Category: 31719-76-3

Li, Jian-Yuan published the artcilePalladium-Catalyzed Hydroxycarbonylation of (Hetero)aryl Halides for DNA-Encoded Chemical Library Synthesis, Application of 4-(Phenoxymethyl)benzoic acid, the publication is Bioconjugate Chemistry (2019), 30(8), 2209-2215, database is CAplus and MEDLINE.

A strategy for DNA-compatible, palladium-catalyzed hydroxycarbonylation of (hetero)aryl halides on DNA-chem. conjugates has been developed. This method generally provided the corresponding carboxylic acids in moderate to very good conversions for (hetero)aryl iodides and bromides, and in poor to moderate conversions for (hetero)aryl chlorides. These conditions were further validated by application within a DNA-encoded chem. library synthesis and subsequent discovery of enriched features from the library in selection experiments against two protein targets.

Bioconjugate Chemistry published new progress about 31719-76-3. 31719-76-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 4-(Phenoxymethyl)benzoic acid, and the molecular formula is C14H12O3, Application of 4-(Phenoxymethyl)benzoic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Seeling, Andreas published the artcilePhysico-chemical, pharmacological, and toxicological properties of fomocaine metabolites, Category: catalysis-chemistry, the publication is Arzneimittel-Forschung (2001), 51(1), 7-17, database is CAplus and MEDLINE.

Fomocaine (4-[3-(4-phenoxymethylphenyl)-propyl]-morpholine, CAS 17692-39-6) is a highly effective local anesthetic of low toxicity. The drug, which causes no allergic response, was introduced in the German Extrapharmacopoeia (DAC). 14 Metabolites are formed after oral administration to rat and beagle dog. Less than 5 % fomocaine are excreted unchanged. The metabolites were synthesized and their physico-chem. properties were investigated. No metabolite caused a surface or conduction anesthesia with the exception of 2-hydroxyfomocaine (O/Se 4). After topical and parenteral administration irritation could not be observed All metabolites except O/Se 10 and O/Se 11 showed a lower toxicity than fomocaine. In both species O/Se 10 and O/Se 11 are formed only in a small amount and are detoxified by conjugation.

Arzneimittel-Forschung published new progress about 31719-76-3. 31719-76-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 4-(Phenoxymethyl)benzoic acid, and the molecular formula is C9H5ClO4S, Category: catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Lupp, Amelie published the artcileIn vitro investigations on the interactions of different fomocaine metabolites with rat microsomal cytochrome P450, HPLC of Formula: 31719-76-3, the publication is Nova Acta Leopoldina (2003), 87(329), 253-264, database is CAplus.

Fomocaine is an ether-type local anesthetic used in dermatol. practice for surface anesthesia. In view of possible new (systemic) applications, e.g. in the therapy of migraine or as an antiarrhythmic, knowledge of interactions also of its metabolites with the cytochrome P 450 system and thus with the metabolism of endogenous or other foreign substances is of importance. Thus, in the present study effects of thirteen fomocaine metabolites on liver P 450 mediated monooxygenase functions were assessed by measuring the influence on the model reactions ethoxyresorufin O-deethylation, ethoxycoumarin O-deethylation, pentoxyresorufin O-depentylation and ethylmorphine N-demethylation. Possible (potentially beneficial) antioxidative capacities of the compounds were evaluated by the influence on luminol and lucigenin amplified chemiluminescence, H₂O₂ production, and stimulated lipid peroxidation in rat liver microsomes and on rat whole blood chemiluminescence. Fomocaine inhibited all four model reactions for P 450 mediated monooxygenase functions in micromolar concentrations In general, the effects of the metabolites were much less pronounced than those of fomocaine. Only 2-hydroxyfomocaine yielded similar effects as fomocaine. A noticeable inhibition of the model reactions was also seen with 4-hydroxyfomocaine. This effect was, however, already distinctly less than that of fomocaine. The overall antioxidative capacity of fomocaine was not very pronounced. Many of the metabolites, especially those containing a phenolic group, displayed a stronger antioxidative capacity than fomocaine. Again, effects were most pronounced with 2-hydroxy- and 4-hydroxyfomocaine. Considering all effects of the metabolites tested, it is to be expected that after systemic application biotransformation of fomocaine to these metabolites will lead to a decrease in the overall interactions with the P 450 system and to an increase in the antioxidative capacity on the whole.

Nova Acta Leopoldina published new progress about 31719-76-3. 31719-76-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 4-(Phenoxymethyl)benzoic acid, and the molecular formula is C14H12O3, HPLC of Formula: 31719-76-3.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Lupp, Amelie published the artcileA synopsis on different homologous series of fomocaine derivatives. In vitro interactions with the cytochrome P450 system, toxicity, and local anesthetic effects in rats., Application of 4-(Phenoxymethyl)benzoic acid, the publication is Arzneimittel Forschung (2007), 57(9), 562-567, database is CAplus.

Fomocaine (CAS 56583-43-6) is a basic ether-type local anesthetic used in dermatol. practice for surface anesthesia. For many years, modifications of the fomocaine mol. have been pursued, e.g. to improve its physicochem. properties and also in view of possible new (systemic) applications, e.g. in the treatment of migraine or as antiarrhythmic. The present paper provides a survey of the investigations undertaken with all the different series of fomocaine derivatives synthesized so far with respect to their in vitro interaction capacity at the cytochrome P 450 system, in vivo toxicity (LD₅₀; paresis of the N. ischiadicus) and local anesthetic effects (conduction anesthesia at the N. ischiadicus; surface anesthesia of the cornea) in rats. The main objective of this systematic comparison of the effects of all these substances was to assess possible basic structure-activity relationships.

Arzneimittel Forschung published new progress about 31719-76-3. 31719-76-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 4-(Phenoxymethyl)benzoic acid, and the molecular formula is C14H12O3, Application of 4-(Phenoxymethyl)benzoic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Fleck, Christian published the artcileLocal anaesthetic effectivity and toxicity of fomocaine, five N-free fomocaine metabolites and two chiral fomocaine derivatives in rats compared with procaine, Name: 4-(Phenoxymethyl)benzoic acid, the publication is Arzneimittel-Forschung (2001), 51(6), 451-458, database is CAplus.

Until now, no optimal local anesthetic drug with long lasting effect and low toxicity has been developed. Fomocaine (CAS 17692-39-6), introduced in the German extrapharmacopoeia (DAC) in 1979, is a local anesthetic, which is largely in accordance with these aspects. Now the basic ether fomocaine, its metabolites O/Se 9 (CAS 3006-96-0), O/Se 10 (CAS 31719-76-3), O/Se 11, O/Se 12 (CAS 64264-21-7) and M5 and its chiral derivatives O/G 3 and O/G 5 were compared with procaine (CAS 59-46-1) and characterized more in detail in rats. The metabolism of fomocaine was investigated earlier with ¹⁴C-fomocaine in rats and beagle dogs. Rac-O/G 3 and Rac-O/G 5 could be separated into the enantiomers via the diastereomeric salts. Based on standard methods for the testing of the local anesthetic effects (estimation of infiltration and conduction anesthesia in rat tail, measurement of corneal anesthesia) and using a couple of tests characterizing the side effects and toxicity of local anesthetic (paresis of the N. ischiadicus, tissue irritation, determination of the approximative i.p. LD₅₀) it can be concluded that: (a) the very good surface anesthesia caused by fomocaine could be stated, but, as expected, concerning conduction anesthesia, procaine is better qualified for clin. use. (b) Fomocaine is much more effective in conduction and surface anesthesia than its chiral derivatives O/G 3 and O/G 5. (c) Differences between the two enantiomers of the O/G-substances have been found, but these little discrepancies are without practical relevance. In the case of O/G 5, agonistic effects of both enantiomers could be shown. (d) Fomocaine undergoes extensive biotransformation with subsequent formation of 14 metabolites. Five of them (O/Se 9-O/Se 12; M5) are N-free and do not show any pharmacol. activity. (e) Compared to other local anesthetics, fomocaine is relatively non-toxic (nearly no tissue irritation, high approximative LD₅₀), however, surprisingly the toxicity of the reference substance procaine has been found to be lower after i.p. administration instead of i.v. administration in comparison with fomocaine.

Arzneimittel-Forschung published new progress about 31719-76-3. 31719-76-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 4-(Phenoxymethyl)benzoic acid, and the molecular formula is C14H12O3, Name: 4-(Phenoxymethyl)benzoic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Yoshikawa, Hiromichi published the artcileLunularic acid analogs exhibit abscisic acid-like activities in higher plants, Recommanded Product: 4-(Phenoxymethyl)benzoic acid, the publication is Proceedings – Plant Growth Regulation Society of America (2000), 133-138, database is CAplus.

Dihydrostilbene carboxylic acids, phenoxymethylbenzoic acids and benzyloxy-benzoic acids were synthesized as lunularic acid analogs and their biol. activities were estimated by the following bioassays: 1) a cress and lettuce assay 2) an ¦Á-amylase induction test and 3) a Lunularia cruciata callus (A-18 strain) growth test. Some analogs with an electron-withdrawing group at the 3-position of the A ring and a carboxyl group at 2′- or 3′-position of B ring inhibited the germination and the growth of cress (Lepidium sativum). Similar tendency was observed in the growth test of Lunularia cruciata callus. Many compounds were more active than lunularic acid. Moreover, these series of compounds inhibited the ¦Á-amylase induction in barley. The 2,6-dichlorobenzyloxybenzoic acid esters stimulated the growth of lettuce roots but they showed no induction on ¦Á-amylase biosynthesis.

Proceedings – Plant Growth Regulation Society of America published new progress about 31719-76-3. 31719-76-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 4-(Phenoxymethyl)benzoic acid, and the molecular formula is C14H14, Recommanded Product: 4-(Phenoxymethyl)benzoic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Exner, O. published the artcileQuantitative evaluation of the inductive effect, Application In Synthesis of 31719-76-3, the publication is Collection of Czechoslovak Chemical Communications (1962), 02296-306, database is CAplus.

The relative pK’ values obtained by measuring the dissociation constants of p-toluic acids, substituted in the Me group, in 50% (by volume) aqueous EtOH (I) and 80% (by weight) Methyl Cellosolve (II), are considered as a measure of the inductive effect of the substituents. From the results it follows that the transmission of the inductive effect takes place predominantly along the ¦Ä-bonds (and not space). Refluxing p-ClCH₂C₆H₄CN (IIa) with azeotropic HBr 12 hrs. gave 62% p-BrCH₂C₆H₄CO₂H, m. 229¡ã (EtOH), also formed in 90% yield by refluxing p-HOCH₂C₆H₄CO₂Me with the same reagent. p-ClCH₂C₆H₄CO₂H (III) (1.71 g.) and 4 g. NaI refluxed 1 hr. in 30 ml. Me₂CO, the solution evaporated to dryness in vacuo, the inorganic salts washed out with H₂O, and the product washed with a dilute solution of Na₂S₂O₃ gave 66% p-ICH₂C₆H₄CO₂H, m. 235¡ã (EtOH). Refluxing 1.71 g. III with 0.46 g. Na in 30 ml. absolute MeOH 3 hrs., evaporating the MeOH in vacuo, and precipitating by HCl gave 70% p-MeOCH₂C₆H₄CO₂H, m. 108¡ã (CHCl₃, petr. ether). Similar procedure with 1.71 g. III, 0.94 g. PhOH, and 0.46 g. Na in 30 ml. MeOH gave 55% p-PhOCH₂C₆H₄CO₂H, m. 216¡ã (dilute EtOH). Adding 0.8 ml. AcCl to 1.52 g. p-HOCH₂C₆H₄C0₂H in 5 ml. C₅H₅N, cooling the mixture after 15 min., and pouring into dilute HCl gave 88% p-AcOCH₂C₆H₄CO₂H, m. 128¡ã (C₆H₆). p-PhCH₂C₆H₄CO₂H, prepared from p-BrCH₂C₆H₄CN (IV) and C₆H₆ in a 68% overall yield, m. 160¡ã (dilute EtOH). Partial hydrolysis of p-NCCH₂C₆H₄CO₂H afforded 51% p-H₂NCOCH₂C₆H₄CO₂H, m. 274¡ã (EtOH). Refluxing 1.71 g. III with 1 g. NaSCN in 30 ml. EtOH 3 hrs., evaporating the solution to dryness in vacuo, eluting the salts with H₂O, and repptg. the crude product from 10% aqueous KOH gave 80% p-NCSCH₂C₆H₄CO₂H, m. 172¡ã (EtOAc). Refluxing 1.61 g. p-BrCH₂C₆H₄CO₂H with 2.2 g. PhSO₂Na in 25 ml. EtOH 8 hrs. yielded 95% p-PhSO₂CH₂C₆H₄CO₂H, m. 306¡ã (decomposition) (EtOH). Adding 4.9 g. IV to a mixture of 8.2 g. Me₂NH.HCl and 3.5 g. NaOH in 10 ml. H₂O and 25 ml. EtOH, allowing the mixture to stand overnight, refluxing 30 min., evaporating the EtOH in vacuo, dissolving the residue in H₂O, extracting the solution with three 15-ml. portions CHCl₃, evaporating the extract, refluxing the residue 3 hrs. with a solution of 3 g. NaOH in 20 ml. 50% EtOH, acidifying the reaction mixture with HCl, evaporating to dryness in vacuo, and extracting the residue with boiling EtOH gave 56% p-Me₂NCH₂C₆H₄CO₂H.HCl, m. 256¡ã (EtOH). Allowing a mixture of 3.03 g. IIa and 2.8 g. (CH₂)₆N₄ in 50 ml. CHCl₃ to stand 2 days at room temperature, concentrating the solution to 10 ml. in vacuo, filtering off 4.11 g. of a salt, dissolving it in 20 ml. 1:2 HCl and EtOH, distg, to dryness in vacuo, and extracting the residue with Me₂CO gave 52% p-H₂NCH₂C₆H₄CN.HCl, m. 269¡ã (EtOH). Hydrolysis by refluxing 16 hrs. with concentrated HCl, followed by acetylation with AcCl in pyridine, gave 43% p-Ac-NHCH₂C₆H₄CO₂H, m. 201¡ã (EtOH). The measurements of the apparent dissociation constants were carried out using an electronic pH meter with a vibrating condenser and a cell having a glass electrode and calomel reference electrode. The substances in concentrations of the order of 10^-3M were titrated with aqueous Me₄OH. The apparent dissociation constants (pK’) in solvents I and II for the appropriate substituents in ¦Á-position of p-MeC₆H₄CO₂H are for: H, 5.78, 6.82; Cl, 5.36, 6.45; Br, 5.36, 6.36; iodine, 5.41, 6.41; Ph, 5.70, 6.73; CN, 5.28, 6.32; CONH₂, 5.44, 6.69; OH, 5.56, 6.70; OMe, 5.50, 6.58; OPh, 5.43, 6.56; OAc, 5.46, 6.50; NHAc, 5.61, 6.68; NMe₂.HCl, 4.67, –; SCN, 5.33, 6.46; and PhSO₂, –, 6.36.

Collection of Czechoslovak Chemical Communications published new progress about 31719-76-3. 31719-76-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 4-(Phenoxymethyl)benzoic acid, and the molecular formula is C14H12O3, Application In Synthesis of 31719-76-3.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Schmid, Kyle M. published the artcileA Self-Immolative Spacer That Enables Tunable Controlled Release of Phenols under Neutral Conditions, Product Details of C14H12O3, the publication is Journal of Organic Chemistry (2012), 77(9), 4363-4374, database is CAplus and MEDLINE.

A current challenge in the area of responsive materials is the design of reagents and polymers that provide controlled release of phenols in environments that are less polar than water. In these contexts, a mol. strategy that enables release of nearly any phenol with predictable and tunable rates and without complication from background hydrolysis would substantially increase the precision with which materials can be designed to respond to a particular signal. This Article addresses this problem at the fundamental level by describing the design, synthesis, and phys.-organic characterization of two small mol. self-immolative spacers that are capable of releasing phenols in organic and mixed organic-aqueous solutions The rate of release from these small mol. model systems is predictable and tunable, such that nearly any type of phenol, regardless of pK_a value, can be released in neutral solutions without complications from nonspecific background release due to hydrolysis. Furthermore, the release properties of the spacers can be predicted from bond length and conformation data (obtained from crystal structures). On the basis of these results, it should now be possible to incorporate these design elements into materials to enable precise response properties in environments that are not 100% aqueous

Journal of Organic Chemistry published new progress about 31719-76-3. 31719-76-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 4-(Phenoxymethyl)benzoic acid, and the molecular formula is C14H12O3, Product Details of C14H12O3.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Kronenberger, Thales published the artcileDesign, synthesis and biological activity of novel substituted 3-benzoic acid derivatives as MtDHFR inhibitors, Related Products of catalysis-chemistry, the publication is Bioorganic & Medicinal Chemistry (2020), 28(15), 115600, database is CAplus and MEDLINE.

The fragment MB872 I [R¹ = H; R² = 3-C(O)OH; W = O; Y = CH₂] was used as a prototype for analog development by bioisosterism/retro-bioisosterism, which resulted in substituted 3-benzoic acid derivatives I [R¹ = H, OH, OMe, NO₂; R² = 3-C(O)OH, 4-C(O)OH, 3-C(O)OMe, 4-C(O)OMe, 3-NO₂; W = O, S, NH, CH₂; Y = O, CH₂]. Compounds I were active against MtDHFR, with IC₅₀ values ranging from 7 to 40¦ÌM, where compound I [R¹ = H; R² = 3-C(O)OH; W = NH; Y = CH₂] not only had the best inhibitory activity (IC₅₀ = 7¦ÌM), but also was 71-fold more active than the original fragment MB872. The compound I [R¹ = H; R² = 3-C(O)OH; W = NH; Y = CH₂] inhibition kinetics indicated an uncompetitive mechanism, which was supported by mol. modeling which suggested that the compounds I could access an independent backpocket from the substrate and competitive inhibitors. Thus, based on these results, substituted 3-benzoic acid derivatives I had strong potential to be developed as novel MtDHFR inhibitors and also anti-TB agents.

Bioorganic & Medicinal Chemistry published new progress about 31719-76-3. 31719-76-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 4-(Phenoxymethyl)benzoic acid, and the molecular formula is C14H12O3, Related Products of catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Wang, Xin published the artcileFlavonoids and antioxidant activity of rare and endangered fern: Isoetes sinensis, Name: 4-(Phenoxymethyl)benzoic acid, the publication is PLoS One (2020), 15(5), e0232185, database is CAplus and MEDLINE.

Isoetes sinensis Palmer is a critically endangered, first-class protected plant in China. Until now, researchers have primarily focused on the ultrastructure, phylogeny, and transcriptomes of the plant. However, flavonoid profiles and bioactivity of I. sinensis have not been extensively investigated. To develop the endangered I. sinensis for edible and medicinal purposes, flavonoid content, chem. constitution, and antioxidant activities were investigated in this study. Results revealed the following. 1) The total flavonoid content was determined as 10.74 ¡À 0.25 mg/g., 2) Antioxidant activities were stronger than most ferns, especially ABTS free radical scavenging activities. 3) Four flavones, containing apigenin, apigenin-7-glucuronide, acacetin-7-O-glcopyranoside, and homoplantageninisoetin; four flavonols, namely, isoetin, kaempferol-3-O-glucoside, quercetin-3-O-[6″-O-(3-hydroxy-3-methylglutaryl)-¦Â-D-glucopyranoside], and limocitrin-Neo; one prodelphinidin (procyanidins;) and one nothofagin (dihydrochalcone) were tentatively identified in the mass spectrometry-DAD (254nm) chromatograms. This study was the first to report on flavonoid content and antioxidant activities of I. sinensis. Stronger antioxidant activity and flavonoid content suggests that the endangered I. sinensis is an important and potentially edible and medicinal plant.

PLoS One published new progress about 31719-76-3. 31719-76-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 4-(Phenoxymethyl)benzoic acid, and the molecular formula is C4H10O2, Name: 4-(Phenoxymethyl)benzoic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia