943-37-3

Usage

Chemical Properties

Yellow to orange flakes or crystalline powder

InChI:InChI=1/C7H7NO5/c1-2-12-7(9)5-3-4-6(13-5)8(10)11/h3-4H,2H2,1H3

Upstream product

• 64-17-5 ethanol 
• 25084-14-4 5-nitrofuran-2-carboxylic chloride 
• 645-12-5 5-nitro-2-furoic acid 
• 5904-69-8 2-acetoxy-5-nitro-2,5-dihydro-furan-2-carboxylic acid ethyl ester 
• 614-99-3 Ethyl 2-furoate 

Downstream Products

• 720-69-4 6-(5-nitro-furan-2-yl)-[1,3,5]triazine-2,4-diamine 
• 5469-78-3 5-nitrofuran-2-carbohydrazide 
• 110-17-8 (2E)-but-2-enedioic acid 
• 123771-00-6 Ethyl 5-(2'-methoxycarbonylphenoxy)furan-2-carboxylate 
• 1187383-36-3 ethyl 5-(2'-methoxycarbonyl-3'-methoxyphenoxy)furan-2-carboxylate 
• 123771-02-8 5-(2'-hydroxycarbonylphenoxy)furan-2-carboxylic acid 
• 15856-35-6 ethyl 2-amino-furan-5-carboxylate 

Relevant academic research and scientific papers

Graphene Oxide: An Efficient Acid Catalyst for the Construction of Esters from Acids and Alcohols

Graphene oxide was found to be an efficient and reusable acid catalyst for the esterification reaction. A wide range of aliphatic and aromatic acids and alcohols were compatible with the standard conditions and afforded the corresponding products in good yields. The heterogeneous catalyst can be easily recovered and recycled in dichloro-ethane solvent with good catalytic activity.

Synthesis, in vitro and in Silico studies of some novel 5-nitrofuran-2-yl hydrazones as antimicrobial and antitubercular agents

In this study, we synthesized two series of novel 5-nitrofuran-2-carbohydrazides 21a-h and 22a-e in addition to a third series of thiophene-2-carbohydrazides 23a-g to develop potent antimicrobial and/or antitubercular agents. The newly synthesized compounds were evaluated in vitro for their antimicrobial and antimycobacterial activities. Most of the 5-nitrofuran-2-carbohydrazides 21a-h and 22a-e displayed variable activity against Aspergillus fumigates, Staphylococcus aureus, Streptococcus pneumonia, Bacillis subtilis, Salmonella typhimurium, Klebsiella pneumonia, Escherichia coli and Mycobacterium tuberculosis. The sulfonamide derivative 21f exhibited superior potency and broad-spectrum antimicrobial activity with minimum inhibitory concentration (MIC)=0.06-0.98 μg/mL and antimycobacterial activity with MIC=3.9 μg/mL. The 5-nitrofuran-2-carbohydrazides 21a, b, g, h and 22a-c exhibited significant antibacterial activity with MIC values in the range of 0.12-7.81 μg/mL. The significances of the 5-nitrofuran moiety and sulfonamide function were explored via the structure-activity relationship (SAR) study. In addition, docking studies revealed that the p-amino benzoic acid (PABA) and binding pockets of the dihydropteroate synthase (DHPS) were successfully occupied by compound 21f. Furthermore, two quantitative structure-activity relationship (QSAR) models were built to explore the structural requirements which controlled the activity.

Rate-product correlations for the solvolysis of 5-nitro-2-furoyl chloride

The solvolysis rate constants of 5-nitro-2-furoyl chloride (5-NO 2(C4H2O)-2-COCl, 1) in 27 different solvents are well correlated with the extended Grunwald-Winstein equation, using the NT solvent nucleophilicity scale and YCl solvent ionizing scale, with sensitivity values of 1.20 ± 0.05 and 0.37 ± 0.02 for l and m, respectively. The activation enthalpies (ΔH≠) were 5.63 to 13.0 kcal·mol-1 and the activation entropies (ΔS ≠) were .25.9 to .43.4 cal·mol-1·K -1, which is consistent with the proposed bimolecular reaction mechanism. The solvent kinetic isotope effect (SKIE, kMeOH/kMeOD) of 2.65 was also in accord with the SN2 mechanism and was possibly assisted using a general-base catalysis. The product selectivity (S) for solvolysis of 1 in alcohol/water mixtures was 1.2 to 11, which is also consistent with the proposed bimolecular reaction mechanism.

5-Nitro-2-furoic acid hydrazones: Design, synthesis and in vitro antimycobacterial evaluation against log and starved phase cultures

Various 5-nitro-2-furoic acid hydrazones were synthesized and evaluated for in vitro activities against log and starved phase culture of two mycobacterial species and Mycobacterium tuberculosis (MTB) isocitrate lyase (ICL) enzyme inhibition studies. Among twenty one compounds, 5-nitro-N′-[(5-nitro-2- furyl)methylidene]-2-furohydrazide (4o) was found to be the most active compound in vitro with MICs of 2.65 and 10.64 μM against log- and starved-phase culture of MTB. Compound 4o also showed good enzyme inhibition of MTB ICL at 10 μM. The docking studies also confirmed the binding potential of the compounds at the ICL active site.

QUINOLONE ANTIBACTERIAL AGENTS

Compounds of formula (I) and methods for their preparation are disclosed. Further disclosed are methods of making biologically active compounds of formula (I) as well as pharmaceutically acceptable compositions comprising compounds of formula (I). Compounds of formula (I) as disclosed herein can be used in a variety of applications including use as antibacterial agents.

QUINOLONE ANTIBACTERIAL AGENTS

Compounds of formula I and methods for their preparation are disclosed. Further disclosed are methods of making biologically active compounds of formula I as well as pharmaceutically acceptable compositions comprising compounds of formula I. Compounds of formula I as disclosed herein can be used in a variety of applications including use as antibacterial agents.

Hypolipidemic and antiatherosclerotic novel (monosubstituted-amino)heteroaryl carboxylic acids and analogs

This disclosure described novel (monosubstituted-amino)heteroaryl carboxylic acids and analogs which are useful as hypolipidemic and antiatherosclerotic agents.

Reaction and Spectral Properties of Ethyl 5-Aminofuroate and its Derivatives

Ethyl 5-aminofuroate (II), prepared by reduction of ethyl 5-nitrofuroate (I), served for preparation of bifunctional α,β-substituted aminofurans IV-IX, acyl derivatives IIIa, IIIb and condensation product X.The later reacted with diazomethane directly to afford the corresponding aziridine derivative XI.The synthesized compounds were characterized by spectral data (IR,UV,(1)H-NMR,(13)C-NMR (XI) and mass spectra).