Green synthesis and anti-inflammatory studies of a series of 1,1-bis(heteroaryl)alkane derivatives

European Journal of Medicinal Chemistry

Volumn 83, Issue , 2014, Pages 561-568

  Jaratjaroonphong, Jaray ^a   Tuengpanya, Surisa ^a   Saeeng, Rungnapha ^a   Udompong, Sarinporn ^a   Srisook, Klaokwan ^a  

^a BURAPHA UNIVERSITY   (Thailand)

Author keywords

1,1 Bis(heteroaryl)alkane; Anti inflammatory agents; Iodine; Nitric oxide

Indexed keywords

1 CYCLOHEXYL 1,1 BIS[(5 METHYL)2 FURYL]METHANE; 1,1 BIS[(5 ETHYL)2 FURYL] 3 PHENYLPROPANE; 1,1 BIS[(5 METHYL)2 FURYL] 3 METHYLBUTANE; 1,1 BIS[(5 METHYL)2 FURYL] 3 PHENYLPROPANE; 1,1 BIS[(5 METHYL)2 FURYL]PENTANE; 1,1 BIS[(5 METHYL)2 FURYL]PROPANE; 1,1 BIS[(5 METHYL)2 THIENYL] 3 PHENYLPROPANE; 2 ETHYL 1,1 BIS[(5 METHYL)2 FURYL]BUTANE; 2,2' (3 PHENYLPROPANE 1,1 DIYL)BIS(1H PYRROLE); 2,2' [(4 NITROPHENYL)METHYLENE]BIS(1H PYRROLE); 3,3' (3 PHENYLPROPANE 1,1 DIYL)BIS(1H INDOLE); 5,5' [(4 NITROPHENYL)METHYLENE]BIS(2 ETHYL 1H PYRROLE); ALKANE DERIVATIVE; ANTIINFLAMMATORY AGENT; BIS[(5 ETHYL)2 FURYL](4 NITROPHENYL) METHANE; BIS[(5 ETHYL)2 FURYL]PHENYL METHANE; NITRIC OXIDE; UNCLASSIFIED DRUG; 1 CYCLOHEXYL 1,1 BIS[(5 METHYL) 2 FURYL]METHANE; 1,1 BIS(HETEROARYL)ALKANE DERIVATIVE; 1,1 BIS[(5 ETHYL) 2 FURYL] 3 PHENYLPROPANE; 1,1 BIS[(5 METHYL) 2 FURYL] 3 METHYLBUTANE; 1,1 BIS[(5 METHYL) 2 FURYL] 3 PHENYLPROPANE; 1,1 BIS[(5 METHYL) 2 FURYL]PENTANE; 1,1 BIS[(5 METHYL) 2 FURYL]PROPANE; 1,1 BIS[(5 METHYL) 2 THIENYL] 3 PHENYLPROPANE; 2 ALKYLFURAN; 2 ETHYL 1,1 BIS[(5 METHYL) 2 FURYL]BUTANE; 2 METHYLFURAN; ALKYLTHIOPHENE; AMINOGUANIDINE; BIS[(5 ETHYL) 2 FURYL](4 NITROPHENYL) METHANE; BIS[(5 ETHYL) 2 FURYL]PHENYL METHANE; BIS[(5 METHYL) 2 FURYL](4 NITROPHENYL) METHANE; INDOLE; IODINE; LIPOPOLYSACCHARIDE; PYRROLE; ALKANE; NONSTEROID ANTIINFLAMMATORY AGENT;

ANIMAL CELL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL VIABILITY; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG MECHANISM; DRUG SYNTHESIS; MACROPHAGE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; THIN LAYER CHROMATOGRAPHY; ANIMAL EXPERIMENT; CATALYST; CHEMICAL REACTION; CYTOTOXICITY; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; ENZYME INHIBITION; FRIEDEL CRAFTS REACTION; GREEN CHEMISTRY; IC50; ANIMAL; BIOSYNTHESIS; CELL LINE; CELL SURVIVAL; CHEMISTRY; CYTOLOGY; DRUG EFFECTS; METABOLISM; MOUSE; SYNTHESIS;

ALKANES; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CELL LINE; CELL SURVIVAL; CHEMISTRY TECHNIQUES, SYNTHETIC; GREEN CHEMISTRY TECHNOLOGY; LIPOPOLYSACCHARIDES; MACROPHAGES; MICE; NITRIC OXIDE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84903779155     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.06.045     Document Type: Article

References (53)

1. W.K. Alderton, C.E. Cooper, and R.G. Knowles Nitric oxide synthases: structure, function and inhibition Biochem. J. 357 2001 593 615 (Pubitemid 32735142)
2. L.-T. Tsao, C.Y. Lee, L.-J. Huang, S.-C. Kuo, and J.P. Wang Inhibition of lipopolysaccharide-stimulated nitric oxide production in RAW 264.7 macrophages by a synthetic carbazole, LCY-2-CHO Biochem. Phamarcol. 63 2002 1961 1968
3. C.E. Wright, D.D. Rees, and S. Moncada Protective and pathological roles of nitric oxide in endotoxin shock Cardiovasc. Res. 26 1992 48 57
4. T.J. Guzik, R. Korbut, and T. Adamek-Guzik Nitric oxide and superoxide in inflammation and immune regulation J. Physiol. Pharmacol. 54 2003 469 487 (Pubitemid 38029745)
5. K.A. Latham, K.B. Whittington, R. Zhou, Z. Qian, and E.F. Rosloniec Ex vivo characterization of the autoimmune T cell response in the HLA-DR1 mouse model of collagen-induced arthritis reveals long-term activation of type II collagen-specific cells and their presence in arthritic joints J. Immunol. 174 2005 3978 3985 (Pubitemid 40395972)
6. V. Nair, S. Thomas, S.C. Mathew, and K.G. Abhilash Recent advanced in the chemistry of triaryl- and triheteroarylmethanes Tetrahedron 62 2006 6731 6747 (Pubitemid 43850561)
7. C.T. Walsh, S. Garneau-Tsodikova, and A.R. Howard-Jones Biological formation of pyrroles: nature's logic and enzymatic machinery Nat. Prod. Rep. 23 2006 517 531 (Pubitemid 44144208)
8. A.V. Butin, T.A. Stroganova, and V.G. Kul'nevich Furyl(aryl)methanes and their analogues Chem. Heterocycl. Compd. 35 1999 757 787
9. M.S. Shchepinov, and V.A. Korshun Recent applications of bifunctional trityl groups Chem. Soc. Rev. 32 2003 170 180 (Pubitemid 38326504)
10. V. Nair, S. Thomas, S.C. Mathew, N. Vidya, and N.P. Rath Electrophilic substitution reactions of trisheteroarylmethanes: an efficient strategy for develop novel synthons for organic synthesis Tetrahedron 61 2005 9533 9540 (Pubitemid 41583472)
11. P.S. Naidu, and P.J. Bhuyan Synthesis of some analogues of (±)-gelliusine F, (±)-gelliusine E, and total synthesis of 2,2-di(6′-bromo-3′-indolyl)ethylamine Tetrahedron Lett. 53 2012 426 428
12. A.R. Katritzky, L. Xie, and W.-Q. Fan Convenient novel synthesis 1,1-bis(heteroaryl)- alkanes J. Org. Chem. 58 1993 4376 4381
13. E. Thiery, D. Harakat, J.L. Bras, and J. Muzart Palladium-catalyzed oxidative coupling of 2-alkylfurans with olefins through C-H activation: synthesis of difurylalkanes Organometallics 27 2008 3996 4004
14. A.V. Butin, A.S. Dmitriev, O.N. Kostyukova, V.T. Abaev, and I.V. Trushkov Synthesis of the 4,10-dihydro-3H-pyridazino[1,6-b]isoquinolin-10-one Synthesis 2007 2208 2214
15. A.V. Gutnov, V.T. Abaev, A.V. Butin, and A.S. Dmitriev Bis(5-alkyl-2-furyl)(2-carboxyphenyl)methanes for the synthesis of tetracyclic isochromone derivatives J. Org. Chem. 66 2001 8685 8686 (Pubitemid 34000680)
16. R. Pajewski, R. Ostaszewski, K. Ziach, A. Kulesza, and J. Jurczak An efficient synthesis of tetraoxaquaterine derivatives starting from 2,2-difurylpropane Synthesis 2004 865 868 (Pubitemid 38594667)
17. N. Arumugam, Y.-S. Jang, and C.-H. Lee Convenient route to super-expanded calixpyrroles: synthesis of calix[n]furano[m]pyrroles (n = 3, 4, 6, 8 and m = 2, 4) Org. Lett. 2 2000 3115 3117
18. J.B. III Pain D. Dolphin, The Porphyrins vol. 1 1978 Academic Press New York
