巴西木素类天然产物的合成研究进展
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摘要
巴西木素类型天然产物是从中药苏木(Caesalpinia sappan)中分离得到的一类化合物,因其独特的结构和良好的生物活性而成为合成化学家关注的焦点.目前,已有许多关于这类天然产物合成的报道.我们主要对巴西木素类型天然产物的合成研究进展进行了综述.
Brazilin-type natural products were isolated from the heartwood of Caesalpinia sappan, a famous traditional Chinese medicine. These compounds have stimulated a great deal of interest on synthetic chemists due to their structural novelty and promising biological activities. Up to now, many methods towards the synthesis of these natural products have been developed. Progress on the synthesis of Brazilin-type natural products are reviewed in this paper.
Brazilin-type natural products were isolated from the heartwood of Caesalpinia sappan, a famous traditional Chinese medicine. These compounds have stimulated a great deal of interest on synthetic chemists due to their structural novelty and promising biological activities. Up to now, many methods towards the synthesis of these natural products have been developed. Progress on the synthesis of Brazilin-type natural products are reviewed in this paper.
引文
[1]Robinson,R.Bull.Soc.Chim.Fr.1958,125.
[2]Masahiro,N.;Seiji,N.Chem.Pharm.Bull.1990,38,1490.
[3]Michio,N.;Hiroyuki,N.;Mariko,N.Chem.Pharm.Bull.1987,35,3568.
[4]Yang,B.O.;Ke,C.Q.;He,Z.S.;Yang,Y.P.;Ye,Y.Tetrahedron Lett.2002,43,1731.
[5]Kim,D.S.;Baek,N.I.;Oh,S.R.;Jung,K.Y.;Lee,I.S.;Lee,H.K.Phytochemistry 1997,46,177.
[6](a)Puchtler,H.;Sweat,F.Histochemistry 1964,4,197.(b)Puchtler,H.;Meloan,S.N.;Waldrop,F.S.Histochemistry1986,85,353.
[7]Kim,B.H.;Kim,S.J.;Jeong,E.J.;Sohn,J.H.;Jung,M.;Lee,H.;Kim,S.H.J.Agric.Food Chem.2012,60,9882.
[8](a)Kim,S.G.;Kim,Y.M.;Khil,L.Y.;Jeon,S.D.;So,D.S.;Moon,C.H.;Moon,C.K.Arch.Pharm.Res.1998,21,140.(b)Hwang,G.S.;Kim,J.Y.;Chang,T.S.;Jeon,S.D.;So,D.S.;Moon,C.K.Arch.Pharm.Res.1998,21,774.
[9]Hikino,H.;Taguchi,T.;Fujimura,H.;Hiramatsu,Y.Planta Med.1977,31,214.
[10]Xu,H.X.;Lee,S.F.Phytother.Res.2004,18,647.
[11]Moon,C.K.;Park,K.S.;Kim,S.G.;Won,H.S.;Chung,J.H.Drug Chem.Taxicol.1992,15,81.
[12]Lee,Y.R.;Noh,E.M.;Han,J.H.;Kim,J.M.;Hwang,J.K.;Hwang,B.M.;Chung,E.Y.;Kim,B.S.;Lee,S.H.;Lee,S.J.;Kim,J.S.Eur.J.Pharmacol.2012,674,80.
[13]Wang,X.;Zhao,H.X.;Bai,H.Acta Chin.Med.Pharmacol.2013,41,164(in Chinese).(王鑫,赵焕新,白虹,中医药学报,2013,41,164.)
[14](a)Zhao,Y.N.;Pan,Y.;Tao,J.L.;Xing,D.M.;Du,L.J.Pharmacology 2006,76,76.(b)Zhong,X.;Wu,B.;Pan,Y.J.;Zheng,S.Neoplasma 2009,56,387.(c)Shen,J.;Zhang,H.;Lin,H.;Su,H.;Xing,D.;Du,L.Eur.J.Pharmacol.2007,558,88.(d)Ye,M.;Xie,W.D.;Lei,F.;Meng,Z.;Zhao,Y.N.;Su,H.;Du,L.J.Int.Immunopharmacol.2006,6,426.(e)Shen,J.;Yip,S.;Wang,Z.X.;Wang,W.;Xing,D.M.;Du,L.J.Eur.J.Pharmacol.2008,580,366.
[15]Hill,R.A.;Parker,M.C.Nat.Prod.Rep.2002,19,ⅲ.
