175276-77-4

Basic information

• Product Name: 5-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]-1,2,4-TRIAZOLE-3-(2H)-THIONE
• Synonyms: 5-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]-1,2,4-TRIAZOLE-3-(2H)-THIONE;Bistrifluoromethylphenyltriazolethione;5-[3,5-Bis(trifluoromethyl)phenyl]-1,2,4-triazole-3(2H)thione 97%;5-[3,5-Bis(trifluoromethyl)phenyl]-1,2,4-triazole-3(2H)thione97%;5-[3,5-di(trifluoromethyl)phenyl]-1H-1,2,4-triazole-3-thiol;3-[3,5-Bis(trifluoromethyl)phenyl]-4,5-dihydro-5-thioxo-1H-1,2,4-triazole;5-[3,5-Bis(trifluoromethyl)phenyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione 97%;5-[3,5-Bis(trifluoromethyl)phenyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione97%
• CAS NO: 175276-77-4
• Molecular Formula: C₁₀H₅F₆N₃S
• Molecular Weight: 313.22
• Mol File: 175276-77-4.mol

Chemical Properties

• Melting Point: 280 °C
• Boiling Point: 267.7°Cat760mmHg
• Flash Point: 115.7°C
• Appearance: /
• Density: 1.66g/cm³
• Vapor Pressure: 0.00805mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: 5-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]-1,2,4-TRIAZOLE-3-(2H)-THIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]-1,2,4-TRIAZOLE-3-(2H)-THIONE(175276-77-4)
• EPA Substance Registry System: 5-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]-1,2,4-TRIAZOLE-3-(2H)-THIONE(175276-77-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 175276-77-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
5-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]-1,2,4-TRIAZOLE-3-(2H)-THIONE is used as a pharmaceutical agent for its antifungal, antibacterial, and antitumor properties. Its diverse biological activities make it a promising candidate for the development of new drugs to treat various diseases and infections.
Used in Agricultural Applications:
In the agricultural industry, 5-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]-1,2,4-TRIAZOLE-3-(2H)-THIONE is used as a bioactive compound for its potential to control fungal and bacterial infections in crops, thereby improving crop yield and quality.
Used in Drug Development:
5-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]-1,2,4-TRIAZOLE-3-(2H)-THIONE is used as a building block in drug development due to its potential to enhance the metabolic stability and bioavailability of new drug candidates. Its presence in the molecular structure can improve the overall pharmacokinetic and pharmacodynamic properties of the drug, leading to more effective treatments.
Used in Synthesis of Heterocyclic Compounds:
In the field of organic chemistry, 5-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]-1,2,4-TRIAZOLE-3-(2H)-THIONE is used as a versatile building block for the synthesis of various heterocyclic compounds with diverse biological activities. Its unique structure allows for the creation of new compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C10H5F6N3S/c11-9(12,13)5-1-4(7-17-8(20)19-18-7)2-6(3-5)10(14,15)16/h1-3H,(H2,17,18,19,20)

Upstream product

• 785-56-8 3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride 
• 79-19-6 thiosemicarbazide 

Relevant articles and documents

Pyrimidine compound as well as preparation method and application thereof

The invention provides a pyrimidine compound and a preparation method and application thereof. The pyrimidine compound has a structure as shown in formula I, and R1 is selected from at least one of hydrogen, halogen, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C1-6 alkoxy, phenyl, cyano, aldehyde and nitro; R2 is selected from hydrogen, halogen, amino substituted by C1-6 alkyl, and substituted or unsubstituted azacycloalkyl; R3 is located at the third position and the fifth position of a benzene ring and is independently selected from trifluoromethyl or fluorine respectively; X is selected from one of oxygen, sulfur and nitrogen; and A, B, C and Z are independently selected from carbon or nitrogen. The pyrimidine compound provided by the invention is an effective SecA inhibitor, has broad-spectrum antibacterial activity, and has good antibacterial activity on drug-resistant strains such as MRSA, MRSE, VISA, VRE and the like.

Design, Synthesis and Evaluation of Triazole-Pyrimidine Analogues as SecA Inhibitors

SecA, a key component of the bacterial Sec-dependent secretion pathway, is an attractive target for the development of new antimicrobial agents. Through a combination of virtual screening and experimental exploration of the surrounding chemical space, we identified a hit bistriazole SecA inhibitor, SCA-21, and studied a series of analogues by systematic dissections of the core scaffold. Evaluation of these analogues allowed us to establish an initial structure-activity relationship in SecA inhibition. The best compounds in this group are potent inhibitors of SecA-dependent protein-conducting channel activity and protein translocation activity at low- to sub-micromolar concentrations. They also have minimal inhibitory concentration (MIC) values against various strains of bacteria that correlate well with the SecA and protein translocation inhibition data. These compounds are effective against methicillin-resistant Staphylococcus aureus strains with various levels of efflux pump activity, indicating the capacity of SecA inhibitors to null the effect of multidrug resistance. Results from studies of drug-affinity-responsive target stability and protein pull-down assays are consistent with SecA as a target for these compounds. One stone, several birds! The SecA inhibitors discovered in this study are broad-spectrum antimicrobials with the intrinsic ability to null the effect of efflux pumps. They are therefore effective against multidrug-resistant bacterial strains, can inhibit virulence factor secretion, and are very active against strains of bacteria that are resistant to antibiotics in current use, including vancomycin.