1233940-89-0Relevant academic research and scientific papers
Synthesis and structure-activity relationship study of 8-hydroxyquinoline- derived Mannich bases as anticancer agents
Shaw, Arthur Y.,Chang, Chun-Yi,Hsu, Mei-Yuan,Lu, Pei-Jung,Yang, Chia-Ning,Chen, Hui-Ling,Lo, Cheng-Wei,Shiau, Chung-Wai,Chern, Ming-Kai
experimental part, p. 2860 - 2867 (2010/08/20)
To continue our early study on the structural modifications of clioquinol, more 8-hydroxyquinoline-derived Mannich bases were synthesized and examined for growth-inhibitory effect. Taken Mannich base 1 as our lead compound, upon replacement of either sulfonyl group with methylene group or piperazine ring with ethylenediamine group resulted in an appreciable increase in potency. On the other hand, as 8-hydroxyquinoline was replaced with phenol, 3-hydroxypyridine and 1-naphthol, a dramatic decrease in activity was observed, indicating that 8-hydroxyquinoline is a crucial scaffold for activity. Further 3D-QSAR analysis on HeLa cells revealed that both steric and electronic effects contributed equally to growth inhibition. Taken together, the structure-activity relationships obtained from both in vitro data and CoMFA model warrant a valuable reference for further study.
