Rothemund and Adler-Longo reactions revisited: synthesis of tetraphenylporphyrins under equilibrium conditions

Lindsey, Jonathan S.; Schreiman, Irwin C.; Hsu, Henry C.; Kearney, Patrick C.; Marguerettaz, Anne M.

doi:10.1021/jo00381a022

Cited by 1,407 publications

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“…Asian J. 2017,12,[6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] Introducing as teric block into the macrocyclic cavity is another strategy for retaining ap lanar configuration. This approach was previouslye xplored by Osuka and co-workers to maintain ap lanar macrocycle (30), but it fell short of ac ompletely conjugated system.…”

Section: Core-modified Octaphyrinsmentioning

confidence: 99%

“…Asian J. 2017,12,[6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] www.chemasianj.org distinctly different, because one of them is complexed by two carbon and nitrogen atoms (NNCC core), whereas the other binds through one carbon atom and three nitrogena toms (NNNC core). Of particulari nterest is the modified topology from Hückel antiaromaticity to Mobiusa romaticityf or the 36 p-conjugated pathway.…”

Section: Metal Complexesmentioning

confidence: 99%

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“To Twist or Not to Twist”: Figure‐of‐Eight and Planar Structures of Octaphyrins

Shivran

Gadekar

Anand

2016

Chemistry An Asian Journal

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Amongst the various porphyrinoids, octaphyrin has attracted significant attention owing to its diverse syntheses, conformations, and metal-ligationp roperties. Octaphyrin is ah igher homologue of porphyrin and is formed by linking together heterocycles such as pyrrole, furan, thiophene, ands elenophene through a-a or a-meso carbon bonds. The planar conformation is mainly achievedt hrough inversion of the heterocyclic units from the center of macrocycle;a voiding meso-bridges;introducing a para-quinodimethane bridge;e mployinganeo-confusion approach; protonation;a nd by generating dianionics pecies. In this Focus Review,r ecent synthetic advancements in the field of octaphyrins are summarized.T he twisted conformation of the octaphyrinb inds to two metal ions in at etracoordinate geometry.T he diphosphorus complex of octaphyrin represents the first example of as table expanded isophlorin.

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Section: Core-modified Octaphyrinsmentioning

confidence: 99%

Section: Metal Complexesmentioning

confidence: 99%

“To Twist or Not to Twist”: Figure‐of‐Eight and Planar Structures of Octaphyrins

Shivran

Gadekar

Anand

2016

Chemistry An Asian Journal

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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] .…”

Section: Porphyrin Chemistrymentioning

confidence: 99%

“…Condensation reactions, notably using Lindsey conditions [137] offer a simple entry into porphyrin systems and have been widely used, especially for meso substituted systems. This requires a combination of pyrrole (delivering the β-pyrrole units) and aldehyde (delivering the meso carbon unit) under acid-catalyzed conditions and obviously is a convenient method for the preparation of A 4 -type porphyrins with the same residue in all meso positions.…”

Section: Synthesis Via Condensation Reactionsmentioning

confidence: 99%

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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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Synthesis of a nickel tetracarboranylphenylporphyrin for boron neutron-capture therapy: Biodistribution and toxicity in tumor-bearing mice

et al. 1996

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BNCT using 'OB-enriched BPA as the neutron-capture agent is being investigated at Brookhaven National Laboratory for the post-operative treatment of human cerebral GBM (Coderre et al., 1996). This therapy is based on the selective accumulation of 1°B carriers such as BPA in tumors and the subsequent production of microscopically localized high linearenergy-transfer radiation from capture of thermalized neutrons by 1°B in the I0B(n,a)'Li reaction. For BNCT of malignant brain tumors, it is crucial that there be robust uptake of boron in tumor relative to normal tissues within the neutronirradiated target volume. Fairchild and Bond (1985) estimated that major advances in BNCT should be possible if ratios of 1°B concentrations in tumor (B1J to those in normal tissue were at least 5. In BNCT of a brain tumor, the dose to normal endothelium is most critical (Slatkin, 1991) and is proportional to two-thirds of the brain parenchymal boron concentration (Bbr) plus one-third of the blood boron concentration (Bbl) (Kitao, 1975). Thus, a major improvement in BNCT would require that B,,/(0.67Bhr + 0.33Bbl) > 5 or Bru/Bbl > 3.33(&,/ Bbl) + 1.67. Therefore, to protect non-edematous zones of the brain using an agent for closed-skull BNCT that respects the blood-brain barrier, Bb, should be close to 0 so that Btu/Bbl > 1.67. However, to protect edematous zones of the brain around a GBM tumor where Bbr/Bbl is nearly 1, Blu/Bbl > 5.We have synthesized a nickel tetraphenylporphyrin, NiTCP, that contains 4 carborane moieties, making the compound 22.3% boron (natural isotopic abundance) by weight. Its biodistribution and toxicity were studied in mice bearing an S.C. transplanted murine tumor. Two different total doses, 160 and 244 pg NiTCP/gbw, were given to tumor-bearing mice by a scries of i.p. injections. Boron concentrations were measured in various tissues removed at necropsy. Indicators of toxicity were sought by assessing changes in body weight and by hematological, chemical and enzymatic assays of the blood. MATERIAL AND METHODS ChemistryAll reagents and solvents were purchased from Aldrich (Milwaukee, WI). IH-NMR was run on a Bruker (Billerica, MA) AM-300 spectrometer, and optical absorption spectra were obtained with a Beckman (Fullerton, CA) DU-8 spectrophotometer. Mass spectra were recorded on a Kratos (Ramsey, NJ) MS 890 instrument equipped with a Sattlefield FAB gun using a nitrobenzyl alcohol matrix at the State University of New York, Stony Brook, by Drs. R.A. Rieger and C. Iden.NiTCP (Fig. l), a non-planar carboranyl tetraphenylporphyrin containing 8 methyl acetate groups, was synthesized by a procedure used for making analogous porphyrins without carborane groups (Miura et al., 1994). In a typical preparation of NiTCP, a method (Lindsey et al., 1987) was used to cyclize 3,4-diacetic acid pyrrole dimethylester (280 mg, 1.32 mmol) (Chiusoli et al., 1989) with 3-o-carboranylmethoxybenzaldehyde (364 mg, 1.32 mmol) (Miura etal., 1990)4 by stirring them in anhydrous dichloromethane (CH;?C12] (35 ml) for 20 min at room te...

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Rothemund and Adler-Longo reactions revisited: synthesis of tetraphenylporphyrins under equilibrium conditions

Cited by 1,407 publications

References 0 publications

“To Twist or Not to Twist”: Figure‐of‐Eight and Planar Structures of Octaphyrins

“To Twist or Not to Twist”: Figure‐of‐Eight and Planar Structures of Octaphyrins

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Synthesis of a nickel tetracarboranylphenylporphyrin for boron neutron-capture therapy: Biodistribution and toxicity in tumor-bearing mice

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