Category: 1772-76-5

Romagnoli, Romeo published the artcileCinnamic acid derivatives linked to arylpiperazines as novel potent inhibitors of tyrosinase activity and melanin synthesis, Related Products of catalysis-chemistry, the publication is European Journal of Medicinal Chemistry (2022), 114147, database is CAplus and MEDLINE.

A novel series of twenty-seven cinnamides constituted by cinnamic acid derivatives liked to 1-aryl piperazines I (R¹ = 4-F, 3-Cl, 3,4-diF, etc.; R² = 4-Cl, 4-NO₂, 3-OMe, etc.) were synthesized and evaluated for their diphenolase inhibitory activity of mushroom tyrosinase. Among them, the presence of a 3-chloro-4-fluorophenyl moiety at the N-1 position of piperazine ring was essential for a potent tyrosinase inhibitory effect, compounds I (R¹ = 3-Cl, 4-F; R² = 3-NO₂) and I (R¹ = 3-Cl, 4-F; R² = 2-Cl, 3-OMe) as the most potent compounds of the series, with IC₅₀ of 0.16 and 0.12¦ÌM, resp., resulting much active than kojic acid, whose IC₅₀ value was 17.76 mM. The mol. docking to the active site of the enzyme has been also performed to investigate the nature of enzyme-inhibitor interactions. Furthermore, for selected highly active compounds, their ability to inhibit melanogenesis in the A375 human melanoma cells and in vivo zebrafish model was also evaluated. One of the most potent compounds of series I (R¹ = 3-Cl, 4-F; R² = 2-Cl, 3-OMe) significantly reduced the pigmentation of zebrafish at 50¦ÌM, unfortunately showing 100% mortality in the Fish Embryo Acute Toxicity (FET) test at the same concentration, Moreover, the zebrafish assay reveals that also I (R¹ = 3-Cl, 4-F; R² = 3-NO₂, 4-OMe) (IC₅₀:0.51¦ÌM against mushroom tyrosinase) effectively reduces melanogenesis with no acute toxicity effects and it could be proposed as potential candidate to treat tyrosinase-mediated hyperpigmentation.

European Journal of Medicinal Chemistry published new progress about 1772-76-5. 1772-76-5 belongs to catalysis-chemistry, auxiliary class Benzenes, name is (E)-3-(3-Nitrophenyl)acrylic acid, and the molecular formula is C9H7NO4, Related Products of catalysis-chemistry.

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

Bokosi, Fostino R. B. published the artcileSynthesis, in silico docking studies, and antiplasmodial activity of hybrid molecules bearing 7-substituted 4-aminoquinoline moiety and cinnamic acid derivatives, Safety of (E)-3-(3-Nitrophenyl)acrylic acid, the publication is Chemical Biology & Drug Design (2022), 100(1), 41-50, database is CAplus and MEDLINE.

This paper reports a series of nine hybrid compounds of 7-substituted 4-aminoquinoline and cinnamic acid as antiplasmodial agents. The synthesized compounds were moderately active, with IC₅₀ values ranging from 1.8 to 16¦ÌM against the Pf3D7 chloroquine-sensitive strain in vitro. Compound I was shown to be the most potent in this investigation, with an IC₅₀ value of 1.8¦ÌM. Mol. docking studies revealed that compounds II and III, with binding energies (¦¤G0) of -7.19 and -7.72 kcal/mol and inhibition constants (Ki) of 5.36 and 2.20¦ÌM, resp., were the best inhibitor candidates. The results of the Frontier MOs revealed that compounds possessed a small HOMO-LUMO energy gap. The HOMO-LUMO energy distributions indicated that the cinnamic acid regions favored the LUMO distribution, while the quinoline regions favored the HOMO energy. The investigation of absorption, distribution, metabolism, excretion, and toxicity based on in silico ADME tools predicted that the compounds have a good drug-like character.

Chemical Biology & Drug Design published new progress about 1772-76-5. 1772-76-5 belongs to catalysis-chemistry, auxiliary class Benzenes, name is (E)-3-(3-Nitrophenyl)acrylic acid, and the molecular formula is C9H7NO4, Safety of (E)-3-(3-Nitrophenyl)acrylic acid.

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

Eibl, Christoph published the artcileThe 3,7-diazabicyclo[3.3.1]nonane scaffold for subtype selective nicotinic acetylcholine receptor ligands. Part 2: Carboxamide derivatives with different spacer motifs, Product Details of C9H7NO4, the publication is Bioorganic & Medicinal Chemistry (2013), 21(23), 7309-7329, database is CAplus and MEDLINE.

