A novel one-pot synthesis and preliminary biological activity evaluation of cis-restricted polyhydroxy stilbenes incorporating protocatechuic acid and cinnamic acid fragments

European Journal of Medicinal Chemistry

Volumn 66, Issue , 2013, Pages 185-192

  Miliovsky, Mitko ^a   Svinyarov, Ivan ^a   Mitrev, Yavor ^b   Evstatieva, Yana ^a   Nikolova, Dilyana ^a   Chochkova, Maya ^c   Bogdanov, Milen G ^a  

^a UNIVERSITY OF SOFIA   (Bulgaria)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Bulgaria)

^c SOUTH WEST UNIVERSITY NEOFIT RILSKI   (Bulgaria)

Author keywords

Antifungal activity; Antioxidant activity; Homophthalic anhydride; Polyhydroxy stilbenes; Tyrosinase inhibitors

Indexed keywords

2 (1 CARBOXY 2 PHENYLVINYL) 4,5 DIHYDROXYBENZOIC ACID; 2 [1 CARBOXY 2 (3,4 DIHYDROXYPHENYL)VINYL] 4,5 DIHYDROXYBENZOIC ACID; 2 [1 CARBOXY 2 (3,4,5 TRIHYDROXYPHENYL)VINYL] 4,5 DIHYDROXYBENZOIC ACID; 2 [1 CARBOXY 2 (3,5 DI TERT BUTYL 4 HYDROXYPHENYL)VINYL] 4,5 DIHYDROXYBENZOIC ACID; 2 [1 CARBOXY 2 (3,5 DI TERT BUTYL 4 HYDROXYPHENYL)VINYL] 4,5 DIMETHOXYBENZOIC ACID; 2 [1 CARBOXY 2 (4 HYDROXYPHENYL)VINYL] 4,5 DIHYDROXYBENZOIC ACID; ANTIFUNGAL AGENT; CINNAMIC ACID; ENZYME INHIBITOR; PROTOCATECHUIC ACID; SCAVENGER; STILBENE DERIVATIVE; UNCLASSIFIED DRUG; 1,1 DIPHENYL 2 PICRYLHYDRAZYL; AMIKACIN; ANTIINFECTIVE AGENT; CINNAMIC ACID DERIVATIVE; HYDROQUINONE; MONOPHENOL MONOOXYGENASE; NYSTATIN;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS FLAVUS; ASPERGILLUS NIGER; BACILLUS SUBTILIS; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SCREENING; DRUG SYNTHESIS; ESCHERICHIA COLI; FUNGUS GROWTH; FUSARIUM GRAMINEARUM; IN VITRO STUDY; NUCLEAR OVERHAUSER EFFECT; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; REACTION TIME; STAPHYLOCOCCUS AUREUS; ANTIOXIDANT ACTIVITY; ASPERGILLUS; BACTERIAL GROWTH; BACTERIAL STRAIN; CANDIDA ALBICANS; CONTROLLED STUDY; DECARBOXYLATION; ENZYME INHIBITION; FUNGAL STRAIN; GROWTH INHIBITION; HECK REACTION; ISOMERIZATION; LIPID PEROXIDATION; NONHUMAN; POLYMERIZATION; PSEUDOMONAS;

EID: 84879466273     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.05.040     Document Type: Article

References (48)

