Synthesis and Cytokinin Activity of New Zeatin Derivatives

Journal of Agricultural and Food Chemistry

Volumn 46, Issue 4, 1998, Pages 1577-1582

  Haidoune, M'Barek ^a,d   Raynaud, Isabelle ^a   O'Connor, Norval ^a   Richomme, Pascal ^b   Mornet, René ^a   Laloue, Michel ^c  

^a UNIVERSITÉ D'ANGERS   (France)

^b SCRMN   (France)

^c CEMAGREF   (France)

^d Hassan II Mohamedia University   (Morocco)

Author keywords

Biological activity; Cytokinins; Fluoro compounds; Synthesis

Indexed keywords

EID: 0040307256     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf970752l     Document Type: Article

References (30)

1. Abraham, R. J.; Ellison, S. L. R.; Barfield, M.; Thomas, W. A. An experimental and theoretical investigation of orientational dependence of H-F couplings in fluoro-olefms. J. Chem. Soc., Perkin Trans. 2 1987, 977-985.
2. Allmendiger, T. Ethyl phenylsulfinyl fluoroacetate, a new and versatile reagent for the preparation of α-fluoro-α,β-unsaturated carboxylic acid esters. Tetrahedron 1991, 47, 4905-4914.
3. 13C NMR spectroscopy. Magn. Reson. Chem. 1987, 25, 347-351.
4. Chau, L. V.; Schlosser, M. Silberion-induzierte ringöffnung von chlorofluorocyclopropanen (Silver ion induced ring opening of chlorofluorocyclopropanes). Synthesis 1974, 115-116.
5. 6-isopentenyladenine. J. Agric. Food Chem. 1996, 44, 320-323.
6. Coutrot, P.; Grison, C.; Sauvêtre, R. 2-Diethoxyphosphoryl alcanoic acid dianions (lithium-α-lithiocarboxylates) [Stereoselective synthesis of (E)-2-fluoro-2,3-ethylenic esters by Wittig-Horner reaction of methyl (diethylphosphono)-2-fluoroacetate. Comparative study with methyl (diphenylphosphono)-2-fluoroacetate]. J. Organomet. Chem. 1987, 332, 1-8.
7. Etemad-Moghadam, G.; Seyden-Penne, J. Synthèse stéréosélective d'esters α,β-ethyléniques α-fluorés E par réaction de Wittig-Horner à partir du diéthyl phosphono α-fluoroacétate de méthyle. Etude comparative avec le diphényl phosphonoxy α-fluoroacétate de méthyle. Bull. Soc. Chim. Fr. 1985, 448-454.
8. Fujii, T.; Ogawa, N. Absolute configuration of (-)-dihydrozeatin. Tetrahedron Lett. 1972, 3075-3078.
9. Fujii, T.; Itaya, T.; Matsubara, S. Purines. XXXIII. Syntheses and cytokinin activities of both enantiomers of 1′-methylzeatin and their 9-β-D-ribofuranosides. Chem. Pharm. Bull. 1989, 37, 1758-1763.
10. 6-substituted adenines and adenosines on their activity in promoting cell growth. Phytochemistry 1970, 9, 1907-1913.
11. Howard, J. A. K.; Hoy, V. J.; O'Hagan, D.; Smith, G. T. How good is fluorine as a hydrogen bond acceptor? Tetrahedron 1996, 52, 12613-12622.
12. Kitazume, T.; Ishikawa, N. One-pot synthesis of α-fluoro-α,β-unsaturated esters from chloromalonic ester and carbonyl compounds using "spray-dried" potassium fluoride. Chem. Lett. 1981, 1259-1260.
13. Leonard, N. J.; Hecht, S. M.; Skoog, F.; Schmitz, R. Y. Cytokinins: Synthesis and biological activities of related derivatives of 2iP, 3iP, and their ribosides. Isr. J. Chem. 1968, 6, 539-550.
14. Letham, D. S. Cytokinins from Zea Mays. Phytochemistry 1973, 12, 2445-2455.
15. Lovey, A. J.; Pawson B. A. Fluorinated retinoic acids and their analogues. 3. Synthesis and biological activity of aromatic 6-fluoro analogues. J. Med. Chem. 1982, 25, 71-75.
16. Machleidt, H.; Wessendorf, R. Organische Fluorverbindungen, IV Carbonyl-fluorolefinierungen (Fluoroorganic compounds, IV. Carbonyl fluoroolefination). Liebigs Ann. Chem. 1964, 674, 1-10.
17. Massoudi, H. H.; Cantacuzène, D.; Wakselman, C.; Bouthier de la Tour, C. Synthesis of the cis-and trans-isomers of homoaconitic and fluorohomoaconitic acid. Synthesis 1983, 1010-1012.
18. Matsubara, S. Structure-activity relationships of Cytokinins. Crit. Rev. Plant Sci. 1990, 9, 17-57.
19. Mornet, R.; Gouin, L. Synthèse de l'acétate du chloro-4 méthyl-2 butène-2-ol-1 (E). Nouvelle voie d'accès à la transzéatine [Synthesis of (E)-4-chloro-2-methyl-2-butenyl acetate. New access to trans-zeatin]. Tetrahedron Lett. 1977a, 167-168.
20. Mornet, R.; Gouin, L. The carbonochloridate cleavage of tertiary amines; a simple step in the preparation of di-and trisubstituted olefinic (allylic) synthons. Synthesis 1977b, 786-787.
21. Müller, C.; Stier, F.; Weyerstahl, P. Darstellung, ringöffnung-sreaktionen und halogen/lithium-austauch von 1-brom-1-fluorcyclopropanen (Synthesis, ring cleavage, and halogen/ lithium exchange of 1-bromo-1-fluorocyclopropanes). Chem. Ber. 1977, 770, 124-137.
22. Nakayama, Y.; Kitazume, T.; Ishikawa, N. Synthesis and useful building blocks for monofluorinated compounds derived from trifluoroethene. J. Fluorine Chem. 1985,29, 445-458.
23. Nogue, F.; Jullien, M.; Mornet, R.; Laloue, M. The response of a cytokinin resistant mutant is highly specific and permits a new bioassay. Plant Growth Regul. 1995, 17, 87-94.
24. Normant, J. F.; Foulon, J. P.; Masure, D.; Sauvêtre, R.; Villiéras, J. A new preparation of trifluorovinyllithium. Applications to the syntheses of trifluorovinylalcohols and of α-fluoro-α-ethylenic acids and derivatives. Synthesis 1975, 122-125.
25. Poulter, C. D.; Argyle, J. C.; Mash, E. A. Prenyltransferase. New evidence for an ionization-condensation-elimination mechanism with 2-fluorogeranyl pyrophosphate. J. Am. Chem. Soc. 1977, 99, 957-959.
26. Schlosser, M.; Chau, L. V. Fluororganische Synthesen. V. Darstellung und abwandlung von chlorfluorcyclopropanen. Ein gezielter zugang zu fluorallylalkoholen (Fluoroorganic syntheses, V. Preparation and transformations of chlorofluorocyclopropanes. A selective approach to fluoroallylic alcohols). Helv. Chim. Acta 1975, 58, 2595-2603.
27. Schlosser, M.; Spahic, B.; Tarchini, C.; Chau, L. V. Insertion of a carbon atom into olefinic double bonds: synthesis of fluorodienes and fluoroalkenes. Angew. Chem., Int. Ed. Engl. 1975, 14, 365-366.
28. Schmitz, R. Y.; Skoog, F.; Playtis, A. J.; Leonard, N. J. Cytokinins: Synthesis and biological activity of geometric and position isomers of zeatin. Plant Physiol. 1972, 50, 702-705.
29. Van Staden, J.; Drewes, S. E. 6-(2,3,4-Trihydroxy-3-methyl-butylamino)purine, a cytokinin with high biological activity. Phytochemistry 1982, 21, 1783-1784.
30. Xu, Z. Q.; DesMarteau, D. D. A convenient one-pot synthesis of α-fluoro-α,β-unsaturated nitriles from diethyl cyanofluoromethanephosphonate. J. Chem. Soc., Perkin Trans, 1 1992, 313-315.