Pyrromethanes and Porphyrins Therefrom<sup>1</sup>

Arsenault, G. P.; Bullock, E.; MacDonald, S. F.

doi:10.1021/ja01501a066

Cited by 346 publications

(187 citation statements)

References 3 publications

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“…For aldehyde-pyrrole condensation reactions, this ranges from the early Rothemund condensation [136] to the now standard Lindsey condensation [137] . Partial and total syntheses were facilitated first by the MacDonald condensation, a [2+2] condensation utilizing dipyrromethenes, dipyrroyl ketones and dipyrromethanes [138] . Condensation methods are continuously improving and almost any desired meso or β-substituted porphyrin can be prepared today [139][140][141][142] .…”

Section: Porphyrin Chemistrymentioning

confidence: 99%

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Moylan¹,

Scanlan²,

Senge

2015

CMC

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Abstract:This review presents an in-depth overview of the modification of porphyrins with bioconjugates and their applications in medicine today. Porphyrin bioconjugates ranging from nucleotides to steroids are under active scrutiny. However, carbohydrates have been at the forefront of such research in recent years and offer significant potential. This is attributed to their own selectivity to lectins on the surface of cancer cells and their influence on the amphiphilicity of the porphyrin macrocycle. These characteristics and the tendency of porphyrin photosensitizers to accumulate in tumor tissues make glycoporphyrins promising candidates for use as photosensitizers. Thus, a detailed overview of the synthesis and biological evaluation of glycoporphyrins is given with a particular focus on their applications in photodynamic therapy and their future prospects as drug candidates have been reported.

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Section: Porphyrin Chemistrymentioning

confidence: 99%

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Moylan¹,

Scanlan²,

Senge

2015

CMC

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“…The solvent was removed, and the anthracenylporphyrins were further purified by recrystallization from dichloromethane/MeOH. [15] 9-anthracenylaldehyde (206 mg, 1 mmol, 4 eq.) was dissolved in 1 L of dry DCM, and 1 mmol (4 eq.)…”

Section: Suzuki Cross-coupling Approach For Anthracenylporphyrinsmentioning

confidence: 99%

“…One method we envisaged to be successful was a standard 2+2 condensation reaction [15]. This method involves the acid-catalyzed condensation of dipyrromethane or dipyrromethane derivatives with an aldehyde to form the porphyrinogen.…”

Section: Introductionmentioning

confidence: 99%

Anthracenylporphyrins

Davis

Senge

Locos

2010

Zeitschrift Für Naturforschung B

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We report the synthesis and characterization of meso-anthracenylporphyrins with zinc and nickel metal centers. A variety of novel aryl and alkyl meso-substituted anthracenylporphyrins were synthesized via step-wise Suzuki cross-coupling reactions using anthracenyl boronates. This method was compared to standard syntheses based on condensation reactions to yield anthracenylporphyrins of the A 2 B 2 -and A 3 B-type. The work was complemented by the synthesis of a number of the functionalized anthracene derivatives via Suzuki couplings. Selected systems were subjected to single-crystal X-ray analysis which revealed an unusual close packing for nickel(II) anthracenylporphyrins.

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“…7,8 After consideration of symmetry issues and monopyrrole availability, we decided that the MacDonald route was the more straightforward approach. Scheme 1 shows the synthetic route which was used.…”

Section: Synthesis Of Corallistin B Dimethyl Ester (2)mentioning

confidence: 99%

“…7,8 However, based on a retrosynthetic analysis of the ease of preparation of the required pyrroles, we chose instead to use a,c-biladiene cyclization 9 as the synthetic route for corallistin C methyl ester (3). Four different, but readily available, pyrroles were required for the synthesis (Scheme 2).…”

Section: Synthesis Of Corallistin C Methyl Ester (3)mentioning

confidence: 99%

Syntheses of porphyrins isolated from the Coral Sea demosponge Corallistes sp.

Pandey¹,

Leung²

2002

Arkivoc

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Methyl esters 2, 3, and 5 of corallistins B, C, and E, respectively, isolated from the Coral Sea demosponge Corallistes sp., were successfully synthesized by the MacDonald method (for corallistin B ester) and via a,c-biladiene cyclization (for corallistins C and E esters). In order to compare with the 1 H-NMR data reported in the literature, zinc(II) complexes of these corallistins were prepared, and their 1 H-NMR spectra were measured. Most chemical shifts were found to be within 0.1 ppm of the reported values, except in the case of corallistin B ester, where signal broadening due to porphyrin aggregation made the comparison with literature values difficult. Overall, the NMR data provided support for the structures proposed for the natural corallistins.Postulates on the biosynthetic origins of the corralistins are also presented.

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Pyrromethanes and Porphyrins Therefrom¹

Cited by 346 publications

References 3 publications

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Anthracenylporphyrins

Syntheses of porphyrins isolated from the Coral Sea demosponge Corallistes sp.

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Pyrromethanes and Porphyrins Therefrom1

Cited by 346 publications

References 3 publications

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Anthracenylporphyrins

Syntheses of porphyrins isolated from the Coral Sea demosponge Corallistes sp.

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About

Pyrromethanes and Porphyrins Therefrom¹