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Studies of N-hydroxy-N'-aminoguanidine Derivatives by Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy and as Ribonucleotide Reductase Inhibitors

Tai, Anna W. and Lien, Eric J. and Moore, E. Colleen and Chun, Yu and Roberts, John D. (1983) Studies of N-hydroxy-N'-aminoguanidine Derivatives by Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy and as Ribonucleotide Reductase Inhibitors. Journal of Medicinal Chemistry, 26 (9). pp. 1326-1329. ISSN 0022-2623. doi:10.1021/jm00363a021.

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Hydroxyguanidine, with the imino group of guanidine and the hydroxyamino group of hydroxyurea, has functional groups believed to be important for both anticancer and antiviral activities (Adamson, R. H. Nature (London) 1972, 236,400-401). Three new N-hydroxy-N‘mninoguanidine derivatives have been synthesized and found to be 20-30 times more active than the hydroxyguanidine itself as inhibitors of ribonucleotide reductase from rat Novikoff tumors (Tai, W. A.; Lai, M. M.; Lien, E. J. “Novel -Hydroxyguanidine Derivatives as Antiviral Agents”, North American Medicinal Chemistry Symposium, University of Toronto, Toronto, Canada, June 20-24,1982; Abstr, p 144). The character of the tautomeric equilibria, the pK_a values, and the protonation sites of these hydroxyguanidine derivatives have been determined by ^(15)N NMR spectroscopy.

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Additional Information:© 1983 American Chemical Society. Received September 7, 1982. Publication Date: September 1983. Taken in part from the Ph.D. dissertation of A.W.T., University of Southern California, 1982. Supported in part by BRSG Grant 2S07RR 05792-05 to the USC School of Pharmacy and by the Clinical Cancer Education Program of the NCI (Grant 5R 25 CA 24426) to A.W.T. (b) Supported by the American Cancer Society (Grant CH122). (c) Supported by the National Science Foundation and by the Public Health Service (Grant No. GM-11072) from the Division of General Medical Sciences. Contribution No. 6720
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NIH2S07RR 05792-05
National Cancer Institute5R 25 CA 24426
American Cancer SocietyCH122
U.S. Public Health Service (USPHS)GM-11072
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Caltech Gates and Crellin Laboratories of Chemistry6720
Issue or Number:9
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Official Citation:Studies of N-hydroxy-N'-aminoguanidine derivatives by nitrogen-15 nuclear magnetic resonance spectroscopy and as ribonucleotide reductase inhibitors Anna W. Tai, Eric J. Lien, E. Colleen Moore, Yu Chun, and John D. Roberts Journal of Medicinal Chemistry 1983 26 (9), 1326-1329 DOI: 10.1021/jm00363a021
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ID Code:60749
Deposited On:05 Oct 2015 18:21
Last Modified:10 Nov 2021 22:38

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