Category: 104-03-0

Cai, Shi published the artcileDesign, synthesis and biological evaluation of bicyclic carboxylic acid derivatives as IDO1 inhibitors, Category: catalysis-chemistry, the publication is Bioorganic Chemistry (2020), 103356, database is CAplus and MEDLINE.

Indoleamine 2,3-dioxygenase 1 (IDO1) plays a vital role in tumor immune escape and has emerged as a promising target for cancer immunotherapy. In this study, a novel series of bicyclic carboxylic acid derivatives were designed, synthesized and evaluated for inhibitory activities against IDO1. Among these, compound 9c exhibited strong IDO1 inhibitory activity (HeLa cellular IC₅₀ = 2.6 nM, THP-1 cellular IC₅₀ = 11.2 nM). Further anti-tumor studies in vivo have shown that compound 9c has a great inhibitory effect on tumor growth in mice CT26 model as a single agent or in combination with 5-fluorouracil (inhibition rate was 53.9% and 92.7%, resp.). These results indicate that compound 9c is a effective IDO1 inhibitor for further investigation.

Bioorganic Chemistry published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C8H7NO4, Category: catalysis-chemistry.

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

Fei, Haiyang published the artcileStereospecific Electrophilic Fluorocyclization of ¦Á,¦¢-Unsaturated Amides with Selectfluor, Application In Synthesis of 104-03-0, the publication is Organic Letters (2020), 22(7), 2651-2656, database is CAplus and MEDLINE.

An efficient fluorocyclization of ¦Á,¦¢-unsaturated amides I (R = Ph, 4-methoxyphenyl, 4-nitrophenyl, i-Pr, n-Bu, Bn; R¹ = H, Me, Et, Ph, n-Pr, cyclopropyl, 4-methylphenyl, 4-nitrophenyl; R² = H, Me, Et, Ph, octyl, etc.; R³ = H, Me, Et, Ph, n-Pr, cyclohexyl, etc.; R⁴ = Me, Et, i-Pr, t-Bu) through a formal halocyclization process is developed. The reaction proceeds under transition-metal-free conditions and leads to the formation of fluorinated oxazolidine-2,4-diones II with excellent regio- and diastereoselectivity. The evaluation of the reaction mechanism based on preliminary experiments and d. functional theory calculations suggests that a synergetic syn-oxo-fluorination occurs and is followed by an anti-oxo substitution reaction. The reaction opens a new window in the field of stereospecific fluorofunctionalization.

Organic Letters published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C8H7NO4, Application In Synthesis of 104-03-0.

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

Liu, Jiang published the artcileEsterification of carboxylic acids with (¦Â-diazo-¦Á,¦Á-difluoroethyl)phosphonates under photochemical conditions, Quality Control of 104-03-0, the publication is Huaxue Xuebao (2021), 79(6), 747-750, database is CAplus.

Fluoroalkyl-substituted diazo compounds belong to one of the most powerful tools in organic synthetic chem. and their transformations have attracted numerous attention. Since the reagent, trifluorodiazoethane, was discovered in 1943, it has attracted many research interests in organic synthesis. On the contrary, the similar difluorodiazoethane (CF₂HCHN₂), which just changes CF₃ group to CF₂H group, however, leads to significant changes on their chem. properties, in particular the stability. Until now, the studies on difluorinated diazo compounds remain less explored. Therefore, the related chem. on difluorodiazoethane emerges as a hot research topic, and the inventory of methods for the preparation and application of new diazo compounds is continuously supplemented. In this communication, a visible-light- promoted esterification reaction of carboxylic acids with in situ generated (¦Â-diazo-¦Á,¦Á-difluoroethyl) phosphonates via O-H insertion has been achieved under mild conditions, which afforded ¦Á,¦Á-difluoromethyl phosphonates (DFMPs)-containing esters with good chem. yields. Several carboxylic acids and amines featuring various functional groups are well compatible in the reaction under photochem. conditions. A control experiment with the addition of D₂O has been performed to verify the proton-transfer process involved in this reaction, and a possible mechanism containing in situ generation of diazo intermediate and protonation is provided. This reaction is operationally simple and shows good functional group compatibility providing an efficient and sustainable strategy for the assembly of ¦Á,¦Á-difluorinated phosphonate derivatives A typical procedure for this visible-light- promoted reaction between (¦Â-diazo-¦Á, ¦Á-difluoroethyl)phosphonates and carboxylic acids is presented as follows: into a vail were taken amine 1 (0.2 mmol), carboxylic acid 2 (0.1 mmol), t-BuONO (0.24 mmol) and CHCl₃ (3 mL). The mixture was heated to 60¡ãC and stirred in the presence of 4.5 W blue LEDs for 4 h. Then, solvent was removed in vacuum. Product 3was purified by TLC plate of 20 cm¡Á20 cm using petroleum ether/ethyl acetate (4:1,V/V) as eluent.

Huaxue Xuebao published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C8H7NO4, Quality Control of 104-03-0.

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

Lei, Jie published the artcileA concise and unexpected one-pot methodology for the synthesis of pyrazinone-fused pyridones, COA of Formula: C8H7NO4, the publication is Organic Chemistry Frontiers (2020), 7(18), 2657-2663, database is CAplus.

A facile one-pot cascade reaction for the synthesis of pyrazinone-fused pyridones I [R¹ = H, 5-Cl, 5-Br; R² = 4-BrC₆H₄, 4-O₂NC₆H₄, 4-NCC₆H₄, etc.; R³ = (CH₂)₃CH₃, cyclohexyl, 4-MeOC₆H₄, 2,6-di-MeC₆H₃, 2-Cl-6-MeC₆H₃, (CH₂)₂C₆H₅]/pyridones II [R⁴ = prop-2-ynyl, 3,5-di-MeC₆H₃, Bn, 1-(2-thienylmethyl); R⁵ = 2,6-di-MeC₆H₃, Bn, (CH₂)₂C₆H₅; R⁶ = H, 5-Br; R⁷ = 4-O₂NC₆H₄, 4-NCC₆H₄] was developed without a metal catalyst. Hydroamination of the Ugi propargyl adducts arising from aromatic isocyanides would be promoted by the intramol. protonation of the alkyne with the amide NH to form an unstable oxazolopyridinium. The cascade reaction was applied to alkyl isocyanide to synthesize pyrazinone-fused pyridones under strongly acidic conditions. This novel cascade reaction proceeded through an Ugi/Michael/Retro-Michael reaction, aromatization and 5-exo-dig cyclization cascade sequence. The reaction features a simple operation procedure, one purification step and good yields, which could be applicable to a broad scope of Ugi starting materials. This was the first report on the intramol. hydroamination occurring between an amide and an alkyne under conditions with an organic base.

Organic Chemistry Frontiers published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C8H7NO4, COA of Formula: C8H7NO4.

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

Cao, Fangyuan published the artcileHDAC/MIF dual inhibitor inhibits NSCLC cell survival and proliferation by blocking the AKT pathway, Quality Control of 104-03-0, the publication is Bioorganic Chemistry (2021), 105396, database is CAplus and MEDLINE.

Non-small-cell lung carcinoma (NSCLC) is one of the most common forms of lung cancer, and a leading cause of cancer death among human beings. There is an urgent demand for novel therapeutics for the treatment of NSCLC to enhance the efficacy of the currently applied Tyrosine kinase inhibitors (TKIs) therapy and to overcome therapy-resistance. Here, we report a novel small-mol. inhibitor that simultaneously targets histone deacetylase (HDAC) and macrophage migration inhibitory factor (MIF). The HDAC/MIF dual inhibitor proved to be toxic for EGFR mutated (H1650, TKI-resistant) or knock out (A549 EGFR-/-) NSCLC cell lines. Further experiments showed that HDAC inhibition inhibits cell survival and proliferation, while MIF inhibition downregulates pAKT or AKT expression level, which both interfere with cell survival. Furthermore, the combination treatment of TKI and HDAC/MIF dual inhibitor showed that the dual inhibitor enhanced TKI inhibitory efficacy, highlighting the advantages of HDAC/MIF dual inhibitor for more effective treatment of NSCLC.

Bioorganic Chemistry published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C8H7NO4, Quality Control of 104-03-0.

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

Zhong, Dayou published the artcileIron-Catalyzed Intramolecular C-H Amidation of N-Benzoyloxyureas, Application of 4-Nitrophenylacetic acid, the publication is Chinese Journal of Chemistry (2021), 39(4), 855-858, database is CAplus.

A redox-neutral Fe-catalyzed intramol. C-H amidation of N-benzoyloxyureas was described. This methodol. employed a simple iron complex in situ generated from Fe(OTf)₂ and bipyridine as the catalyst and N-benzoyloxyureas as the nitrene precursors without using exogenous oxidants. An array of cyclic ureas I [R¹ = Me, n-hexane, Bn, etc.; R² = Me, Ph, 2-naphthyl, etc.; R³ = H, Me] were synthesized via aliphatic C(sp³)-H amidation in excellent yields. In addition, this catalytic system was also amenable to aryl C(sp²)-H nitrene insertion to provide benzimidazolones II [R¹ = Me; R⁴ = H, MeO, t-Bu, C(O)OMe] in moderate yields.

Chinese Journal of Chemistry published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C19H17N3O, Application of 4-Nitrophenylacetic acid.

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

Xu, Biao published the artcileSynthesis, biological evaluation and structure-activity relationship of novel dichloroacetophenones targeting pyruvate dehydrogenase kinases with potent anticancer activity, Related Products of catalysis-chemistry, the publication is European Journal of Medicinal Chemistry (2021), 113225, database is CAplus and MEDLINE.

Pyruvate dehydrogenase kinases (PDKs) are promising therapeutic targets that have received increasing attentions in cancer metabolism In this paper, synthesis and biol. evaluation of a series of novel dichloroacetophenones I (R¹ = cyclopropylamine, piperidin-1-yl, phenylamino, etc.) as potent PDKs inhibitors is reported. Structure-activity relationship anal. enabled to identify a potent compound II, which inhibited PDKs with an EC₅₀ value of 0.09¦ÌM, and reduced various cancer cells proliferation with IC₅₀ values ranging from 1.1 to 3.8¦ÌM, while show weak effect against non-cancerous L02 cell (IC₅₀ > 10¦ÌM). In the A375 xenograft model, II displayed an obvious antitumor activity at a dose of 5 mg/kg, but with no neg. effect to the mice weight Mol. docking suggested that II formed direct hydrogen bond interactions with Ser75 and Gln61 in PDK1, and meanwhile the aniline skeleton in II was sandwiched by the conserved hydrophobic residues Phe78 and Phe65, which contribute to the biochem. activity improvement. Moreover, II induced A375 cell apoptosis and cell arrest in G1 phase, and inhibited cancer cell migration. In addition, II altered glucose metabolic pathway in A375 cell by decreasing lactate formation and increasing ROS production and OCR consumption, which could serve as a potential modulator to reprogram the glycolysis pathway in cancer cell.

European Journal of Medicinal Chemistry published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C9H21NO3, Related Products of catalysis-chemistry.

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

Wang, Xinchao published the artcileNative carboxyl group-assisted C-H acetoxylation of hydrocinnamic and phenylacetic acids, Category: catalysis-chemistry, the publication is Chemical Communications (Cambridge, United Kingdom) (2022), 58(32), 4993-4996, database is CAplus and MEDLINE.

A method of native carboxyl-assisted, Pd(II)-catalyzed ortho-C-H acetoxylation of both hydrocinnamic and phenylacetic acids 2-R-3-R¹-4-R²C₆H₂CH(R³)CH₂C(O)OH (R = H, Me, Cl, OCF₃, etc.; R¹ = Me, Br, CF₃, etc.; R² = Me, F, COOMe, etc.; R³ = H, Me, Et)/2-R⁴-3-R⁵-4-R⁶-5-R⁷C₆HC(R⁸)(R⁹)C(O)OH (R⁴ = H, Me, I, etc.; R⁵ = H, OMe, CF₃, etc.; R⁶ = F, OMe, COOMe, etc.; R⁷ = R⁸ = R⁸ = H, Me) that can be found in many biol. active mols. as the key moieties was reported. Based on the broad scope and the application potential showcased with drug mols., such as (ibuprofen, ketoprofen, and flurbiprofen) it is anticipated that this C-H acetoxylation reaction will find attractive applicability in future synthetic endeavors.

Chemical Communications (Cambridge, United Kingdom) published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C7H5Br2F, Category: catalysis-chemistry.

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

Mirabile, Salvatore published the artcileEvaluation of 4-(4-Fluorobenzyl)piperazin-1-yl]-Based Compounds as Competitive Tyrosinase Inhibitors Endowed with Antimelanogenic Effects, Related Products of catalysis-chemistry, the publication is ChemMedChem (2021), 16(19), 3083-3093, database is CAplus and MEDLINE.

There is a considerable attention for the development of inhibitors of tyrosinase (TYR) as therapeutic strategy for the treatment of hyperpigmentation disorders in humans. Continuing in our efforts to identify TYR inhibitors, we describe the design, synthesis and pharmacophore exploration of new small mols. structurally characterized by the presence of the 4-fluorobenzylpiperazine moiety as key pharmacophoric feature for the inhibition of TYR from Agaricus bisporus (AbTYR). Our investigations resulted in the discovery of the competitive inhibitor [4-(4-fluorobenzyl)piperazin-1-yl]-(3-chloro-2-nitro-phenyl)methanone 26 (I, IC₅₀=0.18¦ÌM) that proved to be ?100-fold more active than reference compound kojic acid (IC₅₀=17.76¦ÌM). Notably, compound 26 exerted antimelanogenic effect on B16F10 cells in absence of cytotoxicity. Docking anal. suggested its binding mode into AbTYR and into modelled human TYR.

ChemMedChem published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C8H7NO4, Related Products of catalysis-chemistry.

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

Matos, Maria Joao published the artcileStructure-Based Optimization of Coumarin hA₃ Adenosine Receptor Antagonists, Product Details of C8H7NO4, the publication is Journal of Medicinal Chemistry (2020), 63(5), 2577-2587, database is CAplus and MEDLINE.

Adenosine receptors are involved in several physiol. processes. Mols. able to selectively modulate one of these receptors represent promising multifunctional agents to treat or slow down the progression of different diseases. 3-Arylcoumarins have already been studied as neuroprotective agents by the group. Here, differently 8-substituted 3-arylcoumarins are complementarily studied as ligands of adenosine receptors, performing radioligand binding assays. Among the synthesized compounds, selective A3 receptor antagonists have been identified. 3-(4-Bromophenyl)-8-hydroxycoumarin (I) proved to be the most potent and selective A3 receptor antagonist (Ki = 258 nM). An anal. of its x-ray diffraction provided detailed information on its structure. Further evaluation of a selected series of compounds indicated that it is the nature and position of the substituents that determine their activity and selectivity. Theor. modeling calculations corroborate and explain the exptl. data, suggesting this novel scaffold has desirable properties for the development of potential multitarget drug candidates.

Journal of Medicinal Chemistry published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C8H7NO4, Product Details of C8H7NO4.

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