胃蛋白酶催化合成2,3-二氢喹唑啉-4(1H)-酮衍生物
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摘要
在乙醇溶剂中,考察了不同的酶对2-氨基苯甲酰胺与醛类物质环缩合反应的催化性能,确定胃蛋白酶为最佳的催化剂.然后对反应温度、酶用量、底物的物质的量比、反应时间等影响因素进行优化,确定了最佳的反应条件:在65℃温度下,10 mg胃蛋白酶可以高效催化2-氨基苯甲酰胺与芳香醛及脂肪醛的反应,合成了一系列2,3-二氢喹唑啉-4(1H)-酮衍生物.
The catalytic property of some hydrolases for the cyclocondensation of aldehydes with 2-aminobenzamide was researched in alcohol solvent, and pepsin was selected as the best catalyst. The reaction conditions were optimized through investigating the temperature, the enzyme loading, the ratio of substrates and the reaction time. Under the optimal conditions, 5 mg of pepsin could catalyze the cyclizing reaction of aldehydes with 2-aminobenzamide, and the corresponding 2,3-dihydroquinazolin-4(1H)-ones were successfully obtained in high yields.
The catalytic property of some hydrolases for the cyclocondensation of aldehydes with 2-aminobenzamide was researched in alcohol solvent, and pepsin was selected as the best catalyst. The reaction conditions were optimized through investigating the temperature, the enzyme loading, the ratio of substrates and the reaction time. Under the optimal conditions, 5 mg of pepsin could catalyze the cyclizing reaction of aldehydes with 2-aminobenzamide, and the corresponding 2,3-dihydroquinazolin-4(1H)-ones were successfully obtained in high yields.
引文
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[2]Abdel-Jalil,R.J.;Voelter,W.;Saeed,M.Tetrahedron Lett.2004,45,3475.
[3]Shi,D.;Rong,L.;Wang,J.;Zhuang,Q.;Wang,X.;Hu,H.Tetrahedron Lett.2003,44,3199.
[4]Shaabani,A.;Maleki,A.;Mofakham,H.Synth.Commun.2008,383751.
[5]Zong,Y.;Zhao,Y.;Luo,W.;Yu,X.H.;Wang,J.K.;Pan,Y.Chin.Chem.Lett.2010,21,778.
[6]Ghashang,M.;Mansoor,S.S.;Aswin,K.Res.Chem.Intermed.2015,41,3347
[7]Xua,B.L.;Chen,J.P.;Qiao,R.Z.;Fu,D.C.Chin.Chem.Lett.2008,19,537.
[8]Zahed,K.-J.;Leila,Z.Acta Chim.Slovaca 2013,60 178.
[9]Labade,V.B.;Shinde,P.V.;Shingare,M.S.Tetrahedron Lett.2013,54,5578.
[10](a)Shaterian,H.R.;Aghakhanizadeh,M.Res.Chem.Intermed.2014,40,1655;(b)Wang,J.;Zong,Y.;Fu,R.;Niu,Y.;Yue,G.;Quan,Z.;Wang,X.;Pan,Y.Ultrason.Sonochem.2014,21,29;(c)Davoodnia,A.;Allameh,S.;Fakhari,A.R.;Tavakoli-Hoseini,N.Chin.Chem.Lett.2010,21,550;(d)Safaei,H.R.;Shekouhy,M.;Shafiee,V.;Davoodi,M.J.Mol.Liq.2013,180,139;(e)Yassaghi,G.;Davoodnia,A.;Allameh,S.;Zare-Bidaki,A.;Tavakoli-Hoseini,N.Bull.Korean Chem.Soc.2012,33,2724;(f)Wang,S.L.;Yang,K.;Wang,X.S.Chin.J.Org.Chem.2011,31,1235(in Chinese).(王树良,杨科,王香善,有机化学,2011,31,1235.)
[11]Dabiri,M.;Salehi,P.;Otokesh,S.;Baghbanzadeh,M.;Kozehgary,G.;Mohammadi,A.A.Tetrahedron Lett.2005,46,6123.
[12]Dabiri,M.;Salehi,P.;Baghbanzadeh,M.;Zolfigol,M.A.;Agheb,M.;Heydari,S.Catal.Commun.2008,9,785.
[13]Abdollahi-Alibeik,M.;Shabani,E.J.Iranian Chem.Soc.2014,11,351.
[14]Dhanunjaya Rao,A.V.;Vykunteswararao,B.P.;Bhaskarkumar,T.;Jogdand,N.R.;Kalita,D.;Lilakar,J.K.D.;Siddaiah,V.;Douglas Sanasi,P.;Raghunadh,A.Tetrahedron Lett.2015,56,4714.
[15]Parthasaradhi,Y.;Rakhi,C.;Suresh,S.;Tangenda,S.J.Eur.J.Chem.2013,4,462.
[16]Branneby,C.;Carlqvist,P.;Magnusson,A.;Hult,K.;Brinck,T.;Berglund,P.J.Am.Chem.Soc.2003,125 874.
[17]Chen,X.;Liu,B.-K.;Kang,H.;Lin,X.-F.J.Mol.Catal.B:Enzym.2011,68,71.
[18]Guan,Z.;Fu,J.-P.;He,Y.-H.Tetrahedron Lett.2012,53,4959.
[19]Purkarthofer,T.;Gruber,K.;Gruber-Khadjawi,M.;Waich,K.;Skranc,W.;Mink,D.;Griengl,H.Angew.Chem.,Int.Ed.2006,45,3454.
[20]Cai,J.-F.;Guan,Z.;He,Y.-H.J.Mol.Catal.B:Enzym.2011,68,240.
[21]Mo,T.;Wang,J.;Gao,B.W.;Zhang,L.;Liu,X.;Wang,X.H.;Tu,P.F.;Shi,S.P.Chin.J.Org.Chem.2015,35,1052(in Chinese).(莫婷,王娟,高博闻,张乐,刘晓,王晓辉,涂鹏飞,史社坡,有机化学,2015,35,1052.)
[22]Wu,Q.;Liu,B.-K.;Lin,X.-F.Curr.Org.Chem.2010,14,1966.
[23]Humble,M.S.;Berglund,P.Eur.J.Org.Chem.2011,3391.
[24]Kapoor,M.;Gupta,M.N.Process Biochem.2012,47,555.
[25]Safari,J.;Gandomi-Ravandi,S.J.Mol.Catal.A:Chem.2014,390,1.