Synthesis and Evaluation of 3,4-Dihydropyrimidin-2(1H)-ones as Sodium Iodide Symporter Inhibitors

ChemMedChem

Volumn 8, Issue 1, 2013, Pages 104-111

  Lacotte, Pierre ^a   Puente, Celine ^a   Ambroise, Yves ^a  

^a SERVICE DE CHIMIE BIOORGANIQUE ET DE MARQUAGE   (France)

Author keywords

Dihydropyrimidones; Inhibitors; Membrane proteins; Sodium iodide symporter; Structure activity relationships

Indexed keywords

3,4 DIHYDROPYRIMIDIN 2(1H) ONE; PROTEIN INHIBITOR; SODIUM IODIDE SYMPORTER; UNCLASSIFIED DRUG;

ARTICLE; DRUG EFFICACY; DRUG SCREENING; DRUG SYNTHESIS; IN VIVO STUDY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANIMALS; CELL LINE; DIHYDROPYRIDINES; HUMANS; IODIDES; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; SYMPORTERS; THYROID GLAND;

EID: 84871649629     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201200417     Document Type: Article

References (29)

1. S. P. Porterfield, C. E. Hendrich, Endocr. Rev. 1993, 14, 94-106.
2. G. Dai, O. Levy, N. Carrasco, Nature 1996, 379, 458-460.
3. P. A. Smanik, Q. Liu, T. L. Furminger, K. Ryu, S. Xing, E. L. Mazaferi, S. M. Jhiang, Biochem. Biophys. Res. Commun. 1996, 226, 339-345.
4. J. Wolff, Physiol. Rev. 1964, 44, 45-90.
5. P. A. Jones, R. U. Pendlington, L. K. Earl, R. K. Sharma, M. D. Barrat, Toxicol. invitro 1996, 10, 149-160.
6. F. Waltz, L. Pillette, Y. Ambroise, Anal. Biochem. 2010, 396, 91-95.
7. T. Kogai, K. Taki, G. A. Brent, Endocr.-Relat. Cancerr 2006, 13, 797-826.
8. O. Dohan, A. de La Vieja, V. Paroder, C. Riedel, M. Artani, M. Reed, C. S. Ginter, N. Carrasco, Endocr. Rev. 2003, 24, 48-77.
9. G. Brumfiel, D. Cyranoski, Nature 2011, 471, 273-275.
10. E. L. Mazzaferri in The Thyroid: a Fundamental and Clinical Text, 7thEd. (Eds.: L.E. Braverman, R.D. Utiger), Lippincott-Raven, Philadelphia, 1996, pp.922-945.
11. D. P. Carvalho, A. C. Ferreira, Arq. Bras. Endocrinol. Metabol. 2007, 51, 672-682.
12. C. Spitzweg, J. C. Morris, Clin. Endocrinol. 2002, 57, 559-574.
13. N. Lecat-Guillet, Y. Ambroise, ChemMedChem 2008, 3, 1211-1216.
14. N. Lecat-Guillet, G. Merer, R. Lopez, T. Pourcher, B. Rousseau, Y. Ambroise, ChemBioChem 2008, 9, 889-895.
15. S. Lindenthal, N. Lecat-Guillet, A. Ondo-Mendez, Y. Ambroise, B. Rousseau, T. Pourcher, J. Endocrinol. 2009, 200, 357-365.
16. P. Biginelli, Gazz. Chim. Ital. 1893, 23, 360-416.
17. C. O. Kappe, Acc. Chem. Res. 2000, 33, 879-888.
18. V. Sridharan, M. Ruiz, J. C. Menéndez, Synthesis 2010, 1053-1057.
19. Y. Oikawa, K. Sugano, O. Yonemitsu, J. Org. Chem. 1978, 43, 2087-2088.
20. V. P. Shamshin, V. A. Aleshina, S. A. Sukhanova, T. I. Kabanova, Pharm. Chem. J. 2001, 35, 349-352.
21. Y. Ma, C. Qian, L. Wang, M. Yang, J. Org. Chem. 2000, 65, 3864-3868.
22. C. O. Kappe, Tetrahedron 1993, 49, 6937-6963.
23. B. Desai, D. Dallinger, C. O. Kappe, Tetrahedron 2006, 62, 4651-4664.
24. K. Yamamoto, Y. G. Chen, F. G. Buono, Org. Lett. 2005, 7, 4673-4676.
25. 50 value of 0.4μM reported in ref.[14] was determined on a sample from a commercial source (Chembridge, San Diego, CA, USA) and with a different type of assay.
26. K. S. Atwal, B. N. Swanson, S. E. Unger, D. M. Floyd, S. Moreland, A. Hedberg, B. C. O'Reilly, J. Med. Chem. 1991, 34, 806-811;
27. T. U. Mayer, T. M. Kapoor, S. J. Haggarty, R. W. King, S. L. Schreiber, T. J. Mitchison, Science 1999, 286, 971-974.
28. F. S. Ambesi-Impiombato, L. A. M. Parks, H. G. Coon, Proc. Natl. Acad. Sci. USA 1980, 77, 3455-3459.
29. T. Mosmann, J. Immunol. Methods 1983, 65, 55-63.