Abstract
The synthesis and physiological activity of some novel 4-substituted triazolo[4,5-d]pyrimidines and 4-substituted pyrazolo[3,4-d]pyrimidines are described. Most of the compounds possessed high anticytokinin activity towards purine (benzyladenine) and phenylurea (4-PU-30) type cytokinins. 1-Benzyl-4-ethoxycarbonylpiperazinyl-1H-1,2,3-triazolo[4,5-d]pyrimidine almost completely removed cytokinin stimulated effects—betacyanin synthesis in Amaranthus caudatus cotyledons; growth of radish cotyledons and retention of chlorophyll in leaf explants. Some chemical structurephysiological activity relationships have been established.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Albert A (1969) 1,2,3,4,6-Pentaazaindenes (8-azapurines). Part V. A comparison of 1,2,3,-triazoles and pyrimidines as intermediates for the preparation of 9-substituted 8-aza purines. Rearrangement of 6-mercapto-8-azapurines and of 4-aminotriazoles. J Chem Soc (C) 152–158
Biddington N, Thomas T (1973) A modified Amaranthus betacyanin bioassay for the rapid determination of cytokinins in plant extracts. Planta 111:183–186
Bruce M, Zwar I, Kefford N (1965) Chemical structure and plant kinin activity—the activity of urea and thiourea derivatives. Life Sci 4:461–466
Christou P, Barton KA (1989) Cytokinin antagonist activity of substituted phenetylamines in plant cell culture. Plant Physiol 89:564–568
El Hedi Jellali M, Van Bac N, Dat-Xoung N (1975) Sur la sylation et 1'alkylation de l'amino-4-pyrazolo[3,4-d]pyrimidine. Tetrahedron 31:587–591
Iwamura H, Murakami S, Koshimizu K, Matsubara S (1985) Quantitative structure-activity relationships in cytokinin agonistic and antagonistic pyrido[2,3-d]pyrimidine derivatives: insights into receptor topology. J Med Chem 28: 577–583
Karanov E, Alexieva A, Golovinsky E, Haimova M (1993) Cytokinin and anticytokinin activity of some 4-substituted 1H-pyrazoles and 8-aza analogues of adenine. Plant Growth Regulation 13:7–11
Karanov E, Alexieva V, Sergiev I (1992) Anticytokinins—chemistry and action. Physiol na Rast XVIII(1):97–107 (in Bulgarian)
Kende H (1965) Kinetin-like factors in the root exudate of sunflowers. Proc Natl Acad Sci USA 53:1302–1307
Klämbt D, Thies G, Skoog F (1966) Isolation of cytokinins from Corynebacterium fascians. Proc Natl Acad Sci USA 56:52–57
Kurosaki F, Takahashi S, Shudo K, Okamoto T, Isogai Y (1981) Structural and biological links between urea- and purinecytokinins. Chem Pharm Bull 29(12):3751–3753
Letham D (1971) Regulators of cell division in plant tissues. XII. A cytokinin bioassay using excised radish cotyledons. Physiol Plant 25:391–396
Shimizu R, Iwamura H, Matsubara S, Fujita T (1989) Development of s-triazine anticytokinins and their quantitative structure-activity relationship. J Agric Food Chem 37: 236–240
Skoog F, Schmitz RY, Hecht SM, Frye RB (1975) Anticytokinin activity of substituted pyrrolo[2,3-d]pyrimidines. Proc Natl Acad Sci USA 72(9):3508–3512
Steel RGD, Tome JH (1960) Principles and procedures of statistics with special reference to the biological sciences. McGraw-Hill Book Company, Inc., New York, Toronto, London
Yamaguchi K, Shudo K (1991) Crystallographic studies on urea cytokinins. J Agric Food Chem 39:793–796
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Alexieva, V., Sergiev, I., Karanov, E. et al. Anticytokinin activity of 4-substituted triazolo[4,5-d]pyrimidines and 4-substituted pyrazolo[3,4-d]pyrimidines. J Plant Growth Regul 13, 123–129 (1994). https://doi.org/10.1007/BF00196375
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00196375