19622-55-0

Basic information

• Product Name: 5-(1-methyl-5-nitro-1H-imidazol-2-yl)-1,3,4-thiadiazol-2-amine
• Synonyms: 1,3,4-thiadiazol-2-amine, 5-(1-methyl-5-nitro-1H-imidazol-2-yl)-; 5-(1-Methyl-5-nitro-1H-imidazol-2-yl)-1,3,4-thiadiazol-2-amine
• CAS NO: 19622-55-0
• Molecular Formula: C₆H₆N₆O₂S
• Molecular Weight: 226.2158
• Mol File: 19622-55-0.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 532.6°C at 760 mmHg
• Flash Point: 275.9°C
• Density: 2g/cm³
• Vapor Pressure: 2.01E-11mmHg at 25°C
• Refractive Index: 1.921
• CAS DataBase Reference: 5-(1-methyl-5-nitro-1H-imidazol-2-yl)-1,3,4-thiadiazol-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(1-methyl-5-nitro-1H-imidazol-2-yl)-1,3,4-thiadiazol-2-amine(19622-55-0)
• EPA Substance Registry System: 5-(1-methyl-5-nitro-1H-imidazol-2-yl)-1,3,4-thiadiazol-2-amine(19622-55-0)

Safety Data

• Hazardous Substances Data: 19622-55-0(Hazardous Substances Data)

Usage

General Description

5-(1-methyl-5-nitro-1H-imidazol-2-yl)-1,3,4-thiadiazol-2-amine is a chemical compound with the molecular formula C6H6N6O2S. It is a member of the thiadiazole family and contains an imidazole ring and a nitro group. 5-(1-methyl-5-nitro-1H-imidazol-2-yl)-1,3,4-thiadiazol-2-amine is commonly used in pharmaceutical research and drug development due to its potential biological activities. It may possess antibacterial, antifungal, and antiparasitic properties, making it a promising candidate for the development of new drugs. Its unique molecular structure and functional groups make it an interesting target for further study and potential medical applications.

Upstream product

• 3994-53-4 1-methyl-5-nitro-imidazole-2-carboxylic acid 
• 1615-60-7 1-methyl-5-nitro-2-imidazolylrbimino ethyl ether 
• 59336-12-8 1-(1-methyl-5-nitro-2-imidazolecarbonyl)-3-thiosemicarbazide 
• 27344-16-7 1-methyl-5-nitro-N'-thiocarbamoyl-1H-imidazole-2-carbohydrazonic acid amide 
• 27344-23-6 1-methyl-5-nitro-N'-thiocarbamoyl-1H-imidazole-2-carbohydrazonic acid ethyl ester 
• 25306-08-5 N-[5-(1H-imidazol-2-yl)-[1,3,4]thiadiazol-2-yl]-acetamide 
• 32539-03-0 5-(1H-imidazol-2-yl)-[1,3,4]thiadiazol-2-ylamine 
• 202408-38-6 2-cyano-4-iodo-1-methyl-5-nitroimidazole 
• 4750-57-6 1-methyl-5-nitro-1H-imidazole-2-carbaldehyde 
• 79-19-6 thiosemicarbazide 
• 1615-42-5 1-methyl-5-nitro-1H-imidazole-2-carbonitrile 
• 4994-21-2 1-methyl-5-nitro-2-imidazolecarboxaldehyde thiosemicarbazone 
• 25306-10-9 5-(1-methyl-1H-2-imidazolyl)-1,3,4-thiadiazol-2-amine 
• 936-05-0 1-methyl-2-hydroxymethyl-5-nitroimidazole 

Downstream Products

• 24033-33-8 5-(1-methyl-5-nitro-1H-imidazol-2-yl)-2-(4-phenylpiperazin-1-yl)-1,3,4-thiadiazole 
• 1294510-70-5 2-(4-benzylpiperazin-1-yl)-5-(1-methyl-5-nitro-1H-imidazol-2-yl)-1,3,4-thiadiazole 

Relevant articles and documents

Trypanosoma cruzi: Effect and mode of action of nitroimidazole and nitrofuran derivatives

With the aim of determining the actual target(s) of nitro-group bearing compounds considered as possible leads for the development of drugs against Chagas' disease, we studied in parallel nitrofurans and nitroimidazoles. We investigated nine representative compounds for the following properties: efficacy on different Trypanosoma cruzi strains, redox cyclers, inhibition of respiration, production of corresponding nitroso derivatives and intracellular thiol scavengers. Our results indicate that nifurtimox and related compounds act as redox cyclers, whereas the most active in the series, the 5-nitroimidazole megazol essentially acts as thiol scavenger particularly for trypanothione, the cofactor for trypanothione reductase, an essential enzyme in the detoxification process.

5-Nitroimidazole-based 1,3,4-Thiadiazoles: Heterocyclic analogs of metronidazole as anti-helicobacter pylori agents

A series of 5-nitroimidazole-based 1,3,4-thiadiazoles were prepared and tested for antibacterial activity against Helicobacter pylori. The anti-H. pylori activity of target compounds along with the commercially available antimicrobial metronidazole was evaluated by comparing the inhibition-zone diameters determined by the paper disc diffusion bioassay. From our bioassay results against 20 clinical isolates it is evident that piperazinyl, 4-methylpiperazinyl, 3-methylpiperazinyl, and 3,5-dimethylpiperazinyl analogs (6a, 6b, 6e, and 6f, respectively) and pyrrolidine derivative 7 had strong activity at 0.5 μg/disc (average of inhibition zone >20 mm) while metronidazole had no activity at this dose. Compound 6f containing the 3,5-dimethylpiperazinyl moiety at the 2-position of the 5-(1-methyl-5-nitro-1H- imidazol-2-yl)-1,3,4-thiadiazole skeleton was the most potent compound tested at low concentrations.

Nitroimidazolyl-1,3,4-thiadiazole-based anti-leishmanial agents: Synthesis and in vitro biological evaluation

A series of 1-[5-(1-methyl-5-nitro-1H-imidazol-2-yl)-1,3,4-thiadiazol-2-yl]-4-aroylpiperazines were synthesized and evaluated in vitro against Leishmania major. Most of the target compounds exhibited good anti-leishmanial activity against the promastigote form of L. major at non-cytotoxic concentrations. The most active compound was 1-[(5-chloro-2-thienyl)carbonyl]-4-[5-(1-methyl-5-nitro-1H-imidazol-2-yl)-1,3,4-thiadiazol-2-yl]piperazine (5f) with an IC50 value of 9.35 ± 0.67 μM against L. major promastigotes. In addition, this compound was effective against intracellular L. major and significantly decreased the infectivity index.

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).