Category: 328-90-5

Wang, Shengzheng published the artcileScaffold diversity inspired by the natural product evodiamine: discovery of highly potent and multitargeting antitumor agents, Recommanded Product: 2-Hydroxy-4-(trifluoromethyl)benzoic acid, the publication is Journal of Medicinal Chemistry (2015), 58(16), 6678-6696, database is CAplus and MEDLINE.

A critical question in natural product-based drug discovery is how to translate the product into drug-like mols. with optimal pharmacol. properties. The generation of natural product-inspired scaffold diversity is an effective but challenging strategy to investigate the broader chem. space and identify promising drug leads. Extending the efforts to the natural product evodiamine, a diverse library containing 11 evodiamine-inspired novel scaffolds and their derivatives were designed and synthesized. Most of them showed good to excellent antitumor activity against various human cancer cell lines. In particular, 3-chloro-10-hydroxyl thio-evodiamine I showed excellent in vitro and in vivo antitumor efficacy with good tolerability and low toxicity. Antitumor mechanism and target profiling studies indicate that compound I is the first-in-class triple topoisomerase I/topoisomerase II/tubulin inhibitor. Overall, this study provided an effective strategy for natural product-based drug discovery.

Journal of Medicinal Chemistry published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C14H17BFNO2, Recommanded Product: 2-Hydroxy-4-(trifluoromethyl)benzoic acid.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Cortes-Arriagada, Diego published the artcileInsights into the luminescent properties of anionic cyclometalated iridium(III) complexes with ligands derived from natural products, Formula: C8H5F3O3, the publication is International Journal of Quantum Chemistry (2018), 118(17), n/a, database is CAplus.

In the search of remarkable anionic electroluminescent semiconductors to be applied in energy conversion devices such as Light Emitting Electrochem. Cells, we report the electronic, photophys., and charge injection/transfer properties of a series of cyclometalated iridium(III) complexes through a DFT/TD-DFT procedure. The proposed semiconductors involve bidentated ligands based on natural products (salicylic acid and boldine), and phenylpyridine and phenylpyrazole as the cyclometalating units. The proposed compounds emit in the range of 446 to 571 nm, where the boldine based compounds have red-shifted emissions compared to their analogs with salicylic acid. Blue phosphors were obtained by the use of phenylpyrazole units; however, the ligand field is weak in these cases compared to the ligand field exerted by the phenylpyridine ligands. The latter allows the accessibility to the radiationless states for emitters below 495 nm as a result of the increased stability of the metal centered excited states; consequently, the luminescent quantum yield could be decreased. Conversely, the semiconductors with phenylpyridine units show a restricted accessibility to radiationless processes, which could result in emitters with a high luminescent quantum yield and low non-radiative constants Finally, the proposed anionic semiconductors show a better balance between hole/electron transfer rate compared to related cationic Ir(III) complexes; while, the easier hole-electron injection is favored for semiconductors with salicylic acid and phenylpyridine units.

International Journal of Quantum Chemistry published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C8H5F3O3, Formula: C8H5F3O3.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Ge, Jie published the artcileEffect of food on the pharmacokinetics of triflusal and its major active metabolite, 2-hydroxy-4-trifluoromethyl benzoic acid, in healthy subjects, SDS of cas: 328-90-5, the publication is International Journal of Clinical Pharmacology and Therapeutics (2015), 53(3), 272-276, database is CAplus and MEDLINE.

Objective: The objective of this study was to evaluate the pharmacokinetic parameters of triflusal and its major active metabolite, 2-hydroxy-4-trifluoromethyl benzoic acid (HTB), following a single oral dose of 900 mg in healthy subjects under fed and fasting conditions. Methods: The study participants (n = 12) were randomized to receive one 900 mg triflusal capsule in a fasting condition (no food for 12 h) or a fed condition (after a high-fat meal); after a 2-wk washout period, participants received the same dose of triflusal capsule under the converse condition. Pharmacokinetic parameters were calculated using WinNonlin 6.2 software. Safety was evaluated through assessment of adverse events, standard laboratory evaluations, vital signs, and 12-lead electrocardiog. Results: The mean Cmax of triflusal and HTB were 13.96, 110.2 ug/mL for the fasting state and 9.546, 97.15 ug/mL for the fed state, resp. The AUC0-144 of triflusal and HTB were 19.66, 5,572 h × μg/mL for the fasting state and 22.20, 5,038 h × μg/mL for the fed state, the AUC0-∞ of triflusal and HTB were 19.79, 6,333 h × μg/mL for the fasting state and 22.44, 5,632 h × μg/mL for the fed state, resp. The results showed that Cmax and AUCs for triflusal were outside the bioequivalency (BE) interval after food intake, but there was no statistically significant change for HTB. Conclusion: High-fat food intake may affect the pharmacokinetics of triflusal capsule in healthy subjects.

International Journal of Clinical Pharmacology and Therapeutics published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C8H5F3O3, SDS of cas: 328-90-5.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Qian, Ya-fang published the artcileDetermination of triflusal and its active metabolite 2-hydroxy-4-(trifluoromethyl)benzoic acid in human plasma by LC-MS, Category: alcohols-buliding-blocks, the publication is Yaowu Fenxi Zazhi (2014), 34(9), 1541-1548, database is CAplus.

A reliable liquid chromatog.-mass spectrometry (LC-MS) method for the determination of triflusal and its active metabolite 2-hydroxy-4-(trifluoromethyl)benzoic acid (HTB) in human plasma was developed. The stability of triflusal in human plasma was evaluated when formic acid of different concentrations was used as the esterase inhibitor. The plasma concentrations of triflusal and HTB were determined by LC-MS, resp. Separation of the analytes was achieved on a Hedera ODS-2 column, and MS determination was carried out in electrospray ionization mode. The stability of triflusal in human plasma was kept by adding 20 μL of 4% formic acid to an aliquot of 400 μL of plasma, and then triflusal was extracted with acetyl acetate. Triflusal was eluted with a mobile phase of acetonitrile (A)-5 mmol·L^-1 ammonium acetate solution containing 0.1 % acetic acid (B) using gradient elution (0-0.1 min, 20%A; 0.1-0.15 min, 20%A→30%A; 0.15-6 min, 30%A; 6-6.5 min, 30% A→100% A; 6.5-9.5 min, 100% A; 9.5-10 min, 100% A→20% A; 10-13.7 min, 20% A) at a flow rate of 0.4 mL·min^-1. The deprotonated ions were at m/z 247.0 and 150.0 for monitoring for triflusal and the internal standard (IS) paracetamol, resp. The protein precipitation method was used for HTB sample treatment. HTB in the treated samples was separated with a mobile phase of methanol-5 mmol·L^-1 ammonium acetate solution containing 3% formic acid (75:25) at a flow rate of 0.25 mL·min^-1. The deprotonated ions were at m/z 205.0 and 137.0 for monitoring for HTB and salicylic acid (IS) resp. The calibration ranges were 0.01-20.37 μg·mL^-1 and 0.7-159.9 μg·mL^-1 for triflusal and HTB, resp. As the lower limit of quantitation for triflusal (0.01 μg·mL^-1) was lower than that by the previous reported methods (0.03 μg·mL^-1), the elimination half-life of triflusal in human could be determined more accurately. The current method was successfully applied to determine the concentration levels of triflusal and HTB in human plasma. The methods can be used for determination of triflusal and HTB in human plasma in pharmacokinetics and bioequivalence studies.

Yaowu Fenxi Zazhi published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C8H5F3O3, Category: alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Giroud, Maude published the artcileRepurposing a Library of Human Cathepsin L Ligands: Identification of Macrocyclic Lactams as Potent Rhodesain and Trypanosoma brucei Inhibitors, Synthetic Route of 328-90-5, the publication is Journal of Medicinal Chemistry (2018), 61(8), 3350-3369, database is CAplus and MEDLINE.

Rhodesain (RD) is a parasitic, human cathepsin L (hCatL) like cysteine protease produced by Trypanosoma brucei (T. b.) species and a potential drug target for the treatment of human African trypanosomiasis (HAT). A library of hCatL inhibitors was screened, and macrocyclic lactams were identified as potent RD inhibitors (K_i < 10 nM), preventing the cell-growth of Trypanosoma brucei rhodesiense (IC₅₀ < 400 nM). SARs addressing the S2 and S3 pockets of RD were established. Three cocrystal structures with RD revealed a noncovalent binding mode of this ligand class due to oxidation of the catalytic Cys 25 to a sulfenic acid (Cys-SOH) during crystallization The P-glycoprotein efflux ratio was measured and the in vivo brain penetration in rats determined When tested in vivo in acute HAT model, the compounds permitted up to 16.25 (vs. 13.0 for untreated controls) mean days of survival.

Journal of Medicinal Chemistry published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C8H5F3O3, Synthetic Route of 328-90-5.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Ferrit, M. published the artcileEffects of long-chains of zwitterionic micelles on binding constants of triflusal and acetylsalicylic acid, Recommanded Product: 2-Hydroxy-4-(trifluoromethyl)benzoic acid, the publication is Colloids and Surfaces, A: Physicochemical and Engineering Aspects (2009), 345(1-3), 26-30, database is CAplus.

A spectrophotometric study of the reaction of the alk. hydrolysis of triflusal (TFL) and acetylsalicylic acid (ASA) in the presence of zwitterionic micelles was carried out, with the objective of determining the effects of the hydrophobic and electrostatic interactions on the micellar union of both drugs. A series of zwitterionic surfactants of alkyldimethylammonio propanesulfonate (SB3-n) was used: decyldimethylammonio propanesulfonate (SB3-10), tetradecyldimethylammonio propanesulfonate (SB3-14), hexadecyldimethylammonio propanesulfonate (SB3-16). This reaction is inhibited at higher surfactant concentrations The exptl. data has been processed according to the micellar pseudophase model. The values of the binding constants of both drugs in the micelle (K _S) determine the importance of the hydrophobic and electrostatic interactions in the micelle solubilization of both drugs.

Colloids and Surfaces, A: Physicochemical and Engineering Aspects published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C8H5F3O3, Recommanded Product: 2-Hydroxy-4-(trifluoromethyl)benzoic acid.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Ferrit, Monica published the artcileThe study of the influence of surfactant charge on alkaline hydrolysis reactions of acetylsalicylic acid (ASA) and triflusal (TFL) using spectrophotometric methods, Application of 2-Hydroxy-4-(trifluoromethyl)benzoic acid, the publication is European Journal of Pharmaceutical Sciences (2007), 31(3-4), 211-220, database is CAplus and MEDLINE.

In this research, the effects of micellar systems on alk. hydrolysis reactions of acetylsalicylic acid (ASA) and triflusal (TFL) were found to be dependant upon the surfactant charge within the micelle. In cationic micelles, there is a catalytic effect at low concentrations of surfactant. However, this reaction is inhibited at higher surfactant concentrations In anionic micelles, a catalytic effect occurs, while in zwitterionic and non-ionic micelles there is an inhibitory effect. Such reactions are attributable to changes in reactants on the micellar surface, or to the fact that both reactants are found in different microenvironments. The pseudophase (PS) and ion-exchange (PPIE) models were found to be consistent with the exptl. result. Furthermore, the association constants for both drugs could be determined together with micellar rate constants in heterogeneous media.

European Journal of Pharmaceutical Sciences published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C8H5F3O3, Application of 2-Hydroxy-4-(trifluoromethyl)benzoic acid.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Palmer, Michael J. published the artcilePotent Antimalarials with Development Potential Identified by Structure-Guided Computational Optimization of a Pyrrole-Based Dihydroorotate Dehydrogenase Inhibitor Series, Synthetic Route of 328-90-5, the publication is Journal of Medicinal Chemistry (2021), 64(9), 6085-6136, database is CAplus and MEDLINE.

Dihydroorotate dehydrogenase (DHODH) has been clin. validated as a target for the development of new antimalarials. Experience with clin. candidate triazolopyrimidine DSM265 (1) suggested that DHODH inhibitors have great potential for use in prophylaxis, which represents an unmet need in the malaria drug discovery portfolio for endemic countries, particularly in areas of high transmission in Africa. We describe a structure-based computationally driven lead optimization program of a pyrrole-based series of DHODH inhibitors, leading to the discovery of two candidates for potential advancement to preclin. development. These compounds have improved physicochem. properties over prior series frontrunners and they show no time-dependent CYP inhibition, characteristic of earlier compounds Frontrunners have potent antimalarial activity in vitro against blood and liver schizont stages and show good efficacy in Plasmodium falciparum SCID mouse models. They are equally active against P. falciparum and Plasmodium vivax field isolates and are selective for Plasmodium DHODHs vs. mammalian enzymes.

Journal of Medicinal Chemistry published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C8H5F3O3, Synthetic Route of 328-90-5.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Hernandez, Marita published the artcileEffect of 4-trifluoromethyl derivatives of salicylate on nuclear factor κB-dependent transcription in human astrocytoma cells, Quality Control of 328-90-5, the publication is British Journal of Pharmacology (2001), 132(2), 547-555, database is CAplus and MEDLINE.

The effect of two derivatives of salicylate, 2-hydroxy-4-trifluoromethylbenzoic acid (HTB) and 2-acetoxy-4-trifluoromethylbenzoic acid (triflusal), on the expression of several proteins displaying proinflammatory activities the regulation of which is associated to the transcription factor NF-κB, was assayed in the human astrocytoma cell line 1321N1. Tumor necrosis factor-α (TNF-α) activated NF-κB as judged from both the appearance of κB-binding activity in the nuclear extracts, the degradation of IκB proteins in the cell lyzates, and the activation of IκB kinases using an immunocomplex kinase assay with glutathione S-transferase (GST)-IκB proteins as substrates. HTB up to 3 mM did not inhibit the nuclear translocation of NK-κB/Rel proteins as judged from electrophoretic mobility-shift assays; however, HTB inhibited the degradation of IκBβ without significantly affecting the degradation of both IκBα and IκBε. In keeping with their inhibitory effect on IκBβ degradation in the cell lyzates, both HTB and triflusal inhibited the phosphorylation of GST-IκBβ elicited by TNF-α, without affecting the phosphorylation of GST-IκBα. The effect of both HTB and triflusal on κB-dependent trans-activation was studied by assaying the expression of both cyclo-oxygenase-2 (COX-2) and vascular cell adhesion mol.-1 (VCAM-1). HTB and triflusal inhibited in a dose-dependent manner the expression of COX-2 and VCAM-1 mRNA and the induction of COX-2 protein at therapeutically relevant concentrations These findings show the complexity of the biochem. mechanisms underlying the activation of NF-κB in the different cell types and extend the anti-inflammatory effects of HTB and triflusal to neural cells.

British Journal of Pharmacology published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C8H5F3O3, Quality Control of 328-90-5.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Bosca, F. published the artcilePhotochemistry of 2-hydroxy-4-trifluoromethylbenzoic acid, major metabolite of the photosensitizing platelet antiaggregant drug triflusal, HPLC of Formula: 328-90-5, the publication is Photochemistry and Photobiology (2001), 73(5), 463-468, database is CAplus.

Triflusal is a platelet antiaggregant drug with photoallergic side effects. However, it is considered a prodrug since it is metabolized to 2-hydroxy-4-trifluoromethyl-benzoic acid (HTB)-the pharmacol. active form. HTB was found to be photolabile under various conditions. Its major photodegradation pathway appears to be the nucleophilic attack at the trifluoromethyl moiety. The involvement of the triplet state in the photodegradation has been unequivocally proved by direct detection of this transient in laser flash photolysis and by quenching experiments with oxygen, cyclohexadiene and naphthalene. Finally, the photobinding of HTB to proteins such as bovine serum albumin has been demonstrated using UV-visible (UV-Vis) and fluorescence spectroscopy. Nucleophilic groups present in the protein appear to be responsible for the formation of covalent drug photoadducts, which is the first step involved in the photoallergy shown by triflusal.

Photochemistry and Photobiology published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C8H5F3O3, HPLC of Formula: 328-90-5.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts