Fungal Metabolites as Pharmaceuticals

Beekman, Andrew M.; Barrow, Russell A.

doi:10.1071/ch13639

Cited by 58 publications

(28 citation statements)

References 110 publications

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“…Simvastatin is a lovastatin analog where the (S)-2-methylbutanoic acid moiety on the decalin core is replaced with a 2,2-dimethylbutanoic acid moiety. Simvastatin obtained US regulatory approval in 1991 and entered the market some time later [1][2][3][4][5][6][7]. From the structural prospective, these natural and semisynthetic statins are chiral 3,5-dihydroxyheptanoic acids that bind at C-7 to the substituted chiral unsaturated decalin core.…”

Section: Discovery Of Statinsmentioning

confidence: 99%

Recent Progress in the Synthesis of Super-Statins

Časar

2015

Topics in Heterocyclic Chemistry

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Super-statins now represent a mature class of marketed drugs that faces the patent cliff, as has already occurred for fluvastatin and atorvastatin and is approaching for rosuvastatin and pitavastatin. However, they continue to trigger huge scientific interest in terms of their efficient preparation. This is not surprising, as easier accessibility of super-statins will promote even bigger demand in the market and consequently the need for higher rates of the production and productivity. Therefore, the stimulus for the development of even more efficient synthetic approaches to the heterocyclic moieties of super-statins and their chiral lateralchain precursors is at a peak, as also for the assembly of the these two parts into super-statins. The present report summarizes recent developments in the field of the synthesis of super-statins published from 2010 to 2015. Emphasis is given to the analysis of novel approaches to the formation of the chiral statin lateral chain, with detailed discussion of the development of new routes to respective heterocyclic cores and the assembly of these key units into the final super-statin structure.

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Section: Discovery Of Statinsmentioning

confidence: 99%

Recent Progress in the Synthesis of Super-Statins

Časar

2015

Topics in Heterocyclic Chemistry

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“…Six more reduced azaphilones, falconensins I-N (9-14) ( Figure 2), along with the three new azaphilones monomethyldihydromitorubrin (15), mitorubrin (16) and monomethylmitorubrin (17) compounds, have been identified from the dichloromethane mycelial extract of E. falconensis and E. fruticulosa [33]. The chemical structures of the isolated compounds (9-16) were elucidated by interpretation of the measured spectra of 1 H and 13 C NMR and MS.…”

Section: Cyclopentenone Pigmentsmentioning

confidence: 99%

“…For example, of the seventy thousand reported compounds of polyketide origin, more than twenty developed substances are now available in medical markets. This hit rate of less than one percent is notably higher than that for screening of synthetic pharmaceutical agents, which is less than 0.001% [15]. Researchers have considered such fungal applications since the discovery of penicillin and the trend has only increased with time.…”

Section: Introductionmentioning

confidence: 95%

Nidulantes of Aspergillus (Formerly Emericella): A Treasure Trove of Chemical Diversity and Biological Activities

et al. 2020

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The genus Emericella (Ascomycota) includes more than thirty species with worldwide distribution across many ecosystems. It is considered a rich source of diverse metabolites. The published classes of natural compounds that are discussed here are organized according to the following biosynthetic pathways: polyketides (azaphilones, cyclopentenone pigments, dicyanides, furan derivatives, phenolic ethers, and xanthones and anthraquinones); shikimate derivatives (bicoumarins); mevalonate derivatives (meroterpenes, sesquiterpenes, sesterterpenes and steroids) and amino acids derivatives (alkaloids (indole-derivatives, isoindolones, and piperazine) and peptides (depsipeptides)). These metabolites produce the wide array of biological effects associated with Emericella, including antioxidant, antiproliferative, antimalarial, antiviral, antibacterial, antioxidant, antihypertensive, anti-inflammatory, antifungal and kinase inhibitors. Careful and extensive study of the diversity and distribution of metabolites produced by the genus Emericella (either marine or terrestrial) revealed that, no matter the source of the fungus, the composition of the culture medium effectively controls the metabolites produced. The topic of this review is the diversity of metabolites that have been identified from Emericella, along with the contextual information on either their biological or geographic sources. This review presents 236 natural compounds, which were reported from marine and terrestrial Emericella. Amongst the reported compounds, only 70.2% were biologically assayed for their effects, including antimicrobial or cytotoxicity. This implies the need for substantial investigation of alternative activities. This review includes a full discussion of compound structures and disease management, based on materials published from 1982 through December 2019.

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“…In the preparation of N-benzylated derivatives we first chose the classical potassium carbonate method, but it did not produce the desired product, so we changed to cesium carbonate, which enabled us to isolate our desired N-benzylated pyridazinone derivatives in medium N-methyl derivatives were also prepared by N-alkylation reactions [52]. By starting from the previously isolated pyridazinone derivatives (8b, 8c, 9, 10) and alkylating them with methyl iodide in tetrahydrofuran in the presence of sodium hydride, the N-methylated compounds (19)(20)(21)(22) were isolated in medium yields. In the preparation of N-benzylated derivatives we first chose the classical potassium carbonate method, but it did not produce the desired product, so we changed to cesium carbonate, which enabled us to isolate our desired N-benzylated pyridazinone derivatives in medium yields (23-27) (Scheme 8) ( Table 3).…”

Section: N-substituted Pyridazinone Derivativesmentioning

confidence: 99%

“…Nowadays there are a few drugs on the market or under development [17][18][19][20][21]. The natural product Griseofulvin has antifungal activity [22]. The steroid derivative spironolactone is used for the treatment of fluid retention, edema, and symptoms of heart failure ( Figure 1) [23].…”

Section: Introductionmentioning

confidence: 99%

New Spiro[cycloalkane-pyridazinone] Derivatives with Favorable Fsp3 Character

Für

Bölcskei

2020

Chemistry

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The large originator pharmaceutical companies need more and more new compounds for their molecule banks, because high throughput screening (HTS) is still a widely used method to find new hits in the course of the lead discovery. In the design and synthesis of a new compound library, important points are in focus nowadays: Lipinski’s rule of five (RO5); the high Fsp3 character; the use of bioisosteric heterocycles instead of aromatic rings. With said aim in mind, we have synthesized a small compound library of new spiro[cycloalkane-pyridazinones] with 36 members. The compounds with this new scaffold may be useful in various drug discovery projects.

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Fungal Metabolites as Pharmaceuticals

Cited by 58 publications

References 110 publications

Recent Progress in the Synthesis of Super-Statins

Recent Progress in the Synthesis of Super-Statins

Nidulantes of Aspergillus (Formerly Emericella): A Treasure Trove of Chemical Diversity and Biological Activities

New Spiro[cycloalkane-pyridazinone] Derivatives with Favorable Fsp3 Character

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