Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2010(16): 2776-2786
DOI: 10.1055/s-0030-1258140
DOI: 10.1055/s-0030-1258140
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Total Synthesis of 3′,3′′′-Binaringenin and Related Biflavonoids
Further Information
Received
18 December 2009
Publication Date:
30 June 2010 (online)
Publication History
Publication Date:
30 June 2010 (online)
Abstract
The synthesis of natural 3′,3′′′-binaringenin and four related biflavonoids was performed in good overall yield (15-35%) starting from readily available phloroglucinol and 4-hydroxy- or 4-methoxybenzaldehyde. Preliminary results indicate that some of these compounds have an interesting activity against S. aureus.
Key words
binaringenin - biapigenin - protecting groups - antibacterial activity
- Supporting Information for this article is available online:
- Supporting Information
- 1
Mabry TJ.Ulubelen A. J. Agric. Food Chem. 1980, 28: 188 - 2
Mabry TJ.Markham KR.Thomas MB. The Systematic Identification of Flavonoids Springer Verlag; Heidelberg: 1970. - 3
Markham KR.Mabry TJ. The FlavonoidsHarborne JB.Mabry TJ.Mabry H. Chapman Hall; London: 1975. - 4
Geissman TA. The Chemistry of Flavonoid Compounds MacMillan; New York: 1962. - 5
Foo LY.Helm R.Karchesy J. Phytochemistry 1992, 31: 1444 - 6
Swamy RC.Kunert O.Schuhly W.Bucar F.Daneel F.Rani VS.Kumar BR.Rao AVNA. Chemistry & Biodiversity 2006, 3: 405 - 7
Seeger T.Geiger H.Zinsmeister HD.Rozdzinski W. Phytochemistry 1993, 34: 295 - 8
Zhao X.Jiang H.-X.Huang H.Zhu R.-L.Jiang B. Chin. J. Chem. 2006, 24: 393 - 9
Brinkmeier E.Geiger H.Zinsmeister HD.
Z. Naturforsch., C: Biosci. 2000, 55: 866 - 10
Zinsmeister HD.Weyand J.Voigt A.Seeger T.Geiger H. Z. Naturforsch., C: Biosci. 1996, 51: 781 - 11
Seeger T.Geiger H.Zinsmeister HD.Frahm JP.Witte L. Z. Naturforsch., C: Biosci. 1992, 47: 667 - 12
Drewes SE.Hudson NA.Bates RB.Linz GS.
J. Chem. Soc., Perkin Trans. 1 1987, 2809 - 13
Niwa M.Otsuji S.Tatematsu H.Liu GQ.Chen XF.Hirata Y. Chem. Pharm. Bull. 1986, 34: 3249 - 14
Niwa M.Chen XF.Liu GQ.Tatematsu H.Hirata Y. Chem. Lett. 1984, 1587 - 15
Jung HJ.Sung WS.Yeo S.-H.Kim HS.Lee I.-S.Woo E.-R.Lee DG. Arch. Pharmacal. Res. 2006, 29: 746 - 16
Qin B.-f.Zhou L.Miao F.Mao P.Wang Y.-x.Tian P.Xiao H.-y. Acta Bot. Bor.-Occid. Sinica 2003, 23: 1977 - 17
Sakasai M.Fukui H.Yamane H.Kyaw AN.Tahara S. Z. Naturforsch., C: Biosci. 2000, 55: 165 - 18
Murakami A.Ohigashi H.Jisaka M.Hirota M.Irie R.Koshimizu K. Cancer Lett. 1991, 58: 101 - 19
Lin Y.-M.Anderson H.Flavin MT.Pai Y.-HS.Mata-Greenwood E.Pengsuparp T.Pezzuto JM. J. Nat. Prod. 1997, 60: 884 - 20
Hayashi K.Hayashi T.Morita N. Antimicrob. Agents Chemother. 1992, 36: 1890 - 21
Sievers H.Burkhardt G.Becker H.Zinsmeister HD. Phytochemistry 1992, 31: 3233 - 22
Sievers H.Burkhardt G.Becker H.Zinsmeister HD. Phytochemistry 1994, 35: 795 - 23
Adaramoye OA.Awogbindin I.Okusaga JO. J. Med. Food 2009, 12: 584 - 24
Liang S.Tang J.Shen Y.-H.Jin H.-Z.Tian J.-M.Wu Z.-J.Zhang W.-D.Yan S.-K. Chem. Pharm. Bull. 2008, 56: 1729 - 25
Chen F.-C.Lin Y.-M.Hung J.-C. Phytochemistry 1975, 14: 300 - 26
Lin L.-C.Chou C.-J. Chin. Pharm. J. 2000, 52: 211 - 27
Lin L.-C.Kuo Y.-C.Chou C.-J. J. Nat. Prod. 2000, 63: 627 - 28
Lale A.Herbert JM.Augereau JM.Billon M.Leconte M.Gleye J. J. Nat. Prod. 1996, 59: 273 - 29
Lin YM.Chen FC.Lee KH. Planta Med. 1989, 55: 166 - 30
Weniger B.Vonthron-Senecheau C.Kaiser M.Brun R.Anton R. Phytomedicine 2006, 13: 176 - 31
Kim HP.Park H.Son KH.Chang HW.Kang SS. Arch. Pharmacal. Res. 2008, 31: 265 - 32
