| 利用脱镁叶绿酸甲酯的化学修饰合成红紫素酰亚胺衍生物 |
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| 引用本文： | 韩光范,王进军,吕俊华,汪芳明,瞿艳,沈荣基. 利用脱镁叶绿酸甲酯的化学修饰合成红紫素酰亚胺衍生物[J]. 中国化学, 2006, 24(8): 1069-1076. DOI: 10.1002/cjoc.200690200 |
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| 作者姓名： | 韩光范 王进军 吕俊华 汪芳明 瞿艳 沈荣基 |
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| 作者单位： | School of Material Science and Engineering Jiangsu University of Science and Technology，Zhenjiang，Jiangsu 212003，China，School of Material Science and Engineering，Jiangsu University of Science and Technology，Zhenjiang，Jiangsu 212003，China，School of Material Science and Engineering，Jiangsu University of Science and Technology，Zhenjiang，Jiangsu 212003，China，Department of Applied Chemistry，Yantai University，Yantai，Shandong 264005，China，School of Pharmaceutical Sciences，Jinan University，Guangzhou，Guangdong 510632，China，School of Nano Engineering，Inji University，Gyongnam 621-749，Korea |
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| 基金项目： | Project supported by the Jiangsu Education Department(No.05KJB350031). |
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| 摘 要： | A series of novel purpurin-18 imide derivatives exhibiting long wavelength absorption and amphiphilicity wereobtained from methyl pheophorbide-a(MPa)by modification of the peripheral functional groups.The vinyl groupat 3-position was oxidized with OsO_4 and NaIO_4 to form the formyl group and the Grignard reaction of this alde-hyde with the alkyl magnesium bromide was carried out to give the corresponding 3-(1-hydroxylalkyl)pheophor-bide-a.The E-ring of these chlorines was converted into anhydride ring to give purpurin derivatives by air oxidation.The trans-3~2-alkyl purpurin derivatives were obtained by dehydration of hydroxyl group at 3~1-position.TheN-hydroxyl purpurin imide was generated by treatment of the anhydride ring with bydroxylamine hydrochloride.The 3~1-alkylacyl-N-hydroxyl purpurin imides were obtained by oxidation of hydroxyl group at 3~1-position.Theacylation of N-hydroxyl group was completed to afford N-acyloxy purpurin imides.The photocytoxicity of severalcompounds in vitro were tested.
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| 关 键 词： | methyl pheophorbide-α purpurin-18 imide photosensitizer photodynamic therapy |
| 收稿时间： | 2005-08-02 |
| 修稿时间： | 2005-08-022006-04-20 |
Synthesis of Purpurin Imide Derivatives by Modification of Peripheral Functional Groups of Methyl Pheophorbide-a |
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| HAN Guang-Fan WANG Jin-Junb L. Synthesis of Purpurin Imide Derivatives by Modification of Peripheral Functional Groups of Methyl Pheophorbide-a[J]. Chinese Journal of Chemistry, 2006, 24(8): 1069-1076. DOI: 10.1002/cjoc.200690200 |
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| Authors: | HAN Guang-Fan WANG Jin-Junb L |
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| Abstract: | A series of novel purpurin-18 imide derivatives exhibiting long wavelength absorption and amphiphilicity were obtained from methyl pheophorbide-a(MPa)by modification of the peripheral functional groups.The vinyl group at 3-position was oxidized with OsO_4 and NaIO_4 to form the formyl group and the Grignard reaction of this alde- hyde with the alkyl magnesium bromide was carried out to give the corresponding 3-(1-hydroxylalkyl)pheophor- bide-a.The E-ring of these chlorines was converted into anhydride ring to give purpurin derivatives by air oxidation. The trans-3~2-alkyl purpurin derivatives were obtained by dehydration of hydroxyl group at 3~1-position.The N-hydroxyl purpurin imide was generated by treatment of the anhydride ring with bydroxylamine hydrochloride. The 3~1-alkylacyl-N-hydroxyl purpurin imides were obtained by oxidation of hydroxyl group at 3~1-position.The acylation of N-hydroxyl group was completed to afford N-acyloxy purpurin imides.The photocytoxicity of several compounds in vitro were tested. |
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| Keywords: | methyl pheophorbide-a purpurin-18 imide photosensitizer photodynamic therapy |
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