135733-34-5

Upstream product

• 135733-32-3 4-phenyl-3-furazanmethanol 
• 104-54-1 3-Phenylpropenol 
• 103-36-6 ethyl 3-phenyl-2-propenoate 
• 100-52-7 benzaldehyde 
• 169614-78-2 3-(bromomethyl)-2-oxido-4-phenyl-1,2,5-oxadiazole 
• 6898-86-8 3-methyl-4-phenylfuroxan 

Downstream Products

• 125520-62-9 4-phenyl-3-furoxancarbonitrile 
• 151733-56-1 4-phenyl-3-furoxanylcarbaldehyde oxime 
• 125520-55-0 3-carboxy-4-phenyl-1,2,5-oxadiazole 2-oxide 
• 143423-14-7 2,6-Dimethyl-4-(2-oxy-4-phenyl-furazan-3-yl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester 

Relevant academic research and scientific papers

An expedient synthesis of new 2-(furoxan-3-yl)thiazolidin-4-one derivatives

A series of new biologically interesting furoxan-3-thiazolidinones have been synthesized via one-pot three-component reaction of furoxan aldehydes, anilines and mercaptoacetic acid. The multi-component reaction involves condensation of furoxan aldehyde with aniline to give imine; the formed imine undergoes nucleophilic addition with mercaptoacetic acid, followed by cyclisation with loss of H2O to obtain the desired products. All the synthesized compounds were well characterized using spectral techniques and confirmed by an X-ray crystal structure for one compound.

Synthesis and preliminary evaluation of N-oxide derivatives for the prevention of atherothrombotic events

Thrombosis is the main outcome of many cardiovascular diseases. Current treatments to prevent thrombotic events involve the long-term use of antiplatelet drugs. However, this therapy has several limitations, thereby justifying the development of new drugs

Synthesis of furoxan derivatives: DABCO-mediated cascade sulfonylation/cyclization reaction of α-nitro-ketoximes

A convenient and efficient method for the synthesis of furoxan derivatives from α-nitro-ketoximes and sulfonyl chlorides is reported. A wide variety of furoxan derivatives were smoothly obtained in good yields via a DABCO-mediated cascade sulfonylation/cy

Design, synthesis and biological evaluation of hybrid bioisoster derivatives of N-acylhydrazone and furoxan groups with potential and selective anti-Trypanosoma cruzi activity

Hybrid bioisoster derivatives from N-acylhydrazones and furoxan groups were designed with the objective of obtaining at least a dual mechanism of action: cruzain inhibition and nitric oxide (NO) releasing activity. Fifteen designed compounds were synthesized varying the substitution in N-acylhydrazone and in furoxan group as well. They had its anti-Trypanosoma cruzi activity in amastigotes forms, NO releasing potential and inhibitory cruzain activity evaluated. The two most active compounds (6, 14) both in the parasite amastigotes and in the enzyme contain the nitro group in para position of the aromatic ring. The permeability screening in Caco-2 cell and cytotoxicity assay in human cells were performed for those most active compounds and both showed to be less cytotoxic than the reference drug, benznidazole. Compound 6 was the most promising, since besides activity it showed good permeability and selectivity index, higher than the reference drug. Thereby the compound 6 was considered as a possible candidate for additional studies.

Leishmanicidal activities of novel synthetic furoxan and benzofuroxan derivatives

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. Copyright

Structure mechanism insights and the role of nitric oxide donation guide the development of oxadiazole-2-oxides as therapeutic agents against schistosomiasis

Schistosomiasis is a chronic parasitic disease affecting hundreds of millions of individuals worldwide. Current treatment depends on a single agent, praziquantel, raising concerns of emergence of resistant parasites. Here, we continue our explorations of an oxadiazole-2-oxide class of compounds we recently identified as inhibitors of thioredoxin glutathione reductase (TGR), a selenocysteine-containing flavoenzyme required by the parasite to maintain proper cellular redox balance. Through systematic evaluation of the core molecular structure of this chemotype, we define the essential pharmacophore, establish a link between the nitric oxide donation and TGR inhibition, determine the selectivity for this chemotype versus related reductase enzymes, and present evidence that these agents can be modified to possess appropriate drug metabolism and pharmacokinetic properties. The mechanistic link between exogenous NO donation and parasite injury is expanded and better defined. The results of these studies verify the utility of oxadiazole-2-oxides as novel inhibitors of TGR and as efficacious antischistosomal agents. 2009 American Chemical Society.

Synthesis and herbicidal activity of N-oxide derivatives

As part of an ongoing program on the chemistry and biological activity of N-oxide-containing molecules, a number of novel 1,2,5-oxadiazole N-oxide, benzo[1,2-c]1,2,5-oxadiazole N-oxide, and quinoxaline N,N'-dioxide derivatives were synthesized and evaluated for their herbicidal activity. Many of these compounds exhibited moderate to good herbicidal pre-emergence activity against Triticum aestivum. Dose - response studies were done on the more representative compounds (12, 20, and 26). The most active compound, butylcarbamoylbenzo[1,2-c]1,2,5-oxadiazole N-oxide, 26, displayed herbicidal activity at concentrations as low as 24 g/ha.

Pharmacochemistry of the furoxan ring: Recent developments

In the present work recent results obtained in the pharmacochemistry of the furoxan system are reported. In particular, after a brief description of the salient points of the furoxan chemistry, the synthesis and the properties of a series of Nifedipine and Prazosin analogues, containing this heterocyclic system, are described. Since we observed that a few furoxan derivatives are able to elicit both a dose-dependent rise in platelet cGMP levels and to promote a dose-dependent inhibition of AA-induced [Ca++] rise, and that many substituted furoxans show potent vasodilating and antiaggregatory activity, the possibility of using the furoxan system as a lead in the design of new vasodilators is also discussed.

Unsymmetrically Substituted Furoxans, XIII. Phenylfuroxancarbaldehydes and Related Compounds

The synthesis and structure of two isomeric phenylfuroxancarbaldehydes 7a and 7b, of the phenylfurazancarbaldehyde 6 and of the corresponding alcohols 3a, 3b and 5 are reported.Thermal equilibration of the furoxan derivatives and their oxidation to the co