4447-45-4

Usage

Uses

Used in Pharmaceutical Research:
5-(2-FURYL)-1,3,4-THIADIAZOL-2-AMINE is used as a key intermediate in the synthesis of various pharmaceutical compounds for its antiviral, antibacterial, and antifungal properties. It aids in the development of treatments for a range of diseases and conditions.
Used in Antimicrobial Applications:
In the medical industry, 5-(2-FURYL)-1,3,4-THIADIAZOL-2-AMINE is used as an antimicrobial agent to combat viral, bacterial, and fungal infections due to its broad-spectrum activity.
Used in Pesticide and Herbicide Development:
5-(2-FURYL)-1,3,4-THIADIAZOL-2-AMINE is used as an active ingredient in pesticides and herbicides for its pesticidal activities, helping to control and manage pests and weeds in agricultural settings.

InChI:InChI=1/C6H5N3OS/c7-6-9-8-5(11-6)4-2-1-3-10-4/h1-3H,(H2,7,9)

Upstream product

• 5419-96-5 furan-2-aldehyde thiosemicarbazone 
• 527-69-5 2-furancarbonyl chloride 
• 79-19-6 thiosemicarbazide 
• 98-01-1 furfural 
• 333-20-0 potassium thioacyanate 
• 617-90-3 2-furancarbonitrile 
• 88-14-2 2-furanoic acid 

Downstream Products

• 4447-47-6 4-amino-N-(5-furan-2-yl-[1,3,4]thiadiazol-2-yl)-benzenesulfonamide 
• 141421-48-9 2-Furan-2-yl-7-hydroxy-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one 
• 73653-51-7 6-(4-chloro-phenyl)-2-furan-2-yl-imidazo[2,1-b][1,3,4]thiadiazole 
• 73653-52-8 2-furan-2-yl-6-(4-methoxy-phenyl)-imidazo[2,1-b][1,3,4]thiadiazole 

Relevant academic research and scientific papers

Synthesis of a Series of Novel 2-Amino-5-substituted 1,3,4-oxadiazole and 1,3,4-thiadiazole Derivatives as Potential Anticancer, Antifungal and Anti-bacterial Agents

Objective: The objective of the present study was to prepare the 5-substituted 2-amino-1,3,4-oxadiazole and 2-amino-1,3,4-thiadiazole derivatives and evaluate their potential anticancer, antibac-terial and antifungal activities. Methods: Twenty-seven derivatives were synthesized by iodine-mediated cyclization of semicarba-zones or thiosemicarbazones obtained from condensation of semicarbazide or thiosemicarbazide and aldehydes. The structures were confirmed by1H-NMR,13C-NMR and MS spectra. The antibacterial and antifungal activities were evaluated by diffusion method and the anticancer activities were evaluated by MTT assay. Results: Twenty-seven derivatives have been synthesized in moderate to good yields. A number of derivatives exhibited potential antibacterial, antifungal and anticancer activities. Conclusion: Compounds (1b, 1e and 1g) showed antibacterial activity against Streptococcus faecal-is, MSSA and MRSA with MIC value ranging between 4 to 64 μg/mL. Compound (2g) showed anti-fungal activity against Candida albicans (8 μg/mL) and Aspergillus niger (64 μg/mL). Compound (1o) exhibited high cytotoxic activity against HepG2 cell line (IC50 value 8.6 μM) which is compara-ble to the activity of paclitaxel, and is non-toxic on LLC-PK1 normal cell line. The structure activity relationship and molecular docking study of the synthesized compounds have also been reported.

Aryl or heteroaryl substituted thiadiazole compound and antibacterial application thereof

The invention belongs to the technical field of medicines, and particularly relates to an aryl or heteroaryl substituted thiadiazole compound, a preparation method and application thereof as an antibacterial drug. The compound is represented by formula (1

N-thiadiazole-4-hydroxy-2-quinolone-3-carboxamides bearing heteroaromatic rings as novel antibacterial agents: Design, synthesis, biological evaluation and target identification

Due to the occurrence of antibiotic resistance, bacterial infectious diseases have become a serious threat to public health. To overcome antibiotic resistance, novel antibiotics are urgently needed. N-thiadiazole-4-hydroxy-2-quinolone-3-carboxamides are a potential new class of antibacterial agents, as one of its derivatives was identified as an antibacterial agent against S. aureus. However, no potency-directed structural optimization has been performed. In this study, we designed and synthesized 37 derivatives, and evaluated their antibacterial activity against S. aureus ATCC29213, which led to the identification of ten potent antibacterial agents with minimum inhibitory concentration (MIC) values below 1 μg/mL. Next, we performed bacterial growth inhibition assays against a panel of drug-resistant clinical isolates, including methicillin-resistant S. aureus, and cytotoxicity assays with HepG2 and HUVEC cells. One of the tested compounds named 1-ethyl-4-hydroxy-2-oxo-N-(5-(thiazol-2-yl)-1,3,4-thiadiazol-2-yl)-1,2-dihydroquinoline-3-carboxamide (g37) showed 2 to 128-times improvement compared with vancomycin in term of antibacterial potency against the tested strains (MICs: 0.25–1 μg/mL vs. 1–64 μg/mL) and an optimal selective toxicity (HepG2/MRSA, 110.6 to 221.2; HUVEC/MRSA, 77.6–155.2). Further, comprehensive evaluation indicated that g37 did not induce resistance development of MRSA over 20 passages, and it has been confirmed as a bactericidal, metabolically stable, orally active antibacterial agent. More importantly, we have identified the S. aureus DNA gyrase B as its potential target and proposed a potential binding mode by molecular docking. Taken together, the present work reports the most potent derivative of this chemical series (g37) and uncovers its potential target, which lays a solid foundation for further lead optimization facilitated by the structure-based drug design technique.

I2 Promoted Synthesis of 2-Aminothiadiazoles Employing KSCN as a Sulfur Source Under Metal-Free Conditions

A new three-component strategy from aldehyde, p-toluenesulfonyl hydrazide and potassium thiocyanate for the synthesis of 2-aminothiadiazoles promoted by I2 under metal-free conditions has been described. Potassium thiocyanate was used as an odo

Synthesis and antifungal activities of drimane-amide derivatives from sclareol

Aim and Objective: Plant diseases are caused by fungal pathogens lead to severe economic losses in many agriculture crops. And the increasing resistance of many fungi to commonly used antifungal agents necessitates the discovery and development of new fungicides. So this study was focused on synthesizing novel skeleton compounds to effectively control plant diseases. Materials and Methods: A series of drimane-amide derivatives were designed, synthesized by aminolysis reaction of amine with intermediate sclareolide which was prepared from sclareol. The structures of all the synthesized compounds were confirmed using1H NMR,13C NMR, and HR-MS (ESI) spectroscopic data. Their in vitro antifungal activity were preliminarily evaluated by using the mycelium growth rate method against five phytopathogenic fungi: Botrytis cinerea, Glomerella cingulata, Alternaria alternate, Alternaria brassicae, and Fusarium graminearum. Results: 23 target compounds were successfully obtained in yields of 52-95%. Compounds358 A2 and A3 displayed favorable inhibitory potency against B. cinerea, G. cingulata and A. brassicae with IC50 values ranging from 3.18 to 10.48 μg/mL. These two compounds displayed higher fungicidal activity than sclareol against all the tested phytopathogenic fungi, and were more effective than the positive control thiabendazole against A. alternate and A. brassicae. The structure-activity relationship studies of compounds A1-10 indicated that both the position and type of substituent on the phenyl ring had significant effects on antifungal activity. Conclusion: The drimane-amide derivatives A2 and A3 were the most promising derivatives and should be selected as new templates for the potential antifungal agents.

5-aryl-1,3,4-thiadiazole-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents: Synthesis, bioevaluation and docking study

The search for newer histone deacetylase (HDAC) inhibitors has attracted a great deal of interest of medicinal chemists worldwide, especially after the first HDAC inhibitor (Zolinza , widely known as SAHA or Suberoylanilide hydroxamic acid) was approved by the FDA for the treatment of Tcell lymphoma in 2006. As a continuity of our ongoing research in this area, we designed and synthesized a series of 5-aryl-1,3,4-thiadiazole-based hydroxamic acids as analogues of SAHA and evaluated their biological activities. Most of the compounds in this series, e.g. compounds with 5-aryl moiety being 2-furfuryl (5a), 5-bromofuran-2-yl (5b), 5-methylfuran-2-yl (5c), thiophen-2-yl (5d), 5-methylthiophen-2-yl (5f) and pyridyl (5g-i), were found to have potent anticancer cytotoxicity with IC50 values of generally 5-to 10-fold lower than that of SAHA in 4 human cancer cell lines assayed. Those compounds with potent cytotoxicity were also found to have strong HDAC inhibition effects. Docking studies revealed that compounds 5a and 5d displayed high affinities towards HDAC2 and 8.

Novel 5-Aryl-1,3,4-Thiadiazole-Based Hydroxamic Acids and Anti-Cancer Composition Comprising the Same As Active Ingredient

The present invention relates to novel 5-aryl-1,3,4-thiadiazole-based hydroxamic acid, and an anti-cancer composition containing the same as an active ingredient. The hydroxamic acid compound of the present invention shows strong activities of inhibiting histone deacetylase (HDAC) and cytotoxicity against various cancer cells, thereby being able to be developed into an active component of strong anticancer drugs.COPYRIGHT KIPO 2016

Synthesis and biological activity of acylthiourea derivatives contain 1,2,3-thiadiazole and 1,3,4-thiadiazole

In order to investigate the biological activity of novel thiourea compounds, some novel 1,2,3-thiadiazole derivatives containing 1,3,4-thiadiazole were synthesized under phase transfer catalyzed condition(PEG-600)by multi-step reactions. The chemical structures of all compounds were established by 1H NMR, FTIR, MS, and elemental analysis, and some of these compounds were investigated for fungicidal activity and plant growth regulatory activity. The bioassay results indicated that some of these compound exhibited moderate activities.

Improved antiproliferative activity of 1,3,4-thiadiazole-containing histone deacetylase (HDAC) inhibitors by introduction of the heteroaromatic surface recognition motif

A series of 1,3,4-thiadiazole-containing hydroxamic acids, in accord with the common pharmacophore of histone deacetylase (HDAC) inhibitors (a Zn2+ binding moiety-a linker-a surface recognition motif), was identified as submicromolar HDAC inhibitors by our group. In this study, we continued our efforts to develop 1,3,4-thiadiazole bearing hydroxamate analogues by modifying the surface recognition motif. We found that 1,3,4-thiadiazoles having a heteroaromatic substituent showed better HDAC inhibitory activity in enzymatic assay and higher antiproliferative potency in cellular assay compared to SAHA.

One-pot synthesis of 5H-1,3,4-thiadiazolo[3,2-a] pyrimidin-5-one derivatives

A novel and efficient one-pot method has been developed for the synthesis of 2-substituted-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5- one derivative by the combination of [3 + 3] cycloaddition, reduction, deamination reactions. The fused heterocyclic compoun