5469-78-3

Basic information

• Product Name: 5-NITROFURAN-2-CARBOHYDRAZIDE
• Synonyms: 5-nitro-2-furohydrazide
• CAS NO: 5469-78-3
• Molecular Formula: C₅H₅N₃O₄
• Molecular Weight: 171.1109
• Mol File: 5469-78-3.mol

Chemical Properties

• Melting Point: 173-174 °C(Solv: methanol (67-56-1))
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.533g/cm³
• Refractive Index: 1.589
• PKA: 10.99±0.10(Predicted)
• CAS DataBase Reference: 5-NITROFURAN-2-CARBOHYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-NITROFURAN-2-CARBOHYDRAZIDE(5469-78-3)
• EPA Substance Registry System: 5-NITROFURAN-2-CARBOHYDRAZIDE(5469-78-3)

Safety Data

• Hazardous Substances Data: 5469-78-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C5H5N3O4/c6-7-5(9)3-1-2-4(12-3)8(10)11/h1-2H,6H2,(H,7,9)

Upstream product

• 1874-23-3 methyl 5-nitrofuran-2-carboxylate 
• 943-37-3 5-nitrofuran-2-carboxylic acid ethyl ester 
• 516465-89-7 N'-(tert-butoxycarbonyl)-5-nitro-2-furancarbohydrazide 
• 645-12-5 5-nitro-2-furoic acid 

Downstream Products

• 83207-21-0 1-(5-Nitro-2-furoyl)-2-acetylhydrazin 
• 125274-01-3 5-nitro-furan-2-carboxylic acid salicylidenehydrazide 
• 133478-77-0 N-benzoyl-N'-(5-nitro-furan-2-carbonyl)-hydrazine 
• 106271-34-5 N-(4-acetylamino-benzoyl)-N'-(5-nitro-furan-2-carbonyl)-hydrazine 
• 3775-55-1 2-Amino-5-(5-nitro-2-furyl)-1,3,4-oxadiazol 
• 78959-38-3 5-nitro-2-furoic acid 2-(2H-1,4-benzoxazin-3-yl)hydrazide 
• 29449-00-1 2-(5-nitrofuran-2-yl)-5-phenyl-1,3,4-oxadiazole 
• 516465-92-2 {2-[N'-(5-nitro-furan-2-carbonyl)-hydrazino]-2-oxo-1-phenyl-ethyl}-carbamic acid tert-butyl ester 
• 78205-35-3 3-(5-Nitro-furan-2-yl)-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole 
• 78205-38-6 3-(5-nitro-2-furyl)-8H-5,6-dihydro<1,2,4>triazolo<3,4-c><1,4>oxazine 
• 1243683-04-6 N'‐[(3‐bromophenyl)methylidene]‐5‐nitrofuran‐2‐carbohydrazide 
• 1243683-07-9 C₁₃H₈F₃N₃O₄ 
• 29448-96-2 5-nitro-furan-2-carboxylic acid (4-methyl-benzylidene)-hydrazide 
• 29448-95-1 N'‐[(4‐chlorophenyl)methylidene]‐5‐nitrofuran‐2‐carbohydrazide 

Relevant articles and documents

Design, synthesis and biological evaluation of nitrofuran-1,3,4-oxadiazole hybrids as new antitubercular agents

Three series of novel nitrofuran-1,3,4-oxadiazole hybrids were designed and synthesized as new anti-TB agents. The structure activity relationship study indicated that the linkers and the substituents on the oxadiazole moiety greatly influence the activity, and the substituted benzenes are more favoured than the cycloalkyl or heterocyclic groups. Besides, the optimal compound in series 2 was active against both MTB H37Rv strain and MDR-MTB 16883 clinical isolate and also displayed low cytotoxicity, low inhibition of hERG and good oral PK, indicating its promising potential to be a lead for further structural modifications.

Synthesis of promising antimicrobial agents: hydrazide-hydrazones of 5-nitrofuran-2-carboxylic acid

In this research, we synthesized and evaluated for in vitro antimicrobial activity a new series of hydrazide-hydrazones obtained from 5-nitrofuran-2-carboxylic acid. New compounds were identified and characterized by spectral methods (1H NMR and 13C NMR). All tested hydrazide-hydrazones proved to be promising antimicrobial agents. Antimicrobial activity and antifungal activity of new derivatives of 5-nitrofuran-2-carboxylic acid were revealed in many cases to be higher than the activity of reference substances (nitrofurantoin, cefuroxime and ampicillin).

Design, synthesis, topoisomerase I & II inhibitory activity, antiproliferative activity, and structure-activity relationship study of pyrazoline derivatives: An ATP-competitive human topoisomerase IIα catalytic inhibitor

A series of pyrazoline derivatives (5) were synthesized in 92-96% yields from chalcones (3) and hydrazides (4). Subsequently, topo-I and IIα-mediated relaxation and antiproliferative activity assays were evaluated for 5. Among the tested compounds, 5h had

Novel pyrazoline derivatives and the use thereof

The present invention relates to a novel pyrazoline derivative compound, a pharmaceutically acceptable salt thereof, and a pharmaceutical composition for preventing or treating cancer, containing the pyrazoline derivative compound or the pharmaceutically

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.

Isatin derivatives and their use in therapy

The present invention relates to compounds of formula (I) wherein R is pyridyl, R1 is selected from Cl or NO2 and R2 is H; or R is 2-nitrofuranosyl, R1 is selected from H, F, Cl, CH3 or OCF3 and R2 is selected from H, phenyl or benzyl; associated pharmaceutical compositions and use of the compounds or compositions in therapy, in particular for the treatment of tuberculosis as well as a method for their preparation.

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.

Antitrypanosomal activities and cytotoxicity of 5-nitro-2-furancarbohydrazides

A series of 5-nitro-2-furancarbohydrazides were synthesized. In vitro antitrypanosomal activities of these compounds were determined against the closely related protozoa Trypanosoma cruzi Trypanosoma brucei and discussed in relation to potential targets.