Synthesis of new plant growth regulator: N-(Fatty acid) O-aryloxyacetyl ethanolamine

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 11, 2007, Pages 3231-3234

  Han, Liang ^a   Gao, Jian Rong ^a   Li, Zheng Ming ^b   Zhang, Yun ^c   Guo, Wei Ming ^c  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

^b NANKAI UNIVERSITY   (China)

^c NANJING AGRICULTURAL UNIVERSITY   (China)

Author keywords

Aryloxyacetic acids; N Acylethanolamines; Plant growth regulator; Synthesis

Indexed keywords

2,4 DICHLOROPHENYLOXYACETIC ACID; ACETIC ACID DERIVATIVE; CHLORINE; ETHANOLAMINE DERIVATIVE; N (FATTY ACID) O ARYLOXYACETYL ETHANOLAMINE; N STEAROYLETHANOLAMINE; PHYTOHORMONE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SOLUBILITY; DRUG SYNTHESIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PLANT GROWTH;

ETHANOLAMINES; FATTY ACIDS; PLANT GROWTH REGULATORS;

EID: 34247882028     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.03.013     Document Type: Article

References (31)

1. Kuehl F.F., Jacob T.A., Ganley O.H., Ormond R.E., and Meisinger M.A.P. J. Am. Chem. Soc. 79 (1957) 5577
2. Parinandi N.L., and Schmid H.H.O. FEBS Lett. 237 (1988) 49
3. Gulaya N.M., Kuzmenko A.I., Margitich V.M., Govseeva N.M., Melnichuk S.D., Goridko T.M., and Zhukov A.D. Chem. Phys. Lipids 97 (1998) 49
4. Skaper S.D., Buriani A., Dal Toso R., Petrelli L., Romanello S., Facci L., and Leon A. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 3984
5. Facci L., and Dal Toso R. Proc. Natl. Acad. Sci. U.S.A. 92 (1995) 3376
6. Mazzari S., Canella R., Petrelli L., Marcolongo G., and Leon A. Eur. J. Pharmacol. 300 (1996) 227
7. Molina-Holgado F., Lledó A., and Guaza C. Neuroreport 8 (1997) 1929
8. Chapman K.D., Venables B., Blair Jr. R., and Berringer C. Plant Physiol. 120 (1999) 1157
9. Schmid H.H., and Berdyshev E.V. Prostaglandins Leukot Essent Fatty Acids 66 (2002) 363
10. Di Marzo V., De Petrocellis L., Fezza F., Ligresti A., and Bisogno T. Prostaglandins Leukot Essent Fatty Acids 66 (2002) 377
11. Chapman K.D., Tripathy S., Venables B., and Desouza A. Plant Physiol. 116 (1998) 1163
12. Stella N., Schweitzer P., and Piomelli D. Nature(London) 388 (1997) 773
13. Tripathy S., Venables B.J., and Chapman K.D. Plant Physiol. 121 (1999) 1299
14. Chapman K.D., Venables B.J., Dian E.E., and Gross G.W. J. Am. Oil. Chem. Soc. (JAOCS) 80 (2003) 223
15. Giuffrida A., Rodriguez de Fonseca F., and Piomelli D. Anal. Biochem. 280 (2000) 87
16. Schmid P.C., Schwartz K.D., Smith C.N., Krebsbach R.J., Berdyshev E.V., and Schmid H.H. Chem. Phys. Lipids 104 (2000) 185
17. Chapman K.D. Chem. Phys. Lipids 108 (2000) 221
18. Tripathy S., Kleppinger-Sparace K., Dixon R.A., and Chapman K.D. Plant Physiol. 131 (2003) 1781
19. Blancaflor E.B., Hou G., and Chapman K.D. Planta 217 (2003) 206
20. Chapman K.D. Prog. Lipid Res. 43 (2004) 302
21. Ryu S., Bjourn K., Ozgen M., and Plata J. Proc. Natl. Acad. Sci. U.S.A. 94 (1997) 12717
22. Austin-Brown S., and Chapman K.D. Plant Physiol. 129 (2002) 1892
23. Sang Y., Zheng S., Li W., Huang B., and Wang X. Plant J. 28 (2001) 1
24. Chapman, K. D. PCT Int. Appl. WO01,301,43 A2, 2001.
25. Krewson C.F., Saggese J.E., Carmichael J.F., Ard J.S., and Drake T.F. J. Agri. Food Chem. 7 (1959) 118
26. Roe E.T., Miles T.D., and Swern D. J. Am. Chem. Soc. 74 (1952) 3442
27. Bao M., He Q.L., He X.-Zh., and Liu B.-D. J. Appl. Chem. (in Chinese) 14 (1997) 90
28. 4: C 73.22, H 10.38, N 2.94; found: C 73.24, H 10.40, N 2.85.
29. Hypocotyls elongation test of rape. After soaking, the seeds with similar magnitude were chosen to use. Tested compounds were dissolved in DMF and later dropped evenly on 6-cm-diameter fitter paper. After air-volatilization of solvent, the filter paper was placed in 6-cm-diameter glass utensil with distilled water to give 10 mg/L compound solutions, and then ten seeds were added. The seeds were cultured at 25 °C in dark. The length of hypocotyls was measured after 3 days and compared with those treated with distilled water to estimate the activity. Two replicates were included in the evaluation.
30. Cotyledon expansion test of cucumber. After soaking, the seeds were germinated in covered enamelware containing 0.7% agar and cultured for 3 days in dark at 26 °C, and then the cotyledons of similar magnitude were chosen to use. Tested compounds were dissolved in DMF and later dropped evenly on 6-cm-diameter fitter paper. After air-volatilization of solvent, the filter paper was placed in 6-cm-diameter glass utensil with distilled water to give 10 mg/L compound solutions and ten pieces of cotyledons were added. The cotyledons were cultured in light (300Lux, 26 °C). After 3 days, the total weight of cotyledon was measured and compared with those treated with distilled water to estimate the activity. Two replicates were included in the evaluation.
31. Coleoptiles growth test of common wheat. After soaking, the seeds were germinated in covered enamelware containing 0.7% agar and cultured for 3 days in dark at 25 °C. When the seedling grew to 2.5-3.0 cm tall, the first 3 mm of coleoptile top was rejected. Coleoptile (5 mm) was truncated and dunked in distilled water for 1 h to remove endogenous hormone, then it was chopped into 10 segments. Tested compounds were dissolved in DMF and later dropped evenly on 6-cm-diameter fitter paper. After air-volatilization of solvent, the filter paper was placed in 10 ml beaker with 0.01 mol/L phosphoric acid-citric acid buffer solution (pH 5) containing 2% sucrose to give 10 mg/L compound solutions and ten coleoptile segments were added afterward. The coleoptiles were cultured at 25 °C in dark for 18-20 h and then the length of coleoptiles was measured and compared with those treated without tested compounds to estimate the activity. Two replicates were included in the evaluation.