Abstract
Paeonol is a major phenolic component isolated from Moutan Cortex, a traditional Chinese medicine. An efficient synthesis of paeonol derivatives linked to a 1,2,3-triazole moiety using a 1,3-dipolar Huisgen-cycloaddition reaction is described. The paeonol derivatives are regioselectively obtained in good yields under mild conditions using Cu(OAc)2·H2O/sodium ascorbate as a catalyst system, and t-BuOH/H2O (1:1, v/v) as a co-solvent.
References
1.
Wang J.J.
,
Li Q.W.
,
Ou Y.T.
,
Li C.J.
,
Tian Y.Z.
, and
Sun X.X.
, Lat. Am. J. Pharm. , 2010 , 29 , 369 .
2.
Sun G.P.
, Eur. J. Pharmacol. , 2008 , 584 , 246 .
3.
Zhang C.H.
,
Hu S.Y.
,
Cao M.Q.
,
Xiao G.L.
, and
Li Y.H.
, Anti-cancer Drugs , 2008 , 19 , 401 .
4.
Tan S.
, Saudi. Med. J. , 2007 , 28 , 642 .
5.
Pan L.L.
, Phytomedicine , 2009 , 16 , 1027 .
6.
Chou T.C.
, Br. J. Pharmacol. , 2003 , 139 , 1146 .
7.
Hsieh C.L.
, J. Ethnopharmacol. , 2006 , 106 , 208 .
8.
Dai M.
, China J. Chin. Mater. Med. , 1999 , 24 , 488 .
9.
Zhou J.
, Brain. Res. , 2011 , 1388 , 141 .
10.
Rehman F.
,
Rastogi S.N.
,
Jetley U.K.
,
Zaidi S.A.
, and
Khan I.A.
, Oriental. J. Chem. , 1988 , 4 , 49 .
11.
Offiong E.O.
,
Emmanuel N.
, and
Ayi A.A.
, Trans. Met. Chem. , 2000 , 25 , 369 .
12.
Zhang Y.K.
,
Lv Z.L.
,
Niu C.J.
, and
Li K.
, Chin. Chem. Lett. , 2010 , 21 , 290 .
13.
Zhang L.J.
,
Qu L.B.
,
Zhang B.J.
,
Chen X.L.
, and
Zhao Y.F.
, Phosphorus, Sulfur Silicon Relat. Elem. , 2008 , 183 , 799 .
14.
Vatmurge N.S.
,
Hazra B.G.
,
Pore V.S.
,
Shirazi F.
,
Chavan P.S.
, and
Deshpande M.V.
, Bioorg. Med. Chem. Lett. , 2008 , 18 , 2043 .
15.
Zhang J.
,
Zhang H.
,
Cai W.
,
Yu L.
,
Zhen X.
, and
Zhang A.
, Bioorg. Med. Chem. , 2009 , 17 , 4873 .
16.
Jagasia R.
,
Holub J.M.
,
Bollinger M.
,
Kirshenbaum K.
, and
Finn M.G.
, J. Org. Chem. , 2009 , 74 , 2964 .
17.
Huber D.
,
Hübner H.
, and
Gmeiner P.
, J. Med. Chem. , 2009 , 52 , 6860 .
18.
Alvarez R.
,
Velazquez S.
,
San-Felix A.
,
Aquaro S.
,
De Clercq E.
,
Perno C.F.
,
Karlsson A.
,
Balzarini J.
, and
Camarasa M.J.
, J. Med. Chem. , 1994 , 37 , 4185 .
19.
Genin M.J.
,
Allwine D.A.
,
Anderson D.J.
,
Barbachyn M.R.
,
Emmert D.E.
,
Garmon S.A.
,
Graber D.R.
,
Grega K.C.
,
Hester J.B.
,
Hutchinson D.K.
,
Morris J.
,
Reischer R.J.
,
Ford C.W.
,
Zurenko G.E.
,
Hamel C.J.
,
Schaadt R.D.
,
Stapert D.
, and
Yagi B.H.
, J. Med. Chem. , 2000 , 43 , 953 .
20.
Buckle D.R.
,
Rockell C.J.M.
,
Smith H.
, and
Spicer B.A.
, J. Med. Chem. , 1984 , 27 , 223 .
21.
Rostovtsev V.V.
,
Green L.G.
,
Fokin V.V.
, and
Sharpless K.B.
, Angew. Chem. Int. Edit. , 2002 , 41 , 2596 .
22.
Tornoe C.W.
,
Christiensen C.
, and
Meldal M.
, J. Org. Chem. , 2002 , 67 , 3057 .
23.
Jiang Y.Q.
,
Chen X.L.
,
Qu L.B.
,
Wang J.L.
,
Yuan J.W.
,
Chen S.S.
,
Li X.
, and
Qu C.
, Ultrason. Sonochem. , 2011 , 18 , 527 .
24.
Jiang Y.Q.
,
Chen X.L.
,
Qu L.B.
,
Wang J.L.
,
Yuan J.W.
,
Chen S.S.
, and
Li X.Z.
, Naturforsch. 2011 , 66b , 77 .
25.
Ahmad-Junan S.A.
, and
Donald A.W.
, J. Chem. Soc., Perkin Trans. 1 , 1992 , 675 .
26.
Meng L.G.
, and
Yang M.M.
, Chin. J. Synth. Chem. , 2011 , 19 , 796 .
27.
Tsutomu I.
,
Keiko N.
,
Naoko O.
, and
Hisashi I.
, Heterocyles , 1994 , 39 , 371 .
28.
Ishikawa T.
,
Mizutani A.
,
Miwa C.
,
Oku Y.
,
Komano N.
,
Takami A.
, and
Watanabe T.
, Heterocycles , 1997 , 45 , 2261 .
29.
Ukhin L.Yu.
,
Suponitskii K. Yu.
, and
Kartsev V.G.
, Chem. Nat. Compd , 2003 , 39 , 482 .
30.
Pal M.
,
Parasuraman K.
, and
Yeleswarapu K.R.
, Org. Lett. , 2003 , 5 , 349 .
31.
Joshi M.C.
,
Joshi P.
, and
Rawat D.S.
, Arkivoc , 2006 , 16 , 65 .