16629-40-6

Usage

Uses

Used in Organic Synthesis:
4-PHENYL-5-PYRIDIN-4-YL-4H-[1,2,4]TRIAZOLE-3-THIOL is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, such as coupling and condensation reactions. Its unique structure allows it to be a versatile building block for the development of new compounds with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-PHENYL-5-PYRIDIN-4-YL-4H-[1,2,4]TRIAZOLE-3-THIOL is used as a key intermediate in the synthesis of novel drug candidates. Its structural diversity and reactivity make it a valuable component in the development of new therapeutic agents, particularly those targeting complex biological systems.
Used in Chemical Research:
4-PHENYL-5-PYRIDIN-4-YL-4H-[1,2,4]TRIAZOLE-3-THIOL is also utilized in academic and industrial research settings as a model compound for studying various chemical reactions and mechanisms. Its unique properties provide insights into the behavior of similar compounds and contribute to the advancement of chemical knowledge.
Used in Material Science:
In the field of material science, 4-PHENYL-5-PYRIDIN-4-YL-4H-[1,2,4]TRIAZOLE-3-THIOL may be employed in the development of new materials with specific properties, such as improved stability, reactivity, or selectivity. Its incorporation into polymers or other materials could lead to innovative applications in various industries, including electronics, coatings, and adhesives.

InChI:InChI=1/C13H10N4S/c18-13-16-15-12(10-6-8-14-9-7-10)17(13)11-4-2-1-3-5-11/h1-9H,(H,16,18)

Upstream product

• 172661-65-3 C₁₆H₁₇N₅S 
• 172661-61-9 C₁₉H₁₇N₅S 
• 172661-62-0 C₂₀H₁₉N₅S 
• 172661-67-5 C₂₀H₁₉N₅S 
• 172661-63-1 C₁₉H₁₆BrN₅S 
• 172661-66-4 C₁₇H₁₉N₅O₂S 
• 172661-64-2 C₁₉H₁₆N₆O₂S 
• 326597-54-0 C₃₂H₂₈N₁₀S₂ 
• 6954-50-3 1-isonicotinoyl-4-phenylthiosemicarbazide 
• 54-85-3 isoniazid 
• 103-72-0 phenyl isothiocyanate 
• 4044-65-9 1 ,4-phenylenediisothiocyanate 
• 62-53-3 aniline 
• 2459-09-8 4-pyridinecarboxylic acid, methyl ester 

Downstream Products

• 325694-00-6 1-(4-fluorophenyl)-2-[(4-phenyl-5-pyridin-4-yl-4H-1,2,4-triazol-3-yl)thio]ethanone 
• 496777-70-9 1-(2,4-dichlorophenyl)-2-[(4-phenyl-5-pyridin-4-yl-4H-1,2,4-triazol-3-yl)thio]ethanone 
• 743477-44-3 N-(4-{2-[(4-phenyl-5-pyridin-4-yl-4H-1,2,4-triazol-3-yl)thio]acetyl}phenyl)acetamide 
• 325693-94-5 1-(4-chlorophenyl)-2-[(4-phenyl-5-pyridin-4-yl-4H-1,2,4-triazol-3-yl)thio]ethanone 
• 743477-45-4 6-{[(4-phenyl-5-pyridin-4-yl-4H-1,2,4-triazol-3-yl)thio]acetyl}-1,3-benzoxazol-2(3H)-one 
• 154626-74-1 tris(3-(4-pyridyl)-4-phenyl-1,2,4-triazole-5-thione)triphenylphosphinepalladium⁽⁰⁾ 
• 1269527-24-3 6-{[4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-ylthio]methyl}-N₂-o-tolyl-1,3,5-triazine-2,4-diamine 
• 1269527-23-2 N₂-(4-methoxyphenyl)-6-{[4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-ylthio]methyl}-1,3,5-triazine-2,4-diamine 
• 1404080-00-7 4-phenyl-5-pyridin-4-yl-2-(pyrrolidin-1-ylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 
• 1404080-01-8 N-methyl-N-[(4-phenyl-5-pyridin-4-yl-3-thioxo-2,4-dihydro-3H-1,2,4-triazol-2-yl)methyl]-2-aminoethanol 
• 1404080-02-9 2-[(4-bromophenylamino)methyl]-4-phenyl-5-pyridin-4-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione 
• 1404080-03-0 2-[(4-chlorobenzylamino)methyl]-4-phenyl-5-pyridin-4-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione 
• 1404079-92-0 3-[(pent-2-yl)thio]-4-phenyl-5-pyridin-4-yl-4H-1,2,4-triazole 
• 552815-53-9 3-methylthio-4-phenyl-5-pyridin-4-yl-4H-1,2,4-triazole 

Relevant academic research and scientific papers

Synthesis and crystal structure of 4-phenyl-3-(pyridin-4-yl)-1H-1,2,4- triazole-5(4H)-thione

A triazole derivative i.e., 4-phenyl-3-(pyridin-4-yl)-1H-1,2,4-triazole- 5(4H)-thione was synthesized and its structure was studied by X-ray diffraction. The crystals are orthorhombic, space group pbcn with a = 11.337 (2), b = 12.789 (3), c = 17.625 (4) ?

