Synthesis and Antimicrobial Activity of 4-Hydroxy-2-[5-Nitrofuran(Thien)-2-Yl]-6h-1,3-Oxazin-6-Ones

Chernov, N. M.; Koshevenko, A. S.; Yakovlev, I. P.; Ананьева, Е. П.; Ksenofontova, G. V.; Shchegolev, A. E.

doi:10.1007/s11094-017-1668-2

Cited by 7 publications

(8 citation statements)

References 7 publications

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“…Examples of antimicrobial agents with thiophene-substituted 1,2,4-triazole, 1,3,4-thiadiazole or tetrazole structure Two triazol-5-ylalkanoic acids 60 (R = CH 3 , n-C 4 H 9 ) (Figure 7) having a nitrothiophene substituent at position 3 of the 1,2,4-triazole ring were obtained from 4-hydroxy-1,3-oxazin-6-ones and phenylhydrazine through a ring opening-ring closing sequence. [67] These compounds were two times more potent against S. aureus and C.…”

Section: Thiophene-substituted Azolesmentioning

confidence: 97%

“…coli and C. albicans was poor. [67] Cyclocondensation of 4-amino-5-[4-(methylsulfonyl)benzyl]-2,4dihydro-3H-1,2,4-triazole-3-thione with thiophene-containing bromoacetyl derivatives afforded two triazole-fused thiadiazines 77…”

Section: Thiophene-substituted Diazines and Heterocycle-fused Ring Sy...mentioning

confidence: 99%

“…Two triazol‐5‐ylalkanoic acids 60 (R = CH 3 , n ‐C 4 H 9 ) (Figure 7) having a nitrothiophene substituent at position 3 of the 1,2,4‐triazole ring were obtained from 4‐hydroxy‐1,3‐oxazin‐6‐ones and phenylhydrazine through a ring opening–ring closing sequence. [ 67 ] These compounds were two times more potent against S. aureus and C. albicans than reference drug furazidine but had no significant effect on E. coli .…”

Section: Antimicrobial Compounds Based On Thiophene‐substituted Heter...mentioning

confidence: 99%

“…The thiophenes were active against S. aureus , but their activity against E. coli and C. albicans was poor. [ 67 ]…”

Section: Antimicrobial Compounds Based On Thiophene‐substituted Heter...mentioning

confidence: 99%

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Thiophene‐containing compounds with antimicrobial activity

Roman¹

2022

Archiv der Pharmazie

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Thiophene, as a member of the group of five-membered heterocycles containing one heteroatom, is one of the simplest heterocyclic systems. Many synthetic strategies allow the accurate positioning of various functionalities onto the thiophene ring. This review provides a comprehensive, systematic and detailed account of the developments in the field of antimicrobial compounds featuring at least one thiophene ring in their structure, over the last decade.

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Section: Thiophene-substituted Azolesmentioning

confidence: 97%

Section: Thiophene-substituted Diazines and Heterocycle-fused Ring Sy...mentioning

confidence: 99%

Section: Antimicrobial Compounds Based On Thiophene‐substituted Heter...mentioning

confidence: 99%

“…The thiophenes were active against S. aureus , but their activity against E. coli and C. albicans was poor. [ 67 ]…”

Section: Antimicrobial Compounds Based On Thiophene‐substituted Heter...mentioning

confidence: 99%

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Thiophene‐containing compounds with antimicrobial activity

Roman¹

2022

Archiv der Pharmazie

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“…Among the new chemotypes, which also exhibited the highest levels of isoform selectivity, were the coumarins 27 , the sulfocoumarins [23][24][25][26] and their congeners, homosulfocoumarins (3H-1,2-benzoxathiepine 2,2dioxides) 31 , and saccharin derivatives [32][33][34] . Considering the fact that this last chemotype was somewhat chemically similar to hydantoin (imidazolidine-2,4-dione) that may serve as zinc binding group (ZBG) we investigated clinically used antibiotic Furagin (Figure 1), also known under names Furazidine, Furamags or Furazidin 35 , that contains hydantoin moiety, as well as newly prepared its derivatives.…”

Section: Introductionmentioning

confidence: 99%

The antibiotic furagin and its derivatives are isoform-selective human carbonic anhydrase inhibitors

Pustenko

Nocentini

Gratteri

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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The clinically used antibiotic Furagin and its derivatives possess inhibitory activity on human (h) carbonic anhydrases (CA, EC 4.2.1.1), some of which are highly expressed in various tissues and malignancies (hCA IX/XII). Furagin exhibited good hCA IX and XII inhibition with K I s of 260 and 57 nM, respectively. It does not inhibit off-target CA I and poorly inhibited CA II (K I ¼ 9.6 lM). Some synthesised Furagin derivatives with aminohydantoin moieties as zinc binding group exhibited weak inhibition of CA I/II, and good inhibition of CA IX/XII with K I s ranging from 350 to 7400 and 150 to 5600 nM, respectively. Docking and molecular dynamics simulations suggest that selectivity for the cancer-associated CA IX/XII over CA II is due to strong H-bond interactions in CA IX/XII, involving the tail orientated towards hydrophobic area of the active site. These results suggest a possible drug repurposing of Furagin as anti-cancer agent.

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