19. C. Marchionni, and P. Vogel Asymmetric synthesis of complicated bicyclic and tricyclic polypropanoates via the double Diels-Alder addition of 2,2′-ethylidenebis[3,5-dimethylfuran] Helv. Chim. Acta 84 2001 431 472 (Pubitemid 32202426)
20. C. Marchionni, P. Vogel, and P. Roversi The simultaneous double Diels-Alder addition of 1,1-bis(3,5-dimethylfur-2-yl)ethane; toward a new, asymmetric synthesis of long-chain polypropionate fragments and analogues Tetrahedron Lett. 37 1996 4149 4152
21. M. Bandini, A. Melloni, S. Tommasi, and A. Umanl-Ronchi A journey across recent advances in catalytic and stereoselective alkylation of indoles Synlett 2005 1199 1222 (Pubitemid 40755295)
22. Q. Kang, Z.-A. Zhao, and S.-L. You Highly enantioselective Friedel-Crafts reaction of indoles with imines by a chiral phosphoric acid J. Am. Chem. Soc. 129 2007 1484 1485
23. N. Saracoglu Functionalization of indole and pyrrole cores via Michael-type additions Top. Heterocycl. Chem. 11 2007 1 61
24. M. Bandini, A. Melloni, and A. Umani-Ronchi New versatile Pd-catalyzed alkylation of indoles via nucleophilic allylic substitution: controlling the regioselectivity Org. Lett. 6 2004 3199 3202 (Pubitemid 39233154)
25. 3-catalyzed highly C3-selective Friedel-Crafts alkylation of indoles with alcohols Tetrahedron Lett. 48 2007 7160 7163 (Pubitemid 47361279)
26. N. Azizi, F. Arynasab, and M.R. Saidi Efficient Friedel-Crafts alkylation of indoles and pyrrole with enones and nitroalkene in water Org. Biomol. Chem. 4 2006 4275 4277 (Pubitemid 44748037)
27. C. Palomo, M. Oiarbide, B.G. Kardak, J.M. Garcia, and A. Linden Highly enantioselective Friedel-Crafts alkylations of pyrroles and indoles with α′-hydroxy enones under Cu(II)-simple bis(oxazoline) catalysis J. Am. Chem. Soc. 127 2005 4154 4155 (Pubitemid 40463024)
28. Y.R. Jorapur, C.-H. Lee, and D.Y. Chi Mono- and dialkylations of pyrrole at C2 and C5 positions by nucleophilic substitution reaction in ionic liquid Org. Lett. 7 2005 1231 1234 (Pubitemid 40544088)
29. 2-catalyzed C-alkylation of pyrroles and indoles with α-diazocarbonyl compounds Tetrahedron Lett. 44 2003 8331 8334 (Pubitemid 37238979)
30. V. Nair, K.G. Abhilash, and N. Vidya Practical synthesis of triaryl- and triheteroaryl-methanes by reaction of aldehydes and activated arenes promoted by gold(III) chloride Org. Lett. 7 2005 5857 5859 (Pubitemid 43052870)
31. V. Nair, N. Vidya, and K.G. Abhilash Efficient condensation reactions of electron-rich arenes with aldehydes and enals promoted by gold(III) chloride: practical synthesis of triaryl- and triheteroarylmethanes and related compounds Synthesis 21 2006 3647 3653 (Pubitemid 44807355)
32. S. Podder, J. Choudhury, U.K. Roy, and S. Roy Dual-reagent catalysis within Ir-Sn domain: highly selective alkylation of arenes and heteroarenes with aromatic aldehydes J. Org. Chem. 72 2007 3100 3103 (Pubitemid 46624448)
33. S. Podder, and S. Roy Efficient and selective alkylation of arenes and heteroarenes with benzyl and allyl ethers using a Ir/Sn bimetallic catalyst Tetrahedron 63 2007 9146 9152 (Pubitemid 47176605)
34. J. Choudhury, S. Podder, and S. Roy Cooperative Friedel-Crafts catalysis in heterobimetallic regime: alkylation of aromatics by π-activated alcohols J. Am. Chem. Soc. 127 2005 6162 6163 (Pubitemid 40627728)
35. P.N. Chatterjee, A.K. Maity, S.S. Mohapatra, and S. Roy Heterobimetallic Ir-Sn catalysis: aza-Fridel-Crafts reaction of N-sulfonyl aldimines Tetrahedron 69 2013 2816 2826