Discovery of antiproliferative and anti-FAK inhibitory activity of 1,2,4-triazole derivatives containing acetamido carboxylic acid skeleton

Small molecule inhibitors of the focal adhesion kinase are regarded as promising tools in our armamentarium for treating cancer. Here, we identified four 1,2,4-triazole derivatives that inhibit FAK kinase significantly and evaluated their therapeutic pote

A first-in-class anticancer dual HDAC2/FAK inhibitors bearing hydroxamates/benzamides capped by pyridinyl-1,2,4-triazoles

Novel 5-pyridinyl-1,2,4-triazoles were designed as dual inhibitors of histone deacetylase 2 (HDAC2) and focal adhesion kinase (FAK). Compounds 5d, 6a, 7c, and 11c were determined as potential inhibitors of both HDAC2 (IC50 = 0.09–1.40 μM) and F

Is Bismuth Really the "green" Metal? Exploring the Antimicrobial Activity and Cytotoxicity of Organobismuth Thiolate Complexes

Antimicrobial resistance is becoming an ever-increasing threat for human health. Metal complexes and, in particular, those that incorporate bismuth offer an attractive alternative to the typically used organic compounds to which bacteria are often able to develop resistance determinants. Herein we report the synthesis, characterization, and biological evaluation of a series of homo- and heteroleptic bismuth(III) thiolates incorporating either one (BiPh2L), two (BiPhL2), or three (BiL3) sulfur-containing azole ligands where LH = tetrazolethiols or triazolethiols (thiones). Despite bismuth typically being considered a nontoxic heavy metal, we demonstrate that the environment surrounding the metal center has a clear influence on the safety of bismuth-containing complexes. In particular, heteroleptic thiolate complexes (BiPh2L and BiPhL2) display strong antibacterial activity yet are also nonselectively cytotoxic to mammalian cells. Interestingly, the homoleptic thiolate complexes (BiL3) were shown to be completely inactive toward both bacterial and mammalian cells. Further biological analysis of the complexes revealed the first insights into the biological mode of action of these particular bismuth thiolates. Scanning electron microscopy images of methicillin-resistant Staphylococcus aureus (MRSA) cells have revealed that the cell membrane is the likely target site of action for bismuth thiolates against bacterial cells. This points toward a nonspecific mode of action that is likely to contribute to the poor selectivity's demonstrated by the bismuth thiolate complexes in vitro. Uptake studies suggest that reduced cellular uptake could explain the marked difference in activity between the homo- and heteroleptic complexes.

Identification of 1,2,4-triazoles as new thymidine phosphorylase inhibitors: Future anti-tumor drugs

Thymidine phosphorylase (TP) is over expressed in several solid tumors and its inhibition can offer unique target suitable for drug discovery in cancer. A series of 1,2,4-triazoles 3a–3l has been synthesized in good yields and subsequently inhibitory potential of synthesized triazoles 3a–3l against thymidine phosphorylase enzyme was evaluated. Out of these twelve analogs five analogues 3b, 3c, 3f, 3l and 3l exhibited a good inhibitory potential against thymidine phosphorylase. Inhibitory potential in term of IC50 values were found in the range of 61.98 ± 0.43 to 273.43 ± 0.96 μM and 7-Deazaxanthine was taken as a standard inhibitor with IC50 = 38.68 ± 4.42 μM. Encouraged by these results, more analogues 1,2,4-triazole-3-mercaptocarboxylic acids 4a–4g were synthesized and their inhibitory potential against thymidine phosphorylase was evaluated. In this series, six analogues 4b–4g exhibited a good inhibitory potential in the range of 43.86 ± 1.11–163.43 ± 2.03 μM. Angiogenic response of 1,2,4-triazole acid 4d was estimated using the chick chorionic allantoic membrane (CAM) assay. In the light of these findings, structure activity relationship and molecular docking studies of selected triazoles to determine the key binding interactions was discussed. Docking studies demonstrate that synthesized analogues interacted with active site residues of thymidine phosphorylase enzyme through π-π stacking, thiolate and hydrogen bonding interactions.

Design, Synthesis and Antibacterial Evaluation of 1-[(1R,2S)-2-Fluorocyclopropyl]ciprofloxacin-1,2,4-triazole-5(4H)-thione Hybrids

A new class of 1-[(1R,2S)-2-fluorocyclopropyl]ciprofloxacin (CPFX)-1,2,4-triazole-5(4H)-thione hybrids 6a?–?6o was designed, synthesized and evaluated for their in?vitro antibacterial activities against a panel of clinically important drug-sensitive and d

Synthesis and antitumor activity of 4-cyclohexyl/aryl-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thiones

The reaction of 2-isonicotinoyl-N-cyclohexyl/arylhydrazinecarbothioamide (2a-r) with sodium hydroxide, in each case, a single product was obtained. The structures of the compounds were confirmed on the basis of their elemental analysis and spectral data.

Narrow SAR in odorant sensing Orco receptor agonists

The systematic exploration of a series of triazole-based agonists of the cation channel insect odorant receptor is reported. The structure-activity relationships of independent sections of the molecules are examined. Very small changes to the compound structure were found to exert a large impact on compound activity. Optimal substitutions were combined using a 'mix-and-match' strategy to produce best-in-class compounds that are capable of potently agonizing odorant receptor activity and may form the basis for the identification of a new mode of insect behavior modification.

Narrow SAR in odorant sensing Orco receptor agonists

The systematic exploration of a series of triazole-based agonists of the cation channel insect odorant receptor is reported. The structure-activity relationships of independent sections of the molecules are examined. Very small changes to the compound structure were found to exert a large impact on compound activity. Optimal substitutions were combined using a 'mix-and-match' strategy to produce best-in-class compounds that are capable of potently agonizing odorant receptor activity and may form the basis for the identification of a new mode of insect behavior modification.

Design, synthesis, and herbicidal activities of 3-aryl-4-substituted-5-[3- (trifluoromethyl)phenoxy]-1,2,4-triazoles

In order to find novel bleaching herbicide lead compounds, a series of novel 3-aryl-4-substituted-5-[3-(trifluoromethyl)phenoxy]-1,2,4-triazoles were designed and synthesized by the multi-step reactions. N-(Arylformamido) phenylthioureas undergo ring clos