Novel macrolides via meso-tetraarylmetalloporphyrin assisted oxidations

Hill, David R.; Celebuski, Joseph E.; Pariza, R. J.; Chorghade, Mukund S.; Levenberg, Milton I.; Pagano, Thomas G.; Cleary, George; West, Paul R.; Whittern, David N.

doi:10.1016/0040-4039(95)02392-5

Cited by 8 publications

(2 citation statements)

References 9 publications

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“…Hydroxylation and epoxidation reactions catalyzed by tetraphenylporphinatoiron(III) chloride (FeTPPCl) with iodosylbenzene as the oxygen donor were reported in 1979 13. Numerous studies of metalloporhyrin/porphine‐catalyzed oxidation reactions have been performed more recently 14–17. Typical systems consist of porphyrin/porphine complexes with metal ions like manganese, iron and chromium, together with oxygen‐donating compounds such as iodosylbenzene, NaClO, amine N ‐oxides and periodate 4.…”

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confidence: 99%

Mimicry of phase I drug metabolism – novel methods for metabolite characterization and synthesis

Johansson

Weidolf

Jurva

2007

Rapid Comm Mass Spectrometry

122

125

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The extent to which electrochemical oxidation, electrochemically assisted Fenton chemistry and synthetic metalloporphines can be used to mimic cytochrome P450 catalyzed oxidations has been investigated for a large range of metabolic reactions. Most relevant metabolic oxidations can be mimicked by at least one of the three investigated systems. The EC oxidation system successfully mimics benzylic hydroxylation, hydroxylation of aromatic rings containing electron-donating groups, N-dealkylation, S-oxidation, dehydrogenation and less efficiently N-oxidation and O-dealkylation. The EC-Fenton system is able to mimic aliphatic hydroxylation, benzylic hydroxylation, aromatic hydroxylation, N-dealkylation, N-oxidation, O-dealkylation, S-oxidation and dehydrogenation. The porphine system mimics all types of reactions although the yields are low for some reactions. In conclusion, these three complementary systems can be used during the drug discovery and development of new drugs to elucidate the structure of metabolites that are difficult to characterize in biological matrices. Moreover, such techniques can replace the classical chemistry strategy, especially when synthesis is complicated or too time-consuming in order to access metabolites for further testing.

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confidence: 99%

Mimicry of phase I drug metabolism – novel methods for metabolite characterization and synthesis

Johansson

Weidolf

Jurva

2007

Rapid Comm Mass Spectrometry

122

125

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“…Drug interactions of clarithromycin are circumstantial to its oral absorption as well as with the concomitant use of other drugs (Hassan et al, 1999). A number of drug interactions of clarithromycin with several drugs have been reported (Cederbrant et al, 1994;Hill et al, 1996). There have been no clari-thromycin±metal interactions reported in the literature although the interactions of erythromycin with antacids containing di-and trivalent metal cations have been reported (Arayne & Sultana, 1993).…”

Section: Commentmentioning

confidence: 99%

Clarithromycin hydrochloride 3.5-hydrate

Parvez¹,

Arayne²,

Sabri³

et al. 2000

Acta Crystallogr C

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The absolute configuration was determined for the title compound, C38H70NO13+·Cl−·3.5H2O. The cation contains a 14‐membered macrocyclic lactone and two sugars, namely cladinose and desosamine. The six‐membered rings of the sugars adopt chair conformations. The structure is stabilized by strong hydrogen bonds, with O⃛O distances in the range 2.486 (9)–2.830 (5) Å; other distances are N⃛O = 2.860 (5), N⃛Cl = 3.134 (4) and O⃛Cl = 3.303 (4) Å.

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Protection for the Amino Group

Wuts

Greene²

2006

Greene's Protective Groups in Organic Synthesis

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Novel macrolides via meso-tetraarylmetalloporphyrin assisted oxidations

Cited by 8 publications

References 9 publications

Mimicry of phase I drug metabolism – novel methods for metabolite characterization and synthesis

Mimicry of phase I drug metabolism – novel methods for metabolite characterization and synthesis

Clarithromycin hydrochloride 3.5-hydrate

Protection for the Amino Group

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