Category: 328-90-5

Boscá, F published the artcilePhotochemistry of 2-hydroxy-4-trifluoromethylbenzoic acid, major metabolite of the photosensitizing platelet antiaggregant drug triflusal., COA of Formula: C8H5F3O3, the publication is Photochemistry and photobiology (2001), 73(5), 463-8, database is MEDLINE.

Triflusal is a platelet antiaggregant drug with photoallergic side effects. However, it is considered a prodrug since it is metabolized to 2-hydroxy-4-trifluoromethylbenzoic acid (HTB)–the pharmacologically 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 ultraviolet-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, COA of Formula: C8H5F3O3.

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

Chae, Hee-Don published the artcileSAR optimization studies on modified salicylamides as a potential treatment for acute myeloid leukemia through inhibition of the CREB pathway, Computed Properties of 328-90-5, the publication is Bioorganic & Medicinal Chemistry Letters (2019), 29(16), 2307-2315, database is CAplus and MEDLINE.

Disruption of cyclic adenosine monophosphate response element binding protein (CREB) provides a potential new strategy to address acute leukemia, a disease associated with poor prognosis, and for which conventional treatment options often carry a significant risk of morbidity and mortality. We describe the structure-activity relationships (SAR) for a series of XX-650-23 derived from naphthol AS-E phosphate that disrupts binding and activation of CREB by the CREB-binding protein (CBP). Through the development of this series, we identified several salicylamides that are potent inhibitors of acute leukemia cell viability through inhibition of CREB-CBP interaction. Among them, a biphenyl salicylamide, compound 71, was identified as a potent inhibitor of CREB-CBP interaction with improved physicochem. properties relative to previously described derivatives of naphthol AS-E phosphate.

Bioorganic & Medicinal Chemistry Letters 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, Computed Properties of 328-90-5.

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

Kim, Seung-Woo published the artcileNeuroprotective effect of triflusal and its main metabolite, 2-hydroxy-4-trifluoromethylbenzoic acid (HTB), in the postischemic brain, Application In Synthesis of 328-90-5, the publication is Neuroscience Letters (2017), 59-64, database is CAplus and MEDLINE.

2-Hydroxy-4-trifluoromethylbenzoic acid (HTB) is a metabolite of triflusal (TF), and has been reported to exert anti-inflammatory effect. In this study, the authors investigated whether HTB has a neuroprotective effect against ischemic brain injuries. We showed that i.v. administration of HTB (5 mg/kg) 30 min before or 1, 3, or 6 h after middle cerebral artery occlusion (MCAO) reduced brain infarct to 10.4 ± 3.3%, 16.9 ± 2.3%, 22.2 ± 1.5% and 40.7 ± 7.5%, resp., of that of treatment-naive MCAO controls, and the therapeutic time window extended to 9 h after MCAO (40.7 ± 7.5%). Furthermore, HTB suppressed infarct formation, protected motor activities, and ameliorated neurol. deficits more effectively than by TF or salicylic acid (SA). HTB markedly suppressed microglial activation and proinflammatory cytokines expressions in the postischemic brain and in BV2 cells and suppressed LPS-induced nitrite production by inhibiting IkB degradation In addition, HTB suppressed NMDA-induced neuronal cell death more effectively than TF or SA in primary cortical neuron cultures. Together, these results indicate that HTB has multi-modal protective effects against ischemic brain damage that encompass anti-inflammatory, anti-excitotoxicity, and anti-Zn²⁺-toxicity effects.

Neuroscience Letters 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 In Synthesis of 328-90-5.

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

Jia, Kangle published the artcileThermal, light and pH triple stimulated changes in self-assembly of a novel small molecular weight amphiphile binary system, Application of 2-Hydroxy-4-(trifluoromethyl)benzoic acid, the publication is RSC Advances (2015), 5(1), 640-642, database is CAplus.

Novel multiple stimuli-responsive fluids based on an azobenzene-contained surfactant 1-[2-(4-decylphenylazo-phenoxy)-ethyl]-3-methylimidazolium bromide (C10AZOC2IMB) and a hydrotrope 4-(trifluoromethyl) salicylic acid (4FS) can be reversibly induced by temperature, light and pH from vesicles to wormlike micelles. UV-vis spectra, rheol. and cryo-TEM measurements were utilized to prove the self-assembly transitions.

RSC Advances 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

Zhong, Yuan-hui published the artcileMethods for synthesis of trifluoromethylsalicylic acid and its intermediate, HPLC of Formula: 328-90-5, the publication is Zhejiang Huagong (2014), 45(1), 7-10, database is CAplus.

A review. 4-(Trifluoromethyl) salicylic acid and m-trifluoromethylphenol are critical intermediate and raw material in the field of pesticide, medicine and others. This article summarizes the methods for synthesis of 4-(trifluoromethyl) salicylic acid, also mainly introduces the synthetic methods of m-trifluoromethylphenol, the synthetic material of 4-(trifluoromethyl) salicylic acid, including the diazotization and hydrolysis of trifluoromethylaniline, the hydroxylation, the trifluoromethylation, the catalytic hydrogenation, the oxidation of benzotrifluoride with hydrogen peroxide, and so on.

Zhejiang Huagong 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 C12H25Br, HPLC of Formula: 328-90-5.

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

Xu, Xiushang published the artcileSynthesis and characterization of dibenzo[hi,st]ovalene as a highly fluorescent polycyclic aromatic hydrocarbon and its π-extension to circumpyrene, Formula: C8H5F3O3, the publication is Yuki Gosei Kagaku Kyokaishi (2020), 78(11), 1094-1104, database is CAplus.

This account described the synthetic approaches to dibenzo[hi,st]ovalene (DBOV) as a novel PAH with a combination of armchair and zigzag edges and the elucidation of its unique optoelectronic and photophys. properties, such as strong red emission with a fluorescence quantum yield of up to 0.89 and stimulated emission. Furthermore, DBOV demonstrated the so-called fluorescence blinking that enables its application as a fluorophore in single-mol. localization microscopy, which is one of the modern superresoln. fluorescence microscopy methods. The self-assembly of a DBOV derivative bearing two 3,4,5-tris(dodecyloxy)phenyl groups was also investigated, showing the formation of helical columnar stacks. On the other hand, the regioselective bromination of DBOV was achieved, allowing the postsynthetic functionalization and modulation of the optoelectronic properties. Moreover, π-extension of the DBOV at the bay regions led to circumpyrene, the largest circumarene synthesized to date.

Yuki Gosei Kagaku Kyokaishi 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 C6H5NO, Formula: C8H5F3O3.

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

Palmer, Ian Arthur published the artcileNovel salicylic acid analogs induce a potent defense response in Arabidopsis, Application of 2-Hydroxy-4-(trifluoromethyl)benzoic acid, the publication is International Journal of Molecular Sciences (2019), 20(13), 3356, database is CAplus and MEDLINE.

The master regulator of salicylic acid (SA)-mediated plant defense, NPR1 (NONEXPRESSER OF PR GENES 1) and its paralogs NPR3 and NPR4, act as SA receptors. After the perception of a pathogen, plant cells produce SA in the chloroplast. In the presence of SA, NPR1 protein is reduced from oligomers to monomers, and translocated into the nucleus. Several of these analogs can induce SA-mediated defense and inhibit growth of Pseudomonas syringae in Arabidopsis. These analogs, when sprayed on Arabidopsis, can induce the accumulation of the master regulator of plant defense NPR1. In a yeast two-hybrid system, these analogs can strengthen the interactions among NPR proteins. We demonstrated that these analogs can induce the expression of the defense marker gene PR1. Furthermore, we hypothesized that these SA analogs could be potent tools against the citrus greening pathogen Candidatus liberibacter spp. In fact, our results suggest that the SA analogs we tested using Arabidopsis may also be effective for inducing a defense response in citrus. Several SA analogs consistently strengthened the interactions between citrus NPR1 and NPR3 proteins in a yeast two-hybrid system. In future assays, we plan to test whether these analogs avoid degradation by SA hydroxylases from plant pathogens. In future assays, we plan to test whether these analogs avoid degradation by SA hydroxylases from plant pathogens.

International Journal of Molecular 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

De Arriba, Alberto Fernandez published the artcileInhibition of cyclooxygenase-2 expression by 4-trifluoromethyl derivatives of salicylate, triflusal, and its deacetylated metabolite, 2-hydroxy-4-trifluoromethylbenzoic acid, HPLC of Formula: 328-90-5, the publication is Molecular Pharmacology (1999), 55(4), 753-760, database is CAplus.

The therapeutic potential of drugs that block the induction of cyclooxygenase-2 has been emphasized. When two 4-trifluoromethyl salicylate derivatives [2-acetoxy-4-trifluoromethylbenzoic acid (triflusal) and its deacetylated metabolite 2-hydroxy-4-trifluoromethylbenzoic acid (HTB)] were compared with aspirin and sodium salicylate as cyclooxygenase-2 (COX-2) inhibitors, we observed that in bacterial lipopolysaccharide-activated human blood, triflusal, aspirin, and HTB, but not sodium salicylate, inhibited COX-2-mediated prostaglandin E₂ (PGE₂) production (IC₅₀ = 0.16, 0.18, 0.39, and > 10 mM, resp.). However, only triflusal and aspirin inhibited purified COX-2 enzyme. To test this apparent discrepancy, we realized that HTB and triflusal (but neither aspirin nor salicylate) produced a concentration-dependent inhibition of COX-2 protein expression in peripheral human mononuclear cells. This observation was further confirmed in a rat air pouch model in vivo, in which both aspirin and triflusal inhibited PGE₂ production (ID₅₀ = 18.9 and 11.4 mg/kg p.o., resp.) but only triflusal-treated animals showed a decrease in COX-2 expression. This different behavior may be, at least in part, due to the ability of HTB and triflusal to block the activation of the transcription factor nuclear factor-κB to a higher extent than aspirin and sodium salicylate. Thus, in addition to inhibiting the COX-2 activity at therapeutic concentrations, triflusal is able to block through its metabolite HTB the expression of new enzyme, and hence the resumption of PGE₂ synthesis. Triflusal and HTB may exert beneficial effects in processes in which de novo COX-2 expression is involved and, in a broader sense, in pathol. situations in which genes under nuclear factor-κB control are up-regulated.

Molecular 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, HPLC of Formula: 328-90-5.

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

Fernández de Arriba, A published the artcileInhibition of cyclooxygenase-2 expression by 4-trifluoromethyl derivatives of salicylate, triflusal, and its deacetylated metabolite, 2-hydroxy-4-trifluoromethylbenzoic acid., Synthetic Route of 328-90-5, the publication is Molecular pharmacology (1999), 55(4), 753-60, database is MEDLINE.

The therapeutic potential of drugs that block the induction of cyclooxygenase-2 has been emphasized. When two 4-trifluoromethyl salicylate derivatives [2-acetoxy-4-trifluoromethyl-benzoic acid (triflusal) and its deacetylated metabolite 2-hydroxy-4-trifluoromethylbenzoic acid (HTB)] were compared with aspirin and sodium salicylate as cyclooxygenase-2 (COX-2) inhibitors, we observed that in bacterial lipopolysaccharide-activated human blood, triflusal, aspirin, and HTB, but not sodium salicylate, inhibited COX-2-mediated prostaglandin E2 (PGE2) production (IC50 = 0.16, 0.18, 0.39, and >10 mM, respectively). However, only triflusal and aspirin inhibited purified COX-2 enzyme. To test this apparent discrepancy, we realized that HTB and triflusal (but neither aspirin nor salicylate) produced a concentration-dependent inhibition of COX-2 protein expression in peripheral human mononuclear cells. This observation was further confirmed in a rat air pouch model in vivo, in which both aspirin and triflusal inhibited PGE2 production (ID50 = 18.9 and 11.4 mg/kg p.o., respectively) but only triflusal-treated animals showed a decrease in COX-2 expression. This different behavior may be, at least in part, due to the ability of HTB and triflusal to block the activation of the transcription factor nuclear factor-kappaB to a higher extent than aspirin and sodium salicylate. Thus, in addition to inhibiting the COX-2 activity at therapeutic concentrations, triflusal is able to block through its metabolite HTB the expression of new enzyme, and hence the resumption of PGE2 synthesis. Triflusal and HTB may exert beneficial effects in processes in which de novo COX-2 expression is involved and, in a broader sense, in pathological situations in which genes under nuclear factor-kappaB control are up-regulated.

Molecular 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, Synthetic Route of 328-90-5.

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

Sanchez de Miguel, Lourdes published the artcileComparison of in vitro effects of triflusal and acetylsalicylic acid on nitric oxide synthesis by human neutrophils, HPLC of Formula: 328-90-5, the publication is European Journal of Pharmacology (1998), 343(1), 57-65, database is CAplus and MEDLINE.

Recent studies have suggested that the protective anti-ischemic effects of acetylsalicylic acid are stronger than the inhibition of platelet thromboxane A₂ synthesis. Since ischemic events still occur in acetylsalicylic acid-treated patients, the development of new drugs with more powerful protective effects is needed. The authors compared the effects of a new platelet antiaggregating drug, 2-acetoxy-4-trifluoromethylbenzoic acid (triflusal) and of acetylsalicylic acid on the interaction between human neutrophils and platelets, examining the capability of neutrophils to generate nitric oxide (NO). Triflusal, in the presence of neutrophils, showed a greater antiplatelet potency than acetylsalicylic acid to inhibit thrombin-induced platelet activation. Significant stimulation of NO-mediated mechanisms in the presence of acetylsalicylic acid or triflusal was demonstrated by the following findings: (1) increased metabolism of arginine to citrulline, (2) increase of cGMP in the platelet/neutrophil system and (3) the inhibitory action of the L-arginine (L-Arg) competitive analog, N^G-nitro-L-arginine-Me ester (L-NAME), which was reversed by L-Arg. Triflusal increased the stimulation of NO synthesis by neutrophils more than did of acetylsalicylic acid. The main metabolite of triflusal, 2-hydroxy-4-trifluoromethylbenzoic acid (HTB), alone or in combination with acetylsalicylic acid, did not modify NO production by neutrophils. Therefore, the whole mol. of triflusal is needed to stimulate NO production by neutrophils. The results show that, in the presence of neutrophils, triflusal exerts an antiplatelet effect greater than that of acetylsalicylic acid, demonstrating a more powerful stimulation of the NO/cGMP system. The present results indicate that it is possible to develop new and more potent acetylsalicylic acid-related antiplatelet drugs for the prevention of the myocardial ischemic/reperfusion processes.

European 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, HPLC of Formula: 328-90-5.

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