Synthetic Approaches to the Neuraminidase Inhibitors Zanamivir (Relenza) and Oseltamivir Phosphate (Tamiflu) for the Treatment of Influenza

Magano, Javier

doi:10.1021/cr800449m

Cited by 207 publications

(126 citation statements)

References 320 publications

Supporting

Mentioning

120

Contrasting

Unclassified

Order By: Relevance

“…Furthermore, SA has a key role in the synthesis of important pharmacological compounds such as anticancer agents, antibacterial agents, and hormones; 3,4,20,21 however, the most important application of SA is its use as the substrate for the chemical synthesis of OSP. 4,11,20,22 Because the chemical structure of ASA is similar to that of SA, it has similar applications, including its potential use as a substrate for OSP synthesis, which might significantly improve the speed and cost of the production of OSP or other oseltamivir carboxylates ( Figure 3). 14,19 However, no other applications …”

Section: Sa Derivatives In the Pharmaceutical Industrymentioning

confidence: 99%

“…SA is extracted at the start of a ten-stage manufacturing process that takes 1 year, and 90% of the production is already used by Roche for the preparation of Tamiflu ® . 20 Approximately 30 kg of star anise is required to generate 1 kg of SA, 22 and the supply of this source is susceptible to weather changes. The demand for Tamiflu ® has increased recently, and Roche cannot meet this demand due to shortage of plant-derived SA.…”

Section: Sa Production Extraction From Plant Sourcesmentioning

confidence: 99%

See 1 more Smart Citation

Current perspectives on applications of shikimic and aminoshikimic acids in pharmaceutical chemistry

Quiroz¹,

Carmona²,

Bolívar³

et al. 2014

RRMC

View full text Add to dashboard Cite

Aromatic metabolism comprises the shikimic acid (SA) and the aminoshikimic acid (ASA) pathways. The SA pathway is the common route for the biosynthesis of aromatic amino acids and other metabolites in bacteria, higher plants, fungi, and Apicomplexa parasites, but this pathway is absent in mammals. A variant of the SA pathway known as the ASA pathway branches off from the normal pathway in some bacteria, and its final product, 3-amino-5-hydroxybenzoic acid, is the precursor for many aminoglycoside antibiotics such as kanamycin, neomycin, butirosin, and spectinomycin. The SA pathway includes the key intermediate SA, which is the precursor for the chemical synthesis of the drug oseltamivir phosphate, known commercially as Tamiflu ® , an efficient inhibitor of the neuraminidase enzyme of the seasonal influenza viruses types A and B, avian influenza virus H5N1, and human influenza virus H1N1. Meanwhile, the intermediate of the ASA pathway, ASA, is an attractive candidate for use as the core scaffold for the synthesis of combinatorial libraries and is a potential alternative to SA as a precursor for oseltamivir phosphate synthesis. In this review, we discuss the relevance of the key intermediates SA and ASA as scaffold molecules for the synthesis of diverse chemicals. We highlight the current and potential pharmaceutical applications of these molecules and discuss the main strategies for the production of these aromatic compounds from natural sources and the application of metabolic engineering strategies in diverse bacterial strains for production through biotechnological processes.

show abstract

Section: Sa Derivatives In the Pharmaceutical Industrymentioning

confidence: 99%

Section: Sa Production Extraction From Plant Sourcesmentioning

confidence: 99%

Current perspectives on applications of shikimic and aminoshikimic acids in pharmaceutical chemistry

Quiroz¹,

Carmona²,

Bolívar³

et al. 2014

RRMC

View full text Add to dashboard Cite

show abstract

“…This adduct then reacts in the next step with 15 to give, after a Wittig reaction and a thio-Michael reaction, the intermediate 16, from which enantiopure oseltamivir 17 is achieved in 57% overall yield. This reaction sequence proceeds by three distinguished one-pot operations and only one column chromatography purification and it is the most efficient synthesis of oseltamivir reported so far [30]. An additional noteworthy application of enamine catalysis is the first catalytic asymmetric α-alkylation of α-branched aldehydes developed by List et al starting from simple racemic α-branched aldehydes and achieving the corresponding enantiomerically enriched products, in a dynamic kinetic asymmetric transformation [31].…”

Section: Covalent Organocatalysismentioning

confidence: 99%

Organocatalysts for enantioselective synthesis of fine chemicals: definitions, trends and developments

Federsel¹

2014

ScienceOpen Research

View full text Add to dashboard Cite

Organocatalysis, that is the use of small organic molecules to catalyse organic transformations, has been included among the most successful concepts in asymmetric catalysis and it has been used for the enantioselective construction of C-C, C-N, C-O, C-S, C-P, and C-halide bonds. Since the seminal works in early 2000, the scientific community has been paying an ever-growing attention to the use of organocatalysts for the synthesis, with high yields and remarkable stereoselectivities, of optically active fine chemicals of interest for the pharmaceutical industry. A brief overview is here presented about the two main classes of substrate activation by the catalyst: covalent organocatalysis and non-covalent organocatalysis, with a more stringent focus on some recent outcomes in the field of the latter and of hydrogen-bond-based catalysis. Finally, some successful examples of heterogenisation of organocatalysts are also discussed, in the view of a potential industrial exploitation.

show abstract

“…The Diels-Alder reaction is one of the most important carbon-carbon bond forming reactions and has been involved in key steps in the making of important intermediates that leads to the synthesis of anti-cancer and anti-viral drugs such as Taxol and Tamiflu, respectively [1,2]. Since then, Diels-Alder reactions have formed an important part of the synthetic repertoire of making intermolecular and intramolecular cyclic compounds.…”

Section: Introductionmentioning

confidence: 99%

The use of optically active O-alkyl ester hydrochlorides of L-phenylalanine and L-tyrosine as chiral micellar media for the catalysis of diels-alder reactions

Caumul¹,

Koonja²,

Namooya³

et al. 2018

Bull. Chem. Soc. Eth.

View full text Add to dashboard Cite

ABSTRACT. The effect of a range of O-alkyl ester hydrochloride surfactants derived from L-phenylalanine and L-tyrosine as catalysts on the Diels-Alder reaction between cyclopentadiene and methyl acrylate was studied. Both chain lengths (C8-C14) and head groups of the surfactants were found to influence the yield and selectivity of the Diels-Alder product. The C10 derivatives of both phenylalanine and tyrosine surfactants gave the highest yields and selectivity. Phenylalanine ester hydrochlorides showed better catalytic activity than the tyrosine derivatives. Adduct optimum yield was obtained at a concentration relating to their critical micelle concentration (CMC) values. The Diels-Alder reaction was also found to be favored in acidic condition (pH 3) as well as in the presence of lithium chloride (LiCl) as salting out agent.

show abstract

Synthetic Approaches to the Neuraminidase Inhibitors Zanamivir (Relenza) and Oseltamivir Phosphate (Tamiflu) for the Treatment of Influenza

Cited by 207 publications

References 320 publications

Current perspectives on applications of shikimic and aminoshikimic acids in pharmaceutical chemistry

Current perspectives on applications of shikimic and aminoshikimic acids in pharmaceutical chemistry

Organocatalysts for enantioselective synthesis of fine chemicals: definitions, trends and developments

The use of optically active O-alkyl ester hydrochlorides of L-phenylalanine and L-tyrosine as chiral micellar media for the catalysis of diels-alder reactions

Contact Info

Product

Resources

About