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Triazoles

Triazoles are a class of heterocyclic organic compounds containing a five-membered ring with three nitrogen atoms.
These compounds have diverse pharmaceutical and agricultural applications, including use as antifungal, antidepressant, and herbicide agents.
Triazoles exhibit a broad spectrum of biological activities and are an important area of research in medicinal chemistry and related fields.
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Most cited protocols related to «Triazoles»

To investigate the COX-2 isozyme templated synthesis, each 5-azido-pyraozle (5, 14, 27, and 31, 1 µl of 3 mM DMSO solution) and alkyne (6a6f, 15a15e, 1 µl of 20 mM DMSO solution) were pairwise mixed with human recombinant COX-2 isozyme (95 µl COX-2) in 1 µl of 1 M Tris-HCl, pH 8.0. The each reaction mixture was vortexed for 1 min, and then incubated at room temperature (For temperature dependency of COX-2 enzyme activity, see Supplementary Fig. 16). Final reagent concentrations were as follows: COX-2 (7 µM), azide (30 µM) alkyne (200 µM). After 3, 6, 9, 12, 15, 18, 21, and 24 h each sample was analyzed in triplicate by injecting (10 µl) into the LC/MS instrument with SIM mode (Water’s Micromass ZQTM 4000 LC−MS instrument, operating in the ESI-positive mode, equipped with a Water’s 2795 separation module). Calibration curve for hit compounds 18 and 21 is given in Supplementary Fig. 17. Summaries of all LC/MS data are presented in Supplementary Tables 37. Separations were performed in triplicate using a Kromasil 100-5-C18 (100 μm pore size, 5 μm particle size) reverse phase column (2.1 mm diameter × 50 mm length), preceded by a Kromasil 100-5-C18 2.1 × guard column. Separations were effected using a gradient MeCN/H2O (0.05% trifluoroacetic acid (TFA))/MeOH in 40/30/30, v/v/v over 15 min at flow rate 0.25 ml min−1. Operating parameters were as follows: capillary voltage = 3.5 kV; cone voltage = 20 V; source temperature = 140 °C; sesolvation temperature = 250 °C; cone nitrogen gas flow = 100 l h−1; desolvation nitrogen gas flow = 550 l h−1. The identities of triazole products (retention time of 6.73 min for 18), (retention time of 4.56 min for 21), and the internal standard (retention time of 10.89 min) were confirmed by molecular weight and comparison of the retention times of the authentic products formed from copper catalyzed reactions. Control experiments in the presence of BSA (1 mg mL−1) instead of the COX-2 enzyme as well as in the absence of COX-2 enzyme and the known COX-2 selective inhibitor (1 µl of celecoxib, 100 µM final concentration) were run as described above. For multicomponent in situ click chemistry reactions, each azide (5, 14, 27, and 31, 1 µL of 3 mM DMSO solution) and eleven alkynes (6a6f and 15a15e, 1 µl of 20 mM DMSO solution) were thoroughly mixed together in the presence of COX-2 isozyme (95 µl COX-2) in 1 µl of 1 M Tris-HCl, pH 8.0 and incubated at room temperature. After 24 h each sample was analyzed in triplicate by injecting (10 µl) into the LC/MS instrument by following the procedure described above, except the ions are monitored for all possible masses. The cyclo addition products were identified by their molecular weights and by comparison of the retention times of authentic products prepared through Cu-catalyzed reactions. Control experiments using BSA (1 mg ml−1) in place of COX-2 isozyme and in the absence of COX-2 isozyme were run consecutively.
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Publication 2017
Alkynes Anabolism Azides Capillaries Celecoxib compound 18 Copper Cyclooxygenase 2 Inhibitors enzyme activity Enzymes Homo sapiens Ions Isoenzymes Nitrogen PTGS2 protein, human Retention (Psychology) Retinal Cone Sulfoxide, Dimethyl Triazoles Trifluoroacetic Acid Tromethamine
The ability of known COX-2 selective inhibitor celecoxib (1), 5-azido-pyraozles (5 and 14) and new triazole products (7–12, 16–25, 28, 29, 32, and 33) to inhibit ovine COX-1 and recombinant human COX-2 was determined using a COX inhibitor assay (Cayman Chemical, Ann Arbor, USA; item number: 700100) following the manufacturer’s protocol. Each compound was assayed in concentration range of 10−9 M to 10−3 M, in triplicate. PRISM5 software was used to calculate IC50 values. In addition to celecoxib, both Dup-697 (potent COX-2 inhibitor) and SC-560 (potent COX-1 inhibitor) were used as internal controls during screening test compounds.
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Publication 2017
Caimans Cardiac Arrest Celecoxib Cyclooxygenase 2 Inhibitors DuP 697 Homo sapiens PTGS1 protein, human PTGS2 protein, human SC 560 Sheep Triazoles
Blood samples were drawn at the examination into serum separator tubes without anticoagulant, centrifuged at 1430 × g for 15 minutes, and 1.8 milliliters of serum transferred to Nunc Cryotubes and stored at −80C for future analysis. 100 μL of serum was mixed with 25D3–[2H6] and 24R,25-(OH)2D3–[2H6] isotopic internal standards dissolved in 5% bovine serum albumin (IsoSciences, Inc., King of Prussia, PA). Total 25D3 and 24,25D3 were extracted away from DBP and other serum binding factors by protein precipitation with 250 μL methanol and cleared by centrifugation. Vitamin D metabolites were isolated from extracted supernatants by solid phase extraction chromatography (Strata C-18E 96-well SPE plates, Phenomenex, Inc., Torrences, CA), and eluted with 1 mL ethyl acetate containing 0.1 mg/mL 4-Phenyl-1,2,4-triazole-3,5-dione (PTAD). PTAD-derivatized samples were dried under vacuum and redissolved with 100 μL of 50% ethanol. Samples were then analyzed for vitamin D metabolites using reverse phase chromatography coupled to tandem mass spectrometry in multiple reaction monitoring mode (intra-assay CV 1.1% and 3.5% for 25D3 and 24,25(OH)2D3,respectively). Assays were calibrated using 25D3 and 24R,25-(OH)2D3 commercial standards (Cerilliant, Inc., Round Rock, TX). Intact PTH levels were measured using the Cobas electrochemiluminescense immunoassay on the Modular Analytics E170 automated analyzer (Roche Diagnostics, Indianapolis, IN, USA; inter-assay CV 2.5%). Additional method details are described in the online Supplementary Materials file.
Publication 2015
4-phenyl-1,2,4-triazoline-3,5-dione Anticoagulants Biological Assay BLOOD Centrifugation Chromatography Chromatography, Reverse-Phase Diagnosis Ergocalciferol Ethanol ethyl acetate Immunoassay Isotopes Methanol Serum Serum Albumin, Bovine Serum Proteins Solid Phase Extraction Tandem Mass Spectrometry Triazoles Vacuum
The deoxynucleoside triazole (0.119 mmol, 1.0 equiv.) and tributylammonium pyrophosphate (0.238 mmol, 2.0 equiv.) were dried under high vacuum for 1 h at ambient temperature in separate round bottom flasks. Throughout the entire experiment, the reaction was maintained under an argon atmosphere. The deoxynucleoside triazole was dissolved in anhydrous pyridine (0.1 mL) and anhydrous dioxane (0.3 mL), a solution of 2-chloro-4H-1,3,2- benzodioxaphosphorin-4-one (0.143 mmol, 1.2 equiv.) in anhydrous dioxane (0.2 mL) was added and stirred at room temperature for 15 min. To the mixture a solution of tributylammonium pyrophosphate (0.213 mmol, 2.0 equiv.) in anhydrous DMF (0.2 mL) was added, which was followed by quick addition of tributylamine (0.596 mmol, 5.0 equiv.) and stirred for 15 min at room temperature. A solution of iodine (1% solution in pyridine/water, 9:1) was then added dropwise till a permanent brown color of iodine was persisted and stirred for 20 min. The excess of iodine was quenched by adding 5% aqueous solution of Na2S2O3. The reaction mixture was evaporated to dryness under vacuum and dissolved in 25% ammonia solution and stirred for 1 h at room temperature. The reaction was monitored by TLC (isopropanol/aq.NH3/H2O = 5:3:2) and MS. The reaction mixture was concentrated under reduced pressure and crude product was purified by reverse-phase preparative HPLC [eluted with a linear gradient of 5% to 40% CH3CN in buffer triethyl ammonium bicarbonate solution (TEAB, 0.1 M, pH=8.0) over 30 min, on a reverse-phase preparative Varian Dynamax Microsorb 100-8 C18 column (250 mm × 44.1 mm, 10 μm) total absorbance at 254 nm at a flow rate of 20.0 mL/min]. The TEAB buffer solution was evaporated by lyophilization afforded the desired 5’-triphosphates triethylammonium salt, which was exchanged into sodium salt by performing Na-ion exchange column chromatography to yield 5’-triphosphates sodium salt as a white solid. The synthesized nucleoside 5’-triphosphates were confirmed by 1H-NMR, 31P-NMR, and HR-MS analyses.
Publication 2013
1H NMR Ammonia Argon Atmosphere Buffers dioxane Diphosphates Freeze Drying High-Performance Liquid Chromatographies Iodine Ion-Exchange Chromatographies Isopropyl Alcohol Nucleosides Pressure Pyridines Sodium Sodium Chloride Triazoles tributylamine triethylammonium bicarbonate triphosphate triphosphoric acid, sodium salt Vacuum
3-Amino-quinazolinone derivatives were prepared according to the procedures shown in Scheme 1 (18 ). Then quinazoline derivatives were treated with chloroacetyl chloride in the presence of dichloromethane/triethylamine to afford the 2-chloro -N-(4-oxo-2-quinazolin3 (3H)-yl) acetamide derivatives. Final products were synthesized by the reaction of 2-chloro -N-(4-oxo-2-quinazolin3 (3H)-yl) acetamide derivatives with 4-mehyl-4-H-1, 2, 4-triazole- 3-thiol in dry acetone and potassium carbonate (19 20 ).
Publication 2019
acetamide Acetone chloroacetyl chloride derivatives Methylene Chloride potassium carbonate Quinazolines Quinazolinones Sulfhydryl Compounds Triazoles triethylamine

Most recents protocols related to «Triazoles»

Example 13

Complex Em7-s*:

[Figure (not displayed)]

0.90 g (2.7 mmol) of 5-methoxy-1,3,4-triphenyl-4,5-dihydro-1H-1,2,4-triazole C1 are heated to 90° C. under reduced pressure for 20 h. After cooling to room temperature, first 800 ml of anhydrous toluene and then 0.99 g (0.9 mmol) of chloro dimer D2 are added. The mixture is stirred under reflux for 3 h. The precipitate formed is filtered off. The filtrate is washed successively with 3×50 ml of saturated NaHCO3 solution and 1×50 ml of distilled water, dried over MgSO4 and freed of the solvent under reduced pressure. The residue is purified by column chromatography (cyclohexane/acetone=2/1). As well as 50 mg of the complex Em6-s, 150 mg of the complex Em7-s* are obtained.

1H NMR (CD2Cl2, 500 MHz):

δ=3.86 (s, 3H), 5.95 (bd, 3JH,H=7.3 Hz, 2H), 6.23 (bd, J=1.4 Hz, 1H), 6.38 (bt, 3JH,H=7.3 Hz, 1H), 6.44 (bd, 3JH,H=7.3 Hz, 1H), 6.54 (bt, 3JH,H=7.5 Hz, 1H), 6.61-6.67 (m, 4H), 6.78-6.91 (m, 5H), 6.96 (bt, 3JH,H=7.5 Hz, 1H), 7.07-7.13 (m, 4H), 7.19-7.36 (m, 12H), 7.53 (bd, 3JH,H=7.0 Hz, 1H), 7.76 (bd, 3JH,H=7.3 Hz, 1H).

Photoluminescence (in a film, 2% in PMMA):

λmax=482, 508 nm, CIE: (0.24; 0.40)

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Patent 2024
1H NMR Acetone Bicarbonate, Sodium carbene Chromatography Cyclohexane Polymethyl Methacrylate Pressure Solvents Sulfate, Magnesium Toluene Triazoles

Example 47

Azide Polymer Synthesis for Click Conjugation to Alkyne Terminated DNA Oligo

A solution of azidohexanoic acid NHS ester (2.5 mg) in anhydrous DMF (100 μL) was added to a solution of the amine-functional polymer (9.9 mg) in anhydrous DMF (100 μL) under argon. Diisopropylethylamine (2 μL) was then added. The reaction was agitated at room temperature for 15 hours. Water was then added (0.8 mL) and the azide-modified polymer was purified over a NAP-10 column. The eluent was freeze dried overnight. Yield 9.4 mg, 95%.

Oligo Synthesis with Pendant Alkyne (Hexyne) for Click Conjugation to Azide Polymer

The 3′ propanol oligo A8885 (sequence YATTTTACCCTCTGAAGGCTCCP, where Y=hexynyl group and P=propanol group) was synthesized using 3′ spacer SynBase™ CPG 1000 column on an Applied Biosystems 394 automated DNA/RNA synthesizer. A standard 1.0 mole phosphoramidite cycle of acid-catalyzed detritylation, coupling, capping and iodine oxidation was used. The coupling time for the standards monomers was 40 s, and the coupling time for the 5′ alkyne monomer was 10 min.

The oligo was cleaved from the solid support and deprotected by exposure to concentrated aqueous ammonia for 60 min at room temperature, followed by heating in a sealed tube for 5 h at 55° C. The oligo was then purified by RP-HPLC under standard conditions. Yield 34 OD.

Solution Phase Click Conjugation: Probe Synthesis

A solution of degassed copper sulphate pentahydrate (0.063 mg) in aqueous sodium chloride (0.2 M, 2.5 μL) was added to a degassed solution of tris-benzo triazole ligand (0.5 mg) and sodium ascorbate (0.5 mg) in aqueous sodium chloride (0.2 M, 12.5 μL). Subsequently, a degassed solution of oligo A8885 (50 nmole) in aqueous sodium chloride (0.2 M, 30 μL) and a degassed solution of azide polymer (4.5 mg) in anhydrous DMF (50 μL) were added, respectively. The reaction was degassed once more with argon for 30 s prior to sealing the tube and incubating at 55° C. for 2 h. Water (0.9 mL) was then added and the modified oligo was purified over a NAP-10 column. The eluent was freeze-dried overnight. The conjugate was isolated as a distinct band using PAGE purification and characterized by mass spectrometry. Yield estimated at 10-20%.

Fluorescence Studies

The oligo-polymer conjugate was used as a probe in fluorescence studies. The probe was hybridized with the target A8090 (sequence GGAGCCTTCAGAGGGTAAAAT-Dabcyl), which was labeled with dabcyl at the 3′ end to act as a fluorescence quencher. The target and probe were hybridized, and fluorescence monitored in a Peltier-controlled variable temperature fluorimeter. The fluorescence was scanned every 5° C. over a temperature range of 30° C. to 80° C. at a rate of 2° C./min. FIG. 25 shows increasing fluorescence intensity or emission with increasing temperature, indicating that as the probe-target pair melt, the polymer and quencher separate and fluorescence is recovered.

