Synthesis and antibacterial activity of oxime ester derivatives from dehydroabietic acid

Letters in Drug Design and Discovery

Volumn 10, Issue 2, 2013, Pages 102-110

  Yan Jie, Cui ^a   Xiao Ping, Rao ^a   Shi Bin, Shang ^a   Jie, Song ^b   Yan Qing, Gao ^a  

^a RESEARCH INSTITUTE OF FORESTRY   (China)

^b UNIVERSITY OF MICHIGAN FLINT   (United States)

Author keywords

Antibacterial activity; Dehydroabietic acid; Oxime ester

Indexed keywords

1 (4 CHLOROPHENYL) ETHANONE OXIMYL DEHYDROABIETATE; 1 (4 METHOXYPHENYL) ETHANONE OXIMYL DEHYDROABIETATE; 1 P TOLYETHANONE OXIMYL DEHYDROABIETATE; AMPICILLIN; ANTIINFECTIVE AGENT; BENZOPHENONE OXIMYL DEHYDROABIETATE; BROMOGERAMINE; BUTANONE OXIMYL DEHYDROABIETATE; DEHYDROABIETIC ACID; ESTER DERIVATIVE; OXIME DERIVATIVE; PROPAN 2 ONE OXIMYL DEHYDROABIETATE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL CELL WALL; DRUG EFFICACY; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; INFRARED SPECTROSCOPY; KLEBSIELLA PNEUMONIAE; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS;

EID: 84875428965     PISSN: 15701808     EISSN: 1875628X     Source Type: Journal    
DOI: 10.2174/157018013804725071     Document Type: Article

References (25)

