|
OALib Journal期刊
ISSN: 2333-9721
费用：99美元
|
|
|
|
Bismuthtriflate:Ahighlyefficientcatalystforthesynthesisofbio-activecoumarincompoundsviaone-potmulti-componentreaction
DOI: 10.1016/S1872-2067(14)60308-9, PP. 1124-1130
Keywords: Coumarin,Chalcone,Pyrazoline,One-potmulti-componentreaction,Salicylaldehyde,α-Ketoester,Bismuthtriflate[Bi(OTf)3]
Abstract:
？Aseriesofcoumarin-chalconehybridcompoundsandcoumarinslinkedtopyrazolinewassynthesizedingoodyieldandshorttimeusingasimpleandefficientmethod.Thismethodinvolvedtheone-potreactionofsalicylaldehyde,anα-ketoesterandanaromaticaldehyde(inthecaseofthecoumarin-chalconederivatives)inadditiontohydrazinehydrate(inthecaseofthepyrazolylcoumarins)inthepresenceofacatalyticamountofbismuthtriflate[Bi(OTf)3,5mol%].Thesynthesizedcompoundsshowedscavengingactivitytowardsthefreeradical2,2-diphenyl-1-picrylhydrazyl.AllcompoundswerecharacterizedusingIR,1HNMRand13CNMRspectroscopy.
| [1] | Riveiro M E, Shayo C, Monczor F, Fernandez N, Baldi A, De Kimpe N, Rossi J, Debenedetti S, Davio C. Cancer Lett, 2004, 210: 179
|
| [2] | Murray R D H, Mendez J, Brown S A. The Natural Coumarins: Occurrence, Chemistry, and Biochemistry. Chichester (UK): Wiley, 1982
|
| [3] | Nguyen V T, Debenedetti S, De Kimpe N. Tetrahedron Lett, 2003, 44: 4199
|
| [4] | Maes D, Vervisch S, Debenedetti S, Davio C. Mangelinckx S, Giubellina N, De Kimpe N. Tetrahedron, 2005, 61: 2505
|
| [5] | Ngameni B, Watchueng J, Boyom F F, Keumedjio F, Ngadjui B T, Gut J, Abegaz B M, Rosenthal P J. ARKIVOC, 2007: 116
|
| [6] | Okwu D E, Ukanwa N. Chem Sin, 2010, 1(2): 21
|
| [7] | Ballesteros J F, Sanz M J, Ubeda A, Miranda M A, Iborra S, Paya M, Alcaraz M. J Med Chem, 1995, 38: 2794
|
| [8] | Go M L, Wu X, Liu X L. Curr Med Chem, 2005, 12: 483
|
| [9] | Mukherjee S, Kumar V, Prasad A K, Raj H G, Bracke M E, Olsen C E, Jain S C, Parmar V S. Bioorg Med Chem, 2001, 9: 337
|
| [10] | Liu M, Wilairat P, Croft S L, Tan A L G, Go M L. Bioorg Med Chem, 2003, 11: 2729
|
| [11] | Sivakumar P M, Babu S K G, Mukesh D. Chem Pharm Bull, 2007, 55: 44
|
| [12] | Viana G S B, Bandeira M A M, Mantos F J A. Phytomedicine, 2003, 10: 189
|
| [13] | Xia Y, Yang Z Y, Xia P, Bastow K F, Nakanishi Y, Lee K H. Bioorg Med Chem lett, 2000, 10: 699
|
| [14] | Ducki S, Forrest R, Hadfield J A, Kendall A, Lawrence N J, McGown A T, Rennison D. Bioorg Med Chem Lett, 1998, 8: 1051
|
| [15] | Wagner B D. Molecules, 2009, 14: 210
|
| [16] | Dorlars A, Schellhammer C W, Schroeder J. Angew Chem Int Ed, 1975, 14: 665
|
| [17] | Kumar S, Bawa S, Drabu S, Kumar R, Gupta H. Recent Patents on Anti-Infective Drug Discovery, 2009, 4: 154
|
| [18] | Zhu J P, Bienayme H. Multicomponent Reactions. Weinheim: WILEY-VCH, 2005
|
