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Studies on Antidiabetic Agents. X. Synthesis and Biological Activities of Pioglitazone and Related Compounds.
Open accessAbstract
Various analogues of a new antidiabetic agent, pioglitazone (AD-4833, U-72107), were synthesized in order to study in more detail the structure-activity relationships of this class of drug. 5-(4-Pyridylalkylthiobenzyl)-2,4-thiazolidinediones (I), thia-analogues of pioglitazone, were prepared via Meerwein arylation of the alkylthioanilines (IV). 5-(4-Pyridylalkoxybenzylidene)-2,4-thiazolidinediones (IIa) and related heterocyclic analogues (IIb) were synthesized by Knoevenagel condensation of the aldehydes (VIII) with the corresponding azolidinones. Compounds I and II were evaluated for hypoglycemic and hypolipidemic activity in genetically obese and diabetic yellow KK (KKAy) mice. Several 5-[4-[2-(2-pyridyl)ethoxy]-benzylidene]-2,4- thiazolidinediones (IIa) were equipotent to pioglitazone. However, the thia-analogues (I) and the benzylideneheterocycles (IIb) had decreased activity. Catalytic hydrogenation of the 5-benzylidene analogue (14) was found to be a convenient new synthetic method for pioglitazone. The configuration of 14 is also discussed.
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Cited by
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
- MOMOSE, Y., MEGURO, K., IKEDA, H., HATANAKA, C., OI, S., & SOHDA, T.
- Venue
- Chemical and Pharmaceutical Bulletin
- Publisher
- Pharmaceutical Society of Japan
- Published
- 1991
- Volume
- 39
- Issue
- 6
- Pages
- 1440-1445
- ISSN
- 0009-2363 (ISSN-L)
- 1347-5223
- OpenAlex
- W2075080580
- Cited by
- 290
- References
- 0
- FWCI
- 1.77
- Type
- journal article
- Language
- en
- Open access
- bronze
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- MOMOSE, Y., MEGURO, K., IKEDA, H., HATANAKA, C., OI, S., & SOHDA, T. (1991). Studies on Antidiabetic Agents. X. Synthesis and Biological Activities of Pioglitazone and Related Compounds. Chemical and Pharmaceutical Bulletin. https://doi.org/10.1248/cpb.39.1440
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