1,3-Dipolar cycloadditions with meso-tetraarylchlorins – site selectivity and mixed bisadducts
The 1,3-dipolar cycloaddition reaction of meso-tetraarylporphyrins with nitrones gives isoxazolidine-fused chlorins. Depending on the substitution pattern on the meso-aryl groups and the nitrone, the chlorins can be obtained in high yields (up to 91%). Bacteriochlorin-type bisadducts are also obtained, although in low yield, from the reaction of meso-tetrakis(pentafluorophenyl)porphyrin with N-methyl, N-cyclohexyl or N-benzyl nitrone. The structure of a bis(N-benzyl isoxazolidine-fused) bacteriochlorin was determined by single-crystal X-ray diffraction and rationalized by DFT calculations. To further explore the nature of site selectivity in the formation of bisadducts, isomeric mixed bacte…
Synthesis, characterization, and cellular investigations of porphyrin– and chlorin–indomethacin conjugates for photodynamic therapy of cancer
Indomethacin is a potent non-steroidal anti-inflammatory drug (NSAID) with a strong selective inhibitor activity towards cyclooxygenase-2 (COX-2), an enzyme that is highly overexpressed in various tumour cells, being involved in tumourigenesis. Concomitantly, porphyrins have gained much attention as promising photosensitizers (PSs) for the non-invasive photodynamic therapy (PDT) of cancer. Herein, we report the design, and determine the singlet oxygen generation capacity and in vitro cellular toxicity of porphyrin- and chlorin-indomethacin conjugates (P2-Ind and C2-Ind). Both the conjugates were obtained in high yields and were characterized by 1H, 19F and 13C NMR as well as by high resolut…
CCDC 1488184: Experimental Crystal Structure Determination
Related Article: José Almeida, António Aguiar, Andreia Leite, André M. N. Silva, Luís Cunha-Silva, Baltazar de Castro, Maria Rangel, Giampaolo Barone, Augusto C. Tomé, Ana M. G. Silva|2017|Org.Chem.Front.|4|534|doi:10.1039/C6QO00771F