Polymer conjugation to nucleic acids can also be performed using methods adapted from the protocols described in Examples 14, 45 and 46.

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Patent 2024
4-(4-dimethylaminophenylazo)benzoic acid Acids Alkynes Amines Ammonia Anabolism Argon Azides DNA Replication Esters Fluorescence Freezing High-Performance Liquid Chromatographies Iodine Ligands Mass Spectrometry Moles Nucleic Acids Oligonucleotides phosphoramidite Polymers Propanols Sodium Ascorbate Sodium Chloride Spacer DNA Sulfate, Copper Triazoles Tromethamine

Example 28

[Figure (not displayed)]

To a solution of (R)-1-(tert-butyl)-N-(8-(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-5-yl)-1H-1,2,3-triazole-4-carboxamide (200 mg, 0.4 mmol) in CH3CN (5 mL) was added 2,2,2-trifluoroethyl trifluoromethanesulfonate (190 mg, 0.6 mmol). The mixture was stirred at 50° C. for 12 h. After concentration of the reaction mixture, the residue was purified by silica gel chromatography (PE:EtOAc=1:1) to give (R)-1-(tert-butyl)-N-(8-(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-5-yl)-1H-1,2,3-triazole-4-carboxamide as a yellow solid (85 mg, yield: 36%). ESI-MS (M+H)+: 569.3. 1H NMR (400 MHz, CD3OD) δ: 8.54 (s, 1H), 8.42 (d, J=5.2 Hz, 1H), 8.03-7.99 (m, 3H), 7.61 (s, 1H), 7.49 (d, J=7.6 Hz, 1H), 7.22 (d, J=5.2 Hz, 1H), 5.60-5.57 (m, 1H), 4.39-4.35 (m, 1H), 4.17-4.12 (m, 1H), 3.89 (s, 3H) 3.43-3.32 (m, 2H), 3.16-3.09 (m, 2H), 2.24-2.20 (m, 1H), 1.98-1.94 (m, 1H), 1.74 (s, 9H).

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Patent 2024
1H NMR Chromatography Gel Chromatography pyrazole Silica Gel Silicon Dioxide TERT protein, human Triazoles trifluoromethanesulfonate

Example 555

(S)-2-(2,5-difluoro-4-(6-((4-fluoro-6-(1-methyl-1H-1,2,3-triazol-4-yl)pyridin-3-yl)methoxy)pyridin-2-yl)benzyl)-1-(4,4-dimethyltetrahydrofuran-3-yl)-1H-benzo[d]imidazole-6-carboxylic acid was prepared in a manner as described in Procedure 41, starting with Intermediate I-1347 and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)triazole. 1H NMR (400 MHz, Methanol-d4) δ 8.89 (d, J=9.8 Hz, 1H), 8.83 (s, 1H), 8.23 (s, 1H), 8.12 (dd, J=8.6, 1.4 Hz, 1H), 8.03-7.90 (m, 1H), 7.88-7.69 (m, 3H), 7.65-7.51 (m, 1H), 7.36 (dd, J=11.2, 6.1 Hz, 1H), 6.94 (dd, J=8.2, 0.7 Hz, 1H), 5.68 (s, 2H), 5.09 (d, J=6.4 Hz, 1H), 4.76-4.56 (m, 3H), 4.52 (dd, J=11.5, 6.7 Hz, 1H), 4.40 (s, 3H), 3.99 (d, J=8.9 Hz, 1H), 3.83 (d, J=8.9 Hz, 1H), 1.40 (s, 3H), 0.74 (s, 3H). ES/MS m/z: 670.1 (M+H+).

