Regioselective reduction of 5-aryl-10,15,20-tris(pyridyl) porphyrin to 5-aryl-10,15,20-tris(pyridyl)dihydroporphyrin (chlorin)
| Autor: | Alexia Moulin, Vincent Sol, Alexis Mailleau, Yves Champavier, Frédérique Brégier, Jérémy Godard, Vincent Chaleix, Soukaina Bouramtane, Jordan Thiais |
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| Přispěvatelé: | PEIRENE (PEIRENE), Institut Génomique, Environnement, Immunité, Santé, Thérapeutique (GEIST), Université de Limoges (UNILIM)-Université de Limoges (UNILIM), Service Commun de Résonance Magnétique Nucléaire (RMN), Université de Limoges (UNILIM) |
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Tris Double bond 010405 organic chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Aryl Regioselectivity General Chemistry Structural difference 010402 general chemistry 01 natural sciences Medicinal chemistry Porphyrin 0104 chemical sciences chemistry.chemical_compound chemistry Chlorin [CHIM]Chemical Sciences ComputingMilieux_MISCELLANEOUS |
| Zdroj: | Journal of Porphyrins and Phthalocyanines Journal of Porphyrins and Phthalocyanines, World Scientific Publishing, 2019, 23 (11n12), pp.1380-1397. ⟨10.1142/S1088424619501438⟩ |
| ISSN: | 1088-4246 1099-1409 |
| Popis: | Dihydroporphyrins or chlorins differ from porphyrins only by saturation of a peripheral double bond of the macrocycle. However, this small structural difference leads to a significant increase of the absorption band at approximately 650 nm, which makes them very interesting candidates for photodynamic therapy applications. The reduction of porphyrins bearing two, three or four pyridyl substituents with tin(II) chloride has been developed for the synthesis of dihydroporphyrins in yields of 15–73%. The reduction of 5-(aryl)-10,15,20-tris(2 or 4-pyridyl)porphyrin with tin(II) chloride dihydrate demonstrated good regioselectivity. Porphyrins with one meso-aryl bearing one electron-donating group (EDG) gave 5-aryl-10,15,20-tris(2- or 4-pyridyl)-17,18-dihydroporphyrins in 17–72% yield. Porphyrins with one meso-aryl bearing one or more electron-withdrawing groups (EWG) gave 5-aryl-10,15,20-tris(4-pyridyl)-17,18-dihydroporphyrins or 5-aryl-10,15,20-tris(4-pyridyl)-7,8-dihydroporphyrins in 15–21% yield and isobacteriochlorin. We have also proven the possibility of functionalizing these compounds to design new regioisomerically pure photosensitizers. |
| Databáze: | OpenAIRE |
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