176980-35-1Relevant academic research and scientific papers
Evaluation of a 99mTc-labelled meso-bisphenylporphyrin as a tumour image agent
Santos, Pedro M.,Laranjo, Mafalda,Serra, Armenio C.,Abrantes, Ana Margarida,Pineiro, Marta,Casalta-Lopes, Joao,Trindade, Dina,Maia, Jorge,Rocha-Gonsalves, Antonio,Botelho, Maria Filomena
, p. 141 - 147 (2014)
Porphyrins are excellent agents for photodynamic treatment of various types of cancer and also good metal chelators that form highly stable metallo-complexes with different radionuclides. Therefore, radiolabelled porphyrins could also be potentially used
Refined synthesis of meso-substituted trans-A2B-corroles bearing electron-withdrawing groups
Gryko, Daniel T.,Koszarna, Beata
, p. 2205 - 2209 (2004)
We have refined a one-pot synthesis of trans-A2B-corroles via the condensation of 5-(pentafluorophenyl)dipyrromethane with aldehydes followed by macrocyclization mediated by DDQ. After thorough examination of reaction parameters and thanks to the identification of key factors influencing the formation of bilanes and the efficiency of their conversion to corroles, we were able to improve yields from ca. 6 to ca. 20% for a broad range of aldehydes. We proved that these conditions work well also for dipyrromethanes possessing cyano and nitro groups. meso-Substituted alkyl aryl corrole has been obtained for the first time using this procedure.
Synthesis of benzodioxepinone analogues via a novel synthetic route with qualitative olfactory evaluation
Drevermann, Britta,Lingham, Anthony R.,Huegel, Helmut M.,Marriott, Philip J.
, p. 1006 - 1027 (2008/02/04)
Marine odorants represent a minor yet diverse class of substances within the fragrance industry, of which 7-methyl-2H-1,5-benzodioxepin-3(4H)-one (1) is commercially known as Calone 1951, a synthetic first in the area of marine-fragrance chemistry. To determine the extent to which the characteristic marine odor of Calone 1951 corresponds to the substitution at the benzo portion of the molecule, a variety of aromatic substituents were incorporated into the benzodioxepinone structure (Scheme 1, Table 3). In light of the difficulty experienced in applying patented literature to deriving the analogues 12-18, particularly those with electron-withdrawing substituents, an alternative synthetic scheme was implemented for the construction of all analogues in favorable yields (Scheme 4, Table 3). Formation of the hydroxy-protected dihalo alkylating agent 24 via epoxide cleavage of epichlorohydrin (Scheme 3) allowed etherification favoring dihalo displacement and subsequent intramolecular ring closure (-→26a-g). THP Deprotection followed by oxidation of the alcohols 27a-g to the ketones 12-18 provided a general pathway to the benzodioxepinone products. The influence of the substituent nature on odor activity revealed a diverse scope of olfactory character (Table 4).
Porphyrin synthesis in surfactant solution: Multicomponent assembly in micelles
Bonar-Law, Richard P.
, p. 3623 - 3634 (2007/10/03)
A synthesis of meso-substituted porphyrins in anionic sodium dodecyl sulfate micelles has been developed. Polar, functionalized aromatic aldehydes condense reversibly with pyrrole in the micellar phase. Oxidation of the porphyrinogen then provides functionalized porphyrins in yields of 10-48%. Hydrophobic aldehydes condense irreversibly to give low yields at practical substrate concentrations. Synthesis in D2O solution results in per-β-deuterated porphyrins. A two-phase model is used to rationalize the dependence of porphyrin yield on reactant and surfactant concentration. Micelles are viewed as potential wells which promote porphyrinogen assembly by binding products more tightly than reactants.