[16]Heller,W.;Tamm,C.Progress in the Chemistry of Organic Natural Products,Vol.40,Eds.:Herz,H.;Criesenbach,H.;Kirby,W,Springer-Verlag,Inc.,New Work,1980,p.105.
[17]Saitoh,T.;Sakashita,S.;Nakata,H.;Shimokawa,T.;Kinjo,J.;Yamahara,J.;Yamasakim,M.;Nohara,T.Chem.Pharm.Bull.1986,34,2506.
[18](a)Kirkiacharian,B.S.C.R.Acad.Ser.C 1972,274,2096.(b)Kirkiacharian,B.S.;Billet,D.;Durgeat,M.;Heitz,S.;Adjangba,M.K.Bull.Soc.Chim.Fr.1975,1770.
[19]Yen,C.T.;Kyoko,N.G.;Hwang,T.L.;Wu,P.C.;Morris-Natschke,S.L.;Lai,W.C.;Bastowd,K.F.;Chang,F.R.;Wu,Y.C.;Lee,K.H.Bioorg.Med.Chem.Lett.2010,20,1037.
[20](a)Davis,F.A.;Chen,B.C.J.Org.Chem.1993,58,1751.(b)Davis,F.A.;Chen,B.C.Tetrahedron Lett.1990,31,6823.
[21]Arnoldi,A.;Bassoli,A.;Borgonovo,G.;Merlini,L.J.Chem.Soc.,Perkin Trans.1 1995,2447.
[22]Ishii,H.;Koyama,H.;Hagiwara,K.;Miura,T.;Xue,G.G.;Hashimoto,Y.;Kitahara,G.;Aida,Y.;Suzuki,M.Bioorg.Med.Chem.Lett.2012,22,1469.
[23]Javed,U.;Karim,M.;Jahng,K.C.;Park,J.G.;Jahng,Y.D.Tetrahedron:Asymmetry 2014,25,1270.
[24]Huang,Y.D.;Zhang,J.S.;Pettus,T.R.R.Org.Lett.2005,7,5841.
[25]Lin,C.C.;Teng,T.M.;Tsai,C.C.;Liao,H.Y.;Liu,R.S.J.Am.Chem.Soc.2008,130,16417.
[26]Pan,C.X.;Zeng,X.H.;Guan,Y.F.;Jiang,X.L.;Li,L.;Zhang,H.B.Synlett 2011,425.
[27]Wang,X.Q.;Zhang,H.B.;Yang,X.D.;Zhao,J.F.;Pan,C.X.Chem.Commun.2013,49,5405.
[28]Li,L.Q.;Li,M.M.;Wang,K.;Qin,H.B.Tetrahedron Lett.2013,54,6029.
[29]Yadav,J.S.;Mishra,A.K.;Das,S.Tetrahedron 2014,70,7560.
[30]Jung,Y.;Kim,I.J.Org.Chem.2015,80,2001.
[2]Masahiro,N.;Seiji,N.Chem.Pharm.Bull.1990,38,1490.
[3]Michio,N.;Hiroyuki,N.;Mariko,N.Chem.Pharm.Bull.1987,35,3568.
[4]Yang,B.O.;Ke,C.Q.;He,Z.S.;Yang,Y.P.;Ye,Y.Tetrahedron Lett.2002,43,1731.
[5]Kim,D.S.;Baek,N.I.;Oh,S.R.;Jung,K.Y.;Lee,I.S.;Lee,H.K.Phytochemistry 1997,46,177.
[6](a)Puchtler,H.;Sweat,F.Histochemistry 1964,4,197.(b)Puchtler,H.;Meloan,S.N.;Waldrop,F.S.Histochemistry1986,85,353.
[7]Kim,B.H.;Kim,S.J.;Jeong,E.J.;Sohn,J.H.;Jung,M.;Lee,H.;Kim,S.H.J.Agric.Food Chem.2012,60,9882.
[8](a)Kim,S.G.;Kim,Y.M.;Khil,L.Y.;Jeon,S.D.;So,D.S.;Moon,C.H.;Moon,C.K.Arch.Pharm.Res.1998,21,140.(b)Hwang,G.S.;Kim,J.Y.;Chang,T.S.;Jeon,S.D.;So,D.S.;Moon,C.K.Arch.Pharm.Res.1998,21,774.
[9]Hikino,H.;Taguchi,T.;Fujimura,H.;Hiramatsu,Y.Planta Med.1977,31,214.
[10]Xu,H.X.;Lee,S.F.Phytother.Res.2004,18,647.
