74270-76-1

Usage

InChI:InChI=1/C13H9ClN4S/c14-10-1-3-11(4-2-10)18-12(16-17-13(18)19)9-5-7-15-8-6-9/h1-8H,(H,17,19)

Upstream product

• 2131-55-7 4-Chlorophenyl isothiocyanate 
• 74270-72-7 N-(4-chlorophenyl)-2-(pyridin-4-ylcarbonyl)hydrazinecarbothioamide 
• 54-85-3 isoniazid 
• 1197-56-4 ammonium (4-chlorophenyl)carbamodithioate 
• 106-47-8 4-chloro-aniline 

Downstream Products

• 743477-53-4 2-{[4-(4-chlorophenyl)-5-pyridin-4-yl-4H-1,2,4-triazol-3-yl]thio}-1-(2,4-dichlorophenyl)ethanone 
• 76226-42-1 1-[4-(4-Chloro-phenyl)-5-pyridin-4-yl-4H-[1,2,4]triazol-3-ylsulfanyl]-3-isopropylamino-propan-2-ol; hydrochloride 
• 1152333-40-8 3-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-(4-pyridyl)-4-p-chlorophenyl-4H-1,2,4-triazole 
• 865571-13-7 C₂₃H₁₇ClN₆OS 
• 74271-11-7 ethyl {[4-(4-chlorophenyl)-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetate 
• 498546-23-9 2-{[4-(4-chlorophenyl)-5-pyridin-4-yl-4H-1,2,4-triazol-3-yl]thio}-1-(4-methoxyphenyl)ethanone 

Relevant academic research and scientific papers

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.

Synthesis, anti-inflammatory, antimicrobial potential and molecular docking studies of 4,5-disubstituted-1,2,4-triazole thioacetate derivatives

Background: In the present study synthesis and biological assessment of nine new ethyl [(4,5-disubstituted-4H-1,2,4-triazol-3-yl)sulfanyl]acetate derivatives 2(a-i) is performed. Methods: The title compounds were characterized by their analytical and spec

Synthesis and antimicrobial activity of some new 1,2,4-trizoles

A series of 1,2,4-triazole derivatives were synthesized using appropriate synthetic route and structures were confirmed by IR,1H NMR and elemental analysis. All the synthesized compounds (6a-6h and 7a-7h) were evaluated for antimicrobial activity by determining their minimum inhibitory concentrations (MICs) against a panel of Gram-positive, Gram-negative bacteria and fungi. Most of the compounds showed significant antimicrobial activity against Gram-positive bacteria viz. S. aureus, B. subtilis, Gram-negative bacteria viz. E. coli, P. aerugenosa and fungi viz. C. albicans, A. niger. Some of the compounds showed better antibacterial activities against Gram-positive bacteria compared to Gram-negative bacteria. Compounds 7g, 6g, 6a exhibited good MICs against Gram-positive bacteria and 7f showed better MICs against Gram-negative bacteria compared to reference norfloxacin. Compounds 7f and 7d exhibited MICs which is equipotent to the reference drug ketoconazole.

Synthesis and anticancer evaluation of 1,3,4-oxadiazoles, 1,3,4-thiadiazoles, 1,2,4-triazoles and mannich bases

A series of 5-(pyridin-4-yl)-N-substituted-1,3,4-oxadiazol-2-amines (3a-d), 5-(pyridin-4-yl)-N-substituted- 1,3,4-thiadiazol-2-amines (4a-d) and 5-(pyridin-4-yl)-4-substituted-1,2,4-triazole-3-thiones (5a-d) were obtained by the cyclization of hydrazinecarbothioamide derivatives 2a-d derived from isonicotinic acid hydrazide. Aminoalkylation of compounds 5a-d with formaldehyde and various secondary amines furnished the Mannich bases 6a-p. The structures of the newly synthesized compounds were confirmed on the basis of their spectral data and elemental analyses. All the compounds were screened for their in vitro anticancer activity against six human cancer cell lines and normal fibroblast cells. Sixteen of the tested compounds exhibited significant cytotoxicity against most cell lines. Among these derivatives, the Mannich bases 6j, 6m and 6p were found to exhibit the most potent activity. The Mannich base 6m showed more potent cytotoxic activity against gastric cancer NUGC (IC50=0.021 μM) than the standard CHS 828 (IC50=0.025 μM). Normal fibroblast cells WI38 were affected to a much lesser extent (IC50>10 μM).

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.

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

AZOLE DERIVATIVES AS WTN PATHWAY INHIBITORS

The present invention relates to new compounds of formula I, to processes for their preparation, to pharmaceutical formulations containing such compounds and to their use in therapy. Such compounds find particular use in the treatment and/or prevention of conditions or diseases which are affected by over-activation of signaling in the Wnt pathway. For example, these may be used in preventing and/or retarding proliferation of tumor cells, for example carcinomas such as colon carcinomas.

Synthesis and molecular structure of new S-nucleosides of 5-(4-pyridyl)-4-aryl-4H-1,2,4-triazole-3-thiols

The synthesis of some new S-nucleosides of 5-(4-pyridyl)-4-aryl-4H-l,2,4- triazole-3-thiols (4a-n) is described. Direct glycosylation of (4a-n) with tetra-O-acetyl-α-D-glucopyranosyl bromide in the presence of potassium hydroxide followed by deacetylation using dry ammonia in methanol gave the corresponding 3-S-(β-D-glucopyranosyl)-5-(4-pyridyl)-4-aryl-4H-l,2,4- triazoles (6a-n) in good yields. All the compounds were fully characterized by means of 1H NMR, 13C NMR spectra and elemental analyses. To assist in the interpretation of the spectroscopic data, the crystal structure of 3-S-(2′,3′,4′,6′-tetra-O-acetyl-β-D- glucopyranosyl)-5-(4-pyridyl)-4-phenyl-4H-l,2,4-triazole (5a) was determined by X-ray diffraction.

Novel anthelmintic and insecticidal compositions

The present invention relates to novel anthelmintic and insecticidal compositions in general, and, more specifically, compositions containing triazole derivatives as active ingredients.

Synthesis and structure elucidation of some new thioether derivatives of 1,2,4-triazoline-3-thiones and their antimicrobial activities.

5-(4-Pyridinyl)-4-substituted-2.4-dihydro-3H-1,2,4-triazole-3-thiones and 5-(4-pyridinyl)-4-substituted-3-(benzoylmethyl)thio-4H-1,2,4-triazoles were synthesized. The structures of original nine compounds were confirmed by IR, 'H NMR, mass spectral methods and elemental analysis. The antibacterial, antifungal and antimycobacterial activities, together with those of known intermediate 1,4-disubstituted thiosemicarbazides, were reported.