RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2012(6): 920-924
DOI: 10.1055/s-0031-1290610
DOI: 10.1055/s-0031-1290610
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New YorkAn Efficient One-Pot Access to Quinazolinone Derivatives Using TiO2 Nanoparticles as Catalyst: Synthesis and Vasorelaxant Activity Evaluation
Weitere Informationen
Received
11 December 2011
Publikationsdatum:
15. März 2012 (online)
Publikationsverlauf
Publikationsdatum:
15. März 2012 (online)
Abstract
A variety of quinazolinone derivatives were successfully synthesized, via a three-component condensation reaction between anthranilic acid, acetic anhydride, and amines. This process was accomplished in the presence of catalytic amount of titanium dioxide nanoparticles (nano-TiO2), under solvent-free conditions. The synthesized compounds were evaluated for their vasorelaxant activity as they revealed a range of activities on the isolated thoracic rat aorta.
Key words
quinazolinone - multicomponent reaction - TiO2 nanoparticles - heterogeneous catalyst - vasorelaxant activity
- Supporting Information for this article is available online:
- Supporting Information (PDF) (opens in new window)
- 1
Zhou H.-B.Liu G.-S.Yao Z.-J. J. Org. Chem. 2007, 72: 6270 - 2
Bandekar PP.Roopnarine KA.Parekh VJ.Mitchell TR.Novak MJ.Sinden RR. J. Med. Chem. 2010, 53: 3558 - 3
McLaughlin NP.Evans P. J. Org. Chem. 2010, 75: 518 - 4
Bergman J.Bergman S. J. Org. Chem. 1985, 50: 1246 - 5a
Kamal A.Ramana KV.Rao MV. J. Org. Chem. 2001, 66: 997 - 5b
Coskun N.Etin MC. Tetrahedron Lett. 2004, 45: 8973 - 6a
Melvin JY.Thrasher J.McCowan JR.Mason NR.Mendelsohn LG. J. Med. Chem. 1991, 34: 1505 - 6b
Parmar SS.Kumar R. J. Med. Chem. 1968, 11: 635 - 6c
Bonola G.Re PD.Magistretti MJ.Massarani E.Setnikar I. J. Med. Chem. 1968, 11: 1136 - 7a
Peet NP.Baugh LE.Sunder S.Lewis JE.Matthews EH.Olberding EL.Shah DN. J. Med. Chem. 1986, 29: 2403 - 7b
Chen K.Aowad AF.Adelstein SJ.Amin I.Kassis AI. J. Med. Chem. 2007, 50: 663 - 8a
Tani J.Yamada Y.Oine T.Ochiai T.Ishida R.Inoue I. J. Med. Chem. 1979, 22: 95 - 8b
Nagase T.Mizutani T.Sekino E.Ishikawa S.Ito S.Mitobe Y.Miyamoto Y.Yoshimoto R.Tanaka T.Ishihara A.Takenaga N.Tokita S.Sato S. J. Med. Chem. 2008, 51: 6889 - 8c
Henderson EA.Bavetsias V.Theti DS.Wilson SC.Clauss R.Jackman AL. Bioorg. Med. Chem. 2006, 14: 5020 - 9a
Martins MAP.Frizzo CP.Moreira DN.Zanatta N.Bonacorso HG. Chem. Rev. 2008, 108: 2015 - 9b
Kim SH.Kim SH.Kim TH.Kim JN. Tetrahedron Lett. 2010, 51: 2774 - 9c
Martins MAP.Frizzo CP.Moreira DN.Buriol L.Machado P. Chem. Rev. 2009, 109: 4140 - 10a
Gopalsamy A.Yang H. J. Comb. Chem. 2000, 2: 378 - 10b
Liu JF.Kaselj M.Isome Y.Ye P.Sargent K.Sprague K.Cherrak D.Wilson CJ.Si Y.Yohannes D.Ng SC. J. Comb. Chem. 2006, 8: 7 - 10c
Hsu NM.Li CY.Yang CM.Lin TS.Hu BH.Tingare YS.Chang WC.Srivastava GK.Li WR. J. Comb. Chem. 2009, 11: 943 - 11
Andrus MB.Mettath SN.Song C. J. Org. Chem. 2002, 67: 8284 - 12
