新型二氢卟吩-5-氟尿嘧啶的合成
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摘要
以系列羟基卟啉为原料,用对甲苯磺酰肼还原,再用四氯对苯醌氧化,制得二氢卟吩(2a~2d);以二环己基碳二亚胺为脱水剂,2与5-氟尿嘧啶-1-基乙酸经酯化反应合成了4个新型二氢卟吩-5-氟尿嘧啶化合物(3a~3d),总收率分别为6.9%,6.9%,7.0%和7.6%,其结构经UV-Vis,1H NMR,IR和MS表征。
Chlorins( 2a ~ 2d) were synthesized by reduction with p-toluenesulfonhydrazide and oxidation with tetrachloro-p-benzoquinone,using hydroxylporphyrins as precursor. Then using N,N'-dicyclohexylcarbdiimide as dehydration agent,four novel chlorins-5-fluorouracil( 3a ~ 3d) were synthesized by esterification of 2a ~ 2d and 5-fluorouracil-1-yl acetic acid in total yield of 6. 9%,6. 9%,7. 0%and 7. 6%,respectively. The structures were characterized by UV-Vis,1H NMR,IR and MS.
Chlorins( 2a ~ 2d) were synthesized by reduction with p-toluenesulfonhydrazide and oxidation with tetrachloro-p-benzoquinone,using hydroxylporphyrins as precursor. Then using N,N'-dicyclohexylcarbdiimide as dehydration agent,four novel chlorins-5-fluorouracil( 3a ~ 3d) were synthesized by esterification of 2a ~ 2d and 5-fluorouracil-1-yl acetic acid in total yield of 6. 9%,6. 9%,7. 0%and 7. 6%,respectively. The structures were characterized by UV-Vis,1H NMR,IR and MS.
引文
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[3]韩军兴,刘彦钦,韩士田.间氯苯基锰卟啉-5-氟尿嘧啶配合物的合成及其对癌细胞的抑制活性[J].应用化学,2012,29(6):718-720.
[4]Belykh D V,Mal’shakova M V,Yudina Y A,et al.Synthesis of potential antitumor agents,dimeric and trimeric chlorins from methylpheophorbide a[J].Russian Chemical Bulletin,2011,60(4),719-728.
[5]武进,殷军港,刘冉冉.β,β-二氰亚甲基取代的叶绿素类二氢卟吩衍生物的合成及其可见光谱[J].有机化学,2012,32:149-155.
[6]马红,韩士田,刘彦钦.新型氯苯基卟啉5-氟尿嘧啶的合成[J].合成化学,2009,17(6):699-701.
[7]刘宏,陈邦银,张汉萍.meso-四(间羟基苯基)二氢卟吩的改良合成[J].中国医药工业杂志,2001,32(4):152-153.
[8]扈靖,刘彦钦,韩士田.5-氟尿嘧啶-1-基乙酸合成方法的改进[J].化学试剂,2005,27(8):500-509.
[9]李雅,申利红,王建森.5-氟尿嘧啶-1-烷氧苯基三间氯苯基卟啉的合成及其体外抗癌活性[J].应用化学,2013,30(1):38-42.
[10]Li X F,Zhuang J P,Li Y L,et al.Synthesis of Isoxazoline-fused chlorins and bacteriochlorins by 1,3-dipolar cycloaddition reaction of porphyrin with nitrile oxide[J].Tetrahedron Lett,2005,46:1555-1559.
[11]Silva A M G,Tome A C,Neves M G P M S,et al.meso-Tetraarylporphyrins as dipolarophiles in 1,3-dipolar cycloaddition reactions[J].Chem Commun,1999:1767-1768.