- Synthesis of meso-tetraphenylthiaporphyrins bearing one inverted pyrrole
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2-Aza-21-thia-23-carba-5,10,15,20-tetraphenylporphyrin and its N-methylated analogue were synthesized and characterized. The synthesis utilizers [3+1] condensation of thiatripyrrin with 2,4-bis(α-hydroxy-α-phenylmethyl)pyrrole or 2,4-bis(α-hydroxy-α-pheny
- Lee, Chang-Hee,Kim, Han-Je
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- Synthesis, characterization, and anti-amoebic screening of core-modified 5,20-bis{2-{[(alkyl)(alkyl′)amino]methyl}ferrocen-1-yl}-10,15-diphenyl-21, 23-dithiaporphyrin (=1,1″-(10,15-diphenyl-21,23-dithiaporphine-5,20-diyl) bis[2-{[(alkyl)(alkyl′)amino]methyl}ferrocene]) derivatives
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The synthesis of the first bis-ferrocenyl-substituted core-modified porphyrins, 5,20-bis{2-{[(alkyl)-(alkyl′)amino]methyl}ferrocen-1-yl}-10, 15-diphenyl-21,23-dithiaporphyrin derivatives 6a - 6j, via a multistep route is reported (Schemes 1, 2, and 4). The synthesis was carried out through acid-catalyzed (BF3 ? Et2O) condensation of 1,1″- [thiophene-2,5-diylbis(hydroxymethyl)]bis[2-{[(alkyl)(alkyl′)amino]methyl} ferrocenes] 4a - 4j with 2,2′-[thiophene-2,5-diylbis(phenylmethylene)] bis[1H-pyrrole] (5b) in presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (=4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile; DDQ). Characterization of the compounds was done at each step by means of various spectroscopic techniques. The final compounds were screened for in vitro anti-amoebic activity against the strain HM1:IMSS of E. histolytica (Table 2).
- Bhat, Abdul R.,Bhat, Asif I.,Athar, Fareeda,Azam, Amir
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experimental part
p. 1644 - 1656
(2009/10/16)
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- Water soluble, core-modified porphyrins. 3. Synthesis, photophysical properties, and in vitro studies of photosensitization, uptake, and localization with carboxylic acid-substituted derivatives
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Water soluble, core-modified porphyrins 1-5 bearing 1-4 carboxylic acid groups were prepared and evaluated in vitro as photosensitizers for photodynamic therapy. The 21,23-core-modified porphyrins 1-5 gave band I absorption maxima with λmax of
- You, Youngjae,Gibson, Scott L.,Hilf, Russell,Davies, Sherry R.,Oseroff, Allan R.,Roy, Indrajit,Ohulchanskyy, Tymish Y.,Bergey, Earl J.,Detty, Michael R.
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p. 3734 - 3747
(2007/10/03)
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- Water-soluble, core-modified porphyrins as novel, longer-wavelength-absorbing sensitizers for photodynamic therapy. II. Effects of core heteroatoms and meso-substituents on biological activity
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Water-soluble, core-modified porphyrins were prepared and evaluated as sensitizers for photodynamic therapy (PDT). The addition of an aromatic aldehyde to 2,5-dilithiothiophene or -selenophene gave diol 3 as a nearly equimolar mixture of meso and d,1 dias
- Hilmey, David G.,Abe, Masako,Nelen, Marina I.,Stilts, Corey E.,Baker, Gary A.,Baker, Sheila N.,Bright, Frank V.,Davies, Sherry R.,Gollnick, Sandra O.,Oseroff, Allan R.,Gibson, Scott L.,Hilf, Russell,Detty, Michael R.
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p. 449 - 461
(2007/10/03)
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- Synthesis of pseudoaromatic expanded porphyrin analogues
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Optically active expanded porphyrins bearing thiophene were synthesized by Schiff base forming reaction. The condensation of thiophene containing 1,14-bisformyl tripyrrane with aromatic diamines failed to give desired macrocycles but condensation with aliphatic 1,2-diamines gave the desired products. The macrocycles synthesized tend to maintain 18π system and the ethylene bridge shows somewhat resistance toward oxidation.
- Lee,Oh
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p. 1921 - 1924
(2007/10/03)
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- Stepwise syntheses of core-modified, meso-substituted porphyrins
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Simple conditions are discovered to afford modified tripyrrin derivatives by condensation of 2,5-bis(α-hydroxymethyl)pyrrole, thiophene and furan derivatives with pyrrole in the presence of acid catalyst. The core-modified porphyrins were synthesized by acid catalyzed 3+1 condensation of modified tripyrrins with 2,5-bis(α-hydroxymethyl)-substituted pyrrole, thiophene or furan. This new process gives a single porphyrin isomer and overcomes the synthetic problems associated with separation and purification of regioisomeric mixtures.
- Heo, Phil-Yeon,Shin, Koo,Lee, Chang-Hee
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p. 197 - 200
(2007/10/02)
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