36. J. Esquivias, R. Gómez-Arrayás, and J.C. Carretero A copper(II)-catalyzed aza-Friedel-Crafts reaction of N-(2-pyridyl)sulfonyl aldimines: synthesis of unsymmetrical diaryl amines and triaryl methanes Angew. Chem. Int. Ed. 45 2006 629 633 (Pubitemid 43121462)
37. II-catalyzed aza-Friedel-Crafts reactions J. Org. Chem. 73 2008 6401 6404
38. 3: an efficient catalyst for reductive alkylation of alkoxy benzenes and for synthesis of triarylmethanes using aldehydes Tetrahedron Lett. 50 2009 6693 6697
39. S. Genovese, F. Epifana, C. Pelucchini, and M. Curini Preparation of triaryl- and triheteroarylmethanes under ytterbium triflate catalysis and solvent-free conditions Eur. J. Org. Chem. 2009 1132 1135
40. B. Temelli, and C. Unaleroglu A novel method for the synthesis of dipyrromethanes by metal triflate catalysis Tetrahedron 62 2006 10130 10135 (Pubitemid 44344780)
41. K. Rad-Moghadam, and M. Sharifi-Kiasaraie Indole 3-alkylation/vinylation under catalysis of the guanidinium ionic liquids Tetrahedron 65 2009 8816 8820
42. 2O: synthesis of triarylmethanes and bis-heteroarylarylmethanes J. Org. Chem. 75 2010 5240 5249
43. H. Togo, and S. Iida Synthetic use of molecular iodine for organic synthesis Synlett 14 2006 2159 2175 (Pubitemid 44393514)
44. M. Jereb, D. Vrazic, and M. Zupan Iodine-catalyzed transformation of molecules containing oxygen functional groups Tetrahedron 67 2011 1355 1387
45. J. Jaratjaroonphong, S. Sathalalai, P. Techasauvapak, and V. Reutrakul Iodine catalyzed Friedel-Crafts alkylation of electron-rich arenes with aldehydes: efficient synthesis of triarylmethanes and diarylalkanes Tetrahedron Lett. 50 2009 6012 6015
46. J. Jaratjaroonphong, S. Krajangsri, V. Reutrakul, and V. Iodine-catalyzed one-pot, three-component aza-Friedel-Crafts reaction of electron-rich arenes with aldehyde/carbamate combinations Tetrahedron Lett. 53 2012 2476 2479
47. C.-J. Li Organic reactions in aqueous media with a focus on carbon-carbon bond formations: a decade update Chem. Rev. 105 2005 3095 3165 (Pubitemid 41222792)
48. S.-J. Ji, S.-Y. Wang, Y. Zhang, and T.-P. Loh Facile synthesis of bis(indolyl)methanes using catalytic amount of iodine at room temperature under solvent-free conditions Tetrahedron 60 2004 2051 2055 (Pubitemid 38201586)
49. P.-A. Faugeras, B. Boëns, P.-H. Elchinger, J. Vergnaud, and K. Teste Synthesis of meso-substituted dipyrromethanes using iodine-catalysis Tetrahedron Lett. 51 2010 4630 4632
50. B. Boëns, P.-A. Faugeras, J. Vergnaud, and R. Lucas Iodine-catalyzed one-pot synthesis of unsymmetrical meso-substituted porphyrins Tetrahedron 66 2010 1994 1996
51. R. Lucas, J. Vergnaud, K. Teste, R. Zerrouki, V. Sol, and P. Krausz A facile and rapid iodine-catalyzed meso-tetraphenylporphyrin synthesis using microwave activation Tetrahedron Lett. 49 2008 5537 5539
52. B.P. Banduar, and K.A.K. Shaikh Molecular iodine-catalyzed efficient and highly rapid synthesis of bis(indolyl)methanes under mild conditions Tetrahedron Lett. 44 2003 1959 1961
53. K. Srisook, M. Palachot, N. Mongkol, E. Srisook, and S. Sarapusit Anti-inflammatory effect of ethyl acetate extract from Cissus quadrangularis Linn may be involved with induction of heme oxygenase-1 and suppression of NF-κB activation J. Ethnopharmacol. 133 2011 1008 1014