Multifunctional aldose reductase inhibitors based on 2H-benzothiazine 1,1-dioxide?
RSC Advances Pub Date: 2016-01-25 DOI: 10.1039/C5RA25984C
Abstract
A series of benzothiazine derivatives were designed and synthesized for the development of drug candidates for diabetic complications. A number of derivatives having a phenolic hydroxyl-substituted N2-aromatic side chain and a C4-acetic acid head group on the core structure were found to be potent and selective aldose reductase inhibitors. 8a with a phenolic 4-hydroxyl at N2-styryl side chain was proved to be the most active with an IC50 value of 0.094 μM. All compounds with the N2-styryl side chain showed good antioxidant activity using the DPPH radical scavenging test, and among them, compounds with phenolic hydroxyl-substituted N2-styryl were potent both in activities of ALR2 inhibition and antioxidation. The results suggest a success in the development of multifunctional aldose reductase inhibitors based on the benzothiazine framework.
Recommended Literature
- [1] Evolution of shape, size, and areal density of a single plane of Si nanocrystals embedded in SiO2 matrix studied by atom probe tomography Bin Han,Yasuo Shimizu,Gabriele Seguini,Celia Castro,Gérard Ben Assayag,Koji Inoue,Yasuyoshi Nagai,Sylvie Schamm-Chardon,Michele PeregoRSC Adv., 2016,6, 3617-3622 10.1039/C5RA26710B
- [2] Essential effect of the electrolyte on the mechanical and chemical degradation of LiNi0.8Co0.15Al0.05O2 cathodes upon long-term cycling?? Xiaoming Liu,Zachary D. Hood,Wangda Li,Donovan N. Leonard,Arumugam Manthiram,Miaofang ChiJ. Mater. Chem. A, 2021,9, 2111-2119 10.1039/D0TA07814J
- [3] Fate of Sb(v) and Sb(iii) species along a gradient of pH and oxygen concentration in the Carnoulès mine waters (Southern France) Eléonore Resongles,Corinne Casiot,Fran?oise Elbaz-Poulichet,Rémi Freydier,Odile Bruneel,Christine Piot,Sophie Delpoux,Aurélie Volant,Angélique DesoeuvreEnviron. Sci.: Processes Impacts, 2013,15, 1536-1544 10.1039/C3EM00215B
- [4] Emulsifier-free, organotellurium-mediated living radical emulsion polymerization (emulsion TERP) of styrene: poly(dimethylaminoethyl methacrylate) macro-TERP agent? Yukiya KitayamaPolym. Chem., 2014,5, 2784-2792 10.1039/C3PY01539D
- [5] Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)? Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. LlewellynChem. Commun., 2007, 3291-3293 10.1039/B703468G
- [6] Fe/Fe3C@C nanoparticles encapsulated in N-doped graphene–CNTs framework as an efficient bifunctional oxygen electrocatalyst for robust rechargeable Zn–air batteries? Zhiyan Chen,Nan Wu,Yaobing Wang,Bing Wang,Yingde WangJ. Mater. Chem. A, 2018,6, 516-526 10.1039/C7TA08423D
- [7] Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings Analyst, 1996,121, 785-788 10.1039/AN9962100785
- [8] Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China? Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing LiFood Funct., 2018,9, 4234-4245 10.1039/C8FO00787J
- [9] Excited state dynamics of symmetric and asymmetric Cr3(dpa)4Cl2 measured using femtosecond transient absorption spectroscopy? Chao-Han Cheng,Wen-Zhen Wang,Shie-Ming Peng,I-Chia ChenPhys. Chem. Chem. Phys., 2017,19, 25471-25477 10.1039/C7CP03968A
- [10] Evidence that the availability of an allylic hydrogen governs the regioselectivity of the Wacker oxidation Matthew J. Gaunt,Jinquan Yu,Jonathan B. SpencerChem. Commun., 2001, 1844-1845 10.1039/B103066N
Journal Name：RSC Advances
research_products
-
CAS no.: 89640-58-4
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)