Mahjoub MA.Ammar S.Edziri H.Mighri N.Bouraoui A.Mighri Z. Med. Chem. Res. 2010, 19: 271 - 33
Anand KK.Gupta VN.Rangari V.Singh B.Chandan BK. Planta Med. 1992, 58: 493 - 34
Iwu MM.Igboko OA.Onwuchekwa UA.Okunji CO. J. Ethnopharmacol. 1987, 21: 127 - 35
Iwu MM.Igboko OA.Elekwa OK.Tempesta MS. Phytother. Res. 1990, 4: 157 - 36
Azebaze AGB.Dongmo AB.Meyer M.Ouahouo BMW.Valentin A.Nguemfo EL.Nkengfack AE.Vierling W. Ann. Trop. Med. Parasitol. 2007, 101: 23 - 37
Adaramoye OA.Medeiros IAJ. Smooth Muscle Res. 2009, 45: 39 - 38
Natarajan S.Murti VVS.Seshadri TR. Phytochemistry 1970, 9: 575 - 39
Natarajan S.Murti VVS.Seshadri TR. Indian J. Chem. 1970, 8: 116 - 40
Natarajan S.Murti VVS.Seshadri TR. Indian J. Chem. 1970, 8: 113 - 41
Natarajan S.Murti VVS.Seshadri TR.Ramaswamy AS. Curr. Sci. 1970, 39: 533 - 42
Kim HP.Mani I.Iversen L.Ziboh VA. Prost. Leuk. Ess. Fatty Acids 1998, 58: 17 - 43
Nakazawa K. Chem. Pharm. Bull. 1962, 10: 1032 - 44
Cabrera M.Simoens M.Falchi G.Lavaggi ML.Piro OE.Castellano EE.Vidal A.Azqueta A.Monge A.Lopez de Ceráin A.Sagrera G.Seoane G.Cerecetto H.González M. Bioorg. Med. Chem. 2007, 15: 3356 - 45
Lopez GV.Pandolfi EM.Seoane GA. Synthesis 2000, 1403 - 46
Sagrera GJ.López GV.Pandolfi EM.Seoane GA.Eicher T. Inf. Tecnol. 1998, 9: 11 - 47
Sagrera GJ.Seoane GA. J. Braz. Chem. Soc. 2005, 16: 851 - 49
Stout GH.Stout VF. Tetrahedron 1961, 14: 296 - 50
Romano JJ.Casillas E. Tetrahedron Lett. 2005, 46: 2323 - 51
Vogel S.Heilmann J. J. Nat. Prod. 2008, 71: 1237 - 52
Bhatt MV.Kulkarni SU. Synthesis 1983, 249 - 53
Burwell RL. Chem. Rev. 1954, 54: 615 - 55
Barros AIRNA.Silva AMS.Alkorta I.Elguero J. Tetrahedron 2004, 60: 6513 - 56
Buchi G.Weinreb SM. J. Am. Chem. Soc. 1971, 93: 746 - 57
Konieczny MT.Horowska B.Kunikowski A.Konopa J.Wierzba K.Yamada Y.Asao T. J. Org. Chem. 1999, 64: 359 - 58
Konieczny MT.Horowska B.Kunikowski A.Konopa J.Wierzba K.Yamada Y.Asao T. Synthesis 2001, 1363 - 59
Sagrera G.Seoane G. Synthesis 2009, 4190 - 60
Sogawa S.Nihro Y.Ueda H.Izumi A.Miki T.Matsumoto H.Satoh T. J. Med. Chem. 1993, 36: 3904 - 61
Mayer F. Chem. Ber. 1912, 45: 1105 - 62
Fanta PE. Chem. Rev. 1964, 64: 613 - 63
Fanta PE. Chem. Rev. 1946, 38: 139 - 64
Fujita E.Fuji K.Tanaka K. J. Chem. Soc. C 1971, 205 - 65
Asolkar R.Kamat VP.Kirtany JK. J. Chem. Res. 2001, 12: 549 - 66
Bredereck H.Hennig I.Rau W. Chem. Ber. 1953, 86: 1085 - 67
Fischer A.Henderson GN. Can. J. Chem. 1983, 61: 1045 - 68
Zhu J.Wang Q.Li Y. J. Chem. Soc., Chem. Commun. 1988, 1549 - 69
Canter FW.Curd FH.Robertson A. J. Chem. Soc., Chem. Commun. 1931, 1245 - 70
Kleiderer EC.Adams R. J. Am. Chem. Soc. 1931, 53: 1575 - 71
Ibrahim A.-R.Abul-Hajj YJ. J. Nat. Prod. 1990, 53: 644 - 72
Huang CS.Zhang Z.Li SH.Li YL. Chin. Chem. Lett. 1998, 9: 799 - 73
Jain AC.Bambah PK. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1987, 26: 488 - 74
Kumazawa T.Kimura T.Matsuba S.Sato S.Onodera J.-i. Carbohydr. Res. 2001, 334: 183 - 75
Adams CJ.Main L. Tetrahedron 1991, 47: 4959
References
Treatment of the hexamethyl ether with 6 to 8 equiv of BBr3 in CH2Cl2 at low temperature always resulted in partial deprotection and further decomposition.
54Treatment with BBr3 (2 equiv) in CH2Cl2 at different temperatures gives no reaction or else ring opening to the chalcone 20; the treatment with 57% HI in glacial AcOH at reflux gives mixtures of chalcone, flavanone, and dihydrochalcone in low yields, and the use of AlCl3 in benzene at reflux resulted in decomposition.