Porphyrin chemistry pertaining to the design of anti-cancer drugs; part 1, the synthesis of porphyrins containing <i>meso</i>-pyridyl and <i>meso</i>-substituted phenyl functional groups

Meng, Guangzhen G.; James, Brian R.; Skov, Kirsten A.

doi:10.1139/v94-241

Cited by 66 publications

(47 citation statements)

References 22 publications

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“…According to data reported by James et al 22 and Lindsay et al 23 for 4-pyridyl protons the double doublet at δ 8.17 (J 4.1 and 1.5 Hz) was attributed to the 4-Py protons H-2 and H-6, while the double doublet at δ 9.07 (J 4.1 and 1.5 Hz) was assigned to the 4-Py protons H-3 and H-5. As for the β-pyrrolic protons of porphyrin 2, the singlet at δ 8.93 was attributed to the β-pyrrolic protons H-7, H-8, H-12 and H-13, which are situated between two pentafluorophenyl substituents and are thus equivalent.…”

Section: A Novel Chlorin Derivative Of Meso-tris(pentafluorophenyl)-4mentioning

confidence: 99%

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A novel chlorin derivative of Meso-tris(pentafluorophenyl)-4-pyridylporphyrin: synthesis, photophysics and photochemical properties

Maestrin¹,

Ribeiro²,

Tedesco³

et al. 2004

J. Braz. Chem. Soc.

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A terapia fotodinâmica (TFD) está baseada na administração e no acúmulo de fotossensibilizador, por exemplo, de tipo porfirina ou clorina, em tecidos doentes. As clorinas apresentam propriedades fotofísicas semelhantes àquelas das porfirinas, mas com intensificação e deslocamento das bandas Q, o que faz com que sejam bons candidatos para TFD. Neste trabalho relata-se a síntese da 5,10,15-tris(pentafluorofenil)-20-(4-piridil)porfirina, (2), e das clorinas isômeras 4, (5,10,20-tris(pentafluorofenil)-15-(4-piridil)-tetra-hidro-1H-N-metil-pirrolo[3,4-b]porfirina e 5, (5,10,15-tris(pentafluorofenil)-20-(4-piridil)-tetra-hidro-1H-N-metil-pirrolo[3,4-b]porfirina, obtidas a partir de 2, por reação de cicloadição 1,3-dipolar com um ileto azometínico, e respectivas caracterizações estruturais por UV-Vis, RMN e EM-FAB. Foram avaliadas as propriedades fotofísicas, fotoquímicas e fotodegradativas para a nova clorina 4, obtida com melhor rendimento que o seu isômero 5. O rendimento quântico de fotodegradação (φ Fd , mol Einstein -1 ) foi de 0,047±0,014. Foram ainda realizados testes com ácido úrico para demonstrar a capacidade do fotossensibilizador na produção de 1 O 2 . Os resultados mostraram que a nova clorina 4 pode ser considerada como um bom fotossensibilizador para TFD.Photodynamic therapy (PDT) is based on the accumulation of a photosensitizer, such as a porphyrin or a chlorin, in a malignant tissue after its administration. Chlorins exhibit photophysical properties similar to those of the porphyrin macrocycles, but with intensified and red-shifted Q bands, making chlorin-containing systems even better candidates for PDT. In this contribution, we report the synthesis of 5,10,15-tris(pentafluorophenyl)-20-(4-pyridyl)porphyrin, (2) and its transformation to the novel chlorin derivatives 4, (5,10,20-tris(pentafluorophenyl)-15-(4-pyridyl)-tetrahydro-1H-N-methyl-pyrrolo [3,4-b]porphyrin and 5, (5,10,15-tris(pentafluorophenyl)-20-(4-pyridyl)-tetrahydro-1H-N-methyl-pyrrolo[3,4-b]porphyrin) by 1,3-dipolar cycloaddition with an azomethine ylide. The new products have been characterized by UV-Vis, 1 H NMR and FAB-MS. The photophysics, photochemical and photobleaching properties of chlorin 4 have been evaluated. Its quantum yield of photobleaching (φ Pb , mol Einstein -1 ) was 0.047±0.014. In order to demonstrate the production of 1 O 2 when 4 is used as a photosensitizer, uric acid tests have been carried out. The results indicate that chlorin 4 can be considered a promising photosensitizer in PDT.

