Structural aspects and rearrangement of radical cations generated from NADH analogues

Journal of the American Chemical Society

Volumn 118, Issue 3, 1996, Pages 691-692

  Gȩbicki, Jerzy ^a   Marcinek, Andrzej ^a   Adamus, Jan ^a   Paneth, Piotr ^a   Rogowski, Jacek ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIHYDROPYRIDINE DERIVATIVE; NICOTINAMIDE ADENINE DINUCLEOTIDE; NICOTINAMIDE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; IONIZATION; MATHEMATICS; STEREOCHEMISTRY; THEORY;

EID: 0030034741     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9532244     Document Type: Article

References (29)

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17. Our experience is that AM1 tends to overestimate the transition-state energy for radical cations as compared with the measured values for 1,5-hydrogen atom shifts; nevertheless, a relative comparison seems to be meaningful.
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21. A description of our system and the methodology of the low-temperature pulse radiolytic studies of radical cations are given elsewhere. Karolczak, S.; Hodyr, K.; Lubis, R.; Kroh, J. J. Radioanal. Nucl. Chem. 1986, 101, 177. Gȩbicki, J.; Marcinek, A.; Rogowski, J. Radiat. Phys. Chem. 1992, 39, 41.
22. A description of our system and the methodology of the low-temperature pulse radiolytic studies of radical cations are given elsewhere. Karolczak, S.; Hodyr, K.; Lubis, R.; Kroh, J. J. Radioanal. Nucl. Chem. 1986, 101, 177. Gȩbicki, J.; Marcinek, A.; Rogowski, J. Radiat. Phys. Chem. 1992, 39, 41.
23. By rapid quenching of the gas phase conformational equilibrium of BAPH on a cold surface we have found by IR matrix isolation spectroscopy that the abundance of the trans-conformer does not exceed 15%.
24. MCPH was prepared by sodium dithionite reduction of the corresponding cycloheptapyridinium iodide prepared from 6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one, which was in turn synthesized according to the known procedures. Epsztajn, J.; Bieniek, A.; Brzeziński, J. Z. Pol. J. Chem. 1980, 54, 341. Caprathe, B. W.; Jaen, J. C.; Wise, L. D.; Heffner, T. G.; Pugsley, T. A.; Meltzer, L. T.; Parvez, M. J. Med. Chem. 1991, 14, 2736.
25. MCPH was prepared by sodium dithionite reduction of the corresponding cycloheptapyridinium iodide prepared from 6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one, which was in turn synthesized according to the known procedures. Epsztajn, J.; Bieniek, A.; Brzeziński, J. Z. Pol. J. Chem. 1980, 54, 341. Caprathe, B. W.; Jaen, J. C.; Wise, L. D.; Heffner, T. G.; Pugsley, T. A.; Meltzer, L. T.; Parvez, M. J. Med. Chem. 1991, 14, 2736.
26. The feasibility of such a reaction is presently being tested in our laboratories.
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