6.53–67.52?μM). Compound 6d showed highest inhibitory activity among the tested series (IC50 2.62?μM) and found more potent as compared to ketamine as standard. The effect of compound 6d was further quantified in I/R injury in Wistar rats, where it dose-dependently improves kidney function of rats with significant amelioration of kidney injury as suggested by histopathologic examination of renal tissues. It further showed reduction in the generation of pro-inflammatory cytokines and improves the antioxidant status of experimental rats. Compound 6d inhibited apoptosis and increases the expression of Bcl2 and decreases Bax, and cleaved caspase-3?level. It further reduces TLR-4 and NF-κB expression in renal cells of rats, with increases in IκB-α level in Western blot analysis as compared to I/R group. In summary, our current study showed the development of a novel class of ketamine-inspired derivatives against renal ischemia/reperfusion injury.
Complex polycyclic lactams from pericyclic cascade reactions of Zincke aldehydes
Steinhardt, Sarah E.,Vanderwal, Christopher D.
supporting information; experimental part, p. 7546 - 7547 (2009/10/17)
(Chemical Equation Presented) In the course of a simple mechanistic study on the rearrangement of Zincke aldehydes to Z-α,β,γ,δ- unsaturated amides, a thermally induced pericyclic cascade rearrangement that converts Zincke aldehydes derived from allylic and homoallylic amines into polycyclic lactams was discovered. The key reaction involves an E-Z alkene isomerization, a 6? electrocyclic ring closure, a[1,5]-sigmatropic shift of hydrogen, a 6? electrocyclic ring-opening , and a Diels-Alder cycloaddition, and proceeds with excellent stereoselectivity. The unusual observation that furans and an indole serve as dienophiles in this cascade reaction permitted the synthesis of complex, functional group-rich tri- and tetracyclic lactams. In all cases, the rigid polycyclic products are available in only two steps from pyridinium salts and the allylic or homoallylic secondary amines.