Chou WC.Tan CW.Chen SF.Ku H. J. Org. Chem. 1998, 63: 10015 - 13
Giardin D.Martarelli D.Sagratini G.Angeli P.Ballinari D.Gulini U.Melchiorre C.Poggesi E.Pompei P. J. Med. Chem. 2009, 52: 4951 - 14a
Gopalsamy A.Yang H. J. Comb. Chem. 2000, 2: 378 - 14b
Yang D.Fu H.Hu L.Jiang Y.Zhao Y. J. Comb. Chem. 2009, 11: 653 - 15a
Larksarp C.Alper H. J. Org. Chem. 2000, 65: 2773 - 15b
Kabri Y.Gellis A.Vanelle V. Green Chem. 2009, 11: 201 - 15c
Chilin A.Marzaro G.Zanatta S.Guiotto A. Tetrahedron Lett. 2007, 48: 3229 - 15d
Adib M.Ansari S.Mohammadi A.Bijanzadeh HR. Tetrahedron Lett. 2010, 51: 30 - 16
Xue S.McKenna J.Shieh WC.Repi O. J. Org. Chem. 2004, 69: 6474 - 17
Couture A.Cornet H.Grandclaudon P. Synthesis 1991, 1009 - 18
Paterson TMC.Smalley RK.Suschitzky H. Synthesis 1975, 187 - 19
Li G.Kakarla R.Gerritz SW.Pendri A.Ma B. Tetrahedron Lett. 2009, 50: 6048 - 20a
Zhang X.Ye D.Sun H.Guo D.Wang J.Huang H.Zhang X.Jianga H.Liu H. Green Chem. 2009, 11: 1881 - 20b
Huang C.Fu Y.Fu H.Jiang Y.Zhao Y. Chem. Commun. 2008, 6333 - 20c
Huang X.Yang H.Fu H.Qiao R.Zhao Y. Synthesis 2009, 2679 - 21
Khalafi-Nezhad A.Panahi F. Synthesis 2011, 984 - 22a
Mehta VP.Modha SG.Ruijter E.Hecke KV.Meervelt LV.Pannecouque C.Balzarini J.Orru RVA.Eycken EV. J. Org. Chem. 2011, 76: 2828 - 22b
Weber L. Curr. Med. Chem. 2002, 9: 2085 - 23a
Dabiri M.Salehi P.Khajavi MS.Mohammadi AA. Heterocycles 2004, 63: 1417 - 23b
Dandia A.Singh R.Sarawgi P. J. Fluorine Chem. 2005, 126: 307 - 23c
Khosropour AR.Mohammadpoor-Baltork I.Ghorbankhani H. Tetrahedron Lett. 2006, 47: 3561 - 24
Mossetti R.Pirali T.Saggiorato D.Tron GC. Chem. Commun. 2011, 47: 6966 - 25a
Khalafi-Nezhad A.Soltani Rad MN.Mohabatkar H.Asrari Z.Hemmateenejad B. Bioorg. Med. Chem. 2005, 13: 1931 - 25b
Khalafi-Nezhad A.Zarea A.Soltani Rad MN.Mokhtari B.Parhami A. Synthesis 2005, 419 - 25c
Khalafi-Nezhad A.Soltani Rad MN.Hakimelahi GH. Helv. Chem. Acta 2003, 86: 2396 - 25d
Oryan A.Khalafi-Nezhad A.Toloo N.Soltani Rad MN. J. Vet. Med. A. 2007, 54: 585 - 26a
Hubert C.Denicourt-Nowicki A.Beaunier P.Roucoux A. Green Chem. 2010, 12: 1167 - 26b
Hosseini-Sarvari M.Sodagar E.Doroodmand MM. J. Org. Chem. 2011, 76: 2853 - 26c
Seh ZW.Liu S.Zhang SY.Shah KW.Han MY. Chem. Commun. 2011, 47: 6689 - 27a
Huang H.Leung DYC. ACS Catal. 2011, 1: 348 - 27b
Hosseini-Sarvari M. Tetrahedron 2008, 64: 5459 - 28a
Yamazaki S. Bull. Chem. Soc. Jpn. 1996, 69: 2955 - 28b
Reich HJ.Chow F.Peake SL. Synthesis 1978, 299 - 28c
Bortolini O.Di Furia F.Modena G.Seraglia R.
J. Org. Chem. 1985, 50: 2688 - 29
Ramanjulu JM.DeMartino MP.Lan Y.Marquis R. Org. Lett. 2010, 12: 2270 - 30
Jatav V.Mishra P.Kashaw S.Stables JP. Eur. J. Med. Chem. 2008, 135 - 31
Mane RS.Ghosh S.Chopade BA.Reiser O.Dhavale DD. J. Org. Chem. 2011, 76: 2892 - 32
Damha MJ.Ogilvie KK. J. Org. Chem. 1986, 51: 3559 - 34
Hansen CP.Jensen AA.Christensen JK.Balle T.Liljefors T.Frølund B. J. Med. Chem. 2008, 51: 7380
References
See Supporting Information.