1. G. Likhtenshtein, Bioactive Stilbenes, in Stilbenes: Applications in Chemistry, Life Sciences and Materials Science, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 2009.
2. J. Chong, A. Poutaraud, P. Hugueney, Metabolism and roles of stilbenes in plants, Plant Sci. 177 (2009) 143-155.
3. F. Mazué, D. Colin, J. Gobbo, M. Wegner, A. Rescifina, C. Spatafora, D. Fasseur, D. Delmas, P. Meunier, C. Tringali, N. Latruffe, Structural determinants of resveratrol for cell proliferation inhibition potency: Experimental and docking studies of new analogs, Eur. J. Med. Chem. 45 (2010) 2972-2980.
4. H. Li, W.K.K. Wu, Z. Zheng, C.T. Che, L. Yu, Z.J. Li, Y.C. Wu, K.-W. Cheng, J. Yu, C.H. Cho, M. Wang, 2,3′,4,4′,5′-Pentamethoxy- trans-stilbene, a resveratrol derivative, is a potent inducer of apoptosis in colon cancer cells via targeting microtubules, Biochem. Pharmacol. 78 (2009) 1224-1232.
5. A. Gosslau, S. Pabbaraja, S. Knapp, K.Y. Chen, trans- and cis-Stilbene polyphenols induced rapid perinuclear mitochondrial clustering and p53-independent apoptosis in cancer cells but not normal cells, Eur. J. Pharmacol. 587 (2008) 25-34.
6. S. Quideau, D. Deffieux, L. Pouysegu, Resveratrol still has something to say about aging!, Angew. Chem. Int. Ed. 51 (2012) 6824-6826.
7. 1-e42 aggregation inhibitors, antioxidants, and neuroprotective agents, Bioorg. Med. Chem. Lett. 22 (2012) 7683-7687.
8. J.-C. Jung, E. Lim, Y. Lee, J.-M. Kang, H. Kim, S. Jang, S. Oh, M. Jung, Synthesis of novel trans-stilbene derivatives and evaluation of their potent antioxidant and neuroprotective effects, Eur. J. Med. Chem. 44 (2009) 3166-3174.
9. D.-J. Ding, X.-Y. Cao, F. Dai, X.-Z. Li, G.-Y. Liu, D. Lin, X. Fu, X.-L. Jin, B. Zhou, Synthesis and antioxidant activity of hydroxylated phenanthrenes as cis-restricted resveratrol analogues, Food Chem. 135 (2012) 1011-1019.
10. S. Sangjun, E. de Jong, S. Nijmeijer, T. Mutarapat, S. Ruchirawat, M. van den Berg, M.B.M. van Duursen, Induction of cell cycle arrest in human MCF-7 breast cancer cells by cis-stilbene derivatives related to VIOXX®, Toxicol. Lett. 186 (2009) 115-122.
11. J. Liu, C.-H. Zheng, X.-H. Ren, F. Zhou, W. Li, J. Zhu, J.-G. Lv, Y.-J. Zhou, Synthesis and biological evaluation of 1-Benzylidene-3,4- dihydronaphthalen-2-one as a new class of MIcrotubule-targeting agents, J. Med. Chem. 55 (2012) 5720-5733.
12. K.V. Balan, Y. Wang, S.W. Chen, J.-C. Chen, L.-F. Zheng, L. Yang, Z.-L. Liu, P. Pantazis, J.H. Wyche, Z. Han, Proteasome-independent down-regulation of estrogen receptor-α (ERα) in breast cancer cells treated with 4,4'-dihydroxy-trans-stilbene, Biochem. Pharmacol. 72 (2006) 573-581. (Pubitemid 44163306)
13. O.I. Petrov, M. Gerova, Ch. Chanev, K.V. Petrova, New efficient synthesis of combretastatin A-4 via colvin rearrangement, Synthesis (2011) 3711-3715.
14. R. Cella, H.A. Stefani, Ultrasound-assisted synthesis of Z and E stilbenes by Suzuki cross-coupling reactions of organotellurides with potassium organo-trifluoroborate salts, Tetrahedron 62 (2006) 5656-5662. (Pubitemid 43668797)
15. K. Gaukroger, J.A. Hadfield, L.A. Hepworth, N.J. Lawrence, A.T. McGown, Novel syntheses of cis and trans isomers of Combretastatin A-4, J. Org. Chem. 66 (2001) 8135-8138. (Pubitemid 34177965)
16. A.G. Myers, D. Tanaka, M.R. Mannion, Development of a decarboxylative palladation reaction and its use in a heck-type olefination of arene carboxylates, J. Am. Chem. Soc. 124 (2002) 11250-11251.
17. G. Bellucci, C. Chiappe, G. Lo Moro, Crown ether catalyzed stereospecific synthesis of Z- and E-stilbenes by Wittig reaction in a solid-liquid two-phases system, Tetrahedron Lett. 37 (1996) 4225-4228. (Pubitemid 26180338)
18. M. Gerova, S. Georgieva, C. Chanev, O.I. Petrov, An improved protocol for the synthesis of natural combretastatin A-4 via modified Wittig reaction, C. R. Acad. Bulg. Sci. 64 (2011) 1415-1420.
19. C. Borrel, S. Thoret, X. Cachet, D. Guernard, F. Tillequin, M. Koch, S. Michel, New antitubulin derivatives in the combretastatin A-4 series: synthesis and biological evaluation, Bioorg. Med. Chem. 13 (2005) 3853-3864. (Pubitemid 40615935)
20. H.-Y. Sun, C.-F. Xiao, Y.-C. Cai, Y. Chen, W. Wei, X.-K. Liu, Z.-L. Lv, Y. Zou, Efficient synthesis of natural polyphenolic stilbenes: resveratrol, piceatannol and oxyresveratrol, Chem. Pharm. Bull. 58 (2010) 1492-1496.
21. C.-F. Xiao, Y. Zou, J.-L. Du, H.-Y. Sun, X.-K. Liu, Hydroxyl substitutional effect on selective synthesis of cis, trans stilbenes and 3-arylcoumarins through Perkin condensation, Synth. Commun. 42 (2012) 1243-1258.
22. A.K. Sinha, V. Kumar, A. Sharma, A. Sharma, R. Kumar, An unusual, mild and convenient one-pot two-step access to (E)-stilbenes from hydroxy-substituted benzaldehydes and phenylacetic acids under microwave activation: a new facet of the classical Perkin reaction, Tetrahedron 63 (2007) 11070-11077. (Pubitemid 47464411)
23. C.S. Letizia, J. Cocchiara, A. Lapczynski, J. Lalko, A.M. Api, Fragrance material review on cinnamic acid, Food Chem. Toxicol. 43 (2005) 925-943. (Pubitemid 40462071)
24. X. Li, X. Wang, D. Chen, S. Chen, Antioxidant activity and mechanism of protocatechuic acid in vitro, Funct. Foods Health Dis. 7 (2011) 232-244.
25. T. Tanaka, T. Tanaka, M. Tanaka, Potential cancer chemopreventive activity of protocatechuic acid, J. Exp. Clin. Med. 3 (2011) 27-33.
26. I. Medina, I. Undeland, K. Larsson, I. Storrø, T. Rustad, C. Jacobsen, V. Kristinová, J.M. Gallardo, Activity of caffeic acid in different fish lipid matrices: a review, Food Chem. 131 (2012) 730-740.
27. M. Touaibia, J. Jean-Francois, J. Doiron, Caffeic acid, a versatile pharmacophore: an overview, Mini Rev. Med. Chem. 11 (2011) 695-713.
28. L.D. Rocha, M.C. Monteiro, A.J. Teodoro, Anticancer properties of hydroxycinnamic acids: a review, Cancer Clin. Oncol. 1 (2012) 1927-4866.
29. Y. Kadoma, S. Fujisawa, A comparative study of the radical-scavenging activity of the phenolcarboxylic acids: caffeic acid, p-coumaric acid, chlorogenic acid and ferulic acid, with or without 2-mercaptoethanol, a thiol, using the induction period method, Molecules 13 (2008) 2488-2499.
30. M.G. Bogdanov, M. Palamareva, cis/trans-Isochromanones. DMAP induced cycloaddition of homophthalic anhydride and aldehydes, Tetrahedron 60 (2004) 2525-2530. (Pubitemid 38249568)
31. M.G. Bogdanov, B. Gocheva, D. Dimitrova, M. Palamareva, New isochromans. 1. Synthesis and antimicrobial activity of 4-substituted (±)-1H-spiro [benzo[c]pyran-3(4H), 1́-cyclohexane]-1-ones, J. Heterocycl. Chem. 44 (2007) 673-677. (Pubitemid 351223674)
32. M.G. Bogdanov, Y. Mitrev, I. Tiritiris, New highly diastereoselective Perkin/ Michael addition domino reaction between homophthalic anhydride and aromatic aldehydes: a facile approach to blue-fluorescent dibenzo[c, h]chromenones, Eur. J. Org. Chem. (2011) 377-384.
