2,3‐Dimethylquinoxaline‐6‐carboxaldehyde 1,4‐dioxide

Edwards, M. L.; Bambury, R. E.

doi:10.1002/jhet.5570120504

Cited by 10 publications

(14 citation statements)

References 4 publications

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“…Culture supernatants from murine L. amazonensis-infected peritoneal macrophages treated with 17 M and 10.4 M concentrations of the compounds 8a and 14a, respectively, were collected after 48 h of incubation, and the nitrite content was determined by the Griess reaction procedure (26)(27)(28). Our results showed that both compounds (8a and 14a) were able to increase nitrite in the medium at 0.75 mM and 1.0 mM (Fig.…”

Section: Nitric Oxide Production (I)mentioning

confidence: 63%

“…Compounds 2, 7, and 12 were synthesized according to a previously described methodology (24)(25)(26)(27). The compounds 2-, 3-, or 4-aminobenzohydrazide and 2-, 3-, or 4-hydroxybenzohydrazide were purchased commercially.…”

Section: Methodsmentioning

confidence: 99%

“…The benzofuroxan (compound 7) and bis-aryl sulfonylfuroxan (compound 12) derivatives were prepared according to the procedures previously described (24)(25)(26)(27)33). The 3-or 4-hydroxybenzaldehyde was reacted with bis-aryl sulfonylfuroxan (compound 12), using 1,8-diazabicyclo [5.4.0]undec-7-ene as a base, to give compound 13a or 13b in yields varying between 46 and 57% (Fig.…”

Section: Chemistrymentioning

confidence: 99%

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Leishmanicidal Activities of Novel Synthetic Furoxan and Benzofuroxan Derivatives

Dutra

Almeida

Passalacqua

et al. 2014

Antimicrob Agents Chemother

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A novel series of furoxan (1,2,5-oxadiazole 2-oxide) (compounds 3, 4a and -b, 13a and -b, and 14a to -f) and benzofuroxan (benzo[c][1,2,5]oxadiazole 1-oxide) (compounds 7 and 8a to -c) derivatives were synthesized, characterized, and evaluated for in vitro activity against promastigote and intracellular amastigote forms of Leishmania amazonensis. The furoxan derivatives exhibited the ability to generate nitric oxide at different levels (7.8% to 27.4%). The benzofuroxan derivative 8a was able to increase nitrite production in medium supernatant from murine macrophages infected with L. amazonensis at 0.75 mM after 48 h. Furoxan and benzofuroxan derivatives showed remarkable leishmanicidal activity against both promastigote and intracellular amastigote forms. Compounds 8a, 14a and -b, and 14d exerted selective leishmanicidal activities superior to those of amphotericin B and pentamidine. In vitro studies at pH 5.4 reveal that compound 8a is stable until 8 h and that compound 14a behaves as a prodrug, releasing the active aldehyde 13a. These compounds have emerged as promising novel drug candidates for the treatment of leishmaniasis.

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Section: Nitric Oxide Production (I)mentioning

confidence: 63%

Section: Methodsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

See 1 more Smart Citation

Leishmanicidal Activities of Novel Synthetic Furoxan and Benzofuroxan Derivatives

Dutra

Almeida

Passalacqua

et al. 2014

Antimicrob Agents Chemother

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“…The expansion process was performed, as previously reported, 5 with sodium methoxide as the base, the mixture of the benzofuroxan derivative [27][28][29][30] and the corresponding phenol in MeOH:THF as the solvent at low temperature. Under these conditions, the products were obtained in moderate yield, except for the highly reactive 5(6)-nitrobenzofuroxan, which produced a complex mixture of products and a low yield of the desired heterocycle (Table 1).…”

Section: Resultsmentioning

confidence: 99%

Preparation of phenazine N5,N10-dioxides: Effects of benzofuroxan substituents in the outcome of their expansion reaction with phenolates

Cerecetto¹,

González²,

Lavaggi³

et al. 2005

J. Braz. Chem. Soc.

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“…The compounds 1, 2a, 2b, 5, 6, 10 and 13 were synthesized according to a previously described methodology [4][5][6][7][8][9]. of aminoguanidine hydrochloride (45mg; 0,4mmol) and 3mL of ethanol was stirred at room temperature for 2 to 3h and monitored by TLC (100% ethyl acetate).…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, biological evaluation and bioavailability prediction of novel furoxan derivatives as leishmanicidal compounds

Pavan

Almeida

Passalacqua

et al. 2017

Proceedings of the 21st International Electronic Conference on Synthetic Organic Chemistry

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Four novel furoxan derivatives were synthesized, characterized and evaluated for in vitro activity against promastigote form of Leishmania amazonensis and Leishmania infantum, and amastigote form of L. infantum. Compound 7 presented low cytotoxicity, being 30 times less toxic than pentamidine. All compounds were more active against L. infantum than L. amazonensis promastigote form, with IC50 reaching values around 8 µM.Regarding amastigote form of L. infantum, the compounds (3b and 7) have exhibited IC50 values around 60 µM. The in silico prediction of ADME properties has shown that all compounds demonstrated drugability according to 'Lipinski rules' and presented intestinal absorption ranging from 67 to 70%. In conclusion, the compounds presented here have demonstrated to be interesting prototypes against the visceral form of leishmaniasis.

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2,3‐Dimethylquinoxaline‐6‐carboxaldehyde 1,4‐dioxide

Abstract: A series of derivatives of 2,3‐dimethylquinoxaline‐6‐carboxaldehyde 1,4‐dioxide was prepared. Derivatives prepared included nitrones, semicarbazide, and aminooxazolidinone.

Cited by 10 publications

References 4 publications

Leishmanicidal Activities of Novel Synthetic Furoxan and Benzofuroxan Derivatives

Leishmanicidal Activities of Novel Synthetic Furoxan and Benzofuroxan Derivatives

Preparation of phenazine N5,N10-dioxides: Effects of benzofuroxan substituents in the outcome of their expansion reaction with phenolates

Synthesis, biological evaluation and bioavailability prediction of novel furoxan derivatives as leishmanicidal compounds

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