Triazoles

Convulsant effects of abused synthetic cannabinoids JWH-018 and 5F-AB-PINACA are mediated by agonist actions at CB1 receptors in mice was written by Wilson, Catheryn D.;Tai, Sherrica;Ewing, Laura;Crane, Jasmine;Lockhart, Taylor;Fujiwara, Ryochi;Radominska-Pandya, Anna;Fantegrossi, William E.. And the article was included in Journal of Pharmacology and Experimental Therapeutics in 2019.Synthetic Route of C6H6N4 This article mentions the following:

Convulsant effects of abused synthetic cannabinoid (SCB) drugs have been reported in humans and laboratory animals, but the mechanism of these effects is not known. We compared convulsant effects of partial CB1R agonist Δ9-tetrahydrocannabinol (THC), full CB1R agonist SCBs JWH-018 and 5F-ABPINACA, and classic chem. convulsant pentylenetetrazol (PTZ) using an observational rating scale in mice. THC did not elicit convulsions, but both SCBs did so as effectively as and more potently than PTZ. SCB-elicited convulsions were attenuated by the CB1R antagonist rimonabant or by THC, or by dose regimens of THC and JWH-018, which downregulate and desensitize CB1Rs. None of these treatments altered the convulsant effects of PTZ, although diazepam attenuated PTZelicited convulsions without altering SCB-induced convulsant effects. Repeated administration of a subthreshold dose of PTZ kindled convulsant effects, but this was not observed with the SCBs, and no cross-kindling was observed Repeated administration of the SCBs resulted in tolerance to convulsant effects, but no cross-tolerance to PTZ was observed Inhibition on Phase I metabolism via nonselective inhibition of CYP450s with 1-aminobenzotriazole potentiated the hypothermic effects of the SCBs and protected against the convulsant effects of JWH-018, but not those of 5F-AB-PINACA or PTZ. Incubation of human liver microsomes with the SCBs showed that JWH-018 is eliminated via oxidation, whereas 5F-ABPINACA is not. In the experiment, the researchers used many compounds, for example, 1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6Synthetic Route of C6H6N4).

1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6) belongs to triazole derivatives. The many free lone pairs in triazoles make them useful as coordination compounds, although not typically as haptic ligands. Triazole growth retardants such as uniconazole and paclobutrazol have been known to inhibit the biosynthesis of gibberellins by blocking kaurene oxidase, an P450 enzymeSynthetic Route of C6H6N4

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Mechanism and pattern of resistance to some ACCase inhibitors in winter wild oat (Avena sterilis subsp. ludoviciana (Durieu) Gillet & Magne) biotypes collected within canola fields was written by Hassanpour-bourkheili, Saeid;Gherekhloo, Javid;Kamkar, Behnam;Ramezanpour, S. Sanaz. And the article was included in Crop Protection in 2021.Quality Control of 1H-Benzo[d][1,2,3]triazol-1-amine This article mentions the following:

Due to the reports regarding unsuccessful control of Avena sterilis subsp. ludoviciana (Durieu) Gillet & Magne by haloxyfop-R-Me in canola fields, the following study was conducted to investigate the resistance of this weed to haloxyfop-R-Me. These biotypes were then subjected to various rates of clodinafop propargyl, sethoxydim, pinoxaden and mesosulfuron Me + iodosulfuron-Me herbicides and their and cross-resistance to clodinafop propargyl and sethoxydim was confirmed. However, no resistance was observed to pinoxaden and mesosulfuron-Me + iodosulfuron-Me herbicides. Indirect study of metabolism by P 450 using 1- aminobenzotriazole and piperonyl butoxide showed that this enzyme had no contribution to occurrence of resistance in the studied biotypes. Allele-specific PCR results indicated that Ile-2041-Asn mutation is responsible for resistance of A. sterilis subsp. ludoviciana biotypes, which was confirmed by sequencing of the samples. Since pinoxaden neg. affects canola, the growers face a serious limitation in their choice for chem. management and thus, implementation of integrated weed management such as introduction of row crops such as faba bean in crop rotation and increasing the diversity of herbicide mode of action by cultivation of crops such as sugar beet in crop rotation may prove helpful. This was the first case of A. sterilis subsp. ludoviciana resistance to ACCase inhibitors in canola fields. In the experiment, the researchers used many compounds, for example, 1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6Quality Control of 1H-Benzo[d][1,2,3]triazol-1-amine).

