Dynamic 1H-NMR conformational study in a series of pyridinium pyrazoles

Revista de Chimie

Volumn 58, Issue 5, 2007, Pages 442-446

  Ilies, Monica ^a   Cáproiu, Miron Teodor ^b  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Romania)

Author keywords

DNMR conformational study; Energetic barriers; Pyridinium pyrazoles

Indexed keywords

EID: 34547807561     PISSN: 00347752     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (19)

1. (a) ILIEŞ, M. A., SEITZ, W. A., CǍPROIU, M. T., WENTZ, M., GARFIELD, R. E., BALABAN,A. T. , Pyridinium-based cationic lipids as gene transfer agents. Eur. J. Org. Chem. 2003, 14, p. 2645;
2. (b) M. A. ILIEŞ, W. A. SEITZ, I. GHIVIRIGǍ, B. H. JOHNSON, A. MILLER, E. B. THOMPSON, A. T. BALABAN, T. Pyridinium cationic lipids in gene delivery: a structure-activity correlation study. J. Med. Chem. 2004, 47, p. 3744
3. (a) SUPURAN, C. T. , ILIEŞ, M. A. , SCOZZAFAVA, A., Carbonic anhydrase inhibitors. Part 29. Interaction of isozymes I, II and IV with benzolamide-like derivatives, possible precursors of inhibitors with applications in positron emission tomography imaging. Eur. J. Med. Chem. 1998, 33, p. 739;
4. (b) SUPURAN, C. T. , SCOZZAFAVA, M. A. ILIEŞ, B. IORGA, T. CRISTEA, F. BRIGANTI, F. CHIRALEU, M. D. BANCIU, Carbonic anhydrase inhibitors. Part 53. Synthesis of substituted-pyridinium derivatives of aromatic sulfonamides: the first nonpolymeric membrane-impermeable inhibitors with selectivity for isozyme IV. Eur. J. Med. Chem. 1998, 33, p. 577;
5. (c) C. T. SUPURAN, A. SCOZZAFAVA, M. A. ILIEŞ, F. BRIGANTI, Carbonic anhydrase inhibitors: synthesis of sulfonamides incorporating 2,4,6-trisubstituted-pyridinium-ethylcarboxamido moieties possessing membrane-impermeability and in vivo selectivity for the membrane-bound (CAIV) versus the cytosolic (CA I and CA II) isozymes. J. Enzyme Inhib. 1999, 15(4), p. 381;
6. (d) A. SCOZZAFAVA, F. BRIGANTI, M. A. ILIEŞ, C. T. SUPURAN, Carbonic anhydrase inhibitors: Synthesis of membrane-impermeant low molecular weight sulfonamides possessing in vivo selectivity for the membrane-bound versus the cytosolic isozymes. J. Med. Chem. 2000, 43, p. 292
7. SUPURAN, C. T. , BRIGANTI, F. , SCOZZAFAVA, A., ILIEŞ, M. A., Protease inhibitors: Part 4. Synthesis of weakly basic thrombin inhibitors incorporating pyridinium-sulfanilylaminoguanidine moieties. J. Enzyme Inhib., 2000, 15, p. 335
8. ILIEŞ, M. A., BANCIU, M. D., ILIEŞ, M. , CHIRALEU, F. , BRIGANTI, F., SCOZZAFAVA, A. , SUPURAN, C. T. , Carbonic anhydrase activators. Part 17. Synthesis and activation study of 1-(1,2,4-triazole-(1H)-3-yl)-2,4,6- trisubstituted-pyridinium salts against isozymes I, II, IV. Eur. J. Med. Chem., 1997, 32, 11, p. 911
9. ILIEŞ, M., BANCIU, M. D., ILIEŞ, M. A., SCOZZAFAVA, M. A., CǍPROIU, M. T., SUPURAN, C. T., Carbonic anhydrase activators: Design of high affinity isozymes I, II and IV activators, incorporating tri-/tetrasubstituted-pyridinium-azole moieties. J. Med. Chem., 2002, 45, 2, p. 504
10. ILIEŞ, M., SCOZZAFAVA, A., SUPURAN, C.T., Carbonic anhydrase activators. In Carbonic anhydrase: Its inhibitors and activators; SUPURAN, C. T., SCOZZAFAVA, A. , CONWAY, J., Eds.; Taylor & Francis/CRC Press, 2004, p. 317
11. (a) BALABAN, A. T., UNCUŢA C., DINCULESCU, A., ELIAN,M., CHIRALEU, F., Rotation barriers in N-substituted 2,4,6-trimethylpyridinium cations. Tetr. Lett. 1980, 21, 16, p. 1553;
12. 3) single bond in 2,4,6-trimethyl-N-alkylpyridinium cations: proton DNMR analysis. Tetrahedron, 1984, 40, 13, p. 2547
13. DUMITRAŞCU, F., DRǍGHICI, C., CRÂNGUŞ, C., CǍPROIU, M.T., MITAN, C.I., DUMITRESCU, D., RǍILEANU, D., Atropisomerism of New Sterically Hindered 1-Arylpyrazoles. Rev. Roum. Chim., 47, 2002, p. 315
14. KATRITZKY, A. R. , The prototropic tautomerism of heteroaromatic compounds. Chimia 1970, 24, p. 134
15. MINKIN, V. I., GARNOVSKII, A. D., ELGUERO, J., KATRITZKY, A.R., DENISKO, O. V., The tautomerism of heterocycles: Five-membered rings with two or more heteroatoms. Adv. Het. Chem. 2000, 76 157-323, and the references cited therein.
16. CHENON, M. T., COUPRY, C., GRANT, D. M. ,PUGMIRE, R. J. , Carbon-13 magnetic resonance study of solvent stabilized tautomerism in pyrazoles. J. Org. Chem. 1977, 42, 4, p. 659
17. OKI, M., Dynamic NMR spectroscopy and diastereotopic nuclei. In Applications of Dynamic NMR Spectroscopy to Organic Chemistry; A. P. Marchand, Ed.; VCH Publishers, Inc. Deerfield Beach, Florida, 1985; p. 1-14;
18. E. L. ELIEL , S. H. WILEN, Stereochemistry of organic compouns, John Wiley & SONS, INC., New York, 1994
19. GHIVIRIGǍ, I., CZERWINSKI, E. W. , BALABAN, A. T. , Rotation Barriers in Pyridinium Salts Depend on the Number of Available Ground State Conformations. Croatica Chem. Acta, 2004, 77, 1-2, p. 391