Synthesis of rubrolide analogues as new inhibitors of the photosynthetic electron transport chain

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 42, 2012, Pages 10555-10563

  Barbosa, Luiz C A ^a   Maltha, Célia R A ^a   Lage, Mateus R ^a   Barcelos, Rosimeire C ^a   Donà, Alice ^c   Carneiro, José W M ^b   Forlani, Giuseppe ^c  

^a FEDERAL UNIVERSITY OF VIÇOSA   (Brazil)

^b FLUMINENSE FEDERAL UNIVERSITY   (Brazil)

^c UNIVERSITY OF FERRARA   (Italy)

Author keywords

alkylidenebutenolides; Hill reaction inhibitors; QSAR; rubrolides

Indexed keywords

ACTIVE PRINCIPLES; BENZENE RING; ELECTRONWITHDRAWING; ELECTROPHILIC REACTION; MODE OF ACTION; MUCOBROMIC ACIDS; NATURAL PRODUCTS; PHOTOSYNTHETIC ELECTRON TRANSPORT; QSAR; QSAR STUDIES; REDUCTION PROCESS; RUBROLIDES;

AGRICULTURAL CHEMICALS; BENZENE; CHLOROPHYLL; COMPUTATIONAL CHEMISTRY; ELECTRON TRANSPORT PROPERTIES; PHOTOSYNTHESIS; UREA; WEED CONTROL;

HERBICIDES;

FURAN DERIVATIVE;

ARTICLE; DRUG EFFECT; ELECTRON TRANSPORT; ELECTROSPRAY MASS SPECTROMETRY; INFRARED SPECTROSCOPY; PHOTOSYNTHESIS; SYNTHESIS;

ELECTRON TRANSPORT; FURANS; PHOTOSYNTHESIS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 84867792118     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf302921n     Document Type: Article

References (44)