3,7-Diazabicyclo[3.3.1]nonane (bispidine) based nicotinic acetylcholine receptor (nAChR) ligands, e.g., I, have been synthesized and evaluated for nAChRs interaction. Diverse spacer motifs were incorporated between the hydrogen bond acceptor (HBA) part and a variety of substituted (hetero)aryl moieties. Bispidine carboxamides bearing spacer motifs often showed high affinity in the low nanomolar range and selectivity for the ¦Á4¦Â2^* nAChR. Compound I and the other two tested compounds with K_i values of about 1 nM displayed the highest affinities for ¦Á4¦Â2* nAChR. All evaluated compounds are partial agonists or antagonists at ¦Á4¦Â2*, with reduced or no effects on ¦Á3¦Â4* with the exception of compound I (agonist), and reduced or no effect at ¦Á7 and muscle subtypes.

Bioorganic & Medicinal Chemistry published new progress about 1772-76-5. 1772-76-5 belongs to catalysis-chemistry, auxiliary class Benzenes, name is (E)-3-(3-Nitrophenyl)acrylic acid, and the molecular formula is C9H7NO4, Product Details of C9H7NO4.

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

Tang, Jie published the artcileBranched Arylalkenes from Cinnamates: Selectivity Inversion in Heck Reactions by Carboxylates as Deciduous Directing Groups, Name: (E)-3-(3-Nitrophenyl)acrylic acid, the publication is Angewandte Chemie, International Edition (2016), 55(37), 11296-11299, database is CAplus and MEDLINE.

A decarboxylative Mizoroki-Heck coupling of aryl halides with cinnamic acids has been developed in which the carboxylate group directs the arylation into its ¦Â-position before being tracelessly removed through protodecarboxylation. In the presence of a copper/palladium catalyst, both electron-rich and electron-deficient aryl bromides and chlorides bearing numerous functionalities were successfully coupled with broadly available cinnamates, with selective formation of 1,1-disubstituted alkenes. This reaction concept, in which the carboxylate acts as a deciduous directing group, ideally complements traditional 1,2-selective Heck reactions of styrenes.

Angewandte Chemie, International Edition published new progress about 1772-76-5. 1772-76-5 belongs to catalysis-chemistry, auxiliary class Benzenes, name is (E)-3-(3-Nitrophenyl)acrylic acid, and the molecular formula is C14H10N2O, Name: (E)-3-(3-Nitrophenyl)acrylic acid.

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

Guo, Ruqing published the artcileSynthesis of Vinylsulfones Via Palladium-Catalyzed Decarboxylative Coupling of Cinnamic Acids with Aromatic Sulfinic Acid Sodium Salts, Computed Properties of 1772-76-5, the publication is Catalysis Letters (2014), 144(8), 1377-1383, database is CAplus.

Abstract: A highly efficient synthesis of vinylsulfones was achieved via decarboxylative cross-coupling reaction of cinnamic acids with aromatic sulfinic acid sodium salts catalyzed by Pd(OAc)₂ and dppb in the presence of Ag₂CO₃. The reaction was found to furnish various vinylsulfones in good yields instead of the expected desulfitative product stilbenes. Mechanistic investigation also suggested that the decarboxylation is likely to take place after the transmetallation step.

Catalysis Letters published new progress about 1772-76-5. 1772-76-5 belongs to catalysis-chemistry, auxiliary class Benzenes, name is (E)-3-(3-Nitrophenyl)acrylic acid, and the molecular formula is C9H7NO4, Computed Properties of 1772-76-5.

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

Xue, Na published the artcileEfficient Synthesis of Vinyl Sulfones by Manganese-Catalyzed Decarboxylative Coupling of Cinnamic Acids with Aromatic Sulfinic Acid Sodium Salts, Formula: C9H7NO4, the publication is Synlett (2016), 27(19), 2695-2698, database is CAplus.

An efficient synthesis of vinyl sulfones is described. Reactions of cinnamic acids with aromatic sulfinic acid sodium salts in the presence of a catalytic amount of manganese(II) acetate tetrahydrate (5 mol%) in DMSO afforded the desired vinyl sulfones in good to excellent yields. Notably, the reaction does not need any base or iodide as additive. The use of DMSO as the solvent and running the reaction under air are critical in achieving good yields.

Synlett published new progress about 1772-76-5. 1772-76-5 belongs to catalysis-chemistry, auxiliary class Benzenes, name is (E)-3-(3-Nitrophenyl)acrylic acid, and the molecular formula is C7H8BBrO3, Formula: C9H7NO4.

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

Xie, Yinjun published the artcileMetal bridging for directing and accelerating electron transfer as exemplified by harnessing the reactivity of AIBN, Category: catalysis-chemistry, the publication is Angewandte Chemie, International Edition (2015), 54(20), 5900-5904, database is CAplus and MEDLINE.

