712-68-5

Basic information

• Product Name: 5-(5-nitro-2-furyl)-1,3,4-thiadiazol-2-ylamine
• Synonyms: 5-(5-nitro-2-furyl)-1,3,4-thiadiazol-2-ylamine;FURIDIAZINE;2-AMINO-5-(5-NITRO-2-FURYL)-1,3,4-THIADIAZOLE;2-amino-5-(-nitro-2-furyl)-1,3,4-thiadiazole;Furidiazina;NF-475;Ph/778;Thiafur
• CAS NO: 712-68-5
• Molecular Formula: C₆H₄N₄O₃S
• Molecular Weight: 212.18596
• EINECS: 211-925-6
• Mol File: 712-68-5.mol
• Article Data: 12

Chemical Properties

• Melting Point: 280°
• Boiling Point: 437.9°C at 760 mmHg
• Flash Point: 218.7°C
• Appearance: /
• Density: 1.655 (estimate)
• Vapor Pressure: 7.18E-08mmHg at 25°C
• Refractive Index: 1.6200 (estimate)
• CAS DataBase Reference: 5-(5-nitro-2-furyl)-1,3,4-thiadiazol-2-ylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(5-nitro-2-furyl)-1,3,4-thiadiazol-2-ylamine(712-68-5)
• EPA Substance Registry System: 5-(5-nitro-2-furyl)-1,3,4-thiadiazol-2-ylamine(712-68-5)

Safety Data

• Hazardous Substances Data: 712-68-5(Hazardous Substances Data)

Usage

Description

5-(5-nitro-2-furyl)-1,3,4-thiadiazol-2-ylamine is a chemical compound with a unique structure that features a thiazol ring fused with a nitro-substituted furyl group. 5-(5-nitro-2-furyl)-1,3,4-thiadiazol-2-ylamine exhibits a range of biological activities, making it a versatile molecule with potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
5-(5-nitro-2-furyl)-1,3,4-thiadiazol-2-ylamine is used as an anti-Heliicobacter pylori agent for treating infections caused by the Helicobacter pylori bacteria. This bacterium is known to cause various gastrointestinal issues, including peptic ulcers and gastritis. 5-(5-nitro-2-furyl)-1,3,4-thiadiazol-2-ylamine's ability to target and eliminate H. pylori makes it a valuable asset in the development of new therapeutic strategies for these conditions.
Used in Agricultural Industry:
5-(5-nitro-2-furyl)-1,3,4-thiadiazol-2-ylamine is used as a fungicide in the agricultural industry to protect crops from fungal infections. Its fungicidal properties help to prevent the growth and spread of various fungi that can damage or destroy crops, ensuring a higher yield and better quality produce.
Used in Pesticide Formulation:
As a pesticide component, 5-(5-nitro-2-furyl)-1,3,4-thiadiazol-2-ylamine is employed in the development of new formulations to control and manage pests in agriculture. Its incorporation into pesticides can enhance their effectiveness against a range of pests, including insects and mites, thereby reducing crop damage and improving overall agricultural productivity.

Safety Profile

Suspected carcinogen with experimental carcinogenic and neoplastigenic data. Experimental reproductive effects. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also NITRO COMPOUNDS OF AROMATIC HYDROCARBONS.

InChI:InChI=1/C6H4N4O3S/c7-6-9-8-5(14-6)3-1-2-4(13-3)10(11)12/h1-2H,(H2,7,9)

Upstream product

• 1673-59-2 1-(5-nitro-furan-2-carbonyl)-thiosemicarbazide 
• 13777-58-7 4-methylbenzenesulfonyl N'-(5-nitrofuran-2-ylmethylene)hydrazide 
• 333-20-0 potassium thioacyanate 
• 92-55-7 5-nitro-2-furfuraldehyde diacetate 
• 79-19-6 thiosemicarbazide 
• 698-63-5 5-nitrofurane-2-carboxaldehyde 
• 146827-83-0 2-[(E)-1-(5-nitro-2-furyl)methylidene]-1-hydrazinecarbothioamide 
• 831-71-0 5-nitro-furfural thiosemicarbazone 

Downstream Products

• 1310494-06-4 N-(2-butyl)-4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)benzamidine hydrochloride 
• 1310494-07-5 N-benzyl-4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)benzamidine hydrochloride 
• 1310494-08-6 N-(4-methoxybenzyl)-4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)benzamidine hydrochloride 
• 1310494-09-7 N-((tetrahydrofuran-2-yl)methyl)-4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)benzamidine hydrochloride 
• 1310494-10-0 morpholino(4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)phenyl)methanimine hydrochloride 
• 1310494-11-1 1-(4-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazine hydrochloride 
• 1310494-12-2 1,4,5,6-tetrahydro-2-(4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)phenyl)pyrimidine hydrochloride 
• 1310494-13-3 4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)benzonitrile 
• 1310494-14-4 O-ethyl 4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)benzimidate hydrochloride 
• 1310494-01-9 4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)benzamidine hydrochloride 
• 1310494-02-0 N-methyl-4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)benzamidine hydrochloride 
• 1310494-03-1 N-ethyl-4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)benzamidine hydrochloride 
• 1310494-04-2 N-(1-propyl)-4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)benzamidine hydrochloride 
• 1310494-05-3 N-(1-butyl)-4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)benzamidine hydrochloride 

Relevant articles and documents

Diversity-Oriented Synthesis of 1,2,4-Triazols, 1,3,4-Thiadiazols, and 1,3,4-Selenadiazoles from N-Tosylhydrazones

The diversity-oriented synthesis of 1,2,4-triazols, 1,3,4-thiadiazols, and 1,3,4-selenadiazoles from N-tosylhydrazones was developed, and the reactions were general for a wide range of substrates, in which NH2CN, KOCN, KSCN, and KSeCN were used as odorless sources. Two different pathways were proposed, and N-tosylhydrazonoyl chlorides were formed in situ in the presence of NCS.

Synthesis and antileishmanial activity of novel 5-(5-nitrofuran-2-y1)-1,3, 4-thiadiazoles with piperazinyl-linked benzamidine substituents

In order to optimize the antileishmanial activity of piperazinyl-linked 5-(5-nitrofuran-2-yl)-1,3,4-thiadiazoles, we synthesized a series of 5-(5-nitrofuran-2-y1)-1,3,4-thiadiazoles with piperazinyl-linked benzamidine substituent as scaffold found in pentamidine related antiprotozoals. The structure of target compounds was confirmed by IR, 1H NMR, 13C NMR and Mass spectral data. All compounds were tested for in vitro activity against the promastigote and amastigote forms of Leishmania major. From the results, we found that the substitution on amidine nitrogen has profound role in the biological activity of these compounds. The 5-nitrofuran-2-yl-1,3,4-thiadiazoles having n-propyl, n-butyl and benzyl side chain on benzamidine (as in compounds 2d, 2e and 2g, respectively) showed very good activity in both forms of promastigote and amastigote. The most active compound was N-propyl-4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl) piperazin-1-yl) benzamidine hydrochloride (2d) with IC50 value of 0.08 μM in promastigote model. This compound showed a very low level of toxicity against macrophages (CC50 = 785 μM), with the highest selectivity index (SI = 78.5) among the tested compounds.

Synthesis and biological activity of 5-nitrofuran-containing (1,3,4-thiadiazol-2-yl)piperazine moieties as a new type of anti-Helicobacter pylori heterocycles

In order to find new and potent drug candidates for the treatment of Helicobacter pylori infections, in this study attention was focused on the synthesis and anti-H. pylori activity of a series of 5-(5-nitrofuran-2-yl)-1,3, 4-thiadiazoles containing piperazinyl functionality at the C-2 position of the 1,3,4-thiadiazole ring. The synthesis of 1-[5-(5-nitrofuran-2-yl)-1,3,4- thiadiazol-2-yl]piperazine derivatives 3a-h and pyrrolidine derivative 3i was achieved with a versatile and efficient synthetic route via 2-chloro-5-(5- nitrofuran-2-yl)-1,3,4-thiadiazole. The inhibitory activity of the new derivatives 3a-i against twenty clinical H. pylori strains was evaluated by the disc diffusion method and compared with the commercially available standard drug metronidazole. Resulting biological data indicated that most compounds exhibited strong inhibitory activity even at doses lower than 2 μg/disc (average zone of inhibition >20 mm) while metronidazole had little or no growth inhibition at this dose. Compound 3c containing the N-benzoylpiperazin-1- yl moiety showed the most potent inhibitory activity.