PMID: 11312962Apr 21, 2001Paper

A simple and efficient approach for the synthesis of fluorinated and nonfluorinated octaethylporphyrin-based benzochlorins with variable lipophilicity, their in vivo tumor uptake, and the preliminary in vitro photosensitizing efficacy

The Journal of Organic Chemistry
G LiR K Pandey

Abstract

Starting from commercially available Ni(II)octaethylporphyrin (OEP), an efficient approach for the preparation of a series of fluorinated and nonfluorinated benzochlorins with variable lipophicity has been developed. Their spectroscopic properties, preliminary in vitro photosensitizing efficacy, and tumor selectivity were determined. Our methodology provides a facile approach for the preparation of the free-base and the related Zn(II) benzochlorins containing alkyl and alkyl ether side chains with variable carbon units. For the preparation of benzochlorins containing alkyl groups attached to the exocyclic phenyl ring, the Ni(II) meso-(2-formylvinyl)octaethyl porphyrin 2 was reacted with various reagents such as (trifluoromethyl)trimethylsilane (TMS-CF3) or the Grignard reagents of various fluorinated or nonfluorinated alkyl halides. The corresponding intermediates 3, 6a-6e, and 8 obtained via intramolecular cyclization under acidic conditions afforded the related benzochlorins 5, 7a-d, and 9 in good yields except for 7e which was obtained in poor yield (11.4%). The alcohol 10 obtained by reacting porphyrin 2 with ethynylmagnesium chloride did not produce the expected acetylenic benzochlorin; instead the corresponding acetyl der...Continue Reading

Citations

Apr 12, 2011·Journal of Photochemistry and Photobiology. B, Biology·Vincent SarrazyPierre Krausz
Dec 23, 2008·Bioorganic & Medicinal Chemistry·Guillaume GarciaPierre Krausz
Jun 7, 2013·Chemistry : a European Journal·Kei MurakamiAtsuhiro Osuka
Jul 4, 2008·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·João Nuno SilvaPatrice Morlière
Feb 20, 2009·Chemical Communications : Chem Comm·Sumito TokujiAtsuhiro Osuka
Oct 14, 2020·ChemPlusChem·Boitumelo F MakumeJan A van den Berg

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