389120-03-0

Basic information

• Product Name: 5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOLE-2-THIOL
• Synonyms: 5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOLE-2-THIOL;1,3,4-Oxadiazole-2(3H)-thione, 5-[4-(trifluoroMethyl)phenyl]-;5-[4-(trifluoromethyl)phenyl]-3H-1,3,4-oxadiazole-2-thione
• CAS NO: 389120-03-0
• Molecular Formula: C₉H₅F₃N₂OS
• Molecular Weight: 246.21
• Mol File: 389120-03-0.mol

Chemical Properties

• Boiling Point: 252.1 °C at 760 mmHg
• Flash Point: 106.3 °C
• Appearance: /
• Density: 1.54 g/cm³
• Vapor Pressure: 0.0197mmHg at 25°C
• Refractive Index: 1.592
• CAS DataBase Reference: 5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOLE-2-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOLE-2-THIOL(389120-03-0)
• EPA Substance Registry System: 5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOLE-2-THIOL(389120-03-0)

Safety Data

• Hazardous Substances Data: 389120-03-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOLE-2-THIOL is used as a key intermediate in the synthesis of various pharmaceuticals for its potential antimicrobial, antifungal, and antitumor properties. Its unique structure allows for the development of new drugs that can target a wide range of diseases and conditions.
Used in Agrochemical Industry:
In the agrochemical field, 5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOLE-2-THIOL serves as a valuable component in the creation of pesticides and other agrochemicals. Its biological activities can be harnessed to protect crops from various pathogens and pests, thereby increasing agricultural productivity and crop yields.
Used in Medicinal Chemistry Research:
5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOLE-2-THIOL is utilized as a subject of study in medicinal chemistry research to explore its potential applications in drug discovery. Its unique structural features and biological activities make it an attractive target for the development of novel therapeutic agents.
Used in Drug Synthesis:
As a building block in drug synthesis, 5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOLE-2-THIOL is used to create new compounds with potential therapeutic effects. Its incorporation into drug molecules can lead to the discovery of innovative treatments for various medical conditions.
Used in Antimicrobial Agents:
5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOLE-2-THIOL is employed as an antimicrobial agent, leveraging its biological activity to combat bacterial infections. Its potential use in this area can contribute to the development of new antibiotics to address the growing issue of antibiotic resistance.
Used in Antifungal Agents:
5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOLE-2-THIOL is also used as an antifungal agent, targeting fungal infections and helping to develop new treatments for a variety of fungal diseases.
Used in Antitumor Agents:
5-[4-(TRIFLUOROMETHYL)PHENYL]-1,3,4-OXADIAZOLE-2-THIOL is utilized in the development of antitumor agents, where its potential to inhibit tumor growth and progression is explored, offering new possibilities for cancer treatment.

InChI:InChI=1/C9H5F3N2OS/c10-9(11,12)6-3-1-5(2-4-6)7-13-14-8(16)15-7/h1-4H,(H,14,16)

Upstream product

• 75-15-0 carbon disulfide 
• 339-59-3 4-(trifluoromethyl)benzoic acid hydrazide 
• 583-02-8 ethyl 4-(trifluoromethyl)benzoate 
• 2967-66-0 methyl 4-(trifluoromethyl)benzoate 
• 455-24-3 4-trifluoromethylbenzoic acid 

Downstream Products

• 389120-02-9 2-(6,6,5-trifluorohex-5-enylthio)-5-(4-trifluoromethylphenyl)-1,3,4-oxadiazole 
• 158668-56-5 E-2-Methoxyimino-2-[(2-[5-(4-trifluoromethylphenyl)-1,3,4-oxadiazol-2-yl]thiomethyl)phenyl]-N-methylacetamide 
• 202823-22-1 5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-(3H)-one 
• 1610410-44-0 2-{[6-(4-Fluorophenyl)thieno[3,2-d]pyrimidin-4-yl]thio}-5-[4-(trifluoromethyl)-phenyl]-1,3,4-oxadiazole 
• 1610730-74-9 2-[(8-phenyl-9H-purin-6-yl)thio]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazole 

Relevant articles and documents

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

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.].

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.

5-Aryl-1,3,4-oxadiazol-2-ylthioalkanoic Acids: A Highly Potent New Class of Inhibitors of Rho/Myocardin-Related Transcription Factor (MRTF)/Serum Response Factor (SRF)-Mediated Gene Transcription as Potential Antifibrotic Agents for Scleroderma

Through a phenotypic high-throughput screen using a serum response element luciferase promoter, we identified a novel 5-aryl-1,3,4-oxadiazol-2-ylthiopropionic acid lead inhibitor of Rho/myocardin-related transcription factor (MRTF)/serum response factor (SRF)-mediated gene transcription with good potency (IC50 = 180 nM). We were able to rapidly improve the cellular potency by 5 orders of magnitude guided by sharply defined and synergistic SAR. The remarkable potency and depth of the SAR, as well as the relatively low molecular weight of the series, suggests, but does not prove, that binding to the unknown molecular target may be occurring through a covalent mechanism. The series nevertheless has no observable cytotoxicity up to 100 μM. Ensuing pharmacokinetic optimization resulted in the development of two potent and orally bioavailable anti-fibrotic agents that were capable of dose-dependently reducing connective tissue growth factor gene expression in vitro as well as significantly reducing the development of bleomycin-induced dermal fibrosis in mice in vivo.

Synthesis and bioactivity of sulfide derivatives containing 1,3,4-oxadiazole and pyridine

A series of novel sulfide derivatives containing 1,3,4-oxadiazole and pyridine were synthesized, characterized, and tested for their antibacterial activity against tobacco bacterial wilt and rice bacterial blight and for insecticidal activity toward diamondback moth. The results showed that some compounds had good insecticidal and bactericidal activity, e.g., the activities of compounds 6e and 6g–6j toward tobacco bacterial wilt were much better than those of commercial thiodiazole-copper, and some of the synthesized compounds possessed good insecticidal activity against Plutella xylostella. Compounds 6d, 6h, 6j, 6l, 6p, 6r, and 6p displayed over 93% activity at 500 mg L? 1.

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.

INHIBITORS OF RHO/MRTF/SRF-MEDIATED GENE TRANSCRIPTION AND METHODS FOR USE OF THE SAME

Disclosed herein are inhibitors of Rho/MRTF/SRF-mediated gene transcription, and methods for their use in treating or preventing diseases such as cancer and fibrosis. In particular, disclosed herein are compounds of Formula (I) and pharmaceutically accept

Synthesis and biological activities of cyclanone O-(2-(3-aryl-4- amino-4H-1,2,4-triazol-3-yl)thio)acetyl)oxime derivatives

Twelve cyclanone O-(2-(3-aryl-4-amino-4H-1,2,4-triazol-3-yl)thio)acetyl)oxime derivatives were synthesized and their structures were confirmed by spectroscopy (IR, 1H NMR, 13C NMR, 19F NMR) and elemental analysis. Their antifungal and antibacterial activities were evaluated against six fungi (Gibberella zeae, Fusarium oxysporum, Clematis mandshurica, Phytophthora infestans, Paralepetopsis sasakii, Sclerotinia sclerotiorum) and two bacteria (Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas citri subsp. Citri (Xcc)). The results indicated that most of the title compounds exhibited good antibacterial activities. Among them, compounds 6d, 6g, 6h, and 6j showed better antibacterial activities against Xoo and Xcc than that of the commercial agent thiodiazole-copper.

Synthesis and biological evaluation of novel resveratrol-oxadiazole hybrid heterocycles as potential antiproliferative agents

A novel class of resveratrol-oxadiazole hybrid compounds was synthesized to screen for their in vitro antiproliferative activity against three human cancer cell lines. All the compounds showed superior antiproliferative activity than the reference compound resveratrol. The most promising active compounds in this series were 1g, 2g, 1c, 2c, 2i and 1a (GI50 0.1 μM), endowed with excellent antiproliferative activity. Thus, we believe that resveratrol-oxadiazole hybrid compounds may possibly be used as a good leads for the development of new antiproliferative agents. Structures of newly synthesized compounds were confirmed by NMR and IR spectral data.

Rational design, synthesis and biological evaluation of 1,3,4-oxadiazole pyrimidine derivatives as novel pyruvate dehydrogenase complex E1 inhibitors

On the basis of previous study on 2-methylpyrimidine-4-ylamine derivatives I, further synthetic optimization was done to find potent PDHc-E1 inhibitors with antibacterial activity. Three series of novel pyrimidine derivatives 6, 11 and 14 were designed and synthesized as potential Escherichia coli PDHc-E1 inhibitors by introducing 1,3,4-oxadiazole-thioether, 2,4-disubstituted-1,3-thiazole or 1,2,4-triazol-4-amine-thioether moiety into lead structure I, respectively. Most of 6, 11 and 14 exhibited good inhibitory activity against E. coli PHDc-E1 (IC50 0.97-19.21 μM) and obvious inhibitory activity against cyanobacteria (EC50 0.83-9.86 μM). Their inhibitory activities were much higher than that of lead structure I. 11 showed more potent inhibitory activity against both E. coli PDHc-E1 (IC50 50 50 = 0.97 μM) and cyanobacteria (EC50 = 0.83 μM). The possible interactions of the important residues of PDHc-E1 with title compounds were studied by molecular docking, site-directed mutagenesis, and enzymatic assays. The results indicated that 11d had more potent inhibitory activity than that of 14d or I due to its 1,3,4-oxadiazole moiety with more binding position and stronger interaction with Lsy392 and His106 at active site of E. coli PDHc-E1.