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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (01): 65-70. 上一篇    下一篇

研究论文

3-位环庚烷(酰)基取代的焦脱镁叶绿酸-a甲酯的合成

王进军*,1，刘万卉2，韩光范3，沈荣基d   

  1. (1 烟台大学应用化学系 烟台 264005)
    (2 烟台大学药学院 烟台 264005)
    (3 华中船舶工业学院材料与工程学院 镇江 212003)
    (4 仁济大学纳米工程学院 釜山 韩国)
  • 收稿日期:2004-04-05 修回日期:2004-07-09 发布日期:2004-12-30
  • 通讯作者: 王进军

Synthesis of Methyl Pyropheophorbide-a with Cycloheptyl(acyl)Group at 3-Position

WANG Jin-Jun*,1,LIU Wan-Hui2,HAN Guang-Fan3,SHIM Yong Key4   

  1. (1 Department of Applied Chemistry, Yantai University, Yantai 264005)
    (2 School of Pharmacy, Yantai University, Yantai 264005)
    (3 School of Materials Science and Engineering, East China Shipbuilding Institute, Zhenjiang 212003)
    (4 School of Nano Engineering, Inji University, Pusan, Korea)
  • Received:2004-04-05 Revised:2004-07-09 Published:2004-12-30
  • Contact: WANG Jin-Jun

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以焦脱镁叶绿酸-a甲酯(MPP-a)为起始原料, 在对其E-环羰基进行保护的前提下, 经焦脱镁叶绿酸-d甲酯与环庚基溴化镁进行Grignard反应; 所生成新的卟吩仲醇再经脱保护、脱水和氧化等诸多反应, 将3-位仲羟基转化成碳碳双键和羰基, 其碳氧双键再行Grignard反应并脱水成烯, 完成一系列未见报道的3-位环庚基取代的焦脱镁叶绿酸-a甲酯衍生物的合成. 其化学结构均经UV, IR, 1H NMR及元素分析予以证实.

关键词: 环庚烷, 焦脱镁叶绿酸-a甲酯衍生物, 光动力疗法(PDT), Grignard反应

Methyl pyropheophorbide-a (MPP-a) was used as starting material. The carbonyl group on E-ring of methyl pyropheophorbide-d was protected and the Grignard reaction with cycloheptyl magnesium bromide was performed. The sec-alcohol obtained from Grignard reaction was subjected to deprotection, dehydration, oxidation and other more reaction for converting hydroxyl group at 3-position into carbon-carbon double bond and carbonyl group. The Grignard reaction of the carbon-oxygen double bond and following dehydration were carried out to form olefin. The synthesis of a series of new methyl pyropheophorbide-a substituted by cycloheptyl group at 3-position was completed. The structures of the compounds were characterized by elemental analysis, UV, IR and 1H NMR spectra.

Key words: cycloheptane, Grignard reaction, photodynamic therapy (PDT), methyl pyropheophorbide-a