Bromination Reaction of Methyl Pyropheophorbide-a

Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (5): 537-542. Previous Articles Next Articles

焦脱镁叶绿酸-a甲酯的溴化反应

王进军^*,a, 韩光范^b, 邬旭然^a, 王鲁敏^a, 沈荣基^c

^a烟台大学应用化学系烟台 264005
^b华中船舶工业学院材料科学与工程学院镇江 212003
^c仁济大学釜山韩国

收稿日期:2003-07-23 修回日期:2003-10-13 接受日期:2003-11-26 发布日期:2022-09-20
基金资助:
国家科技部中韩政府间合作研究(2002)资助项目.

Bromination Reaction of Methyl Pyropheophorbide-a

WANG, Jin-Jun^*,a, HAN, Guang-Fan^b, WU, Xu-Ran^a, WANG, Lu-Min^a, SHIM, Young-Key^c

^aDepartment of Applied Chemistry, Yantai University, Yantai 264005
^bSchool of Material and Environmental Engineering, East China Shipbuilding, Zhenjiang 212003
^cLnie University, Pusan, Korea

Received:2003-07-23 Revised:2003-10-13 Accepted:2003-11-26 Published:2022-09-20
Contact: *E-mail: wjj1955@163.com

Abstract

Methyl pyropheophorbide-a (MPP-a) was usedas starting material for the synthesis of new bromine-substituted chlorin compounds. The bromines were introduced into 3-position and meso-position of the chlorin chromophore by addition reaction and substitution reaction with the bromide reagents to give mono-bromine- and tri-bromine-substituted chlorines.The formal addition product, hydrolyzate and esterified product were obtained by addition reaction with 30% hydrogen bromide in acetic acid. MPP-a was oxidized with OsO₄ in THF containing catalytic pyridine at 0 ℃ and followed by glycol cleavage with sodium periodate in aqueous THF to give the methyl pyropheophorbide-d (MPP-d) which was reacted with carbon tetrabromide and triphenylphosphine to generate gem-dibromine substituted product at 3^b-position. The structures of all new compounds were characterized by elemental analysis, UV, IR and ¹H NMR spectra.

Key words: methyl pyropheophorbide-a, bromination reaction, visiblespectra, photodynamic therapy (PDT)

Cite this article

WANG, Jin-Jun, HAN, Guang-Fan, WU, Xu-Ran, WANG, Lu-Min, SHIM, Young-Key. Bromination Reaction of Methyl Pyropheophorbide-a[J]. Chinese Journal of Organic Chemistry, 2004, 24(5): 537-542.

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焦脱镁叶绿酸-a甲酯的溴化反应

Bromination Reaction of Methyl Pyropheophorbide-a

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