1. Wang, W.; He, H. W.; Zuo, N.; He, H. F.; Peng, H.; Tan, X. Synthesis and herbicidal activity of 2-(substituted phenoxyacetoxy)alkyl-5,5-dimethyl-1,3,2- dioxaphosphinan-2-one J. Agric. Food Chem. 2012, 60, 7581-7587
2. He, H. W.; Yuan, J. L.; Peng, H.; Chen, T.; Shen, P.; Wan, S. Q.; Li, Y. J.; Tan, H. L.; He, Y. H.; He, J. B.; Li, Y. Studies of O, O -dimethyl α-(2,4-dichlorophenoxy acetoxy)ethylphosphonate (HW02) as a new herbicide. 1. Synthesis and herbicidal activity of HW02 and analogues as novel inhibitors of pyruvate dehydrogenase complex J. Agric. Food Chem. 2011, 59, 4801-4813
3. Yu, H.; Yang, H.; Cui, D.; Lv, L.; Li, B. Synthesis and herbicidal activity of diphenyl ether derivatives containing unsaturated carboxylates J. Agric. Food Chem. 2011, 59, 11718-11726
4. Shang, J.; Wang, W. M.; Li, Y. H.; Song, H. B.; Li, Z. M.; Wang, J. G. Synthesis, crystal structure, in vitro acetohydroxy acid synthase inhibition, in vivo herbicidal activity, and 3D-QSAR of new aymmetric aryl disulfides J. Agric. Food Chem. 2012, 60, 8286-8293
5. Wang, J.; Tan, H.; Li, Y.; Ma, Y.; Li, Z.; Guddat, L. W. Chemical synthesis, in vitro acetohydroxyacid synthase (AHAS) inhibition, herbicidal activity, and computational studies of isatin derivatives J. Agric. Food Chem. 2011, 59, 9892-9900
6. Chaves, F. C.; Barbosa, L. C. A.; Demuner, A. J.; Silva, A. A. New helminthosporal analogues with plant-growth regulatory properties synthesized via oxyallyl cation Z. Naturforsch. 2006, 61, 1287-1294
7. Barbosa, L. C. A.; Demuner, A. J.; Maltha, C. R. A.; Da Silva, P. S.; Silva, A. A. Sintese e avaliação da ativadade fitotóxica de novos análogos oxigenados do ácido helmintospórico Quim. Nova 2003, 26, 655-660
8. Barbosa, L. C. A.; Costa, A. V.; Veloso, D. P.; Lopes, J. L. C.; Hernandez-Terrones, M. G. H.; King-Diaz, B.; Lotina-Hennsen, B. Phytogrowth-inhibitory lactones derivatives of glaucolide B Z. Naturforsch. 2004, 59C, 803-810
9. Lima, L. S.; Barbosa, L. C. A.; Alvarenga, E. S.; Demuner, A. J.; Silva, A. A. Synthesis and phytotoxicity evaluation of substituted para -benzoquinones Aust. J. Chem. 2003, 36, 625-630
10. Vyvyan, J. R. Allelochemicals as leads for new herbicides and agrochemicals Tetrahedron 2002, 58, 1631-1646
11. Barbosa, L. C. A.; Rocha, M. E.; Teixeira, R. R.; Maltha, C. R. A.; Forlani, G. Synthesis of 3-(4-bromobenzyl)-5-(aryl methylene)-5 H -furan-2-ones and their activity as inhibitors of the photosynthetic electron transport chain J. Agric. Food Chem. 2007, 55, 8562-8569
12. Barbosa, L. C. A.; Demuner, A. J.; Maltha, C. R. A.; Teixeira, R. R.; Souza, K. A. P.; Bicalho, K. U. Phytogrowth activity of 3-(3-chlorobenzyl)-5- arylidenofuran-2(5 H)-ones Z. Naturforsch. 2009, 64B, 245-251
13. Barbosa, L. C. A.; Teixeira, R. R.; Forlani, G.; Veloso, D. P.; Carneiro, J. W. M. Synthesis of photosynthesis-inhibiting nostoclide analogues J. Agric. Food Chem. 2008, 56, 2321-2329
14. Teixeira, R. R.; Pinheiro, P. F.; Barbosa, L. C. A.; Carneiro, J. W. M.; Forlani, G. QSAR modeling of photosynthesis-inhibiting nostoclide derivatives Pest Manag. Sci. 2010, 66, 196-202
15. Barbosa, L. C. A.; Varejão, J. O. S.; Petrollino, D.; Pinheiro, P. F.; Demuner, A. J.; Maltha, C. R. A.; Forlani, G. Tailoring nostoclide structure to target the chloroplastic electron transport chain Arkivok 2012, 10, 15-32
16. Miao, S.; Andersen, R. J. Metabolites of the colonial tunicate Ritterella rubra J. Org. Chem. 1991, 56, 6275-6280
17. Ortega, M. J.; Zubía, E.; Ocaña, J. M.; Naranjo, S.; Salvá, J. New rubrolides from the ascidian Synoicum blochmanni Tetrahedron 2000, 56, 3963-3967
18. Pearce, A. N.; Chia, E. W.; Berridge, M. V.; Maas, E. W.; Page, M. J.; Webb, V. L.; Harper, J. L.; Copp, B. R. E / Z -Rubrolide O, an anti-inflammatory halogenated furanone from the New Zealand ascidian Synoicum n. sp J. Nat. Prod. 2007, 70, 111-113
19. Boukouvalas, J.; Mccann, L. C. Synthesis of the human aldose reductase inhibitor rubrolide L Tetrahedron Lett. 2010, 51, 4636-4639
20. Kar, A.; Gogoi, S.; Argade, N. P. Synthesis of naturally occurring bioactive butyrolactones: maculactones A-C and nostoclides I Tetrahedron 2005, 61, 5297-5302
21. Bellina, F.; Rossi, R. Synthetic applications of 3,4-dihalo-2(5 H)-furanone derivatives. A formal total synthesis of nostoclides I and II Synthesis 2002, 18, 2729-2732
22. Boukouvalas, J.; Lachance, N.; Oullet, M.; Trudeau, M. Facile acess to 4-aryl-2(5 H)-furanones by Suzuki cross coupling: efficient synthesis of rubrolides C and E Tetrahedron Lett. 1998, 39, 7665-7668
23. Krieger-Liszkay, A.; Rutherford, A. W. Influence of herbicide binding on the redox potential of the quinone acceptor in photosystem II: relevance to photodamage and phytotoxicity Biochemistry 1998, 37, 17339-17344
24. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 5.edBodmin; Butterworth-Heinemann: Oxford, UK, 2003; 609 pp.
25. Bellina, F.; Anselmi, C.; Stéphane, V.; Mannina, L.; Rossi, R. Selective synthesis of (Z)-4-aryl-5-[1-(aryl)methylidene]-3-bromo-2-(5 H)-furanones Tetrahedron 2001, 57, 9997-10007
26. Shao, Y.; Molnar, L. F.; Jung, Y.; Kussmann, J.; Ochsenfeld, C.; Brown, S. T.; Gilbert, A. T. B.; Slipchenko, L. V.; Levchenko, S. V.; ONeill, D. P.; DiStasio, R. A., Jr.; Lochan, R. C.; Wang, R.; Beran, G. J. O.; Besley, N. A.; Herbert, J. M.; Lin, C. Y.; Van Voorhis, T.; Chien, S. H.; Sodt, A.; Steele, R. P.; Rassolov, V. A.; Maslen, P. E.; Korambath, P. P.; Adamson, R. D.; Austin, B.; Baker, J.; Byrd, E. F. C.; Dachsel, H.; Doerksen, R. J.; Dreuw, A.; Dunietz, B. D.; Dutoi, A. D.; Furlani, T. R.; Gwaltney, S. R.; Heyden, A.; Hirata, S.; Hsu, C.-P.; Kedziora, G.; Khalliulin, R. Z.; Klunzinger, P.; Lee, A. M.; Lee, M. S.; Liang, W. Z.; Lotan, I.; Nair, N.; Peters, B.; Proynov, E. I.; Pieniazek, P. A.; Rhee, Y. M.; Ritchie, J.; Rosta, E.; Sherrill, C. D.; Simmonett, A. C.; Subotnik, J. E.; Woodcock, H. L., III; Zhang, W.; Bell, A. T.; Chakraborty, A. K.; Chipman, D. M.; Keil, F. J.; Warshel, A.; Hehre, W. J.; Schaefer, H. F.; Kong, J.; Krylov, A. I.; Gill, P. M. W.; Head-Gordon, M. Advances in methods and algorithms in a modern quantum chemistry program package Phys. Chem. Chem. Phys. 2006, 8, 3172-3191
27. Stewart, J. J. P. MOPAC 2007, version 7, 290 W. Stewart Computational Chemistry, Colorado Springs, CO, 2007.
28. Dewar, M. J. S.; Thiel, W. Ground states of molecules. 38. The MNDO method. Approximations and parameters J. Am. Chem. Soc. 1977, 99, 4899-4907
29. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F. AM1: a new quantum chemical molecular model J. Am. Chem. Soc. 1985, 107, 3902-3909
30. Katritsky, A.; Karelson, M.; Lobanov, V. S.; Dennington, R.; Keith, T. CODESSA 2.7.10., Semichem, Inc., Shawnee, KS, 2004.
31. Bellina, F.; Rossi, R. An efficient and inexpensive multigram synthesis of 3,4-dibromo- and 3,4-dichlorofuran-2(5 H)-one Synthesis 2007, 12, 1887-1889
32. Bellina, F.; Rossi, R. Mucochloric and mucobromic acids: inexpensive, highly functionalised starting materials for the selective synthesis of variously substituted 2(5 H)-furanone derivatives, sulfur- or nitrogen-containing heterocycles and stereodefined acyclic unsaturated dihalogenated compounds Curr. Org. Chem. 2004, 8 (12) 1-15
33. Cunha, S.; Oliveira, C. C. Aplicações sintéticas do ácido mucobrômico e da 3,4-dibromofuran-2(5 H)-ona Quim. Nova 2011, 34, 1425-1438
34. Rossi, R.; Bellina, F.; Raugei, E. Selective synthesis of unsymmetrical 3,4-disubstituted and 4-substituted 2(5 H)-furanones Synlet 2000, 12, 1749-1752
35. Teixeira, R. R.; Barbosa, L. C. A.; Maltha, C. R. A.; Rocha, M. E.; Bezerra, D. P.; Costa-Lotufo, L. V.; Pessoa, C.; Moraes, M. O. Synthesis and cytotoxic activity of some 3-benzyl-5-arylidenefuran-2(5 H)-ones Molecules 2007, 12, 1101-1116
36. Boukouvalas, J.; Maltais, F.; Lachance, N. Furanolate-based strategy for sequential 2,3,4-trisubstitution of butenolide: total synthesis of nostoclide I and II Tetrahedron Lett. 1994, 35, 7897-7900
37. Barbosa, L. C. A.; Demuner, A. J.; Alvarenga, E. S.; Oliveira, A.; King-Diaz, B.; Lotina-Hennsen, B. Phytogrowth- and photosynthesis-inhibiting properties of nostoclide analogues Pest Manag. Sci. 2006, 62, 214-222
38. Ghose, A. K.; Pritchett, A.; Crippen, G. M. Atomic physicochemical parameters for three dimensional structure directed quantitative structure-activity relationships III: modeling hydrophobic interactions J. Comput. Chem. 1988, 9, 80-90
39. Vicentini, C. B.; Mares, D.; Tartari, A.; Manfrini, M.; Forlani, G. Synthesis of pyrazole derivatives and their evaluation as photosynthetic electron transport inhibitors J. Agric. Food Chem. 2004, 52, 1898-1906
40. Xia, B.; Ma, W.; Zheng, B.; Zhang, X.; Fan, B. Quantitative structure-activity relationship studies of a series of non-benzodiazepine structural ligands binding to benzodiazepine receptor Eur. J. Med. Chem. 2008, 43, 1489-1498
41. Katritsky, A.; Karelson, M.; Lobanov, V. S. Semichem, Inc., http://www.semichem.com/codessa/cfeatures.php (accessed Nov 16, 2011).
42. Stanton, D. T.; Jurs, P. C. Development and use of charged partial surface area structural descriptors in computer-assisted quantitative structure-property relationship studies Anal. Chem. 1990, 62, 2323-2329
43. Stanton, D. T.; Egolf, L. M.; Jurs, P. C.; Hicks, M. G. Computer-assisted prediction of normal boiling points of pyrans and pyrroles J. Chem. Inf. Comput. Sci. 1992, 32, 306-316
44. Katritzky, A. R.; Pacureanu, L.; Dobchev., D.; Karelson, M. QSPR Modeling of hyperpolarizabilities J. Mol. Model. 2007, 13, 951-963