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Azachlorins: Synthesis of a novel type of hydroporphyrins from the bile pigment bilirubin
Author(s) -
Gerlach Benjamin,
Montforts FranzPeter
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199508206
Subject(s) - chemistry , singlet oxygen , regioselectivity , photodynamic therapy , pigment , chlorin , bile pigments , amide , cycloaddition , combinatorial chemistry , stereochemistry , photochemistry , organic chemistry , oxygen , catalysis
Azachlorins rac ‐ 10a,b , rac ‐ 11 , and rac ‐ 16 , a novel type of hydroporphinoid compounds, were synthesized from azaporphyrins 8 and 13 by regioselective cycloaddition of singlet oxygen and further transformation by amide acetal Claisen rearrangement. The azaporphyrins are readily accessible from the naturally occurring bile pigment bilirubin ( 5 ). The photophysical properties of the azachlorins recommend these chlorin derivatives as potential photosensitizers for Photodynamic Therapy (PDT).