Formycins and their Analogues: Purine Nucleoside Phosphorylase Inhibitors and their Potential Application in Immunosuppression and Cancer

Bzowska, Agnieszka

doi:10.1002/9783527623112.ch19

Cited by 6 publications

(5 citation statements)

References 186 publications

(138 reference statements)

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“…Together, formycins A and B possess a vast degree of biological activity. Formycin A in particular exhibits antitumor effects, cytotoxic potential in tumor islet cells, and insulinotropic action in rats . Both 142 and 143 possess antiviral and antibacterial activity .…”

Section: Natural Products Containing An N–n Bondmentioning

confidence: 99%

“…Formycin A in particular exhibits antitumor effects, cytotoxic potential in tumor islet cells, and insulinotropic action in rats . Both 142 and 143 possess antiviral and antibacterial activity . Formycin B alone exhibits antiparasitic effects, owing to its inhibition of purine nucleoside phosphorylases .…”

Section: Natural Products Containing An N–n Bondmentioning

confidence: 99%

“…Both 142 and 143 possess antiviral and antibacterial activity . Formycin B alone exhibits antiparasitic effects, owing to its inhibition of purine nucleoside phosphorylases . The C -nucleoside pyrazomycin ( 145 ) (also known as Pyrazofurin) was first isolated in 1969 from Streptomyces candidus fermentations, followed by its α-anomer pyrazomycin B ( 146 ) in 1973, isolated from the identical strain of bacteria .…”

Section: Natural Products Containing An N–n Bondmentioning

confidence: 99%

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Natural Products Containing a Nitrogen–Nitrogen Bond

2013

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Section: Natural Products Containing An N–n Bondmentioning

confidence: 99%

Section: Natural Products Containing An N–n Bondmentioning

confidence: 99%

Section: Natural Products Containing An N–n Bondmentioning

confidence: 99%

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Natural Products Containing a Nitrogen–Nitrogen Bond

2013

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“…Some interesting results were obtained on a compound with the 4-aminopyrazolo[1,5- a ][1,3,5]triazin-2-one skeleton (a triazine-based 5-aza-9-deaza-isostere of isoguanine) [21]. This compound was an efficient inhibitor of purine nucleoside phosphorylase, which is a valid target for anticancer and antiparasitic therapy [22,23,24,25]. This brought our attention to a similar purine-like heterocyclic system, i.e., 5-aza-isoguanine.…”

Section: Introductionmentioning

confidence: 99%

Fused Heterocyclic Systems with an s-Triazine Ring. 34. Development of a Practical Approach for the Synthesis of 5-Aza-isoguanines

et al. 2019

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Purine isosteres present excellent opportunities in drug design and development. Using isosteres of natural purines as scaffolds for the construction of new therapeutic agents has been a valid strategy of medicinal chemistry. Inspired by the similarity to isoguanine, we attempted to develop a practical method for the preparation of 5-aza-isoguanines. Several synthetic approaches were explored to establish a robust general protocol for the preparation of these compounds. The significant difference in the reactivity of the C-5 and C-7 electrophilic centers of 1,2,4-triazolo[1,5-a][1,3,5]triazines (5-azapurines) towards nucleophiles was demonstrated. The most practical and general method for the preparation of 5-aza-isoguanines involved a regioselective reaction of ethoxycarbonyl isothiocyanate with a 5-aminotriazole. The intramolecular ring closure of the resulted product followed by the S-methylation afforded 7-methylthio-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-one, which could be effectively aminated with various amines. The resulted 5-aza-isoguanines resemble a known purine nucleoside phosphorylase inhibitor and could be interesting for further investigations as potential anticancer agents.

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“…Many natural and synthetic C -nucleosides, also containing modified heterocyclic bases, biologically active, have been described in literature. Natural antibiotics formycins [ 11 ] (in particular FA , FB , and oxoformycin B OFB ) have been known since the early 1960s to possess antibiotic and cytotoxic properties; their antiparasitic activity (antimalarial, antischisostoma, etc. ) was unraveled later.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Properties of 5-(1H-1,2,3-Triazol-4-yl)isoxazolidines: A New Class of C-Nucleosides

et al. 2015

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A novel series of C-nucleosides, featuring the presence of a 1,2,3-triazole ring linked to an isoxazolidine system, has been designed as mimetics of the pyrimidine nucleobases. An antiproliferative effect was observed for compounds 17a and 17b: the growth inhibitory effect reaches the 50% in HepG2 and HT-29 cells and increases up to 56% in the SH-SY5Y cell line after 72 h of incubation at a 100 µM concentration.

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Formycins and their Analogues: Purine Nucleoside Phosphorylase Inhibitors and their Potential Application in Immunosuppression and Cancer

Cited by 6 publications

References 186 publications

Natural Products Containing a Nitrogen–Nitrogen Bond

Natural Products Containing a Nitrogen–Nitrogen Bond

Fused Heterocyclic Systems with an s-Triazine Ring. 34. Development of a Practical Approach for the Synthesis of 5-Aza-isoguanines

Synthesis and Biological Properties of 5-(1H-1,2,3-Triazol-4-yl)isoxazolidines: A New Class of C-Nucleosides

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