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Studies on hindered phenols and analogs. 1. Hypolipidemic and hypoglycemic agents with ability to inhibit lipid peroxidation
Abstract
A series of hindered phenols were investigated as hypolipidemic and/or hypoglycemic agents with ability to inhibit lipid peroxidation. 1,3-Benzoxathioles (9 and 22), phenoxypentanoic acid (34), phenoxypentanol (35a), phenoxynonanol (35b), phenylchloropropionic acid having a chromanyl group (25), and a thiazolidine compound (27) derived from 25, all having a hindered phenol group, were prepared and examined. Compound 27 showed the expected biological properties in vivo and in vitro without any liver weight increase. Biological activities of the analogous thiazolidine compounds, 43-58, were compared. Thus, (+/-)-5-[4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]- benzyl]-2,4-thiazolidinedione (27) (CS-045) was found to have all of our expected properties and was selected as a candidate for further development as a hypoglycemic and hypolipidemic agent.
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Citations
Cited by
Pathophysiology and Pharmacological Treatment of Insulin Resistance*
Matthaei, S., Stumvoll, M., Kellerer, M., & Häring, H.-U. (2000) · Endocrine Reviews · doi:10.1210/edrv.21.6.0413 · Cited by 377
Kassahun, K., Pearson, P. G., Tang, W., McIntosh, I., Leung, K., Elmore, C., Dean, D., Wang, R., Doss, G., & Baillie, T. A. (2001) · Chemical Research in Toxicology · doi:10.1021/tx000180q · Cited by 311
Henke, B. R., Blanchard, S. G., Brackeen, M. F., Brown, K. K., Cobb, J. E., Collins, J. L., Harrington, Hashim, M. A., Hull-Ryde, E. A., Kaldor, I., et al. (1998) · Journal of Medicinal Chemistry · doi:10.1021/jm9804127 · Cited by 301
Targeting Peroxisome Proliferator-Activated Receptors (PPARs): Development of Modulators
Pirat, C., Farce, A., Lebègue, N., Renault, N., Furman, C., Millet, R., Yous, S., Speca, S., Berthelot, P., Desreumaux, P., et al. (2012) · Journal of Medicinal Chemistry · doi:10.1021/jm101360s · Cited by 198
Metadata
- Authors
- Yoshioka, T., Fujita, T., Kanai, T., Aizawa, Y., Kurumada, T., Hasegawa, K., & Horikoshi, H.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1989-02
- Volume
- 32
- Issue
- 2
- Pages
- 421-428
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2001881588
- Cited by
- 221
- References
- 0
- FWCI
- 3.91
- Type
- journal article
- Language
- en
- Open access
- closed
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- Yoshioka, T., Fujita, T., Kanai, T., Aizawa, Y., Kurumada, T., Hasegawa, K., & Horikoshi, H. (1989). Studies on hindered phenols and analogs. 1. Hypolipidemic and hypoglycemic agents with ability to inhibit lipid peroxidation. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm00122a022
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