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Synthesis of Porphyrins Di‐ and Tetra‐Functionalized with Nucleobases
Author(s) -
Tufenkjian Elsa,
Kahlfuss Christophe,
Kyritsakas Nathalie,
Hosseini Mir Wais,
Bulach Véronique
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001406
Subject(s) - nucleobase , chemistry , porphyrin , sonogashira coupling , thymine , guanine , stereochemistry , cytosine , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , dna , nucleotide , palladium , biochemistry , gene
A library composed of ten porphyrins bearing nucleobases is prepared, following two strategies: substitution or Sonogashira cross‐coupling reactions. The former strategy led to the synthesis of four porphyrins ( T 2 −Po1 , A 2 −Po1 , C 2 −Po1 and P 2 −Po1 ) bearing nucleobases (NBs) at two trans meso ‐positions. These 4 porphyrins were obtained by reacting 5,15‐di(4‐(bromomethyl)phenyl)‐10,20‐dimesitylporphyrin ( Po1 ) with thymine ( T ), adenine ( A ), cytosine ( C ) and 2‐amino‐6‐chloropurine ( P ), a precursor of guanine ( G ), respectively in the presence of a suitable base. A fifth porphyrin, 5,15‐di(N9‐methylphenylguanine)‐10,20‐dimesitylporphyrin ( G 2 −Po1 ) was obtained by hydrolysis of P 2 −Po1 . A thymine tetra‐functionalized porphyrin was also synthesized following the same strategy starting from T and 5,10,15,20‐tetrakis[4‐(bromomethyl)phenyl]porphyrin ( Po2 ). The second strategy based on Sonogashira cross‐coupling reactions between 5,15‐dibromo‐10,20‐dipentylporphyrin ( Po3 ) and ethynyl‐substituted nucleobases resulted in four rigid porphyrins ( U 2 −Po3 , C 2 −ZnPo3 , A 2 −ZnPo3 , and G 2 −ZnPo3 ).