Efficient synthesis and free-radical scavenging capacity of new 2, 4-substituted tetrahydroquinolines prepared via BiCl 3-catalyzed three-component Povarov reaction, using N-vinylamides

Molecular Diversity

Volumn 15, Issue 4, 2011, Pages 1007-1016

  Kouznetsov, Vladimir V ^a   Gómez, Carlos M Meléndez ^b   Parada, Luz K Luna ^a   Bermudez, John H ^a   Méndez, Leonor Y Vargas ^c   Acevedo, Amner Muñoz ^d  

^a UNIVERSIDAD INDUSTRIAL DE SANTANDER   (Colombia)

^b UNIVERSIDAD DEL ATLÁNTICO   (Colombia)

^c UNIVERSIDAD SANTO TOMÁS   (Colombia)

^d UNIVERSIDAD DEL NORTE   (Colombia)

Author keywords

2,4 disubstituted tetrahydroquinolines; Antioxidant agents; DOS methodology; MCRs; Reaction imino Diels Alder (Povarov); Structural diversity

Indexed keywords

ALDEHYDE; ALPHA TOCOPHEROL; AMIDE; ANILINE DERIVATIVE; ENAMIDE; N [2 (3',4' METHYLENEDIOXYPHENYL) 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]PYRROLIDIN 2 ONE; N [2 (ALPHA FURANVINYL) 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]ACETAMIDE; N [2 (ALPHA FURANVINYL) 6 METHYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]ACETAMIDE; N [2 (ALPHA FURANYL) 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]ACETAMIDE; N [2 (ALPHA FURANYL) 5,7 DIMETHYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]ACETAMIDE; N [2 (ALPHA FURANYL) 6 CHLORO 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]ACETAMIDE; N [2 (ALPHA FURANYL) 6 ETHYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]ACETAMIDE; N [2 (ALPHA FURANYL) 6 METHOXY 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]ACETAMIDE; N [2 (ALPHA FURANYL) 6 METHYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]ACETAMIDE; N [2 (ALPHA FURANYL) 6 NITRO 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]ACETAMIDE; N [2 (ALPHA FURANYL) 6,7 METHILENEDIOXY 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]ACETAMIDE; N [5,7 DIMETHYL 2 (3',4' METHYLENDIOXYPHENYL) 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]PYRROLIDIN 2 ONE; N [5,8 DIMETHYL 2 (3',4' METHYLENDIOXYPHENYL) 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]PYRROLIDIN 2 ONE; N [6 CHLORO 2 (3',4' METHYLENDIOXYPHENYL) 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]PYRROLIDIN 2 ONE; N [6 FLUORO 2 (3',4' METHYLENDIOXYPHENYL) 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]PYRROLIDIN 2 ONE; N [6 METHOXY 2 (3',4' METHYLENDIOXYPHENYL) 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]PYRROLIDIN 2 ONE; N [6 METHYL 2 (3',4' METHYLENDIOXYPHENYL) 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]PYRROLIDIN 2 ONE; N [6,8 DIMETHOXY 2 (3',4' METHYLENDIOXYPHENYL) 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]PYRROLIDIN 2 ONE; N [7 ETHYL 2 (3',4' METHYLENDIOXYPHENYL) 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]PYRROLIDIN 2 ONE; N VINYLACETAMIDE; N VINYLPYRROLIDIN 2 ONE; QUINOLINE DERIVATIVE; SCAVENGER; TETRAHYDROQUINOLINE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DIELS ALDER REACTION; DRUG POTENCY; DRUG SYNTHESIS; POVAROV REACTION; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

AMIDES; BISMUTH; CATALYSIS; CHEMISTRY TECHNIQUES, SYNTHETIC; CHLORIDES; FREE RADICAL SCAVENGERS; QUINOLINES;

EID: 84855247779     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-011-9330-5     Document Type: Article

References (38)

