Category: 1860-58-8

Gandomkar, Somayyeh published the artcileEnantioselective Oxidative Aerobic Dealkylation of N-Ethyl Benzylisoquinolines by Employing the Berberine Bridge Enzyme, Category: catalysis-chemistry, the publication is Angewandte Chemie, International Edition (2015), 54(50), 15051-15054, database is CAplus and MEDLINE.

N-Dealkylation methods are well described for organic chem. and the reaction is known in nature and drug metabolism; however, to our knowledge, enantioselective N-dealkylation has not been yet reported. In this study, exclusively the (S)-enantiomers of racemic N-Et tertiary amines (1-benzyl-N-ethyl-1,2,3,4-tetrahydroisoquinolines) were dealkylated to give the corresponding secondary (S)-amines in an enantioselective fashion at the expense of mol. oxygen. The reaction is catalyzed by the berberine bridge enzyme, which is known for C-C bond formation. The dealkylation was demonstrated on a 100 mg scale and gave optically pure dealkylated products (ee>99 %).

Angewandte Chemie, International Edition 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

Woods, Lucy A. published the artcileNative State Mass Spectrometry, Surface Plasmon Resonance, and X-ray Crystallography Correlate Strongly as a Fragment Screening Combination, Application of 2-(3-(Benzyloxy)phenyl)acetic acid, the publication is Journal of Medicinal Chemistry (2016), 59(5), 2192-2204, database is CAplus and MEDLINE.

Fragment-based drug discovery (FBDD) is contingent on the development of anal. methods to identify weak protein-fragment noncovalent interactions. Herein we have combined an underutilized fragment screening method, native state mass spectrometry, together with two proven and popular fragment screening methods, surface plasmon resonance and X-ray crystallog., in a fragment screening campaign against human carbonic anhydrase II (CA II). In an initial fragment screen against a 720-member fragment library (the “CSIRO Fragment Library”) seven CA II binding fragments, including a selection of nonclassical CA II binding chemotypes, were identified. A further 70 compounds that comprised the initial hit chemotypes were subsequently sourced from the full CSIRO compound collection and screened. The fragment results were extremely well correlated across the three methods. Our findings demonstrate that there is a tremendous opportunity to apply native state mass spectrometry as a complementary fragment screening method to accelerate drug discovery.

Journal of 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 C6H13N3O2, Application of 2-(3-(Benzyloxy)phenyl)acetic acid.

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

Passarella, Daniele published the artcileA Convenient Synthesis of ¦¤^7,8-Morphinan-6-one and Its Direct Oxidation to 14-Hydroxy-¦¤^7,8-morphinan-6-one, Formula: C15H14O3, the publication is Bioorganic & Medicinal Chemistry Letters (2002), 12(15), 1981-1983, database is CAplus and MEDLINE.

Synthesis of ¦¤^7,8-morphinan-6-one I (R₂ = bond) by Grewe cyclization of quinolinecarboxaldehyde derivative II and bromoketalization reaction of I (R = H) as crucial steps is described. Introduction of a hydroxyl group at 14-position is demonstrated by direct oxidation with MnO₂ in the presence of silica gel.

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

Tadpetch, Kwanruthai published the artcileCytotoxic naphthoquinone and a new succinate ester from the soil fungus Fusarium solani PSU-RSPG227, Product Details of C15H14O3, the publication is Phytochemistry Letters (2015), 106-110, database is CAplus.

A new naphthoquinone, solaninaphthoquione (1), and a new succinate ester derivative, 4-(4-hydroxyphenethoxy)-4-oxobutanoic acid (2), were isolated from the soil fungus Fusarium solani PSU-RSPG227 together with five previously reported compounds; javanicin (3), monaspilosin (4), aspergillol B (5), tyrosol (6) and 4-hydroxyphenylacetic acid (7). Their structures were elucidated primarily by NMR spectroscopic data. Due to paucity of materials, compounds 2, 4 and 5 as well as analogs of 5 were prepared for biol. activity evaluation. Compound 1 showed significant cytotoxic activity against breast cancer (MCF-7) cells and mild cytotoxic activity against oral human carcinoma (KB) cells (IC₅₀ values of 21.3 and 22.6 ¦ÌM, resp.) compared to standard compounds Compound 1 also displayed weak antimalarial activity (IC₅₀ of 26.1 ¦ÌM).

Phytochemistry 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 C11H10N4, Product Details of C15H14O3.

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

Hill, Robert A. published the artcileBiosynthesis of fungal metabolites. Terrein, a metabolite of Aspergillus terreus Thom, SDS of cas: 1860-58-8, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1981), 2570-6, database is CAplus.

Terrein (I), a metabolite of A. terreus, was shown by incorporation experiments with labeled precursors to be biosynthesized from 3,4-dihydro-6,8-dihydroxy-3-methylisocoumarin (II) by contraction of an aryl ring. The direction of the ring contraction was studied with acetate-1,2–¹³C₂ as precursor.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) 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, SDS of cas: 1860-58-8.

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

O’Boyle, Niamh M. published the artcileSynthesis and Evaluation of Azetidinone Analogues of Combretastatin A-4 as Tubulin Targeting Agents, Synthetic Route of 1860-58-8, the publication is Journal of Medicinal Chemistry (2010), 53(24), 8569-8584, database is CAplus and MEDLINE.

The synthesis and antiproliferative activity of a new series of rigid analogs of combretastatin A-4 are described which contain the 1,4-diaryl-2-azetidinone (¦Â-lactam) ring system in place of the usual ethylene bridge present in the natural combretastatin stilbene products. These novel compounds are also substituted at position 3 of the ¦Â-lactam ring with an aryl ring. A number of analogs showed potent nanomolar activity in human MCF-7 and MDA-MB-231 breast cancer cell lines, displayed in vitro inhibition of tubulin polymerization, and did not cause significant cytotoxicity in normal murine breast epithelial cells. 4-(4-Methoxyphenyl)-substituted compound, 4-(3-hydroxy-4-methoxyphenyl)-substituted compounds, and the 3-(4-aminophenyl)-substituted compounds displayed the most potent antiproliferative activity of the series. ¦Â-Lactam I in particular showed subnanomolar activity in MCF-7 breast cancer cells (IC₅₀ = 0.8 nM) together with significant in vitro inhibition of tubulin polymerization and has been selected for further biochem. assessment. These novel ¦Â-lactam compounds are identified as potentially useful scaffolds for the further development of antitumor agents that target tubulin.

Journal of 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, Synthetic Route of 1860-58-8.

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

Renaud, Johanne published the artcileSelective Estrogen Receptor Modulators with Conformationally Restricted Side Chains. Synthesis and Structure-Activity Relationship of ERα-Selective Tetrahydroisoquinoline Ligands, Formula: C15H14O3, the publication is Journal of Medicinal Chemistry (2005), 48(2), 364-379, database is CAplus and MEDLINE.

The authors disclose herein the discovery of estrogen receptor α (ERα) selective estrogen receptor modulators (SERMs) of the tetrahydroisoquinoline series that incorporate novel conformationally restricted side chains as replacement of the aminoethoxy residue typical of SERMs. Mol. modeling studies used in conjunction with the x-ray crystal structure of the ERα ligand binding domain (LBD) with raloxifene (7) suggested a diazadecaline moiety as a viable mimic of the SERM side chain. On the basis of this knowledge, the piperidinylethoxy moiety of our lead compound I was replaced by a diazadecaline subunit, providing the novel tetrahydroisoquinoline II. In addition to exhibiting a binding affinity to ERα and antagonistic properties in the estrogen response element and MCF-7 assays similar to those of the parent compound I, ligand II showed a reduced agonist behavior in the MCF-7 assay in the absence of 17β-estradiol. These data point toward the fact that II may have a potential for breast cancer prevention/treatment in vivo, a feature which is particularly attractive in the quest for safe alternatives to hormone replacement therapy. In a pharmacokinetic experiment carried out in rats, II displayed an interesting profile, with a bioavailability of 49%. The authors also disclose the x-ray crystal structure of II in complex with ERα-LBD, which reveals the preferred configurations of II at the two chiral centers and the details of its interactions with the receptor. Finally, our structure-activity relationship studies show that other analogs bearing constrained side chains retain potency and antagonist activity and that a 3-OH substituted Ph D-ring increases the selectivity of a set of piperazinyl-containing ligands in favor of ERα over ERβ.

Journal of 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, Formula: C15H14O3.

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

Guanti, Giuseppe published the artcileRegioselective synthesis of 1,8-dihydroxytetralins through a tandem reduction/intramolecular hydroxyalkylation of 4-(3-hydroxyphenyl)alkanoates, Name: 2-(3-(Benzyloxy)phenyl)acetic acid, the publication is Tetrahedron (1994), 50(41), 11945-66, database is CAplus.

A series of 4-(3-hydroxyphenyl)butanoates, e.g., 3-HOC₆H₄(CH₂)₃CO₂Et, has been prepared and transformed into 1,8-dihydroxytetralins, e.g., I, by treatment with 2 equiv of DIBALH followed by quenching with aqueous NH₄Cl. A possible mechanism for this novel, totally regioselective intramol. hydroxyalkylation is suggested and the factors affecting the stability of 1,8-dihydroxytetralins are also discussed.

Tetrahedron 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

Rakowitz, Dietmar published the artcileSynthesis and aldose reductase inhibitory activities of novel O-substituted hydroxyphenylacetic acid derivatives, Quality Control of 1860-58-8, the publication is Archiv der Pharmazie (Weinheim, Germany) (2006), 339(10), 547-558, database is CAplus and MEDLINE.

In continuation of our work aimed towards the preparation of novel aldose reductase inhibitors, several O-substituted hydroxyphenylacetic acid derivatives were investigated. The highest inhibitory activity was found for compounds 7b (3-(cyclohexylmethoxy)benzeneacetic acid) and 7c (4-(cyclohexylmethoxy)benzeneacetic acid). This result demonstrates that within these series, this moiety is a useful surrogate for the 4-bromo-2-fluorobenzyl residue which can be often found in potent aldose reductase inhibitors.

Archiv der Pharmazie (Weinheim, Germany) 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, Quality Control of 1860-58-8.

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

Juvonen, Risto O. published the artcileDevelopment of new Coumarin-based profluorescent substrates for human cytochrome P450 enzymes, COA of Formula: C15H14O3, the publication is Xenobiotica (2019), 49(9), 1015-1024, database is CAplus and MEDLINE.

Cytochrome P 450 (CYP) enzymes constitute an essential xenobiotic metabolizing system that regulates the elimination of lipophilic compounds from the body. Convenient and affordable assays for CYP enzymes are important for assessing these metabolic pathways. In this study, 10 novel profluorescent coumarin derivatives with various substitutions at carbons 3, 6 and 7 were developed. Mol. modeling indicated that 3-phenylcoumarin offers an excellent scaffold for the development of selective substrate compounds for various human CYP forms, as they could be metabolized to fluorescent 7-hydroxycoumarin derivatives Oxidation of profluorescent coumarin derivatives to fluorescent metabolites by 13 important human liver xenobiotic-metabolizing CYP forms was determined by enzyme kinetic assays. Four of the coumarin derivatives were converted to fluorescent metabolites by CYP1 family enzymes, with 6-methoxy-3-(4-trifluoromethylphenyl)coumarin being oxidized selectively by CYP1A2 in human liver microsomes. Another set of four compounds were metabolized by CYP2A6 and CYP1 enzymes. 7-Methoxy-3-(3-methoxyphenyl)coumarin was oxidized efficiently by CYP2C19 and CYP2D6 in a non-selective fashion. The advantages of the novel substrates were (1) an excellent signal-to-background ratio, (2) selectivity for CYP1 forms, and (3) convenient multiwell plate measurement, allowing for precise determination of potential inhibitors of important human hepatic forms CYP1A2, CYP2C19 and CYP2D6.

Xenobiotica 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