13239-11-7

Usage

InChI:InChI=1/C6H4N2O2S/c11-6-8-7-5(10-6)4-2-1-3-9-4/h1-3H,(H,8,11)

Upstream product

• 3326-71-4 2-furoic acid hydrazide 
• 75-15-0 carbon disulfide 
• 88-14-2 2-furanoic acid 
• 611-13-2 2-furoic acid methyl ester 
• 614-99-3 Ethyl 2-furoate 
• 140-92-1 potassium isopropylxanthate 
• 63467-57-2 potassium ethyldithiocarbamate 

Downstream Products

• 1355947-56-6 1,2,4,5-tetrakis[5-(2-furyl)-1,3,4-oxadiazol-2-ylthiomethyl]benzene 
• 33621-24-8 (5-furan-2-yl-[1,3,4]oxadiazol-2-ylsulfanyl)-acetic acid 
• 1222827-75-9 4-(5-(furan-2-yl)-1,3,4-oxadiazol-2-ylthio)but-2-ynyl 4-fluorobenzoate 
• 80809-38-7 4-amino-3-(2-furyl)-5-mercapto[4H]-1,2,4-triazole 
• 1610730-73-8 2-(furan-2-yl)-5-[(8-phenyl-9H-purin-6-yl)thio]-1,3,4-oxadiazole 

Relevant academic research and scientific papers

5-Furan-2yl[1,3,4]oxadiazole-2-thiol, 5-furan-2yl-4h [1,2,4] triazole-3-thiol and their thiol-thione tautomerism

5-Furan-2-yl[1,3,4]oxadiazole-2-thiol (Ia) and 5-furan-2-yl-4H-[1,2,4]- triazole-3-thiol (Ib) were synthesized from furan-2-carboxylic acid hydrazide. Mannich bases and methyl derivatives were then prepared. The structures of the synthesized compounds were confirmed by elemental analyses, IR and 1H-NMR spectra. Their thiol-thione tautomeric equilibrium is described.

Synthesis, characterization, and nonlinear optical properties of some new series of S-(5-aryl-1,3,4-oxadiazol-2-yl) 2-chloroethanethioate derivatives

In the present investigation, some novel S-(5-aryl-1,3,4-oxadiazol-2-yl)2-chloroethanethioate (3a–3e) derivatives were synthesized and their impact on optical properties was studied. They have also been characterized by elemental analysis and various spectroscopic methods including FTIR, 1 H NMR, 13 C NMR, and UV-Vis techniques. The nonlinear refractive indexes of 3a–3e were also measured in dichloromethane via Z-scan method using a continuous wave diode-pumped laser at 532 nm wavelength. The nonlinear refractive coefficient of compounds was obtained from 1011 m2/W order. Regarding the appropriate nonlinearity of these compounds, they could be considered good candidates for biooptical and photonic applications. All the synthesized compounds (3a–3e) have also been evaluated for their antimicrobial and antifungal activities. The bioactive assay showed that the synthetic compounds displayed variable inhibition zones against tested bacterium Escherichia coli and fungus Aspergillus fumigatus in comparison to enrofloxacin and amphotericin as reference drugs, which are normally used for treating such infections.

Synthesis, crystal structure and 3D-QSAR studies of antifungal (bis-)1,2,4-triazole Mannich bases containing furyl and substituted piperazine moieties

A series of novel title compounds 6a-6r and 7a-7c have been synthesized by Mannich reaction of the new triazole Schiff base intermidiates, substituted piperazine and formaldehyde under mild conditions in excellent yields. The crystal structure of compound 6i was determined to show a chair conformation of the piperazine ring and an (E)-configuration of the C[dbnd]N double bond. The bioassay results indicated that most of the newly synthesized compounds exhibited excellent in vitro inhibitory activities and broader spectrum against several plant fungi, and were more effective than the control Triadimefon. Several compounds also displayed favourable in vivo antifungal activities. The relationships between the compound structures and various biological activities were discussed. Furthermore, the CoMFA calculation based on the antifungal activity data of compounds 6 against R. cerealis was carried out to establish a 3D-QSAR model, which revealed that steric and electrostatic fields were two most important factors for contributing the bioactivity of the compounds. The present work will provide significant information for guiding optimization of such new structures to develop novel agrochemicals with higher antifungal activities.

Synthesis and biological activities of novel 5-substituted-1,3,4-oxadiazole Mannich bases and bis-Mannich bases as ketol-acid reductoisomerase inhibitors

A series of novel 5-substituted-1,3,4-oxadiazole Mannich bases and bis-Mannich bases have been conveniently synthesized in good yields. Their structures were characterized by IR,1H NMR,13C NMR and elemental analysis. The preliminary bioassay results indicated that some of the compounds showed promising in vitro fungicidal activities towards several test plant fungi; some of them exhibited significant herbicidal activities against Brassica campestris and excellent in vitro inhibitory activities against rice ketol-acid reductoisomerase (KARI). Among 14 novel compounds, 8c, 8d and 8m showed potent KARI inhibitory activities with Kivalue of (0.96?±?0.42), (3.86?±?0.49) and (3.10?±?0.71) μmol/L, respectively, and were comparable with IpOHA. These compounds could be novel KARI inhibitors for further investigation. The density functional theory (DFT) calculations and molecular docking were carried out to study the structure–activity relationship (SAR) of the active inhibitors in this Letter.

Design, synthesis, in vitro and in vivo evaluation against MRSA and molecular docking studies of novel pleuromutilin derivatives bearing 1, 3, 4-oxadiazole linker

A class of pleuromutilin derivatives containing 1, 3, 4-oxadiazole were designed and synthesized as potential antibacterial agents against Methicillin-resistant staphylococcus aureus (MRSA). The ultrasound-assisted reaction was proposed as a green chemistry method to synthesize 1, 3, 4-oxadiazole derivatives (intermediates 85–110). Among these pleuromutilin derivatives, compound 133 was found to be the strongest antibacterial derivative against MRSA (MIC = 0.125 μg/mL). Furthermore, the result of the time-kill curves displayed that compound 133 could inhibit the growth of MRSA in vitro quickly (- 4.36 log10 CFU/mL reduction). Then, compound 133 (- 1.82 log10 CFU/mL) displayed superior in vivo antibacterial efficacy than tiamulin (- 0.82 log10 CFU/mL) in reducing MRSA load in mice thigh model. Besides, compound 133 exhibited low cytotoxicity to RAW 264.7 cells. Molecular docking studies revealed that compound 133 was successfully localized in the binding pocket of 50S ribosomal subunit (ΔGb = -10.50 kcal/mol). The results indicated that these pleuromutilin derivatives containing 1, 3, 4-oxadiazole might be further developed into novel antibiotics against MRSA.

Ultrasound-assisted, low-solvent and acid/base-free synthesis of 5-substituted 1,3,4-oxadiazole-2-thiols as potent antimicrobial and antioxidant agents

Abstract: One of the goals of green chemistry is to use environmentally friendly solvents or remove and reduce the volume of harmful spent solvents. In this study, a novel process for the synthesis of 5-substituted 1,3,4-oxadiazole-2-thiol derivatives was proposed via ultrasound-assisted reaction of aryl hydrazides with CS2 (1:1 molar ratio) in some drops of DMF in the absence of basic or acidic catalysts. They were produced in good to excellent yields under easy workup and purification conditions. In order to prove the usefulness of the prepared compounds, their antioxidant, antibacterial, and antifungal potentials were screened by DPPH free radical scavenging, serial twofold microdilution and streak plate methods. Acceptable to significant inhibitory activities were observed with synthesized heterocycles. The results showed that 5-(4-fluorophenyl)-1,3,4-oxadiazole-2-thiol (3c) is an broad-spectrum antimicrobial agent. Many of them displayed remarkable antioxidant properties comparable to standard controls (ascorbic acid and α-tocopherol). Synthesized 1,3,4-oxadiazoles are also potent candidates to treat cancer, Parkinson, inflammatory, and diabetes diseases. Graphic Abstract: Eighteen 5-substituted 1,3,4-oxadiazole-2-thiol derivatives as potent antimicrobial and antioxidant agents were prepared via a new, efficient and green procedure.[Figure not available: see fulltext.].