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Section: A Novel Chlorin Derivative Of Meso-tris(pentafluorophenyl)-4mentioning

confidence: 99%

“…[20][21][22] This synthesis involves the condensation of pyrrole with 4-pyridinecarbaldehyde and pentafluorobenzaldehyde, under reflux for 30 min in acetic acid at 118 °C. Under such conditions, a mixture of porphyrin 1 and the desired porphyrin 2 were directly obtained.…”

Section: Synthesis and Characterization Of Porphyrinmentioning

confidence: 99%

A novel chlorin derivative of Meso-tris(pentafluorophenyl)-4-pyridylporphyrin: synthesis, photophysics and photochemical properties

Maestrin¹,

Ribeiro²,

Tedesco³

et al. 2004

J. Braz. Chem. Soc.

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“…UV-visible (see Table 4). 'H NMR (see Table 1 H4,N7OlO~O.5H2O: C 67.89,H 4.77,N 10.08;found: C 67.82,H 4.74,3,4, Table 4). 'H NMR (see Table 1).…”

Section: -(2346-tetra-o-acetyl-p-~-glucopyranosyloxy)-mentioning

confidence: 93%

“…Aldehyde l a was prepared from commercially available helicin (2-(P-D-glucopyranosyloxy)benzaldehyde) by acetylation at 0°C during 1.5 h with acetic anhydride in dry pyridine (yield 90%). 3,4,acetyl-P-D-glucopyranosyloxy)benzaldehyde l b was synthesized from 2,3,4,6-tetra-0-acetyl-a-D-glucopyranosyl bromide and 4-hydroxybenzaldehyde (2.5 equiv. ) in acetone in the presence of 7% aqueous NaOH.…”

Section: Acomentioning

confidence: 99%

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Synthesis of glycosylated cationic porphyrins as potential agents in photodynamic therapy

Driaf¹,

Granet²,

Krausz³

et al. 1996

Can. J. Chem.

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Trisalkylpyridiniurn porphyrins substituted by one glycosyl (glucosyl, maltosyl, and lactosyl) moiety have been prepared in acceptable yields. These glycosylated cationic porphyrins have been synthesized from pyrrole condensed with 4-pyridinecarboxaldehyde, and suitable ortho-orpara peracetylglycosyloxybenzaldehyde derivatives in refluxing propionic acid -Ac20 followed by action of alkyliodide in DMF. Deprotection of the glycosylated moieties led to a new class of representative glycosylated porphyrins.Key words: porphyrins, cationic, glycosylated; phototherapy, cancer.RCsumk : On a prCparC des tris(alky1pyridiniurn)porphyrines substituCes par une portion glycosyle (glucosyle, maltosyle et lactosyle) avec des rendements acceptables. On a synthttist ces porphyrines cationiques glycosylCes a partir de pyrrole condens6 avec un pyridine-4-carboxyaldChyde et des derives ortho-ou para-peracCtylglycosyloxybenzaldChydes approprits, par reflux dans de l'acide propanoi'que -Ac20, suivi par l'action d'un iodure d'alkyle dans le DMF. La dkprotection des portions glycosylCes conduit a une nouvelle classe de porphyrines glycosyltes representatives.

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Nitration of Porphyrin Systems: A Toolbox of Synthetic Methods

Mikus

Łopuszyńska

2020

Chemistry An Asian Journal

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This review addresses nitration reactions of porphyrin derivatives. Simple porphyrins modifications afford valuable intermediates in this area of chemistry. They are useful materials for further transformations, as the NO2 group introduced into parent porphyrin system increases its electrophilic character, thus allowing a broad spectrum of subsequent reactions, e. g. reduction of NO2 to NH2, subsequent diazotisation, nucleophilic substitution of hydrogen (in ortho‐position to NO2), a variety of cyclizations, etc. Such reactions are often utilized in the first steps of the designed syntheses, leading to attractive and useful target porphyrin molecules. This approach (via nitro‐derivatives) allows synthesizing numerous porphyrin‐like compounds of a high degree of complexity, and has thus become one of the methods choice. The substitution by NO2 group can take place at all positions of the porphyrin systems: four meso‐positions (5, 10, 15, 20) and eight positions β (2, 3, 7, 8, 12, 13, 17, 18). The third possibility includes the nitration in meso‐aryl rings attached to positions 5, 10, 15, and 20. The latter derivatives (meso‐aryl substituted ones) are a large, well‐known group of synthetic porphyrins. The nitration reactions described herein follow three various mechanisms: (a) radical, (b) via π‐cation radicals and π‐dications, and (c) electrophilic. All the above cases are discussed in detail. According to our knowledge, this is the first such systematic account concerning these reactions.

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Porphyrin chemistry pertaining to the design of anti-cancer drugs; part 1, the synthesis of porphyrins containing meso-pyridyl and meso-substituted phenyl functional groups

Cited by 66 publications

References 22 publications

A novel chlorin derivative of Meso-tris(pentafluorophenyl)-4-pyridylporphyrin: synthesis, photophysics and photochemical properties

A novel chlorin derivative of Meso-tris(pentafluorophenyl)-4-pyridylporphyrin: synthesis, photophysics and photochemical properties

Synthesis of glycosylated cationic porphyrins as potential agents in photodynamic therapy

Nitration of Porphyrin Systems: A Toolbox of Synthetic Methods

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