Special Issue Reviews and Accounts ARKIVOC 2008 (i) 153-194
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Aminoguanidine is an important precursor for many useful compounds,149 among them the plant growth regulator, 3-amino-1,2,4-triazole.150 Amidrazones derived from nicotinic and isonicotinic acids among others have been tested for their pharmacological activity.151,152 Pyridine-4-carboxamidrazone is reported to be about half as effective as isoniazid in its tuberculostatic properties but only about one-half to one-third as toxic. Moreover, the isonicotinamidrazone-rifamycin-O reaction product has been found to be very active against gram positive microorganisms.153,154 Pteridine amidrazone or their aldehyde or ketone condensation products have been the subject of several patents as compounds that have diuretic and natiuretic properties.155
References
1. Patai, S., Ed. The Chemistry of Carboxylic Acids and Esters; Interscience: London, 1969. 2. Patai, S., Ed. The Chemistry of the Carbon-Nitrogen Double Bond; Interscience: London, 1970. 3. Zabicky, J., Ed. The Chemistry of Amides; Interscience: London, 1972. 4. Kotera, A.; Morita, T.; Aoyagi, S.; Kakiuchi, Y.; Nagakura, S.; Kume, K.. Nippon Kagaku Zasshi, 1961, 82, 298; Chem. Abstr. 1961, 55, 15128e. 5. Kiro, Z. B.; Teterin, Yu. A.; Nikolenko, L. N.; Stepanov, B. I. Zh. Org. Khim. 1972, 8, 2573; Chem. Abstr. 1973, 78, 135210z. 6. Hantzsch, A.; Geidel, W. Ber. Dtsch. Chem. Ges. 1930, 63, 1782. 7. Runner, M. E.; Kilpatrick, M. L.; Wagner, E. C. J. Am. Chem. Soc. 1947, 69, 1406. 8. Neuman, R. C., Jr.; Hammond, G. S. J. Phys. Chem. 1963, 67, 1659. 9. (a) Gauter, J. A.; Miocque, M.; Farnoux, C. C. In The Chemistry of Amidines and Imidates, Vol. 1; Patai, S., Ed.; John Wiley & Sons: New York, 1975, p 283. (b) Boyd, G. V. In The Chemistry of Amidines and Imidates, Vol. 2; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: New York, 1991, p 367. (c) Granik, V. G. Russ. Chem. Rev. 1983, 52, 377. (d) Dunn, P. J. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R.; Meth- Cohn, O.; Rees, C. W.; Eds.; Pergamon: New York, 1995, Vol. 5, Chapter 5.19. 10. (a) Partridge, M. W.; Smith, A. J. Chem. Soc., Perkin Trans. 1 1973, 453. (b) Hill, A. J.; Johnston, J. V. J. Am. Chem. Soc. 1954, 76, 920. (c) Tsatsas, G.; Delaby, R.; Quevauviller, A.; Damiens, R.; Blanpin, O. Ann. Pharm. Fr. 1956, 14, 607. (d) Mandel, H. G.; Hill, A. J. J. Am. Chem. Soc. 1954, 76, 3978. 11. Weintraub, L.; Oles, S. R.; Kalish, N. J. Org. Chem. 1968, 33, 1679. ISSN 1551-7012 Page 187 ©ARKAT USA, Inc.