1. Arya P, Joseph R, Gan Z, Rakic B (2005) Exploring new chemical space by stereocontrolled diversity-oriented synthesis. Chem Biol 12:163-180. doi:10.1016/j.chembiol.2005.01.011 (Pubitemid 40281324)
2. Boger DL, Weinreb S (1987) Hetero Diels-Alder methodology in organic synthesis. Academic Press, San Diego
3. Weinreb SM (1991) [4 + 2] Cycloadditions. In: Trost BM, Fleming I (eds) Comprehensive organic synthesis. Pergamon, Oxford, pp 401-512
4. Tan DS (2005) Diversity-oriented synthesis exploring the intersections between chemistry and biology. Nat Chem Biol 1:74-84. doi:10.1038/nchembio0705- 74
5. Arya P, Durieux P, Chen Z-X, Joseph R, Leek D (2004) Stereoselective diversity-oriented solution and solid-phase synthesis of tetrahydroquinoline- based polycyclic derivatives. J Comb Chem 6:54-64. doi:10.1021/cc034053z (Pubitemid 38142640)
6. Arya P, Couve-Bonnaire S, Durieux P, Laforce O, Kumar R, Leek DM (2004) Solution- and solid-phase synthesis of natural productlike tetrahydroquinoline- based polycyclics having a medium size ring. J Comb Chem 6:735-745. doi:10.1021/cc049935s (Pubitemid 39329428)
7. Spring DR (2003) Diversity-oriented synthesis; a challenge for synthetic chemists. Org Biomol Chem 1:3867-3870. doi:10.1039/B310752N
8. Spandl RJ, Bender A, Spring DR (2008) Diversity-oriented synthesis; a spectrum of approaches and results. Org Biomol Chem 6:1149-1158. doi:10.1039/B719372F (Pubitemid 351432832)
9. Kouznetsov VV, Astudillo L, Vargas LY, Cazar ME (2004) Synthesis of some secondary amine derivatives bearing a heteroaryl fragment. J Chil Chem Soc 49:107-203. doi:10.4067/S0717- 97072004000400010
10. Inserra PF, Ardestani SK, Watson RR (1997) Antioxidants and immune function. In: Garewal HS (ed) Antioxidant and disease prevention. CRC Press, Boca Raton, pp 19-29
11. MDLDrugDataReport (MDDR)database: http://www.akosgmbh.de/Symyx/software/ databases/mddr.htm
12. Meier HR, Evans S (1989) N-Substituted tetrahydroquinolines for use as antioxidants in lubricants. U.S. Patent 4828741, 9 May
13. Meier HR, Evans S (1990) N-Substituted tetrahydroquinolines for use as antioxidants in lubricants. U.S. Patent 4919832, 24 Apr
14. Rasberger M (1983) Tetrahydroquinoline as an antioxidant for lubricants. EP0072349A2, 16 Feb
15. Nishiyama T, Suzuki T, Hasiguchi Y, Shiotsu S, Fujioka M (2002) Antioxidant activity of aromatic cyclic amine derivatives. Polym Degrad Stab 75:549-554. doi:10.1016/S0141-3910(01)00258-0 (Pubitemid 34100058)
16. Nishiyama T, Hasiguchi Y, Sakata T, Sakaguchi T (2003) Antioxidant activity of the fused heterocyclic compounds, 1, 2, 3, 4- tetahydroquinolines, and related compounds-effect of ortho-substituents. Polym Degrad Stab 79:225-230. doi:10.1016/S0141-3910(02)00285-9 (Pubitemid 35452393)
17. De Koning AJ (2002) The antioxidant ethoxyquin and its analogues: A review. Int J Food Properties 5:451-461. doi:10.1081/JFP-120005797
18. B?aszczyk A, Skolimowski J (2006) Comparative analysis of cytotoxic, genotoxic and antioxidant effects of 2, 2, 4, 7-tetramethyl- 1, 2, 3, 4-tetrahydroquinoline and ethoxyquin on human lymphocytes. Chem-Biol Interact 162:70-80. doi:10.1016/j.cbi.2006.05.008 (Pubitemid 44080168)
19. Dorey G, Lockhart B, Lestage P, Casara P (2000) New quinolinic derivatives as centrally active antioxidants. BioorgMed Chem Lett 10:935-939. doi:10.1016/S0960-894X(00)00122-0 (Pubitemid 30301597)
20. Panteleon V, Marakos P, Pouli N, Mikros E, Andreadou I (2003) Synthesis, conformational analysis and free radical scavenging activity of some new Spiropyranoquinolinones. Chem Pharm Bull 51:522-529. doi:10.1248/cpb.51.522 (Pubitemid 41656803)
21. Kouznetsov VV, Vargas Méndez LY, Muñoz Acevedo A (2010) 3′4′-Dihydrospiro[piperidine-42′-(1′H quinoline] derivatives as new antioxidant agents with acetylcholinesterase inhibitory property. Lett Drug Des Discov 7:710-715
