| 红紫素-18的卤化反应及其二氢卟吩类衍生物的合成 |
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| 引用本文： | 刘冉冉,殷军港,李家柱,武进,陈冠龙,金英学,王进军.红紫素-18的卤化反应及其二氢卟吩类衍生物的合成[J].有机化学,2012,32(3):544-551. |
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| 作者姓名： | 刘冉冉 殷军港 李家柱 武进 陈冠龙 金英学 王进军 |
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| 作者单位： | 1. 烟台大学化学化工学院 烟台264005
2. 哈尔滨师范大学化学化工学院 哈尔滨150025 |
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| 基金项目： | 山东省自然科学基金(No.Y2008B49);科技部中匈政府间科技合作(No.2009-2010年度)资助项目~~ |
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| 摘 要： | 从红紫素-18甲酯开始,通过对其3-位乙烯基和20-meso-位的亲电加成和亲电取代反应,区域选择性地给出相应的氯代或者溴代产物.红紫素-18甲酯与重氮甲烷的1,3偶极环加成反应生成C(3)-吡唑啉基取代的红紫素-18,继续与N-溴代丁二酰亚胺(NBS)和N-氯代丁二酰亚胺(NCS)进行亲电取代反应,生成相应的卤代吡唑啉基取代二氢卟吩.3-吡唑啉基红紫素-18热裂解后的卤代反应则给出3-环丙基-20-卤代二氢卟吩.选择脱镁叶绿酸-a甲酯为另一起始反应物,通过C(3)-乙烯基和E-环结构的一系列化学转换和20-meso-位的溴代反应,区域选择性地得到20-溴代红紫素-18衍生物.新报道的标题化合物均经UV,IR,1H NMR及元素分析证明其结构.
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| 关 键 词： | 叶绿素-a 红紫素-18 焦脱镁叶绿酸-a甲酯 化学修饰 二氢卟吩 光动力疗法(PDT) |
Halogenation Reaction of Purpurin-18 and Synthesis of Chlorin Derivatives |
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| Liu, Ranran
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Yin, Jungang
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Li, Jiazhu
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Wu, Jin
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Chen, Guanlong
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Jin, Yingxue
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Wang, Jinjun.Halogenation Reaction of Purpurin-18 and Synthesis of Chlorin Derivatives[J].Chinese Journal of Organic Chemistry,2012,32(3):544-551. |
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| Authors: | Liu Ranran Yin Jungang Li Jiazhu Wu Jin Chen Guanlong Jin Yingxue Wang Jinjun |
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| Institution: | Liu,Ranrana Yin,Junganga Li,Jiazhua Wu,Jina Chen,Guanlonga Jin,Yingxueb Wang,Jinjun,a(aColledge of Chemistry and Chemical Engineering,Yantai University,Yantai 264005)(bCollege of Chemistry and Chemical Engineering,Harbin Normal University,Harbin 150025) |
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| Abstract: | From purpurin-18 methyl ester the electrophilic addition of C(3)-vinyl group and electrophilic substitution at 20-meso-position produced regioselectively corresponding chloro-substituted or bromo-substituted products.The 3-pyrazolinylpurpurin-18 ester,obtained by 1,3-dipolar cycloaddition of purpurin-18 with diazomethane,reacted with N-bromosuccinimide(NCS) or N-chlorosuccinimide(NBS) to generate halogenated pyrazolinyl-substituted chlorins.After pyrolysis the halogenations of 3-pyrazolinylpurpurin-18 ester gave 20-halogenated 3-cyclopropylchlorins.Methyl pheophorbide-a was used another starting material and converted into 20-bromopurpurin-18 derivatives by a series of chemical conversion for C(3)vinyl group and bromination at 20-position.The structures of newly-reported title compounds were characterized by elemental analysis,UV,IR and1H NMR spectra. |
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| Keywords: | chlorophyll-a purpurin-18 methyl pyropheophorbide-a chemical modification chlorin photodynamic therapy(PDT) |
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