16865-27-3

Basic information

• Product Name: 5-(5-NITRO-2-FURYL)-1,3,4-THIADIAZOLE-2-THIOL
• Synonyms: 5-(5-NITROFURAN-2-YL)-1,3,4-THIADIAZOLE-2-THIOL;5-(5-NITRO-2-FURYL)-1,3,4-THIADIAZOLE-2-THIOL;5-(5-nitrofuran-2-yl)-3H-1,3,4-thiadiazole-2-thione
• CAS NO: 16865-27-3
• Molecular Formula: C₆H₃N₃O₃S₂
• Molecular Weight: 229.24
• Mol File: 16865-27-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 175 °C
• Boiling Point: 363.9°Cat760mmHg
• Flash Point: 173.9°C
• Appearance: /
• Density: 1.96g/cm³
• Vapor Pressure: 1.75E-05mmHg at 25°C
• Refractive Index: 1.879
• PKA: 5.42±0.40(Predicted)
• CAS DataBase Reference: 5-(5-NITRO-2-FURYL)-1,3,4-THIADIAZOLE-2-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(5-NITRO-2-FURYL)-1,3,4-THIADIAZOLE-2-THIOL(16865-27-3)
• EPA Substance Registry System: 5-(5-NITRO-2-FURYL)-1,3,4-THIADIAZOLE-2-THIOL(16865-27-3)

Safety Data

• Hazard Codes: Xi
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39:Wear suitable g
• Hazardous Substances Data: 16865-27-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H3N3O3S2/c10-9(11)4-2-1-3(12-4)5-7-8-6(13)14-5/h1-2H,(H,8,13)

Upstream product

• 4015-11-6 2-chloro-5-(5-nitrofuran-2-yl)-1,3,4-thiadiazole 
• 712-68-5 2-amino-5-(5-nitro-2-furyl)-1,3,4-thiadiazole 
• 831-71-0 5-nitro-furfural thiosemicarbazone 
• 92-55-7 5-nitro-2-furfuraldehyde diacetate 
• 698-63-5 5-nitrofurane-2-carboxaldehyde 

Relevant articles and documents

Synthesis and in vitro urease inhibitory activity of 5-nitrofuran-2-yl-thiadiazole linked to different cyclohexyl-2-(phenylamino)acetamides, in silico and kinetic studies

A series of 5-nitrofuran-2-yl-thiadiazole linked to different cyclohexyl-2-(phenylamino)acetamides were rationally designed and synthesized. All synthetic compounds were evaluated for their urease inhibitory activity and exhibited good inhibitory potential against urease with IC50 values in the range of 0.94 – 6.78 μM as compared to the standard thiourea (IC50 = 22.50 μM). Compound 8g (IC50 = 0.94 μM) with a thiophene substituent at the R2 position was found to be the most active member of the series. Kinetic studies exhibited that the compound 8g was a non-competitive inhibitor. In silico study showed the critical interactions of potent inhibitors with the active site of the enzyme. These newly identified inhibitors of the urease enzyme can serve as leads for further research and development.

Synthesis and antimycobacterial activity of some alkyl [5-(nitroaryl)-1,3, 4-thiadiazol-2-ylthio]propionates

Two series of 2- and 3-[5-(nitroaryl)-1,3,4-thiadiazol-2-ylthio, sulfinyl and sulfonyl] propionic acid alkyl esters were synthesized and screened for antituberculosis activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system. The MIC values for the compounds showing more than 90% inhibition were determined. The result of comparison between two groups of data exhibited that among the synthesized derivatives, the compound propyl 3-[5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-ylthio]propionate was the most active one (MIC = 1.56 μg ml-1).

Synthesis and antifungal activity of 2-aryl-1,3,4-thiadiazole-5-sulphides, sulphoxides and sulphones

2-Aryl-1,3,4-thiadiazole-5-sulphides, sulphoxides and sulphones were synthesized and tested against a variety of fungal strains, Miconazole and fluconazole were used as reference drugs. The most active compounds against Candida albicans, Candida spp., Cryptococcus neoformans and Aspergillus niger were 2-(1-methyl-5-nitro-2-imidazolyl)-5-methylsulphonyl-1 ,3,4-thiadiazole (8h) and 2-(5-nitro-2-furyl)-5-methylsulphonyl-1,3,4-thiadiazole (8f). Our results showed that compounds 8h and 8f were several times more active than fluconazole in most fungal strains.