Überführung von Porphyrinen in Dioxy‐chlorine durch Einwirkung von Osmiumtetroxyd

Fischer, Hans; Eckoldt, Hans

doi:10.1002/jlac.19405440109

Cited by 35 publications

(12 citation statements)

References 11 publications

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“…More synthetically useful is the 2,3-dihydroxylation of porphyrins and follow-up chemistry [263][264][265] . Some of the earlier examples of hydroxychlorins derived from octaethylporphyrin were substituted with glycerol, D-glucose and D-mannitol via ether linkages as outlined in Scheme 25 [39,266] rearrangement yielding the oxochlorin 521 in 75 % yield.…”

Section: Dihydroxylationmentioning

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: Dihydroxylationmentioning

confidence: 99%

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Moylan¹,

Scanlan²,

Senge

2015

CMC

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“…Although the oxidation of -substituted porphyrins by hydrogen peroxide in the presence of acid [27] or by OsO 4 [28] was reported for the first time more than 60 years ago, until 1995 no oxidation procedure for meso-substituted porphyrins was known. Brückner and Dolphin reported that the use of a stoichiometric amount of OsO 4 led to the formation of 2,3-vic-dihydroxy-meso-tetraphenylchlorin (16) in 50% yield.…”

Section: Oxidation Of Porphyrinsmentioning

confidence: 99%

Recent Advances in the Synthesis of Hydroporphyrins

Gałęzowski¹,

Gryko

2007

COC

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The various approaches to the synthesis of hydroporphyrins are summarized. Transformations of synthetic porphyrins have been extensively studied in the last decade due to their easy availability. Many two and three step reaction sequences have been developed, which have allowed access to a broad variety of structures including not only chlorins but also benzochlorins, secochlorins etc. The fact that porphyrins can act as dienophiles or dipolarophiles has been broadly investigated and utilized. On the other hand 'total syntheses' of chlorins from pyrrole and other simple starting materials have been pursued by only a few research groups. Generally a [2+2] approach has been investigated and usually chlorins possessing two geminal methyl groups on the reduced pyrrole ring ('locked' chlorins) were the targets of the studies. The synthesis of tetrahydrodipyrrin derivatives as popular building blocks was the subject of intense investigation. Overall, a few interesting and ingenious approaches toward 'total synthesis' of chlorins were proposed, reaching total yields on the level of 1-5%. Some derivatives with auxochromic groups were prepared, which allowed the study of the relationship between structure and spectroscopic properties. Bacteriochlorin synthesis, probably due to their limited stability, has been studied less extensively.

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“…In 1940 Fischer and Eckoldt reported on the oxidation of some naturally occurring porphyrins with OsO 4 giving vic-dihydroxychlorins [6]; more recently the oxidations of octaethylporphyrin [7,8] and corrins [9] have been reported. Chang and his colleagues have prepared a variety of dihydroxychlorins [10] prepared from octaethylporphyrins and have examined in detail the biodistribution and PDT efficacy of ketochlorins obtained by an acid catalyzed pinacol rearrangement [10].…”

Section: Introductionmentioning

confidence: 99%

Evaluation of tetraphenyl-2,3-dihydroxychlorins as potential photosensitizers

MacAlpine

Boch

Dolphin

2002

J. Porphyrins Phthalocyanines

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A series of β,β-dihydroxychlorins derived from meso-tetraphenylporphyrins (TPPs) have been synthesized. Their in vitro cytotoxicity has been measured and compared to BPDMA (verteporfin). Under the assay conditions BPDMA had an LD 50 (lethal dose to kill 50% of cells) value of 0.007 μM (5 ng/mL). The LD 50 values for the TPP derivatives varied from 1.7 × 10-2 to 9.9 μM depending upon the substituents and their position on the phenyl groups. One example of the dihydroxychlorin prepared from unsubstituted 5,15-diphenylporphyrin was examined and this exhibited an LD 50 of 2.4 × 10-3 μ M !

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Überführung von Porphyrinen in Dioxy‐chlorine durch Einwirkung von Osmiumtetroxyd

Cited by 35 publications

References 11 publications

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Recent Advances in the Synthesis of Hydroporphyrins

Evaluation of tetraphenyl-2,3-dihydroxychlorins as potential photosensitizers

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