Synthesis and hypoglycemic activity evaluation of rhein amide derivatives
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Med Chem Res (2013) 22:2228–2234 DOI 10.1007/s00044-012-0215-7
ORIGINAL RESEARCH
Synthesis and hypoglycemic activity evaluation of rhein amide derivatives Xiaokang Zhu • Xiaoli Ye • Liu Song • Yonghuang Luo Qing Tang • Yanan Jin • Xuegang Li
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Received: 1 November 2011 / Accepted: 24 August 2012 / Published online: 5 September 2012 Ó Springer Science+Business Media, LLC 2012
Abstract In order to investigate the relationship of the structure and hypoglycemic activity, rhein amide derivatives 2a–2e were synthesized and their hypoglycemic activities were evaluated by glucose consumption in HepG2. Their structures were characterized by 1H-, 13C NMR, IR, mass and elemental analysis. All the compounds exhibited strong hypoglycemic activity in improving glucose consumption in HepG2 cell assays in vitro, which was influenced by the diversity of rhein amide derivatives. The compounds 2a–c, 2f, and 2g bearing heterocyclic ring were proved to be more potentially useful in glucose consumption than dimethyldiguanide. Among all the compounds, compound 2f exhibited the strongest activity on glucose consumption, while compound 2d showed the weakest activity. Keywords Rhein derivatives Glucose consumption Hypoglycemic activity
X. Zhu Y. Luo Q. Tang Y. Jin X. Li (&) College of Pharmaceutical Sciences, Southwest University, Chongqing 400716, People’s Republic of China e-mail: [email protected] X. Zhu e-mail: [email protected] X. Ye School of Life Sciences, Southwest University, Chongqing 400715, People’s Republic of China L. Song School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People’s Republic of China
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Introduction Diabetes is a metabolic disease, seriously affecting people’s health and quality of life. Type II diabetes, the more prevalent form of diabetes, is characterized by insulin resistance of internal organs and peripheral tissues that results in impaired glucose utilization, and consequently, in abnormally high blood glucose levels between and especially after meals (Jan-Willem et al., 2011). It has been estimated that the number of adults affected by diabetes will grow from 135 million in 1995 to 300 million in 2025 worldwide (King et al., 1998; Benson et al., 2010). Hyperglycemia resulting from uncontrolled glucose regulation, which cause the disorder of fat and protein metabolism and even lead to cardiovascular disease, is widely recognized as the causal link between diabetes and diabetic complications (Anabela and Carlos, 2006; Brownlee, 2001). Therefore, it is of great importance to explore more effective and safer antihyperglycemic drugs, as a pharmacological tool to provide important information regarding treatment for diabetes. Currently, the diabetic drugs are structurally divided into two major classes, sulfonylureas and biguanides. Furthermore, other drugs such as a-glucosidase inhibitors are used as an auxiliary type for diabetes treatment. The development of more effective and safe hypoglycemic agents is still a challenge, due to fe
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