[11]Moon,C.K.;Park,K.S.;Kim,S.G.;Won,H.S.;Chung,J.H.Drug Chem.Taxicol.1992,15,81.
[12]Lee,Y.R.;Noh,E.M.;Han,J.H.;Kim,J.M.;Hwang,J.K.;Hwang,B.M.;Chung,E.Y.;Kim,B.S.;Lee,S.H.;Lee,S.J.;Kim,J.S.Eur.J.Pharmacol.2012,674,80.
[13]Wang,X.;Zhao,H.X.;Bai,H.Acta Chin.Med.Pharmacol.2013,41,164(in Chinese).(王鑫,赵焕新,白虹,中医药学报,2013,41,164.)
[14](a)Zhao,Y.N.;Pan,Y.;Tao,J.L.;Xing,D.M.;Du,L.J.Pharmacology 2006,76,76.(b)Zhong,X.;Wu,B.;Pan,Y.J.;Zheng,S.Neoplasma 2009,56,387.(c)Shen,J.;Zhang,H.;Lin,H.;Su,H.;Xing,D.;Du,L.Eur.J.Pharmacol.2007,558,88.(d)Ye,M.;Xie,W.D.;Lei,F.;Meng,Z.;Zhao,Y.N.;Su,H.;Du,L.J.Int.Immunopharmacol.2006,6,426.(e)Shen,J.;Yip,S.;Wang,Z.X.;Wang,W.;Xing,D.M.;Du,L.J.Eur.J.Pharmacol.2008,580,366.
[15]Hill,R.A.;Parker,M.C.Nat.Prod.Rep.2002,19,ⅲ.
[16]Heller,W.;Tamm,C.Progress in the Chemistry of Organic Natural Products,Vol.40,Eds.:Herz,H.;Criesenbach,H.;Kirby,W,Springer-Verlag,Inc.,New Work,1980,p.105.
[17]Saitoh,T.;Sakashita,S.;Nakata,H.;Shimokawa,T.;Kinjo,J.;Yamahara,J.;Yamasakim,M.;Nohara,T.Chem.Pharm.Bull.1986,34,2506.
[18](a)Kirkiacharian,B.S.C.R.Acad.Ser.C 1972,274,2096.(b)Kirkiacharian,B.S.;Billet,D.;Durgeat,M.;Heitz,S.;Adjangba,M.K.Bull.Soc.Chim.Fr.1975,1770.
[19]Yen,C.T.;Kyoko,N.G.;Hwang,T.L.;Wu,P.C.;Morris-Natschke,S.L.;Lai,W.C.;Bastowd,K.F.;Chang,F.R.;Wu,Y.C.;Lee,K.H.Bioorg.Med.Chem.Lett.2010,20,1037.
[20](a)Davis,F.A.;Chen,B.C.J.Org.Chem.1993,58,1751.(b)Davis,F.A.;Chen,B.C.Tetrahedron Lett.1990,31,6823.
[21]Arnoldi,A.;Bassoli,A.;Borgonovo,G.;Merlini,L.J.Chem.Soc.,Perkin Trans.1 1995,2447.
[22]Ishii,H.;Koyama,H.;Hagiwara,K.;Miura,T.;Xue,G.G.;Hashimoto,Y.;Kitahara,G.;Aida,Y.;Suzuki,M.Bioorg.Med.Chem.Lett.2012,22,1469.
[23]Javed,U.;Karim,M.;Jahng,K.C.;Park,J.G.;Jahng,Y.D.Tetrahedron:Asymmetry 2014,25,1270.
[24]Huang,Y.D.;Zhang,J.S.;Pettus,T.R.R.Org.Lett.2005,7,5841.
[25]Lin,C.C.;Teng,T.M.;Tsai,C.C.;Liao,H.Y.;Liu,R.S.J.Am.Chem.Soc.2008,130,16417.
[26]Pan,C.X.;Zeng,X.H.;Guan,Y.F.;Jiang,X.L.;Li,L.;Zhang,H.B.Synlett 2011,425.
[27]Wang,X.Q.;Zhang,H.B.;Yang,X.D.;Zhao,J.F.;Pan,C.X.Chem.Commun.2013,49,5405.
[28]Li,L.Q.;Li,M.M.;Wang,K.;Qin,H.B.Tetrahedron Lett.2013,54,6029.
[29]Yadav,J.S.;Mishra,A.K.;Das,S.Tetrahedron 2014,70,7560.
[30]Jung,Y.;Kim,I.J.Org.Chem.2015,80,2001.