Synthesis of galactopyranosyl substituted porphyrins

Hombrecher, Hermann K.; Ohm, Stefan; Koll, Daniela

doi:10.1016/0040-4020(96)00174-3

Cited by 36 publications

(15 citation statements)

References 14 publications

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“…Compounds 188 and 189, however, were produced in 7 % yield due to increased formation of the carboxylic acid [197] . Alternative routes were explored using condensation reactions which produced compound 189 in a yield of 20 % by using the 4-[di-O-isopropylidene-α-Dgalactopyranosyl]benzaldehyde.…”

Section: Scheme 9 Synthesis Of Bis(d-glucosyl)isohematoporphyrin Andmentioning

confidence: 97%

“…Alternative routes were explored using condensation reactions which produced compound 189 in a yield of 20 % by using the 4-[di-O-isopropylidene-α-Dgalactopyranosyl]benzaldehyde. They also used Lindsey's procedure, treating the aldehyde in a mixed condensation with p-tolyl aldehyde and pyrrole which proved unsuccessful in increasing the yields [197] . Hombrecher later extended his studies with the porphyrin framework shown for 402.…”

Section: Scheme 9 Synthesis Of Bis(d-glucosyl)isohematoporphyrin Andmentioning

confidence: 99%

“…Similarly, four series of meso-tetraaryl-glycoporphyrins were synthesized with protected and de-protected hydroxyl groups to evaluate their photo-inactivation of HSV-1 and HSV-2 herpes simplex virus [30] . Three different classes of porphyrins (83,190,197) were prepared by Rothemund or cross-Rothemund reactions and porphyrin 190 was reacted with hexafluorobenzene affording 198 in addition to the series. The first two series of glycoporphyrins were synthesized via the coupling of tetraphenylporphyrins with a hydroxyl group (190) [30] .…”

Section: Glycosidation Reactions O-linked Systemsmentioning

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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Section: Scheme 9 Synthesis Of Bis(d-glucosyl)isohematoporphyrin Andmentioning

confidence: 97%

Section: Scheme 9 Synthesis Of Bis(d-glucosyl)isohematoporphyrin Andmentioning

confidence: 99%

Section: Glycosidation Reactions O-linked Systemsmentioning

confidence: 99%

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Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Moylan¹,

Scanlan²,

Senge

2015

CMC

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“…for C 79 H 90 N 10 O 6 Zn = 1338.6336 found = 1338.6379; UV-vis (CH 2 Cl 2 ): λ max (log ε) = 426 (5.69), 558 (4.14), 598 nm (3.63). 5,10,15,porphyrin, m-THPP (1 eq. ), was placed in a 50 mL round-bottom flask with a magnetic stirrer flashed with Ar.…”

Section: 46mentioning

confidence: 99%

“…The functionalization of pre-prepared porphyrins has emerged as the most efficient approach to the synthesis of glycoporphyrins. Several examples of such an approach exist including post-modification of carboxyl functionalities 15 and functionalization of hydroxyl porphyrins, 16 to name a few. While limited examples of glycosylated lipid porphyrin conjugates have been published, some include a subset of hydrophilic AB 3 porphyrins synthesized with aryl and short carbon chains as hydrophobic groups 17 and a similar strategy was invoked by Maillard and co-workers to prepare diethylene glycol linked glycoporphyrins.…”

Section: Introductionmentioning

confidence: 99%

Lead structures for applications in photodynamic therapy 7. Efficient synthesis of amphiphilic glycosylated lipid porphyrin derivatives: refining linker conjugation for potential PDT applications

et al. 2015

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Synthesis of meso-nitrophenylporphyrins covalently linked to a polyphenylene chain bearing methoxy groups

Durantini

2000

J. Porphyrins Phthalocyanines

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A convenient procedure for the synthesis of polyphenylene porphyrin dyads is described. The dyads consist of a meso-nitrophenylporphyrin covalently linked to a polyphenylene chain by an amide bond. The final phenyl group in the chain bears electron donor methoxy groups. The π-conjugated chain was obtained in excellent yield via a Wittig–Horner reaction, which produces a new double bond (E isomer) incorporating either — COOCH 3 or E isomer) incorporating either — CON ( OCH 3)( CH 3) functional groups. Expansion of the conjugated chain involves the reduction of these groups to aldehydes followed by a second Wittig–Horner reaction. 5-(4-Aminophenyl)-10,15,20-tris(4-nitrophenyl)porphyrin was synthesized from meso-(4-nitrophenyl)dipyrromethane. The E isomer) incorporating either — NO 2 groups in para positions of the peripheral phenyl rings give extra electron-withdrawing character to the porphyrin macrocycles. Coupling of the polyphenylene acids with aminoporphyrin results in the desired dyads. These dyads have moieties with different electron donor–acceptor properties. This present strategy may be easily used for preparation of other similar dyad derivatives. These compounds can be suitable for photodynamic therapy.

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Synthesis of galactopyranosyl substituted porphyrins

Cited by 36 publications

References 14 publications

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Lead structures for applications in photodynamic therapy 7. Efficient synthesis of amphiphilic glycosylated lipid porphyrin derivatives: refining linker conjugation for potential PDT applications

Synthesis of meso-nitrophenylporphyrins covalently linked to a polyphenylene chain bearing methoxy groups

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