1. Ma, J. A., Huang, R.Q., and Chai, Y. X. Synthesis and insecticidal activities of new pyrethroid acid oxime ester derivatives[J]. Progress in Natural Science. 2002, 12(4), 271-277.
2. Jin, G.Y., Li, Y. C., Liu, Z. F., and Zheng, J. Y. (1997). Synthesis and biological activity of oximino-phosphorothioate containing 1, 2, 4-triazole[J]. Chin. J. Appl. Chem. 1997, 14(6), 5-8.
3. Bromidge, S. M., Brown, F., Cassidy, F., Clark, M. S., Dabbs, S., Hadley, M. S., Hawkins, J., Loudon, J. M., Naylor, C. B., Orlek, B. S., Riley, G. J. Design of [R-(Z)]-(+)-α-(methoxyimino)-1-azabicyclo[2.2.2] octane-3-acetonitrile (SB 202026), a functionally selective azabicyclic muscarinic M1 agonist incorporating the N-methoxy imidoyl nitrile group as a novel ester Bioisostere[J]. J. Med. Chem. 1997, 40(26), 4265-4280.
4. Bekhit, A. A., Abdel-Rahman, H. M., and Guemei, A. A. Synthesis and biological evaluation of some hydroxypyrazole derivatives as anti-inflammatory-antimicrobial agents[J]. Arch. Pham. (Weinheim). 2006, 339(2), 81-87.
5. Vonhoff, S.; Piens, K.; Pipelier, M.; Braef, C.; Claeyssens, M.; Vusella, A. Inhibition of Cellobiohydrolases from Trichoderma reesei. Synthesis and Evaluation of Some Glucose-, Cellobiose-, and Cellotriose-Derived Hydroximolactams and Imidazoles [J]. Helv. chim. Acta.1999, 82(7), 963-980.
6. Song, B. A., Liu, X. H., Yang, S., Hu, D. Y., Jin, L. H., and Zhang, Y. T. Recent advance in synthesis and biological activity of oxime derivatives[J]. Chin. J. Org. Chem. 2005, 25(5), 507-525.
7. Li, T. G., Liu, J. P., Han, J. T., Fu, B., Wang, D. Q., and Wang, M. G. Synthesis and herbicidal activity of α-phenylsulfonyl-cyclododecanone oxime esters[J] Chin. J. Org. Chem. 2009, 29(6), 898-903.
8. Liu, X. H., Zhi, L. P., Song, B. A., and Xu, H. L. Synthesis, characterization and antibacterial activity of 5 -aryl pyrazole oxime esters derivatives [J]. Chemical Research in Chinese Universities. 2008, 24(4), 454-458.
9. Liu, X. G.; Wang, J. P.; Li, X. M.; Wang, D. Q. Synthesis and insecticidal activity of 5-acyloxyimino-5-deoxyavermectin B1 derivatives[J]. Pest Manag. Sci. 2004, 60 (7), 697-702.
10. Wood, J. L.; Stoltz, B. M.; Goodman, S. N.; 0nwneme, K. Design and Implementation of an Efficient Synthetic Approach to Pyranosylated Indolocarbazoles: Total Synthesis of (+)-RK286c, (+)-MLR-52, (+)-Staurosporine, and(-)-TAN-1030a[J]. J. Am. Chem. Soc. 1997, 119, 9652-9661.
11. Koenig. G.; Leonard, K. A.; Lovr, R. S.; Ausfin, D. J. Synthesis of 3, 4-substituted cyclopentenones via an intramolecular Pauson-Khand reaction of N-O linked enynes[J]. Tetrahedron Lett. 2000, 41, 9393-9396.
12. Benkli, K., Karaburum, N. G. K., Ucucu, U., Demirayak, S., Kiraz, N. Synthesis and Antifungal Activities of Some Aryl (3-Methyl-Benzofuran-2-yl) Ketoximes [J]. Arch. Pharm. Res. 2003, 26(3), 202-206.
13. α [J]. J. Pestic. Sci. 1980, 11, 249-256.
14. Savluchinske-Feio S, Curto M J, Gigante B, Roseiro JC. Antimicrobial activity of resin acid derivatives[J]. Applied Microbiology and Biotechnology. 2006, 72, 430-436.
15. Fonseca, T., Gigantea, B., Gilchrist, T. L. A short synthesis of phenanthro[2,3-d]imidazoles from dehydroabietic acid. Application of the methodology as a convenient route to benzimidazoles[J]. Tetrahedronv. 2001, 57. 1793-1799.
16. Gouiric, S. C., Feresin, G. E., Tapia, A. A., Gouiric, S.C., Feresin, G. E., Tapia, A.A., Rossomando, P.C., Schmeda-Hirschmann, G., Bustos D.A. 1β, 7β -Dihydroxydehydroabietic acid, a new biotransformation product of dehydroabietic acid by Aspergillus niger[J]. World Journal of Microbiology & Biotechnology.2004, 20(3). 281-284.
17. Duan, W. G., Li, X. R., Mo, Q. J., SU, J. F., LUO, D. C., HUANG, D. P. Microwave-assisted synthesis of 5-dehydroabietyl-1, 3, 4-oxadiazole-2-thiol and its antibacterial activity [J]. Journal of Guang Xi University. Nat Sci Ed. 2009, 34(2). 201-204,210.
18. Gigante, B., Santos, C., Silva, A. M. Catechols from abietic acid:Synthesis and evaluation as bioactive compounds [J]. Bioorganie & Medicinal Chemistry. 2003, 11, 1631-1638.
19. Fonseca, T., Gigante, B., Marques, MM., Gilchrist, TL, De., Clercq, E. Synthesis and antiviral evaluation of benzimidazoles, quinoxalines and indoles from dehydroabietic acid[J]. Bioorganic & Medicinal Chemistry. 2004, 12, 103-112
20. Wada, H., Kodato, S., Kawamori, M. Antiulceractivity ofdehydroabietic acid derivatives[J]. Chemical & Pharmaceutical Bulletin. 1985, 33(4), 1472-1487.
21. Su, G. F., Huo, L. N., Qin, J. K., PAN, C.X., GUAN. Y. F. Synthesis and Antibacterial Activity of 1-Dehydryabieticacyl-3-aroylthiosemicarbazides Compounds and Their 1, 3, 4-Thiadiazole Derivatives [J]. Chinese Journal of Applied Chemistry. 2008, 25(7), 803-809.
22. Chen, L., Cen, B.; Duan, W. G.; DONG, S. Q. Synthesis and Characterization of Pinic Acid Diacyl-didehydroabietyl-bisoxadiazole [J]. Chemistry and Industry of Forest Products. 2010, 30 (5), 61-64.
23. Jia, W. H., Rao, X. P., Song, Z. Q., SHANG, S. B. Antimicrobial activities of rosin-based gemini cationic surfactants [J]. Chemistry and Industry of Forest Products. 2010, 30(1), l-4.
24. Han, C. R., Song, Z. Q., Li, H. T., YANG, D. M. Synthesis and Bioactivity of Sulfodehydroabietates [J]. Chemistry and Industry of Forest Products. Nanjing China. 2007, 27(6), 8l-84.
25. Noah, J. H., Ray, V. L. The isolation of dehydroabietic acid from disproportionate rosin.[J]. J. Org.Chem. 1996, 31, 4246-4247.