142569-86-6Relevant articles and documents
Synthesis of Porphyrinyl-Nucleosides
Czuchajowski, Leszek,Habdas, Jan,Niedbala, Halina,Wandrekar, Vinay
, p. 479 - 486 (2007/10/02)
Several porphyrinyl-nucleosides were prepared in the reaction of the OH group of one, two or four meso-p-hydroxyphenyl substituents of porphyrin with 5'-O-tosylates of 2',3'-O-isopropylidene-adenosine or -uridine, or 5'-O-tosylthymidine; the remaining porphyrin meso-substituents were p-tolyl, p-hydroxyphenyl or 4-pyridyl.The following porphyrinyl-nucleosides were obtained with 8-17percent yield: meso-di(p-tolyl)di(p-phenylene-5'-O-2',3'-O-isopropylidene-adenosine) (or -uridine)porphyrins 1,2, the respective meso-tetranucleosideporphyrins 3,4-meso-mono(p-phenylene-5'-O-thymidine)porphyrins 5-7, meso-di(p-tolyl)di(p-phenylene-5'-O-thymidine)porphyrins 8,9 and the meso-di(p-hydroxyphenyl)di(p-phenylene-5'-O-thymidine)porphyrins 10.Other compounds prepared belonged to the series: meso(4-pyridyl)4-n(p-phenylene-5'-O-2',3'-O-isopropylideneuridine)nporphyrin, n = 1,2 or 4, 11-13.N-Methylation gave the water soluble iodide salts: (N-methyl-4-pyridinium)4-n(p-phenylene-5'-O-2',3'-isopropylideneuridine)nporphyrins, n = 1,2 or 4, 14-16.The ms fab showed in most cases stepwise detachment of the CH2(5')-nucleoside fragments.The porphyrins meso disubstituted by thymidine represent a convenient substrate for the build-up of both nucleoside units into the oligo/polynucleotide chains.