69829-90-9

Usage

Uses

Used in Pharmaceutical Industry:
4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenol is used as a bioisostere for enhancing the biological activity of pharmaceutical compounds. Its oxadiazole ring can improve the efficacy and pharmacokinetics of drugs, making it a valuable component in the development of new medications.
Used in Materials Industry:
In the materials industry, 4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenol is used for its versatility in synthesis and modification. The thiol group allows for a range of chemical reactions, facilitating the creation of new materials with tailored properties.
Used in Antioxidant Applications:
4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenol is used as an antioxidant, leveraging its potential to protect against oxidative stress and damage. This makes it a candidate for use in various applications where oxidative stability is crucial, such as in the food industry, cosmetics, and pharmaceuticals.
Used in Antimicrobial Applications:
4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenol is also used as an antimicrobial agent, capitalizing on its potential to inhibit the growth of microorganisms. This application is particularly relevant in healthcare, food preservation, and material coatings that require antibacterial properties.

InChI:InChI=1/C8H6N2O2S/c11-6-3-1-5(2-4-6)7-9-10-8(13)12-7/h1-4,9H,(H,10,13)

Upstream product

• 75-15-0 carbon disulfide 
• 5351-23-5 4-hydroxybenzoic acid hydrazide 
• 79-19-6 thiosemicarbazide 
• 99-96-7 4-hydroxy-benzoic acid 
• 120-47-8 Ethyl 4-hydroxybenzoate 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 137-26-8 Thiram 

Downstream Products

• 136413-99-5 4-(5-Butylsulfanyl-[1,3,4]oxadiazol-2-yl)-phenol 
• 121477-86-9 4-(5-Propylsulfanyl-[1,3,4]oxadiazol-2-yl)-phenol 
• 136413-82-6 3-[1-(3,4-Dichloro-phenylamino)-ethyl]-5-(4-hydroxy-phenyl)-3H-[1,3,4]oxadiazole-2-thione 
• 136413-81-5 3-[(3,4-Dichloro-phenylamino)-methyl]-5-(4-hydroxy-phenyl)-3H-[1,3,4]oxadiazole-2-thione 
• 136413-92-8 C₃₀H₂₄N₆O₄S₂ 
• 92792-66-0 C₁₆H₁₀N₄O₄S₂ 
• 206346-95-4 C₂₂H₂₂N₄O₄S₂ 
• 206346-97-6 C₂₄H₂₆N₄O₄S₂ 
• 206346-99-8 C₂₆H₃₀N₄O₄S₂ 

Relevant academic research and scientific papers

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 and Biological Evaluation of Oxadiazole Clubbed Thiadiazole Derivatives as Antimicrobial Agents

A series of 1,3,4-oxadiazole clubbed 1,3,4-thiadiazole derivatives were synthesized and assessed in vitro for their activity as antimicrobial agents. The target compounds 2-(5-(substituted aryl)-1, 3, 4-oxadiazol-2-ylthio)-N-(5-(substituted aryl)-1, 3, 4-thiadiazol-2-yl) acetamides (5a-5s) were synthesized using a basic condensation reaction between 5-(substituted aryl)-1,3,4-oxadiazole-2-thiol and 2-chloro-N-(5-(substituted aryl)-1,3,4-thiadiazol-2-yl)acetamide in presence of K2CO3 as a scavenging agent and acetone as reaction solvent. The titled compounds synthesized here, exhibited excellent to moderate antimicrobial activity against a broad panel of antibacterial strains of Gram-positive and Gram-negative bacteria and fungi.

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 neuraminidase inhibitor as well as preparation method and application thereof

The invention relates to a 1, 3, 4-oxadiazole neuraminidase inhibitor as well as a preparation method and an application thereof. The inhibitor has a structure as shown in a formula (I). The preparation method specifically comprises the following steps: (1) reacting aniline, chloroacetyl chloride and triethylamine, and performing post-treatment to obtain an intermediate as shown in a formula (II); (2) performing reaction on benzoyl hydrazine, carbon disulfide and potassium hydroxide, and performing post-treatment to obtain an intermediate as shown in a formula (III); and (3) dissolving the intermediate shown in the formula (II) and the intermediate shown in the formula (III) in an organic solvent, reacting, and performing post-treatment to obtain the inhibitor shown in the formula (I). Compared with the prior art, the compound is novel in structure, and experiments show that the compound has good neuraminidase inhibitory activity and can be used for preparing drugs for inhibiting neuraminidase activity.

Design, synthesis, and in vitro evaluation of novel 1,3,4-oxadiazolecarbamothioate derivatives of Rivastigmine as selective inhibitors of BuChE

Rivastigmine has been prescribed for the therapy of Alzheimer’s disease (AD) symptoms. This drug is classified in the carbamate derivative group that has dual activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). According to the structure of Rivastigmine and its performance, a new series of 5-aryl-1,3,4-oxadiazole-2-carbamothioate compounds I–XI was synthesized using structure-based drug discovery approaches. For this purpose a set of these compounds were designed with computational docking method and their interactions with amino acid residues in the active sites of AChE and BuChE checked out. The structures of synthesized compounds were established by physicochemical and spectroscopic methods. The carbamoyl moiety of Rivastigmine structure was modified to carbamothioate and the effects of 1,3,4-oxadiazole heterocycle as a pharmacophoric nucleus were investigated. The potential of the synthesized compounds I–XI was evaluated against two most known agents of AD (AChE and BuChE) to determine their IC50 values. The results of the docking showed the range of binding affinity for the best poses of ten individual conformers for any compounds (I–XI) was between ?7.81 (VI) and ?6.75 (II) kcal/mol. The results of biological experiments displayed that most synthetic compounds (I–VIII) showed moderate to excellent selective activity range against BuChE (0.51–69.44 μM). In vitro cytotoxicity evaluation of these compounds (I–XI) by MTT assay on human dermal fibroblast (HDF) cell line exhibited no activity against HDF. The compound VI [S-(5-(p-tolyl)-1,3,4-oxadiazol-2-yl) ethyl(methyl)carbamothioate] showed the most stable binding affinity (?7.81 kcal/mol) and the lowest IC50 value (0.51 μM) in comparison with Rivastigmine with 7.72 μM and Donepezil with 5.20 μM against BuChE.

COMPOUNDS COMPRISING CLEAVABLE LINKER AND USES THEREOF

Provided are a compound including a cleavable linker, a use thereof, and an intermediate compound for preparing the same, and more particularly, the compound including a cleavable linker of the present invention may include an active agent (for example, a drug, a toxin, a ligand, a probe for detection, etc.) having a specific function or activity, a SO2 functional group which is capable of selectively releasing the active agent, and a functional group which triggers a chemical reaction, a physicochemical reaction and/or a biological reaction by external stimulation, and may further include a ligand (for example, oligopeptide, polypeptide, antibody, etc.) having binding specificity for a desired target receptor.

COMPOUNDS COMPRISING CLEAVABLE LINKER AND USES THEREOF

Provided are a compound including a cleavable linker, a use thereof, and an intermediate compound for preparing the same, and more particularly, the compound including a cleavable linker of the present invention may include an active agent (for example, a drug, a toxin, a ligand, a probe for detection, etc.) having a specific function or activity, a -S(=0)(=N-)- functional group which is capable of selectively releasing the active agent, and a functional group which triggers a chemical reaction, a physicochemical reaction and/or a biological reaction by external stimulation, and may further include a ligand (for example, oligopeptide, polypeptide, antibody, etc.) having binding specificity for a desired target receptor.

Tunable Heteroaromatic Sulfones Enhance in-Cell Cysteine Profiling

Heteroaromatic sulfones react with cysteine via nucleophilic aromatic substitution, providing a mechanistically selective and irreversible scaffold for cysteine conjugation. Here we evaluate a library of heteroaromatic sulfides with different oxidation st