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The synthesis of new potential photosensitizers. 1. Mono-carboxylic acid derivatives of tetraphenylporphyrin.

Zięba G, Rojkiewicz M, Kozik V, Jarzembek K, Jarczyk A, Sochanik A, Kuś P - Monatsh. Chem. (2011)

Bottom Line: A series of mono-alkylcarboxylic acid derivatives of tetraphenylporphyrin have been prepared.Experimental log P were determined by use of reversed-phase thin-layer chromatography with use of log P Rekker.These porphyrins are potential photosensitizers in photodynamic therapy. .

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Silesia, 9, Szkolna Street, 40-006 Katowice, Poland.

ABSTRACT

Abstract: A series of mono-alkylcarboxylic acid derivatives of tetraphenylporphyrin have been prepared. All the porphyrins were completely characterized by use of mass, (1)H NMR, UV-visible, and fluorescence spectroscopy. Experimental log P were determined by use of reversed-phase thin-layer chromatography with use of log P Rekker. These porphyrins are potential photosensitizers in photodynamic therapy.

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Sch1:  

Mentions: To the best of our knowledge no derivatives with carboxyl groups at the distal ends of alkyl chains have been investigated for their usefulness in PDT. We thus decided to investigate compounds with alkyl chains of different lengths separating the porphyrin fragment from the carboxyl group. To synthesize alkyl precursors with n = 4, 5, 6, 7, and 11 we used the classic method of obtaining carboxyl derivatives starting from suitable dibromoalkyl derivatives and malonic acid diethyl ester [19, 20]. The yields of the obtained diethyl (bromoalkyl)malonates were not very high but this could be expected, especially for shorter alkyl chains. These compounds quite easily undergo intramolecular cyclization reaction under the reaction conditions [21, 22]. Hydroxyphenyltritolylporphyrin (3) was obtained according to Ref. [23]. Diethyl (ω-bromoalkyl)malonates were coupled to a hydroxyl fragment of porphyrin using NaOH in DMF (Scheme 1). Under the reaction conditions the monocarboxy derivatives were obtained directly; in the presence of NaOH hydrolysis of the ester took place, whereas DMF distillation at an elevated temperature led to simultaneous decarboxylation of the malonic acid derivative. Exceptional for this synthetic route were the reactions of diethyl (3-bromopropyl)malonate leading to a malonic acid derivative and of diethyl (4-bromobutyl)malonate which gave a pentyloxy derivative of tetraphenylporphyrin. The properties of the obtained derivative were compared with those of the similar compound obtained by direct alkylation of the hydroxyphenyl derivative of porphyrin with 1-bromopentane.Scheme 1


The synthesis of new potential photosensitizers. 1. Mono-carboxylic acid derivatives of tetraphenylporphyrin.

Zięba G, Rojkiewicz M, Kozik V, Jarzembek K, Jarczyk A, Sochanik A, Kuś P - Monatsh. Chem. (2011)

 
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4494763&req=5

Sch1:  
Mentions: To the best of our knowledge no derivatives with carboxyl groups at the distal ends of alkyl chains have been investigated for their usefulness in PDT. We thus decided to investigate compounds with alkyl chains of different lengths separating the porphyrin fragment from the carboxyl group. To synthesize alkyl precursors with n = 4, 5, 6, 7, and 11 we used the classic method of obtaining carboxyl derivatives starting from suitable dibromoalkyl derivatives and malonic acid diethyl ester [19, 20]. The yields of the obtained diethyl (bromoalkyl)malonates were not very high but this could be expected, especially for shorter alkyl chains. These compounds quite easily undergo intramolecular cyclization reaction under the reaction conditions [21, 22]. Hydroxyphenyltritolylporphyrin (3) was obtained according to Ref. [23]. Diethyl (ω-bromoalkyl)malonates were coupled to a hydroxyl fragment of porphyrin using NaOH in DMF (Scheme 1). Under the reaction conditions the monocarboxy derivatives were obtained directly; in the presence of NaOH hydrolysis of the ester took place, whereas DMF distillation at an elevated temperature led to simultaneous decarboxylation of the malonic acid derivative. Exceptional for this synthetic route were the reactions of diethyl (3-bromopropyl)malonate leading to a malonic acid derivative and of diethyl (4-bromobutyl)malonate which gave a pentyloxy derivative of tetraphenylporphyrin. The properties of the obtained derivative were compared with those of the similar compound obtained by direct alkylation of the hydroxyphenyl derivative of porphyrin with 1-bromopentane.Scheme 1

Bottom Line: A series of mono-alkylcarboxylic acid derivatives of tetraphenylporphyrin have been prepared.Experimental log P were determined by use of reversed-phase thin-layer chromatography with use of log P Rekker.These porphyrins are potential photosensitizers in photodynamic therapy. .

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Silesia, 9, Szkolna Street, 40-006 Katowice, Poland.

ABSTRACT

Abstract: A series of mono-alkylcarboxylic acid derivatives of tetraphenylporphyrin have been prepared. All the porphyrins were completely characterized by use of mass, (1)H NMR, UV-visible, and fluorescence spectroscopy. Experimental log P were determined by use of reversed-phase thin-layer chromatography with use of log P Rekker. These porphyrins are potential photosensitizers in photodynamic therapy.

Graphical abstract: .

No MeSH data available.