16629-43-9

Usage

InChI:InChI=1/C14H12N4S/c1-10-2-4-12(5-3-10)18-13(16-17-14(18)19)11-6-8-15-9-7-11/h2-9H,1H3,(H,17,19)

Upstream product

• 106-49-0 p-toluidine 
• 13036-91-4 ammonium (4-methylphenyl)carbamodithioate 
• 54-85-3 isoniazid 
• 622-59-3 1-isothiocyanato-4-methylbenzene 
• 74270-71-6 N-isonicotinyl-N'-p-methylphenylthiosemicarbazide 
• 172661-69-7 C₂₀H₁₈N₆O₂S 
• 172661-68-6 C₂₀H₁₈BrN₅S 
• 172661-71-1 C₁₈H₂₁N₅O₂S 
• 172661-74-4 C₂₁H₂₁N₅S 
• 172661-67-5 C₂₀H₁₉N₅S 
• 172661-62-0 C₂₀H₁₉N₅S 
• 172661-70-0 C₁₇H₁₉N₅S 

Downstream Products

• 76226-41-0 1-Piperidin-1-yl-3-(5-pyridin-4-yl-4-p-tolyl-4H-[1,2,4]triazol-3-ylsulfanyl)-propan-2-ol 
• 76226-38-5 1-Cyclohexylamino-3-(5-pyridin-4-yl-4-p-tolyl-4H-[1,2,4]triazol-3-ylsulfanyl)-propan-2-ol 
• 76226-39-6 1-Phenylamino-3-(5-pyridin-4-yl-4-p-tolyl-4H-[1,2,4]triazol-3-ylsulfanyl)-propan-2-ol 
• 1152333-34-0 3-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-(4-pyridyl)-4-p-methylphenyl-4H-1,2,4-triazole 
• 890-24-4 5-(4-pyridyl)-4-(p-tolyl)-1,2,4-triazole 
• 743477-52-3 1-(2,4-dichlorophenyl)-2-{[4-(4-methylphenyl)-5-pyridin-4-yl-4H-1,2,4-triazol-3-yl]thio}ethanone 
• 338426-02-1 1-(4-methoxyphenyl)-2-{[4-(4-methylphenyl)-5-pyridin-4-yl-4H-1,2,4-triazol-3-yl]thio}ethanone 

Relevant academic research and scientific papers

4-(4-Methylphenyl)-3-(4-pyridyl)-1H,2,4-triazole-5(4H)-thione

The title compound, C14H12N4S, crystallizes with two independent molecules which differ slightly in conformation. The methyl-substituted phenyl ring is inclined at angles of 67(1) and 76(1)° with respect to the 1,2,4-triaz

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 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

Novel syntheses of some 1, 2, 4-triazoles as potent bacteriocidal agents

A facile syntheses of 4-aryl-5-(isomeric pyridoyl)-3H-1, 2, 4-triazoles as potent bacteriocidal agents are described. The newly synthesized compounds were characterized by spectral and elemental analyses. Some compounds were screened for their antibacterial activity against S. aureus, E. coli, B. subtilis and P.aeruginosa. All compounds carrying 1, 2, 4- triazole moiety showed significant biological activity.

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.

Photochemical synthesis of triazolo[3,4-b]-1,3(4H)-benzothiazines: A detailed mechanistic study on photocyclization/photodesulfurisation of triazole-3-thiones

Irradiation of 4-(2-halobenzyl)-5-substituted-1,2,4-triazole-3-thiones under base mediated (CH3CN/2 M NaOH) condition afforded triazolo[3,4-b]-1,3(4H)-benzothiazines and desulfurized triazoles. Benzophenone sensitized photolysis of triazole-3-thiones gave desulfurized triazoles exclusively. The mechanism of the photocyclization/photodesulfurization and the involvement of singlet and triplet energy levels are discussed.