| [19] | Wang Z Z, Fang S Y. Eur J Org Chem, 2009: 5505
|
| [20] | Ollevier T. Org Biomol Chem, 2013, 11: 2740
|
| [21] | Tiwari A K. Curr Sci, 2004, 86: 1092
|
| [22] | Sethna S M, Shah N M. Chem Rev, 1945, 36: 1
|
| [23] | Riveiro M E, De Kimpe N, Moglioni A, Vazquez R, Monczor F, Shayo C, Davio C. Curr Med Chem, 2010, 17: 1325
|
| [24] | Riveiro M E, Maes D, Vazquez R, Vermeulen M, Mangelinckx S, Jacobs J, Debenedetti S, Shayo C, De Kimpe N, Davio C. Bioorg Med Chem,2009, 17: 6547
|
| [25] | O'Kennedy R, Thornes R D. Coumarins: Biology, Applications, and Mode of Action. Chichester (UK): Wiley, 1997
|
| [26] | Yu D L, Suzuki M, Xie L, Morris-Natschke S L, Lee K H. Med Res Rev, 2003, 23: 322
|
| [27] | Zhang Q Y, Qin L P, He W D, Van Puywelde L, Maes D, Adams A, De Kimpe N. Planta Medica, 2007, 73: 13
|
| [28] | Tejedor D, Garcia-Tellado F. Chem Soc Rev, 2007, 36: 484
|
| [29] | Ugi I. Pure Appl Chem, 2001, 73: 187
|
| [30] | Lieby-Muller F, Simon C, Constantieux T, Rodriguez, J. QSAR Comb Sci, 2006, 25: 432
|
| [31] | Trost B M. Angew Chem Int Ed, 1995, 34: 259
|
| [32] | Wender P A, Handy S T, Wright D L. Chem Ind, 1997: 767
|
| [33] | Weber L. Curr Opin Chem Biol, 2000, 4: 295-302
|
| [34] | El-Remaily M A A. Tetrahedron, 2014, 70: 2971
|
| [35] | Domling A. Curr Opin Chem Biol, 2002, 6: 306
|
| [36] | Leonard N M, Wieland L C, Mohan R S. Tetrahedron, 2002, 58: 8373
|
| [37] | Thirupathi P, Kim S S. Tetrahedron, 2009, 65: 5168
|
| [38] | Rivera S, Bandyopadhyay D, Banik B K. Tetrahedron Lett, 2009, 50: 5445
|
| [39] | Antoniotti S, Dunach E. C R Chim, 2004, 7: 679
|
| [40] | Mohammadpoor-Baltork I, Khosropour A R, Moghadam M, Tangestaninejad S, Mirkhani V, Baghersad S, Mirjafari A. C R Chim, 2011, 14: 944
|
| [41] | Ollevier T. Top Curr Chem, 2012, 311: 69
|
| [42] | Pin F, Comesse S, Garrigues B, Marchaln S, Daich A. J Org Chem, 2007, 72: 1181
|
| [43] | Anzalone P W, Baru A R, Danielson E M, Hayes P D, Nguyen M P, Panico A F, Smith R C, Mohan R S. J Org Chem, 2005, 70: 2091
|
| [44] | Rueping M, Nachtsheim B J, Ieawsuwan W. Adv Synth Catal, 2006, 348: 1033
|
| [45] | Ollevier T, Li Z Y. Adv Synth Catal, 2009, 351: 3251
|
| [46] | Venkat Narsaiah A, Reddy B V S, Premalatha K, Reddy S S, Yadav J S. Catal Lett, 2009, 131: 480
|
| [47] | Podgorski D M, Krabbe S W, Le L N, Sierszulski P R, Mohan R S. Synthesis, 2010: 2771
|
| [48] | Sugino T, Tanaka K. Chem Lett, 2001, 30: 110
|
| [49] | Bhatnagar A, Sharma P K, Kumar N, Upadhyay A. Pharm Chem J, 2012, 46: 482
|
| [50] | Blois M S. Nature, 1958, 181: 1199
|
| [51] | Samshuddin S, Narayana B, Sarojini B K, Yathirajan H S, Raghavendra R. Pharm Chem, 2012, 4: 1445
|
Full-Text
|
|
Contact Us
[email protected] QQ:3279437679 
WhatsApp +8615387084133
|
|