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Patent 2024
1H NMR Carboxylic Acids imidazole Methanol Triazoles

Example 554

(S)-2-(2,5-difluoro-4-(6-((2-fluoro-4-(1-methyl-1H-1,2,3-triazol-5-yl)benzyl)oxy)pyridin-2-yl)benzyl)-1-(4,4-dimethyltetrahydrofuran-3-yl)-1H-benzo[d]imidazole-6-carboxylic acid was prepared in a manner as described in Procedure 41, starting with Intermediate I-1220 and 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)triazole. 1H NMR (400 MHz, Methanol-d4) δ 8.88 (s, 1H), 8.16 (dd, J=8.6, 1.4 Hz, 1H), 7.97-7.86 (m, 2H), 7.84 (dd, J=8.3, 7.5 Hz, 1H), 7.80-7.68 (m, 2H), 7.59 (dd, J=7.2, 1.6 Hz, 1H), 7.49-7.33 (m, 3H), 6.95 (dd, J=8.3, 0.6 Hz, 1H), 5.64 (s, 2H), 5.13 (d, J=6.6 Hz, 1H), 4.81-4.57 (m, 3H), 4.52 (dd, J=11.6, 6.7 Hz, 1H), 4.13 (s, 3H), 3.99 (d, J=8.9 Hz, 1H), 3.84 (d, J=8.9 Hz, 1H), 1.41 (s, 3H), 0.75 (s, 3H). ES/MS m/z: 669.1 (M+H+).

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Patent 2024
1H NMR Carboxylic Acids imidazole Methanol Triazoles

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3-amino-1,2,4-triazole (3-AT) is a chemical compound that is commonly used as a fungicide and herbicide. It is a crystalline solid with a molecular formula of C2H4N4. 3-AT functions as an inhibitor of the enzyme imidazoleglycerol-phosphate dehydratase, which is involved in the biosynthesis of histidine. This property makes it useful in various research and laboratory applications.
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3-amino-1,2,4-triazole is a heterocyclic organic compound. It is a white crystalline solid soluble in water and various organic solvents.
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The PGADT7 vector is a plasmid used for gene expression in yeast. It contains a GAL4 DNA-binding domain and a transcriptional activation domain, which can be used to study protein-protein interactions.
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The PGBKT7 is a plasmid vector used for gene expression in yeast cells. It contains a yeast selectable marker and a multiple cloning site for the insertion of DNA sequences.
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The PGADT7 is a plasmid vector used in yeast two-hybrid systems for the detection of protein-protein interactions. It contains the GAL4 DNA-binding domain, a multiple cloning site, and various genetic markers for selection in yeast.
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The Triazole reagent is a laboratory chemical compound used in various analytical and synthetic procedures. It serves as a versatile building block in organic chemistry and biochemistry applications. The core function of the Triazole reagent is to facilitate specific chemical transformations and reactions.
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More about "Triazoles"

Triazoles are a class of nitrogen-containing heterocyclic organic compounds that have garnered significant attention in the scientific community.
These five-membered ring structures, consisting of three nitrogen atoms, exhibit a diverse range of pharmaceutical and agricultural applications, including use as antifungal, antidepressant, and herbicide agents.
The versatility of triazoles can be attributed to their broad spectrum of biological activities, making them an important area of research in medicinal chemistry and related fields.
Compounds such as 3-amino-1,2,4-triazole (3-AT), a commonly used triazole reagent, have found applications in various experimental procedures, including the PGADT7 and PGBKT7 vectors, which are crucial tools in yeast two-hybrid assays.
Triazole-based molecules can also be combined with solvents like DMSO (dimethyl sulfoxide) to create effective formulations, as exemplified by the triazole reagent A8056.
Researchers in the field of triazoles often leverage these diverse compounds and their derivatives to explore novel therapeutic avenues and tackle agricultural challenges.
With the growing importance of triazoles, platforms like PubCompare.ai have emerged as valuable resources, empowering scientists to optimize their research by locating relevant protocols from literature, preprints, and patents, and leveraging AI-driven comparisons to identify the most effective protocols and products.
This can significantly enhance the reproducibility and accuracy of triazoles-related studies, supporting advancements in this dynamic and impactful area of scientific inquiry.