Total syntheses of 8-formyl-8-demethylprotoporphyrin IX, 8-(hydroxymethyl)-8-demethylprotoporphyrin IX, and 8-fluoromethyl analogs of protoporphyrin IX

Snow, Kevin M.; Smith, Kevin M.

doi:10.1021/jo00275a009

Cited by 15 publications

(9 citation statements)

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“…No satisfactory melting point could be obtained for this compound. The 1 H NMR matched published values. , The mass specrum (MH +• = 582) was also consistent with 4 . Anal.…”

Section: Methodssupporting

confidence: 78%

“…This very mild, clean method causes no hydrolysis of the ester side chains and produces virtually no side products. Snow and Smith reported that dialdehyde 4 decomposed in solution over time and could not be crystallized, but we found that 4 could be crystallized from hexane/methylene chloride and was stable for at least six weeks on storage at −20 °C. They did not report a yield in their transacetylation of the bis-acetal to give 4 , and the procedure involves chromatographic separation .…”

Section: Resultsmentioning

confidence: 63%

“…Snow and Smith reported that dialdehyde 4 decomposed in solution over time and could not be crystallized, but we found that 4 could be crystallized from hexane/methylene chloride and was stable for at least six weeks on storage at −20 °C. They did not report a yield in their transacetylation of the bis-acetal to give 4 , and the procedure involves chromatographic separation . In all the drawings of this Note, the symbol POMe represents a methyl propionate residue.…”

Section: Resultsmentioning

confidence: 63%

“…At 1 h the once again heterogenous solution was reduced in volume in vacuo , diluted with chloroform, and washed three times with water. The solvent was removed and the crude porphyrin was dissolved in hot CHCl 3 and precipitated with hexane to obtain 72 mg, 80%: mp 283−286 °C (lit. , 284−286 °C). The 1 H NMR spectra match the published values .…”

Section: Methodsmentioning

confidence: 99%

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Improved Methods for the Synthesis of Porphyrin Alcohols and Aldehydes from Protoporphyrin IX Dimethyl Ester and Their Further Modification

1997

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“…No satisfactory melting point could be obtained for this compound. The 1 H NMR matched published values. , The mass specrum (MH +• = 582) was also consistent with 4 . Anal.…”

Section: Methodssupporting

confidence: 78%

Section: Resultsmentioning

confidence: 63%

Section: Resultsmentioning

confidence: 63%

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Improved Methods for the Synthesis of Porphyrin Alcohols and Aldehydes from Protoporphyrin IX Dimethyl Ester and Their Further Modification

1997

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“…The second series of thio-glycosylated porphyrins was synthesized from protoporphyrin IX dimethylester 450 which was converted to the isohematoporphyrin 451 via modifications using methods from Smith's group [245,246] (Scheme 17). The latter was brominated to form 452 and was subsequently glycosylated yielding 453-455 in 64-93 %.…”

Section: S-linked Systemsmentioning

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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Iron Porphyrin Chemistry

Walker¹,

Simonis²

2005

Encyclopedia of Inorganic Chemistry

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This article reviews most aspects of the chemistry of iron porphyrins, from Fe(0) to Fe(V), including occurrence and roles of natural iron porphyrins (hemes) and their synthetic analogs, structures and electron configurations of iron porphyrins of all oxidation and spin states, π electron configuration of the porphyrin ring, synthesis of metal‐free porphyrins and other related macrocycles, insertion of iron into free‐base porphyrins and related macrocycles, the properties, reactions, uses and biological relevance of iron(0), ‐(I), ‐(II) porphyrins (the latter with S = 0, 1, and 2 spin state possibilities), of iron(II) porphyrin π‐cation radicals, of iron(III) porphyrins (with S = 1/2, 3/2, and 5/2 spin state possibilities), of iron(III) porphyrin and corrole π‐cation radicals, of iron(IV) porphyrins (including five‐ and six‐coordinate ferryl (FeO) 2+ , iron(IV) phenyl, carbene and hydrazine complexes, and the bis‐methoxide complex) and a comparison of iron(IV) porphyrins to iron(III) porphyrin π‐cation radicals, of iron(IV) porphyrin π‐cation radicals, and of the possible existence of iron(V) porphyrins. Included in the Fe(II) part are sections on addition of ligands to four‐coordinate iron(II) porphyrins, including equilibrium binding constants, photodissociation of ligands from PFeL 2 complexes, binding of small molecules (O 2 , CO, NO, HNO) to 5‐coordinate iron(II) porphyrins and design of porphyrin ligands that will mimic the active sites of heme proteins such as myoglobin and hemoglobin, the cytochromes P450 and nitric oxide synthases, and the nitrophorins and guanylyl cyclases. Included in the iron(III) part are sections on both 5‐ and 6‐coordinate high‐spin complexes and their similarities and differences, bridged or through‐space magnetically coupled complexes of high‐spin iron(III) porphyrins with other metal complexes as possible models for cytochrome oxidase and the assimilatory sulfite reductases, coupled oxidation of hemes by hydrogen peroxide or its equivalent, and the relationship of this reactivity to the reactions of heme oxygenase, iron(III) porphyrins as reduction catalysts, and photochemistry of iron(III) porphyrins, possible electron configurations of low‐spin iron(III) porphyrins, the phenomenon and possible electronic consequences of ruffling of the porphinato core in iron(III) porphyrins, the preferred orientation of planar axial ligands bound to low‐spin iron(III) porphyrins, NO complexes of iron(III) porphyrins, reduction potentials, equilibrium constants and rates of axial‐ligand addition and exchange, kinetics of axial‐ligand rotation and porphyrin ring inversion, kinetics of reduction and autoreduction of iron(III) porphyrins, electron self‐exchange between low‐spin iron(III) and iron(II) porphyrins, synthetic ferriheme proteins, and synthesis of five‐coordinate low‐spin iron(III) porphyrins having σ‐alkyl or σ‐aryl groups as axial ligands. The iron(IV) and iron(IV) cation radical sections discuss the high‐valent states of cytochromes P450 and related enzymes.

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Total syntheses of 8-formyl-8-demethylprotoporphyrin IX, 8-(hydroxymethyl)-8-demethylprotoporphyrin IX, and 8-fluoromethyl analogs of protoporphyrin IX

Cited by 15 publications

References 1 publication

Improved Methods for the Synthesis of Porphyrin Alcohols and Aldehydes from Protoporphyrin IX Dimethyl Ester and Their Further Modification

Improved Methods for the Synthesis of Porphyrin Alcohols and Aldehydes from Protoporphyrin IX Dimethyl Ester and Their Further Modification

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Iron Porphyrin Chemistry

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