1, 3, 4-oxadiazole-2 (3H)-thioketone-norfloxacin heterozygote and preparation method and application thereof

The invention discloses a 1, 3, 4-oxadiazole-2 (3H)-thioketone-norfloxacin heterozygote and a preparation method and application thereof, and the structural formula of the 1, 3, 4-oxadiazole-2 (3H)-thioketone-norfloxacin heterozygote is shown as a formula

Pleuromutilin derivative with 1, 3, 4-oxadiazole side chain and preparation and application thereof

The invention belongs to the field of medicinal chemistry, and particularly relates to a pleuromutilin derivative with a 1, 3, 4-oxadiazole side chain and preparation and application thereof The pleuromutilin derivative with the 1, 3, 4-oxadiazole side chain is a compound shown in a formula 2 or a pharmaceutically acceptable salt thereof, and a solvent compound, an enantiomer, a diastereoisomer and a tautomer of the compound shown in the formula 2 or the pharmaceutically acceptable salt thereof or a mixture of the solvent compound, the enantiomer, the diastereoisomer and the tautomer in any proportion, including a racemic mixture. The pleuromutilin derivative has good antibacterial activity, is especially suitable for being used as a novel antibacterial agent for systemic system infection of animals or human beings, and has good water solubility.

Synthesis, antifungal and antibacterial activity of calix[4]arene-based 1,3,4-oxadiazole derivatives

We describe the synthesis of some novel p-tert-butylcalix[4]arene-based (5-aryl-1,3,4-oxadiazol-2-yl)2-chloroethanethioate derivatives (4a–e). These compounds were synthesized by the reaction of tetra-tert-butyl calix[4]arene (1) with (5-aryl-1,3,4-oxadiazol-2-yl)2-chloroethanethioate (3a–e) in the presence of potassium carbonate as a weak base and dry acetone as the solvent. All the newly synthesized calix[4]arene derivatives were characterized by elemental analysis and various spectroscopic methods such as FT-IR, 1H NMR,13C NMR, DEPT, and ESI-MS. The synthesized compounds were tested in vitro for their antibacterial and antifungal activities against Escherichia coli and Aspergillus fumigates in comparison with enrofloxacin and amphotericin as reference drugs, which are normally used for treating such infections. The synthesized compounds showed different inhibition zones against the tested bacteria and fungi. Compound 4c was found to be most effective against A. fumigates, whereas compound 4e was found to be equally effective against E. coli and A. fumigates.

Rational Optimization and Action Mechanism of Novel Imidazole (or Imidazolium)-Labeled 1,3,4-Oxadiazole Thioethers as Promising Antibacterial Agents against Plant Bacterial Diseases

The emergence and widespread occurrence of plant bacterial diseases that cause global production constraints have become major challenges to agriculture worldwide. To promote the discovery and development of new bactericides, imidazole-labeled 1,3,4-oxadiazole thioethers were first fabricated by integrating the crucially bioactive scaffolds of the imidazole motif and 1,3,4-oxadiazole skeleton in a single molecular architecture. Subsequently, a superior antibacterial compound A6 was gradually discovered possessing excellent competence against plant pathogens Xanthomonas oryzae pv oryzae and Xanthomonas axonopodis pv citri with EC50 values of 0.734 and 1.79 μg/mL, respectively. These values were better than those of commercial agents bismerthiazol (92.6 μg/mL) and thiodiazole copper (77.0 μg/mL). Further modifying the imidazole moiety into the imidazolium scaffold led to the discovery of an array of potent antibacterial compounds providing the corresponding minimum EC50 values of 0.295 and 0.607 μg/mL against the two strains. Moreover, a plausible action mechanism for attacking pathogens was proposed based on the concentration dependence of scanning electron microscopy, transmission electron microscopy, and fluorescence microscopy images. Given the simple molecular structures, easy synthetic procedure, and highly efficient bioactivity, imidazole (or imidazolium)-labeled 1,3,4-oxadiazole thioethers can be further explored and developed as promising indicators for the development of commercial drugs.