6243-07-8Relevant academic research and scientific papers
Dihydrobenzoxazinone derivatives as aldose reductase inhibitors with antioxidant activity
Chen, Huan,Fan, Zhenya,Lei, Yanqi,Liu, Wenchao,Ma, Bing,Zhang, Xiaonan,Zhang, Xin,Zhu, Changjin
, (2020)
Dihydrobenzoxazinone based design and synthesis produced two series of compounds as aldose reductase (ALR2) inhibitor candidates. In particular, phenolic residues were embodied into the compounds for the combination of strengthening the inhibitory acitvity and antioxidant ability to retard the progression of diabetic complications. Most of the derivatives with styryl side chains exhibited excellent activities on selective ALR2 inhibition with IC50 values ranging from 0.082 to 0.308 μM, and {8-[2-(4-hydroxy-phenyl)-vinyl]-2-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl}-acetic acid (3a) was the most potent. More significantly, most of dihydrobenzoxazinone compounds revealed not only good inhibitory effect on ALR2, but also showed powerful antioxidant activity. Notably, phenolic compound 3a was even comparable to the well-known antioxidant Trolox, confirming that the C8 p-hydroxystyryl substitution was key structure of lowering oxidative stress. Therefore, these results provided an achievement of multifunctional ALR2 inhibitors possessing capacities for both ALR2 inhibition and as antioxidants.
Synthesis and metal complexation properties of bisbenzospiropyran chelators in water
Kumar, Satish,Chau, Cindy,Chau, Gordon,McCurdy, Alison
, p. 7097 - 7105 (2008/12/20)
As a step towards developing a light-controlled reversible binding switch based on photochromic bisbenzospiropyran for investigating intracellular calcium signaling, substituted bisbenzospiropyran and phenolic chelators were synthesized and examined for metal binding strength. The complexation of these compounds with alkaline earth and zinc ions in methanol and buffer was characterized using NMR and luminescence spectroscopies. An increased length of convergent ligands on the rigid scaffold maintained binding affinity for Ca2+ but decreased selectivity for Ca2+ over Mg2+. Results indicate that at least three carboxylate ligands are required for significant binding, and increased length of the ligands will result in a fully water-soluble photoswitch that exhibits two states with approximately 300-fold difference in binding affinity for Ca2+.
