| Literature DB >> 20359788 |
Arthur Y Shaw1, Chun-Yi Chang, Mei-Yuan Hsu, Pei-Jung Lu, Chia-Ning Yang, Hui-Ling Chen, Cheng-Wei Lo, Chung-Wai Shiau, Ming-Kai Chern.
Abstract
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. Copyright (c) 2010 Elsevier Masson SAS. All rights reserved.Entities:
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Year: 2010 PMID： 20359788 DOI： 10.1016/j.ejmech.2010.03.008
Source DB: PubMed Journal: Eur J Med Chem ISSN： 0223-5234 Impact factor: 6.514