1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6) belongs to triazole derivatives. Triazoles are important five-member nitrogen heterocycles involved in a wide range of industrial applications such as agrochemicals, corrosion inhibitors, dyes, optical brighteners, as well as biologically active agents. Due to the structural characteristics, both 1,2,3- and 1,2,4-triazoles are able to accommodate a broad range of substituents (electrophiles and nucleophiles) around the core structures and pave the way for the construction of diverse novel bioactive molecules.Quality Control of 1H-Benzo[d][1,2,3]triazol-1-amine

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Determination of metabolic profile of novel triethylamine containing thiophene S006-830 in rat, rabbit, dog and human liver microsomes was written by Hidau, Mahendra Kumar;Singh, Yeshwant;Singh, Shio Kumar. And the article was included in Drug Testing and Analysis in 2016.Formula: C6H6N4 This article mentions the following:

CDRI S006-830 is a potent triethylamine containing thiophene antitubercular compound of the Central Drug Research Institute, India. The present study aimed to conduct comprehensive metabolic investigations of CDRI S006-830 to corroborate its preclin. investigations. Preliminary metabolic investigations were performed to assess the metabolic stability, enzyme kinetics, reaction phenotyping, and metabolite identification of CDRI S006-830 in rat, rabbit, dog, and human liver microsomes using liquid chromatog. with mass spectrometry. The observed in vitro t_1/2 and Cl_int values were 9.9 ± 1.29, 4.5 ± 0.52, 4.5 ± 0.86, 17 ± 5.21 min and 69.60 ± 8.37, 152.0 ± 17.26, 152.34 ± 27.63, 33.62 ± 21.04 μL/min/mg in rat, rabbit, dog and human liver microsomes resp. These observations suggested that CDRI S006-830 rapidly metabolized in the presence of NADPH in liver microsomes of rat, rabbit and dog while moderately metabolized in human liver microsomes. It was observed that CDRI S006-830 exhibited monophasic Michaelis-Menten kinetics. The metabolism of CDRI S006-830 was primarily mediated by CYP3A4 and was deduced by CYP reaction phenotyping with known potent inhibitors. CYP3A4 involvement was also confirmed by cDNA-expressed recombinant human isoenzyme activity with different CYPs. Four major phase-I metabolites of S006-830, (M-1 to M-4) were detected in rat, rabbit, dog (except M4) and human liver microsomes. Copyright © 2015 John Wiley & Sons, Ltd. In the experiment, the researchers used many compounds, for example, 1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6Formula: C6H6N4).

1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6) belongs to triazole derivatives. However, triazoles are also useful in bioorthogonal chemistry, because the large number of nitrogen atoms causes triazoles to react similar to azides. Triazoles are compounds with a vast spectrum of applications, varying from materials (polymers), agricultural chemicals, pharmaceuticals, photoactive chemicals and dyes.Formula: C6H6N4

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Sequential phase I metabolism of pyrethroids by duplicated CYP6P9 variants results in the loss of the terminal benzene moiety and determines resistance in the malaria mosquito Anopheles funestus was written by Nolden, Melanie;Paine, Mark J. I.;Nauen, Ralf. And the article was included in Insect Biochemistry and Molecular Biology in 2022.Category: triazoles This article mentions the following:

Pyrethroid resistance in Anopheles funestus is threatening the eradication of malaria. One of the major drivers of pyrethroid resistance in An. funestus are cytochrome P 450 monooxygenases CYP6P9a and CYP6P9b, which are found upregulated in resistant An. funestus populations from Sub-Saharan Africa and are known to metabolise pyrethroids. Here, we have functionally expressed CYP6P9a and CYP6P9b variants and investigated their interactions with azole-fungicides and pyrethroids. Some azole fungicides such as prochloraz inhibited CYP6P9a and CYP6P9b at nanomolar concentrations, whereas pyrethroids were weak inhibitors (>100μM). Amino acid sequence comparisons suggested that a valine to isoleucine substitution at position 310 in the active site cavity of CYP6P9a and CYP6P9b, resp., might affect substrate binding and metabolism We therefore swapped the residues by site directed mutagenesis to produce CYP6P9aI310V and CYP6P9bV310I. CYP6P9bV310I produced stronger metabolic activity towards coumarin substrates and pyrethroids, particularly permethrin. The V310I mutation was previously also detected in a pyrethroid resistant field population of An. funestus in Benin. Addnl., we found the first metabolite of permethrin and deltamethrin after hydroxylation, 4OH permethrin and 4OH deltamethrin, were also suitable substrates for CYP6P9-variants, and were depleted by both enzymes to a higher extent than as their resp. parent compounds (approx. 20% more active). Further, we found that both metabolites were toxic against An. funestus FANG (pyrethroid susceptible) but not towards FUMOZ-R (pyrethroid resistant) mosquitoes, the latter suggesting detoxification by overexpressed CYP6P9a and CYP6P9b. We confirmed by mass-spectrometric anal. that CYP6P9a and CYP6P9b are capable of cleaving phenoxybenzyl-ethers in type I pyrethroid permethrin and type II pyrethroid deltamethrin and that both enzymes preferentially metabolise trans-permethrin. This provides new insight into the metabolism of pyrethroids and a greater understanding of the mol. mechanisms of pyrethroid resistance in An. funestus. In the experiment, the researchers used many compounds, for example, 1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6Category: triazoles).

1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6) belongs to triazole derivatives. Triazoles exhibit substantial isomerism, depending on the positioning of the nitrogen atoms within the ring. Due to the structural characteristics, both 1,2,3- and 1,2,4-triazoles are able to accommodate a broad range of substituents (electrophiles and nucleophiles) around the core structures and pave the way for the construction of diverse novel bioactive molecules.Category: triazoles

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Biodegradation of fluoroquinolone antibiotics and the climbazole fungicide by Trichoderma species was written by Manasfi, Rayana;Chiron, Serge;Montemurro, Nicola;Perez, Sandra;Brienza, Monica. And the article was included in Environmental Science and Pollution Research in 2020.Reference of 1614-12-6 This article mentions the following:

Abstract: Filamentous fungi Trichoderma have been able to efficiently degrade fluoroquinolone antibiotics namely ciprofloxacin (CIP) and ofloxacin (OFL) as well as the fungicide climbazole (CLB) that are persistent in conventional activated sludge processes. All targeted compounds were biotransformed by whole cells of Trichoderma spp., exactly T. harzanium and T. asperellum, and biosorption played a limited role in their elimination. However, contrasting results were obtained with the two strains. T. asperellum was more efficient against CIP, with a 81% degradation rate in 13 days of incubation, while T. harzianum was more efficient against CLB, with a 91% degradation rate. While in the case of OFL, both strains showed same efficiency with degradation rate around 40%. Adding a cytochrome P 450 enzyme inhibitor hardly resulted in the modification of degradation kinetics supporting the implication of extracellular enzymes in chem. biotransformation. Transformation products were identified by liquid chromatog.-high resolution-mass spectrometry and transformation pathways were proposed. Biotransformation of selected compounds included hydroxylation, oxidation/reduction and N- and O-dealkylation reactions, similarly to those reported with white rot fungi. CIP underwent transformations at the piperazinyl ring through oxidation and conjugation reactions, while OFL mainly underwent hydroxylation processes and CLB carbonyl reduction into alc. In the experiment, the researchers used many compounds, for example, 1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6Reference of 1614-12-6).

1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6) belongs to triazole derivatives. Among the nitrogen-containing heterocyclic compounds, triazoles emerge with superior pharmacological applications. Due to the structural characteristics, both 1,2,3- and 1,2,4-triazoles are able to accommodate a broad range of substituents (electrophiles and nucleophiles) around the core structures and pave the way for the construction of diverse novel bioactive molecules.Reference of 1614-12-6

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthesis and characterization of a novel one-dimensional Zn(II) coordination polymer based on in situ generated 1-methyl-2-(3H-[1,2,3]triazol-4-yl)-1H-benzoimidazole was written by Sun, Chen-guang;Xu, Kang-zhen;Yin, Zheng;Song, Ji-rong;Zeng, Ming-hua. And the article was included in Inorganic Chemistry Communications in 2012.Application of 4546-95-6 This article mentions the following:

One novel 1-dimensional chain of {[Zn₂(L)₃(H₂O)(NO₃)]·2.5H₂O}_n (1)(HL = 1-methyl-2-(3H-[1,2,3]triazol-4-yl)-1H-benzoimidazole) was hydrothermally constructed from in situ generated 1-methyl-2-(3H-[1,2,3]triazol-4-yl)-1H-benzoimidazole ligand at 160°. Compound 1 exhibits a 1-dimensional butterfly-like chain architecture, which is further assembled into a 3-dimensional supermol. network by interchain H bonds. TGA studies show that compound 1 is highly thermally stable. The fluorescent property in the solid state is also explored, and the emission spectrum shows a blue shift of 62 nm compared with that of HL, which may be assigned to ligand-to-metal charge transfer. In the experiment, the researchers used many compounds, for example, 1H-1,2,3-Triazole-4,5-dicarboxylic acid (cas: 4546-95-6Application of 4546-95-6).

1H-1,2,3-Triazole-4,5-dicarboxylic acid (cas: 4546-95-6) belongs to triazole derivatives. Many triazoles are versatile, biologically active compounds commonly used as fungicides and plant retardants. 1,2,3-Triazoles are usually prepared following (3+2) cycloaddition protocols. A common technique for unsubstituted triazoles is the Huisgen azide-alkyne 1,3-dipolar cycloaddition: a azide and an alkyne react at high temperature to form a ring. However, the Huisgen strategy produces a mixture of isomers (typically 1,4- and 1,5-disubstituted) when used to produce substituted triazoles.Application of 4546-95-6

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

In vitro and in vivo studies of triacetone triperoxide (TATP) metabolism in humans was written by Gonsalves, Michelle D.;Colizza, Kevin;Smith, James L.;Oxley, Jimmie C.. And the article was included in Forensic Toxicology in 2021.Recommanded Product: 1614-12-6 This article mentions the following:

Triacetone triperoxide (TATP) is a volatile but powerful explosive that appeals to terrorists due to its ease of synthesis from household items. For this reason, bomb squad, canine (K9) units, and scientists must work with this material to mitigate this threat. However, no information on the metabolism of TATP is available. Methods: In vitro experiments using human liver microsomes and recombinant enzymes were performed on TATP and TATP-OH for metabolite identification and enzyme phenotyping. Enzyme kinetics for TATP hydroxylation were also investigated. Urine from laboratory personnel collected before and after working with TATP was analyzed for TATP and its metabolites. Results: While experiments with flavin monooxygenases were inconclusive, those with recombinant cytochrome P450s (CYPs) strongly suggested that CYP2B6 was the principle enzyme responsible for TATP hydroxylation. TATP-O-glucuronide was also identified and incubations with recombinant uridine diphosphoglucuronosyltransferases (UGTs) indicated that UGT2B7 catalyzes this reaction. Michaelis-Menten kinetics were determined for TATP hydroxylation, with Km = 1.4μM and Vmax = 8.7 nmol/min/nmol CYP2B6. TATP-O-glucuronide was present in the urine of all three volunteers after being exposed to TATP vapors showing good in vivo correlation to in vitro data. TATP and TATP-OH were not observed Conclusions: Since scientists working to characterize and detect TATP to prevent terrorist attacks are constantly exposed to this volatile compound, attention should be paid to its metabolism This paper is the first to elucidate some exposure, metabolism and excretion of TATP in humans and to identify a marker of TATP exposure, TATP-O-glucuronide in urine. In the experiment, the researchers used many compounds, for example, 1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6Recommanded Product: 1614-12-6).

1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6) belongs to triazole derivatives. Many triazoles are versatile, biologically active compounds commonly used as fungicides and plant retardants. The presence of the three nitrogen atoms in triazole structures afforded opportunities for a plethora of structural modification with the generation of novel therapeutically potential agents, which is different from other heterocyclic compounds.Recommanded Product: 1614-12-6

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A cage-based cationic body-centered tetragonal metal-organic framework: single-crystal to single-crystal transformation and selective uptake of organic dyes was written by Chen, Di-ming;Shi, Wei;Cheng, Peng. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2015.Recommanded Product: 4-(4H-1,2,4-Triazol-4-yl)benzoic acid This article mentions the following:

A cage-based cationic body-centered metal-organic framework, {[(Cu₄Cl)(CPT)₄(H₂O)₄]·3NO₃·5NMP·3.5H₂O} (1)(HCPT = 4-(4-carboxyphenyl)-1,2,4-triazole, NMP = N-methyl-2-pyrrolidone), was successfully synthesized using a custom-designed bifunctional triazolcarboxylate ligand. It shows interesting single-crystal-to-single-crystal transformation upon solvent exchange process and selective uptake of organic dyes. In the experiment, the researchers used many compounds, for example, 4-(4H-1,2,4-Triazol-4-yl)benzoic acid (cas: 157069-48-2Recommanded Product: 4-(4H-1,2,4-Triazol-4-yl)benzoic acid).

4-(4H-1,2,4-Triazol-4-yl)benzoic acid (cas: 157069-48-2) belongs to triazole derivatives. The triazole ring is a relatively stable functional group, and the triazole bond can be used for a variety of applications, such as replacing the phosphate backbone of DNA. Both the triazoles and their derivatives have significant biological properties including antimicrobial, antiviral, antitubercular, anticancer, anticonvulsant, analgesic, antioxidant, anti-inflammatory, and antidepressant activities.Recommanded Product: 4-(4H-1,2,4-Triazol-4-yl)benzoic acid

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Nonclinical pharmacokinetics, disposition, and drug-drug interaction potential of a novel D-amino acid peptide agonist of the calcium-sensing receptor AMG 416 (Etelcalcetide) was written by Subramanian, Raju;Zhu, Xiaochun;Kerr, Savannah J.;Esmay, Joel D.;Louie, Steven W.;Edson, Katheryne Z.;Walter, Sarah;Fitzsimmons, Michael;Wagner, Mylo;Soto, Marcus;Pham, Roger;Wilson, Sarah F.;Skiles, Gary L.. And the article was included in Drug Metabolism & Disposition in 2016.Quality Control of 1H-Benzo[d][1,2,3]triazol-1-amine This article mentions the following:

AMG 416 (etelcalcetide) is a novel synthetic peptide agonist of the calcium-sensing receptor composed of a linear chain of seven D-amino acids (referred to as the D-amino acid backbone) with a D-cysteine linked to an L-cysteine via a disulfide bond. AMG 416 contains four basic D-arginine residues and is a +4 charged peptide at physiol. pH with a mol. weight of 1048.3 Da. The pharmacokinetics (PK), disposition, and potential of AMG 416 to cause drug-drug interaction were investigated in nonclin. studies with two single ¹⁴C-labels placed either at a potentially metabolically labile acetyl position or on the D-alanine next to D-cysteine in the interior of the D-amino acid backbone. After i.v. dosing, the PK and disposition of AMG 416 were similar in male and female rats. Radioactivity rapidly distributed to most tissues in rats with intact kidneys, and renal elimination was the predominant clearance pathway. No strain-dependent differences were observed In bilaterally nephrectomized rats, minimal radioactivity (1.2%) was excreted via nonrenal pathways. Biotransformation occurred primarily via disulfide exchange with endogenous thiol-containing mols. in whole blood rather than metabolism by enzymes, such as proteases or cytochrome P450s; the D-amino acid backbone remained unaltered. A substantial proportion of the plasma radioactivity was covalently conjugated to albumin. AMG 416 presents a low risk for P 450 or transporter-mediated drug-drug interactions because it showed no interactions in vitro. These studies demonstrated a ¹⁴C label on either the acetyl or the D-alanine in the D-amino acid backbone would be appropriate for clin. studies. In the experiment, the researchers used many compounds, for example, 1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6Quality Control of 1H-Benzo[d][1,2,3]triazol-1-amine).

1H-Benzo[d][1,2,3]triazol-1-amine (cas: 1614-12-6) belongs to triazole derivatives. The many free lone pairs in triazoles make them useful as coordination compounds, although not typically as haptic ligands. Both the triazoles and their derivatives have significant biological properties including antimicrobial, antiviral, antitubercular, anticancer, anticonvulsant, analgesic, antioxidant, anti-inflammatory, and antidepressant activities.Quality Control of 1H-Benzo[d][1,2,3]triazol-1-amine

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics