Ready syntheses of benzoporphyrins via Diels–Alder reactions with protoporphyrin IX

Morgan, Alan R.; Pangka, Veronica Scherrer; Dolphin, David

doi:10.1039/c39840001047

Cited by 45 publications

(27 citation statements)

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“…In addition, the vinyl and cross-conjugated porphyrinic P, P' double bonds of protoporphyrin IX (I) have been shown (10, 1 1) to undergo [4+2] cvcloaddition reactions with electron-deficient dieno~hiles to give compounds (3) having essentially a chlorin chromophore (Scheme 1). With alkynes (2), the initially formed cycloadducts, under certain reaction conditions, undergo aromatization (12) with the concomitant loss of the angular methyl group to give benzoporphyrins (4). To study this cycloaddition reaction further, we have developed, and describe here, an efficient synthesis of vinylporphyrins .…”

Section: Introductionmentioning

confidence: 99%

“…Following catalytic debenzylation using 10% Pd-C, the resulting pyrrole-4-carboxylic acid (12) was decarboxylated by an indirect iodinative-deiodinative procedure (the electron-withdrawing 2-ethoxycarbonyl group prevents direct decarboxylation) to give the P-unsubstituted pyrrole (14) in 60% overall yield (from 11). To manipulate the a-ester for pyrrole coupling, compound 14 was transbenzylated to the bis-benzyl ester 15 and preferentially transmethylated with sodium methoxide in methanol-THF at room temperature to give benzyl3-(methoxycarbony1)methyl-5-methylpyrrole-2-carboxlate (16) in 77% overall yield.…”

Section: Introductionmentioning

confidence: 99%

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An efficient route to vinylporphyrins

Yon-Hin¹,

Wijesekera²,

Dolphin³

1990

Can. J. Chem.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

An efficient route to vinylporphyrins

Yon-Hin¹,

Wijesekera²,

Dolphin³

1990

Can. J. Chem.

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“…These can be obtained from the Diels-Alder mono-cycloaddition of protoporphyrin IX dimethyl ester with dimethyl acetylenedicarboxylate (Morgan et al 1984). Visudyne can be activated at 690 nm but PDT studies with it did not demonstrate promising applications in that area; however Visudyne became a clinically approved PS with ophthalmic significance.…”

Section: Visudynementioning

confidence: 99%

Cancer, Photodynamic Therapy and Porphyrin-Type Derivatives

Gomes

Cavaleiro

2018

An. Acad. Bras. Ciênc.

110

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This review has two parts. The first one gives an approach to interdisciplinary studies against cancer carried out by many scientists using porphyrin-type substrates as photosensitizers in PDT. Intensive studies were performed for almost six decades. The successes really started in 1993 with the first formulation patented under the trade name Photofrin, which was immediately approved in several countries to treat certain types of cancer. Photofrin is still used although certain negative features soon became well known. That has motivated the search for better new photosensitizers. Several ones were developed, evaluated and a few of them had clinical approval. This group includes porphyrin derivatives and pro-drugs (aminolevulinic acid and its alkyl esters). Oncological, dermatological and ophthalmic applications are now taking place for the benefit of mankind. The second part of this review is related with the work carried out in Aveiro at the authors University on the synthesis and biological evaluation of several potential PDT photosensitizers. Not only new synthetic methodologies mainly for porphyrins and chlorins were developed but also other related macrocycles of the phthalocyanine and corrole types have entered in the same "pipeline". In vivo and in vitro biological evaluations also took place under interdisciplinary studies.

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“…A more 'classic' approach is the preparation of benzochlorins [275,276] . Maillard et al regioselectively synthesized an amphiphilic glycoconjugated meso-monoarylbenzochlorin from the meso-monoaryl-nickel(II) porphyrin [277] .…”

Section: Benzochlorinsmentioning

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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Ready syntheses of benzoporphyrins via Diels–Alder reactions with protoporphyrin IX

Abstract: Reaction of protoporphyrin IX dimethyl ester with strongly activated dienophiles causes a Diels-Alder reaction to occur with the porphyrin periphery; elimination of the angular methyl group from these adducts gives mono benzoporphyrins.

Cited by 45 publications

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An efficient route to vinylporphyrins

An efficient route to vinylporphyrins

Cancer, Photodynamic Therapy and Porphyrin-Type Derivatives

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

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