33. U. Vogeli, W. von Philipsborn, C. Vicinal, H spin coupling in substituted alkenes. Stereochemical significance and structural effects, Org. Magn. Reson. 7 (1975) 617-627.
34. R.L. Prior, X. Wu, K. Schaich, Standardized methods for the determination of antioxidant capacity and phenolics in foods and dietary supplements, J. Agric. Food Chem. 53 (2005) 4290-4302. (Pubitemid 40936797)
35. L.M. Reid, R.W. Nicol, T. Ouellet, M. Savard, J.D. Miller, J.C. Young, D.W. Stewart, A.W. Schaafsma, Interaction of F. graminearum and F. moniliforme in Maize ears: disease progress, fungal biomass, and mycotoxin accumulation, Phytopathology 89 (1999) 1028-1037. (Pubitemid 29514853)
36. A. Zinedine, J.M. Soriano, J.C. Molto, J. Manes, Review on the toxicity, occurrence, metabolism, detoxification, regulations and intake of zearalenone: an oestrogenic mycotoxin, Food Chem. Toxicol. 45 (2007) 1-18. (Pubitemid 44792326)
37. J.J. Pestka, A.T. Smolinski, Deoxynivalenol: toxicology and potential effects on humans, J. Toxicol. Environ. Health Part B: Crit. Rev. 8 (2005) 39-69. (Pubitemid 40066025)
38. S.-Y. Kwak, J.-K. Yang, H.-R. Choi, K.-C. Park, Y.-B. Kim, Y.-S. Lee, Synthesis and dual biological effects of hydroxycinnamoyl phenylalanyl/prolyl hydroxamic acid derivatives as tyrosinase inhibitor and antioxidant, Bioorg. Med. Chem. Lett. 23 (2013) 1136-1142.
39. S. Okombi, D. Rival, S. Bonnet, A.-M. Mariotte, E. Perrier, A. Boumendjel, Analogues of N-hydroxycinnamoylphenalkylamides as inhibitors of human melanocyte-tyrosinase, Bioorg. Med. Chem. Lett. 16 (2006) 2252-2255. (Pubitemid 43351089)
40. J.-M. Noh, Y.-S. Lee, Inhibitory activities of hydroxyphenolic acid-amino acid conjugates on tyrosinase, Food Chem. 125 (2011) 953-957.
41. S. Kermasha, M. Goetghebeur, A. Monfette, M. Metche, B. Rovel, Inhibitory effects of cysteine and aromatic acids on tyrosinase activity, Phytochemistry 34 (1993) 349-353.
42. L. Georgiev, M. Chochkova, I. Totseva, K. Seizova, E. Marinova, G. Ivanova, M. Ninova, H. Najdenski, T. Milkova, Anti-tyrosinase, antioxidant and antimicrobial activities of hydroxycinnamoylamides, Med. Chem. Res. (2012), http://dx.doi.org/10.1007/s00044-012-0419-x.
43. Q. Fan, H. Jiang, E.-D. Yuan, J.-X. Zhang, Z.-X. Ning, S.-J. Qi, Q.-Y. Wei, Tyrosinase inhibitory effects and antioxidative activities of novel cinnamoyl amides with amino acid ester moiety, Food Chem. 134 (2012) 1081-1087.
44. K. Iwai, N. Kishimoto, Y. Kakino, K. Mochida, T. Fujita, In vitro antioxidative effects and tyrosinase inhibitory activities of seven hydroxycinnamoyl derivatives in green coffee beans, J. Agric. Food Chem. 52 (2004) 4893-4898.
45. I. Kubo, I. Kinst-Hori, Tyrosinase inhibitory activity of the olive oil flavor compounds, J. Agric. Food Chem. 47 (1999) 4574-4578.
46. G.-Z. Liu, J. Zhang, L.-Y. Wang, A comparison of the coordination preference of Cd, Zn, Cu(II) with flexible homophthalic acid and rigid bipyridine ligands, Polyhedron 30 (2011) 1487-1493.
47. C.M. Rogers, C.Y. Wang, G.A. Farnum, R.L. LaDuca, Divalent metal homophthalate coordination polymers with long-spanning dipyridyl ligands containing piperazine moieties, Inorg. Chim. Acta 403 (2013) 78-84.
48. Y. Wang, S.-Q. Shen, J.-H. Zhou, T. Wang, S.-N. Wang, G.-X. Liu, Synthesis, structural diversities and properties of a series of transition metal-organic frameworks based on asymmetric dicarboxylic acid and N-donor auxiliary ligand, Inorg. Chem. Commun. 30 (2013) 5-12.