22. Kouznetsov VV, Bohórquez A, Astudillo L, Fierro R (2006) An efficient synthesis of new C-2 aryl substituted quinolines based on three component imino Diels-Alder reaction. Mol Divers 10:29-37. doi:10.1007/s11030- 006-2344-8 (Pubitemid 43096171)
23. Kouznetsov VV, Mora Cruz U, Zubkov FI, Nikitina EV (2007) An Efficient synthesis of isoindolo[2, 1-a]quinoline derivatives via imino Diels-Alder and intramolecular Diels-Alder with furan methodologies. Synthesis 375-384. doi:10.1055/s-2007-965875 (Pubitemid 46474219)
24. Kouznetsov VV, Meléndez Gómez CM, Bermúdez Jaimes JH (2010) Transformations of 2-aryl-4-(2-oxopyrrolinidyl-1)- 1, 2, 3, 4-tetrahydro-quinolines, cycloadducts of the BiCl3-catalyzed three component Povarov reaction: oxidation and reduction processes towards new potentially bioactive 2-arylquinoline derivatives. J Heterocycl Chem 47:1148-1152. doi:10.1002/jhet.44
25. Salvador JAR, Pinto RMA, Silvestre SM (2009) Recent advances of bismuth(III) salts in organic chemistry: application to the synthesis of heterocycles of pharmaceutical interest. Curr Org Synth 6:426-470
26. Katritzky A, Rachwal B, Rachwal S (1995) Reactions of N-alkyl- N-phenyl-1H-benzotriazole-1-methanamineswith N-vinylamides and N-vinylcarbazole. A convenient synthesis of 4-(dialkylamino)- tetrahydroquinolines. J Org Chem 60:3993-4001. doi:10.1021/jo00118a014
27. Talukdar S, Chen C-T, Fang J-M (2000) A stereoselective route to polysubstituted tetrahydroquinolines by benzotriazole-promoted condensation of aliphatic aldehydes and aromatic amines. J Org Chem 65:3148-3153. doi:10.1021/jo000033x (Pubitemid 30329180)
28. Zhang W, Guo Y, Liu Z, Jin X, Yang L, Liu Z-L (2005) Photochemically catalyzed Diels-Alder reaction of arylimines with N-Vinylpyrrolidinone and N-vinylcarbazole by 2, 4, 6-triphenylpyrylium salt: synthesis of 4-heterocycle-substituted tetrahydroquinoline derivatives. Tetrahedron 61:1325-1333. doi:10.1016/j. tet.2004.11.042 (Pubitemid 40126735)
29. +) initiated and cation radical-mediated imino Diels-Alder reaction. Tetrahedron Lett 46:8937-8939. doi:10.1016/j.tetlet.2005.10.083 (Pubitemid 41665934)
30. Damon DB, Dugger R, Magnus-Aryitey G, Ruggeri R, Wester R, Tu M, Abramov Y (2006) Synthesis of the CETP inhibitor Torcetrapib: the resolution route and origin of stereoselectivity in the iminium ion cyclization. Org Process Res Dev 10:464-471. doi:10.1021/op060014a (Pubitemid 44012684)
31. HaddenM, Nieuwenhuyezen M, PottsD, Stevenson PJ, Thompson N (2001) Synthesis and reactivity of hexahydropyrroloquinolines. Tetrahedron 57:5615-5624 (Pubitemid 32537810)
32. Guo C, Yang J, Wei J, Li Y, Xu J, Jiang Y (2003) Antioxidant activities of peel, pulp and seed fractions of common fruits as determined by FRAP assay. Nutr Res 23:1719-1726. doi:10.1016/j.nutres.2003.08.005 (Pubitemid 38018625)
33. Prior RL, HoangH, Gu L, WuX, Bacchiocca M, Howard L, Hampsch- Woodill M, Huang D, Ou B, Jacob R (2003) Assays for hydrophilic and lipophilic antioxidant capacity (oxygen radical absorbance capacity (ORACFL)) of plasma and other biological and food samples. J Agric Food Chem 51:3273-3279. doi:10.1021/jf0262256
34. Sanchez-Moreno C, Larrauri JA, Saura-Calixto F (1998) A procedure to measure the antiradical efficiency of polyphenol. J Sci Food Agric 76:270-276. doi:10.1002/(SICI)1097-0010(199802)76:2< 270 (Pubitemid 28126648)
35. Mulabagal V, Alexander-Lindo RL, DeWitt DL, Nair MG (2008) Functional food components of Antigonon leptopustea. Food Chem 106:487-492. doi:10.1016/j.foodchem.2007.06.013 (Pubitemid 47332858)
36. Re R, PellegriniN, ProteggenteA, Pannala A, Yang M, Rice-Evans C (1999) Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biol Med 26:1231-1237 (Pubitemid 29262709)
37. Muñoz-Acevedo A, Vargas Méndez LY, Stashenko EE, Kouznetsov VV (2011) Improved Trolox™ equivalent antioxidant capacity assay for efficient and fast search of new antioxidant agents. Anal Chem Lett 1:86-102
38. Thorisson S, Gunstone FD, Hardy R (1992) Some oxidation products of ethoxyquin including those found in autoxidising systems. Chem Phys Lipids 60:263-271