Category: 1860-58-8

Leimbacher, Markus published the artcileDiscovery of Small-Molecule Interleukin-2 Inhibitors from a DNA-Encoded Chemical Library, Application In Synthesis of 1860-58-8, the publication is Chemistry – A European Journal (2012), 18(25), 7729-7737, S7729/1-S7729/120, database is CAplus and MEDLINE.

Libraries of chem. compounds individually coupled to encoding DNA tags (DNA-encoded chem. libraries) hold promise to facilitate exceptionally efficient ligand discovery. We constructed a high-quality DNA-encoded chem. library comprising 30 000 drug-like compounds; this was screened in 170 different affinity capture experiments High-throughput sequencing allowed the evaluation of 120 million DNA codes for a systematic anal. of selection strategies and statistically robust identification of binding mols. Selections performed against the tumor-associated antigen carbonic anhydrase IX (CA IX) and the pro-inflammatory cytokine interleukin-2 (IL-2) yielded potent inhibitors with exquisite target specificity. The binding mode of the revealed pharmacophore against IL-2 was confirmed by mol. docking. Our findings suggest that DNA-encoded chem. libraries allow the facile identification of drug-like ligands principally to any protein of choice, including mols. capable of disrupting high-affinity protein-protein interactions.

Chemistry – A European Journal published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C15H14O3, Application In Synthesis of 1860-58-8.

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

Rit, Raja K. published the artcilePd(II)-Catalyzed ortho-C-H Oxidation of Arylacetic Acid Derivatives: Synthesis of Benzofuranones, COA of Formula: C15H14O3, the publication is Organic Letters (2014), 16(3), 968-971, database is CAplus and MEDLINE.

Pd(II)-catalyzed ortho-C-H acetoxylation of arylacetic acid derivatives, e.g., I (X= H), is demonstrated with the aid of a novel S-methyl-S-2-pyridylsulfoximine (MPyS) directing group (DG). The ¦Á-mono- and ¦Á-unsubstituted arylacetic acid derivatives were readily employed in the ortho-C-H acetoxylations. The oxidation products, e.g., I (X= OAc), are hydrolyzed, and the MPyS-DG is easily recovered, providing ready access to o-hydroxyarylacetic acids. 3-Mono- and 3-unsubstituted benzofuranones, e.g., II, are synthesized from o-hydroxyarylacetic acids.

Organic Letters published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C15H14O3, COA of Formula: C15H14O3.

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

Chen, Weibin published the artcileEthers of 3-hydroxyphenylacetic acid as selective gamma-hydroxybutyric acid receptor ligands, Application In Synthesis of 1860-58-8, the publication is Bioorganic & Medicinal Chemistry Letters (2005), 15(13), 3201-3202, database is CAplus and MEDLINE.

Gamma-hydroxybutyric acid (GHB) is a drug of abuse, a therapeutic, and purportedly a neurotransmitter with a complex mechanism of action in vivo due to direct actions at GABA_B as well as GHB receptors and because of its metabolism to GABA. Herein, the authors describe 3-ethers of 3-hydroxyphenylacetic acid, which have relatively high affinity at GHB sites, no significant affinity at GABA receptors, and would not be expected to be rapidly metabolized to GABAergic ligands. The selectivity of these compounds (UMB108, UMB109, and UMB119) could prove to be useful for studying the biol. of GHB receptors, free from GABAergic effects.

Bioorganic & Medicinal Chemistry Letters published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C15H14O3, Application In Synthesis of 1860-58-8.

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

Tangdenpaisal, Kassrin published the artcileDesigning New Analogs for Streamlining the Structure of Cytotoxic Lamellarin Natural Products, Application of 2-(3-(Benzyloxy)phenyl)acetic acid, the publication is Chemistry – An Asian Journal (2015), 10(4), 925-937, database is CAplus and MEDLINE.

Despite the therapeutic potential of marine-derived lamellarin natural products, their preclin. development has been hampered by their lipophilic nature, causing very poor aqueous solubility In order to develop more drug-like analogs, their structure was streamlined in this study from both the cytotoxic activity and lipophilicity standpoints. First, a modified total synthetic route was successfully devised to construct a library of 59 systematically designed lamellarin analogs, which were then subjected to cytotoxicity and log P determinations [e.g., I with single or double bond as indicated by dotted line; R = H, Me; X = H, OH; Y = H, OMe; A, B = H, OH]. Along with the 25 first-generation lamellarins previously synthesized in our laboratory, the structure-activity and structure-lipophilicity relationships were extensively evaluated. Our results clearly indicated the addnl. structural requirements around the lamellarin skeleton which, when combined with those reported previously, can provide invaluable guidance for further modifications to increase the aqueous solubility of these compounds

Chemistry – An Asian Journal published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C17H14O5, Application of 2-(3-(Benzyloxy)phenyl)acetic acid.

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

Wang, Xu-Dong published the artcileSynthesis, molecular docking and biological evaluation of 3-arylfuran-2(5H)-ones as anti-gastric ulcer agent, Name: 2-(3-(Benzyloxy)phenyl)acetic acid, the publication is Bioorganic & Medicinal Chemistry (2015), 23(15), 4860-4865, database is CAplus and MEDLINE.

3-Arylfuran-2(5H)-one derivatives show good antibacterial activity and were determined as tyrosyl-tRNA synthetase (TyrRS) inhibitors. In a systematic medicinal chem. exploration, we demonstrated chem. opportunities to treat infections caused by Helicobacter pylori. Twenty 3-arylfuran-2(5H)-ones were synthesized and evaluated for anti-H. pylori, antioxidant and anti-urease activities which are closely interconnected with H. pylori infection. The results displayed that some of the compounds show excellent antioxidant activity, and good anti-H. pylori and urease inhibitory activities. Out of these compounds, 3-(3-methylphenyl)furan-2(5H)-one (I) showed the most potent antioxidant activity (IC₅₀ = 8.2 ¦ÌM) and good anti-H. pylori activity (MIC₅₀ = 2.6 ¦Ìg/mL), and it can be used as a good candidate for discovering novel anti-gastric ulcer agent.

Bioorganic & Medicinal Chemistry published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C8H11BO2, Name: 2-(3-(Benzyloxy)phenyl)acetic acid.

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

Mannekens, Els published the artcileEfficient synthesis of 1-benzyloxyphenyl-3-phenylacetones, Category: catalysis-chemistry, the publication is Synthesis (2000), 1214-1216, database is CAplus.

1-[(Benzyloxy)phenyl]-3-phenylacetones (I) were conveniently synthesized by acylation of the PhCH₂Li-DABCO complex with their resp. N-Me O-Me hydroxamates. In four steps, the ketones I having ortho-, meta- and para-benzyloxy substituents were obtained in 42-51% overall yields from com. available 2-(hydroxyphenyl)acetic acids.

Synthesis published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C15H14O3, Category: catalysis-chemistry.

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

Matsufuji, Tetsuyoshi published the artcileDiscovery of novel chiral diazepines as bombesin receptor subtype-3 (BRS-3) agonists with low brain penetration, Formula: C15H14O3, the publication is Bioorganic & Medicinal Chemistry Letters (2014), 24(3), 750-755, database is CAplus and MEDLINE.

The discovery and optimization of a novel series of BRS-3 agonists are described. We explored a potent BRS-3 agonist with low brain penetration to avoid an adverse effect derived from central nervous system exposure. Through the derivatization process, chiral diazepines I (R¹ = iso-Bu, 2-methylpyridin-5-yl) were identified as possessing low brain penetration as well as potent in vitro activity against human and mouse BRS-3s.

Bioorganic & Medicinal Chemistry Letters published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C15H14O3, Formula: C15H14O3.

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

Matsufuji, Tetsuyoshi published the artcileSynthesis and biological evaluation of novel chiral diazepine derivatives as bombesin receptor subtype-3 (BRS-3) agonists incorporating an antedrug approach, Recommanded Product: 2-(3-(Benzyloxy)phenyl)acetic acid, the publication is Bioorganic & Medicinal Chemistry (2015), 23(1), 89-104, database is CAplus and MEDLINE.

Novel compounds based on the lead BRS-3 agonists from our HTS compounds have been synthesized with the focus on obtaining peripheral BRS-3 agonists. To identify potent anti-obesity compounds without adverse effects on the central nerve system, a labile carboxylic ester with an antedrug functionality was introduced onto the terminal position. Through the extensive synthetic exploration and the pharmacokinetic studies of oral administration in mice, the phenol ester I was selected due to the most suitable pharmacol. profile. In the evaluation of food intake suppression in B6 mice, I showed significant in vivo efficacy and no clear adverse effect on heart rate and blood pressure change in dog iv infusion. Our study paved the way for development of anti-diabetes and obesity drugs with a safer profile.

Bioorganic & Medicinal Chemistry published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C15H14O3, Recommanded Product: 2-(3-(Benzyloxy)phenyl)acetic acid.

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

Neumann, William L. published the artcileSynthesis and structure-activity relationships of 3,4,5-trisubstituted-1,2,4-triazoles: high affinity and selective somatostatin receptor-4 agonists for Alzheimer¡äs disease treatment, Name: 2-(3-(Benzyloxy)phenyl)acetic acid, the publication is RSC Medicinal Chemistry (2021), 12(8), 1352-1365, database is CAplus and MEDLINE.

Somatostatin receptor-4 (SST₄) is highly expressed in brain regions affiliated with learning and memory. SST₄ agonist treatment may act to mitigate Alzheimer¡äs disease (AD) pathol. An integrated approach to SST₄ agonist lead optimization is presented herein. High affinity and selective agonists with biol. efficacy were identified through iterative cycles of a structure-based design strategy encompassing computational methods, chem., and preclin. pharmacol. 1,2,4-Triazole derivatives of our previously reported hit (4) showed enhanced SST₄ binding affinity, activity, and selectivity. Thirty-five compounds showed low nanomolar range SST₄ binding affinity, 12 having a K_i < 1 nM. These compounds showed >500-fold affinity for SST₄ as compared to SST_2A. SST₄ activities were consistent with the resp. SST₄ binding affinities (EC₅₀ < 10 nM for 34 compounds). Compound 208 (SST₄K_i = 0.7 nM; EC₅₀ = 2.5 nM; >600-fold selectivity over SST_2A) display a favorable physiochem. profile, and was advanced to learning and memory behavior evaluations in the senescence accelerated mouse-prone 8 model of AD-related cognitive decline. Chronic administration enhanced learning with i.p. dosing (1 mg kg^-1) compared to vehicle. Chronic administration enhanced memory with both i.p. (0.01, 0.1, 1 mg kg^-1) and oral (0.01, 10 mg kg^-1) dosing compared to vehicle. This study identified a novel series of SST₄ agonists with high affinity, selectivity, and biol. activity that may be useful in the treatment of AD.

RSC Medicinal Chemistry published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C15H14O3, Name: 2-(3-(Benzyloxy)phenyl)acetic acid.

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

Rapson, Wm. Sage published the artcileSynthesis of substances related to the sterols. VII, Recommanded Product: 2-(3-(Benzyloxy)phenyl)acetic acid, the publication is Journal of the Chemical Society (1935), 1533-43, database is CAplus.

Et 1-methyl-¦¤²-cyclopentene-1-carboxylate (I), b₁₃ 70-1¡ã, results from the HO ester and P₂O₆ in C₆H₆; the acid b₁₄ 110¡ã. Reduction of the Et ester gives 70% of 1-methyl-¦¤²-cyclopentenyl-1-carbinol (II), b₇₆₀ 162-5¡ã (p-nitrobenzoate, m. 67¡ã); PCl₅ in petr. ether gives the chloride, b₁₈ 40-56¡ã, which does not condense with AcCHNaCO₂Et in EtOH or C₆H₆. Dehydration of II with KHSO₄ gives a dihydrotoluene(?), b. 112-13¡ã. Electrolytic reduction of 35 g. of m-MeOC₆H₄CHO (4 amps., c. d., 0.025 amp./sq. cm.) for 3 hrs. gives 20 g. m-MeOC₆H₄CH₂OH (III) and 9 g. of 3,3′-dimethoxyhydrobenzoin ¦Á,¦Á’-di-Me ether, m. 112-13¡ã. III was converted through the chloride and nitrile to Et m-methoxyphenylacetate, which was reduced with Na and EtOH to ¦Â-m-methoxyphenylethyl alc., b₁₂ 135-7¡ã; the chloride, b₁₄ 128-30¡ã, reacts sluggishly with AcCHNaCO₂Et; Et ¦Â-m-methoxyphenylethylacetoacetate b₂ 180¡ã; hydrolysis gives ¦Ã-m-methoxyphenylpropyl Me ketone, b₁₉ 168¡ã (semicarbazone, m. 109¡ã); condensation with I did not give a pure ¦Â-diketone. The K salt of Et trans-cyclopentane-1-carboxylate-2-cyanoacetate and PhCH₂Ch₂Br give Et ¦Á-cyano-¦Á-(trans-2-carbethoxycyclopentyl)-¦Ã-phenylbutyrate, b₁ 195-200¡ã; hydrolysis with concentrated HCl (boiling 30 hrs.) gives ¦Á-cyano-¦Á-(trans-2-carboxycyclopentyl)-¦Ã-phenylbutyric acid, m. 210¡ã (decomposition); boiling with H₂SO₄ and AcOH gives ¦Á-(trans-2-carboxycyclopentyl)-¦Ã-phenylbutyric acid, m. 160-1¡ã; the trans-anhydride, m. 112¡ã, on heating at 250¡ã for 15 min., gives the cis-anhydride, which did not crystallize; the cis-acid m. 133¡ã. The trans-acid with H₂SO₄ gives 1-keto-2-(trans – 2′ – carboxycyclopentyl) – 1,2,3,4 – tetrahydronaphthalene, m. 164-5¡ã; heating with Ac₂O and AcONa and decomposition of the anhydride gives the cis-isomer, m. 155-6¡ã. The Me ester of the trans-acid m. 45¡ã; this did not react with BrCH₂CO₂Et and Zn. Both acids react with SOCl₂ in CHCl₃ to yield the trans- and cis- forms of 1-hydroxy – 2 – (2′ – carboxycyclopentyl) – 3,4 – dihydroxynaphthalene lactone, m. 162¡ã and 66¡ã, resp. The transform, monoclinic needles elongated along a, with the faces {021}, {100} developed; the dimensions of the unit cell are a = 8.2, b = 23.4, c = 13.6, ¦Â = 68¡ã; with a density of about 1.315, the number of mols. in the cell is 8; the cis-form crystallizes in triclinic plates, a = 7.27, b = 16.75; d. (001) = 11.0, ¦Ã = 75¡ã; d. 1.267, number of mols. in the unit cell, 4. Catalytic reduction of the trans-lactone yields 2-(2′-trans-carboxycyclopentyl)-1,2,3,4-tetrahydronaphthalene, m. 107¡ã. Et cyclopentan-2-one-1-carboxylate in PCl₅ in light petroleum gives Et 2-chloro-¦¤¹-cyclopentene-1-carboxylate, b₁₂ 95-8¡ã, and a small quantity of the acid, m. 115-16¡ã; this ester did not condense with AcCHNaCO₂Et or CHNa(CO₂Et)₂. m-HOC₆H₄CHO and PhCH₂Cl with Na give m-benzyloxybenzaldehyde, b₂₀ 215-18¡ã, m. 54¡ã; hippuric acid and Ac₂O give m-methoxybenzylidenephenylisoxazolone, yellow, m. 129¡ã; hydrolysis gives m-benzyloxyphenylpyruvic acid, m. 145¡ã but it decomposes on keeping; alk. H₂O₂ gives m-benzyloxyphenylacetic acid (IV), m. 126¡ã. Since debenzylation could not be avoided in further work methoxylated intermediates were used. The dry Na salt of IV, 6,3-O₂N-(MeO)C₆H₃CHO (V) and Ac₂O, heated on the water bath for 24 hrs., give 2-nitro-5-methoxy-¦Á-(m-benzyloxyphenyl)cinnamic acid, pale yellow, m. 148¡ã; 2-NH₂ derivative, m. 137¡ã. m-MeOC₆H₄CH₂CO₂Na, V and Ac₂O give 2-nitro-5-methoxy-¦Á-(m-methoxyphenyl)cinnamic acid, yellow, m. 148¡ã; 2-NH₂ derivative, m. 185¡ã; the diazo reaction gives 63% of a mixture of 44% 2,7-dimethoxyphenanthrene-9-carboxylic acid, pale yellow, m. 265¡ã, and 56% of the 2,5-isomer, pale yellow, m. 191¡ã. Decarboxylation gives 2,7-dimethoxyphenanthrene and the 2,5-isomer, m. 117¡ã (picrate, orange-red, m. 154-6¡ã). 2,5-Dihydroxyphenanthrene, m. 180¡ã; di-Ac derivative, m. 144¡ã. In the preparation of ¦Â-2-hydroxy-1-naphthylethyl Me ketone a by-product is 2-methyl-5,6-(1,2-naphtho)-¦Ã-pyran, b₁₆ 190¡ã, m. 44-5¡ã. The K derivative of Et cyclopentanonecarboxylate and octyl bromide, boiled 7 hrs. in C₆H₄Me₂, give Et 1-octylcyclopentan-2-one-1-carboxylate, b₁ 157-65¡ã (85% yield) (semicarbazone, m. 117¡ã); hydrolysis with Ba(OH)₂ gives ¦Á-octyladipic acid, m. 74¡ã, and 2-octylcyclopentanone, b₁₁ 135-8¡ã (semicarbazone, m. 183¡ã); reduction of the ketone yields 2-octylcyclopentanol, b₂₃ 161¡ã, b₈ 140¡ã; bromide, b₈ 135-40¡ã. Octyl-¦¤¹-cyclopentene and MeO₂CCH₂CH₂COCl with SnCl₂ or AlCl₃ give 2-(¦Â-carbomethoxypropionyl)-1-octyl-¦¤¹-cyclopentene, b₁ 173-7¡ã, n_D¹⁵ 1.4818. Work of R. Hirt on cyclopentanone-2-¦Â-propionic acid is described. Refluxing the acid with AcCl gives the enolic lactone, b₁₇ 116-7¡ã; cyclopentanol-2-¦Â-propionic acid lactone, b₁₈ 138-9¡ã. PhCH₂CH₂CH₂Ac and 85% H₂SO₄ at 0¡ã give 74% of 1-methyl-3,4-dihydronaphthalene, b₁₄ 107-8¡ã.

Journal of the Chemical Society published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C15H14O3, Recommanded Product: 2-(3-(Benzyloxy)phenyl)acetic acid.

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