A new strategy for tuning the electron transfer between radicals and enolates has been developed. This method elicits the innate reactivity of AIBN with a copper catalyst and enables a cascade reaction with cinnamic acids. ESR studies and control experiments indicate that the redox-active copper species not only activates the radical by coordination, but also serves as a bridge to bring the radical and nucleophile within close proximity to facilitate electron transfer. By exploiting possible combinations of redox-active metals and radical entities with suitable coordinating functional groups, this strategy should contribute to the development of a broad range of radical-based reactions.

Angewandte Chemie, International Edition published new progress about 1772-76-5. 1772-76-5 belongs to catalysis-chemistry, auxiliary class Benzenes, name is (E)-3-(3-Nitrophenyl)acrylic acid, and the molecular formula is C8H5IO, Category: catalysis-chemistry.

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

Rowles, Ian published the artcileEngineering of phenylalanine ammonia lyase from Rhodotorula graminis for the enhanced synthesis of unnatural L-amino acids, Recommanded Product: (E)-3-(3-Nitrophenyl)acrylic acid, the publication is Tetrahedron (2016), 72(46), 7343-7347, database is CAplus.

Phenylalanine ammonia lyase (PAL) catalyzes the reversible non-oxidative deamination of phenylalanine to trans-cinnamic acid and ammonia. Analogs of L-phenylalanine are incorporated as pharmacophores in several peptidomimetic drug mols. and are therefore of particular interest to the fine chem. industry. PAL from Rhodotorula graminis (RgrPAL) has shown an ability to accept analogs of L-phenylalanine. Our aim was to increase enzymic activity with directed evolution towards a specific non-natural substrate through the cloning and over-production of PAL in Escherichia coli. The identified variants of RgrPAL with significantly showed more catalytic efficient compared to the wild-type enzyme. These variants were used in a preparative scale biotransformation resulting in a 94% conversion to L-4-Br-phenylalanine (>99% ee).

Tetrahedron published new progress about 1772-76-5. 1772-76-5 belongs to catalysis-chemistry, auxiliary class Benzenes, name is (E)-3-(3-Nitrophenyl)acrylic acid, and the molecular formula is C9H7NO4, Recommanded Product: (E)-3-(3-Nitrophenyl)acrylic acid.

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

Wang, Shuiliang published the artcileFacile synthesis of methylthiomethyl esters through Pummerer-type rearrangement of carboxylic acids and DMSO under metal-free conditions, Safety of (E)-3-(3-Nitrophenyl)acrylic acid, the publication is Synthetic Communications (2019), 49(7), 950-958, database is CAplus.

A green and cost-effective Pummerer-type rearrangement between readily accessible carboxylic acids and DMSO has been achieved under metal-free conditions in satisfactory to excellent yields. The transformation for the synthesis of valuable methylthiomethyl esters is shown to be a convenient strategy for various (hetero)aromatic acids, ¦Á,¦Â-unsaturated carboxylic acids and saturated alkyl carboxylic acids with good functional group tolerance.

Synthetic Communications published new progress about 1772-76-5. 1772-76-5 belongs to catalysis-chemistry, auxiliary class Benzenes, name is (E)-3-(3-Nitrophenyl)acrylic acid, and the molecular formula is C27H39ClN2, Safety of (E)-3-(3-Nitrophenyl)acrylic acid.

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

Liu, Wenjuan published the artcileCopper-catalyzed highly selective synthesis of 2-benzyl- and 2-benzylidene-substituted benzo[b]thiazinones from 2-iodophenylcinnamamides and potassium sulfide, Synthetic Route of 1772-76-5, the publication is Organic & Biomolecular Chemistry (2017), 15(46), 9804-9808, database is CAplus and MEDLINE.

An efficient and practical procedure for the synthesis of 2-benzyl benzo[b]thiazinones and 2-benzylidene benzo[b]thiazinones I [R¹ = Ph, 2-MeC₆H₄, 3,4-(MeO)₂C₆H₃, etc.; R² = H, 7-Me, 6-F, etc.; R³ = H, Me, Ph, PhCH₂] from easily available 2-iodophenylcinnamamides II and potassium sulfide has been developed. In the presence of DBU, the reaction proceeds via electrophilic addition, followed by dehydrogenation and reduction to give 2-benzyl benzo[b]thiazinones. Furthermore, 2-benzylidenebenzo[b]thiazinones were obtained in moderate to good yields without the addition of DBU.

Organic & Biomolecular Chemistry published new progress about 1772-76-5. 1772-76-5 belongs to catalysis-chemistry, auxiliary class Benzenes, name is (E)-3-(3-Nitrophenyl)acrylic acid, and the molecular formula is C9H7NO4, Synthetic Route of 1772-76-5.

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