Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (3): 562-571.DOI: 10.6023/cjoc201508032 Previous Articles     Next Articles



李彦龙a, 李家柱a, 张善国a, 王进军a,b   

  1. a 烟台大学化学化工学院 烟台 264005;
    b 烟台大学文经学院食品与生物工程系 烟台 264005
  • 收稿日期:2015-08-31 修回日期:2015-11-10 发布日期:2015-11-20
  • 通讯作者: 王进军
  • 基金资助:

    国家自然科学基金(No. 21272048)和山东省黄金工程技术研究中心(2011年度)资助项目.

Synthesis of (Methylenated)vinylated Chlorophyllous Chlorins and Study on Their Photosensitive Bactericidal Activities

Li Yanlonga, Li Jiazhua, Zhang Shanguoa, Wang Jinjuna,b   

  1. a College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
    b Department of Food & Biological Engineering, Wenjing College, Yantai University, Yantai 264005
  • Received:2015-08-31 Revised:2015-11-10 Published:2015-11-20
  • Supported by:

    Project supported by the National Natural Science Foundations of China (No. 21272048) and the Project of Shandong Applied Resarch Centre of Gold Nanotechnology (2011).

Pheophorbide-a and b methyl esters, as initial degraded products from chlorophyll-a and b, were used as starting materials, and the hydroxylmethylic or formylic structures were established making use of the active reaction regions on chlorin periphery by some common reactions, such as aldol condensation, allomerization, oxidant oxidation. The methylene or vinyl groups possessing higher reactivity were introduced at different site around chlorin pericycle by Grignard reavtion, acid-catalyzed dehydration and rearrangement reaction in E-ring. A series of unreported chlorophyllous chlorins substituted by multi-terminal alkenyl group were synthesized and their chemical structures were characterized by elemental analysis, UV, IR and 1H NMR spectra. The in vitro photosensitive bactericidal activities of new chlorins were discussed and the possible mechanisms about corresponding reactions were tentatively proposed.

Key words: chlorophyll-a, chlorin, chemical modification, photosensitive bactericidal activity, synthesis