Biosynthesestudien an Pyridazomycin

Bockholt, Heike; Beale, John M.; Rohr, Jürgen

doi:10.1002/ange.19941061542

Cited by 10 publications

(4 citation statements)

References 21 publications

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“…Biosynthetic investigations of the azoxy‐containing antibiotic valanimycin ( 1 )2 and the antifungal antibiotic pyridazomycin ( 2 )3a (Figure 1) have shown that both of these natural products are derived from the condensation of amino acids. Pyridazomycin3b was the only natural product known to contain a pyridazine ring until the phthalazinone meroterpenoid azamerone ( 3 ) was isolated from the marine sediment‐derived bacterium Streptomyces sp.…”

Section: Methodsmentioning

confidence: 99%

Formation of the Pyridazine Natural Product Azamerone by Biosynthetic Rearrangement of an Aryl Diazoketone

et al. 2009

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Familienbande: Über die Biosynthese von Naturstoffen mit N‐N‐Bindungen ist wenig bekannt. Fütterungsexperimente mit 13C‐ und 15N‐markierten Verbindungen belegen nun, dass das Phthalazinon‐System von Azameron aus dem Diazo‐ und Chlor‐substituierten Meroterpenoid SF2415 A3 entsteht (siehe Schema). Ein Biosynthesemechanismus mit oxidativer Umlagerung des Aryldiazoketons und anschließender Rearomatisierung des N‐N‐Heterocyclus wird vorgeschlagen.

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Section: Methodsmentioning

confidence: 99%

Formation of the Pyridazine Natural Product Azamerone by Biosynthetic Rearrangement of an Aryl Diazoketone

et al. 2009

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“…griseofuscus , inhibited the growth of Mucor hiemalis [ 95 ]. Pyridazomycin ( 86 ) and its analog ( 87 ), as chloride salts showed antimicrobial activity [ 96 ]. Compounds ( 88 or 89 ), also known as 8-azaguanine, is produced from guanine by Spteptomyces albus [ 97 ].…”

Section: Azo Metabolites Derived From Actinomycetes and Fungal Speciementioning

confidence: 99%

Pharmacological and Predicted Activities of Natural Azo Compounds

Dembitsky

Gloriozova

Poroikov

2017

Nat. Prod. Bioprospect.

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This paper describes research on natural azo compounds isolated from fungi, plant, bacteria, and invertebrates. More than 120 biologically active diazene containing alkaloids demonstrate confirmed pharmacological activity, including antitumor, antimicrobial, and antibacterial effects. The structures, origin, and biological activities of azo compounds are reviewed. Utilizing the computer program PASS, some structure–activity relationship new activities are also predicted, pointing toward possible new applications of these compounds. This article emphasizes the role of natural azo compounds as an important source of drug prototypes and leads for drug discovery.

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“…166 The biosynthesis of pyridazomycin (175) has also been studied. 167 Pyridazocidin (176) was isolated almost a decade after the discovery of 175 from a strain of Streptomyces sp., collected from loam soil in Honduras. 168 Pyridazocidin exhibits significant phytotoxicity, which operates via reversible redox reaction linked to photosynthetic electron transport, a highly unique mode of action among natural products.…”

Section: Journal Of Natural Productsmentioning

confidence: 99%

“…Studies showed that 175 exhibits significant antifungal activity, along with minor inhibitory effects against B. subtilis . The biosynthesis of pyridazomycin ( 175 ) has also been studied . Pyridazocidin ( 176 ) was isolated almost a decade after the discovery of 175 from a strain of Streptomyces sp., collected from loam soil in Honduras .…”

Section: Natural Products Containing An N–n Bondmentioning

confidence: 99%