Category: 16909-09-4

Leong, Sze Wei published the artcileSynthesis and SAR study of diarylpentanoid analogues as new anti-inflammatory agents, Recommanded Product: (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, the publication is Molecules (2014), 19(10), 16058-16081, 24 pp., database is CAplus and MEDLINE.

A series of ninety-seven diarylpentanoid derivatives I (R = H, 4-Cl, 4-Br, 5-OCH₃, 3,5-(OCH₃)₂, 4-OCH₃, 4,6-(Cl)₂; Ar = 3,4,5-trimethoxyphenyl, 2-chlorophenyl, 1-naphthyl, 2-furyl, 5-chloro-2-thienyl, etc.) were synthesized and evaluated for their anti-inflammatory activity through NO suppression assay using interferon gamma (IFN-¦Ã)/lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. Some of the compounds I exhibited greater or similar NO inhibitory activity in comparison with curcumin (14.7 ¡À 0.2 ¦ÌM), notably compounds I (R = 4-Cl; Ar = 2,3-(OH)₂-C₆H₃) and I (R = H; Ar = 2,3-(OH)₂-C₆H₃), which demonstrated the most significant NO suppression activity with IC₅₀ values of 4.9 ¡À 0.3 ¦ÌM and 9.6 ¡À 0.5 ¦ÌM, resp. A structure-activity relationship (SAR) study revealed that the presence of a hydroxyl group in both aromatic rings is critical for bioactivity of these mols. With the exception of the polyphenolic derivatives, low electron d. in ring-A and high electron d. in ring-B are important for enhancing NO inhibition. The pharmacophore mapping showed that hydroxyl substituents at both meta- and para-positions of ring-B could be the marker for highly active diarylpentanoid derivatives

Molecules published new progress about 16909-09-4. 16909-09-4 belongs to catalysis-chemistry, auxiliary class Alkenyl,Carboxylic acid,Benzene,Ether, name is (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, and the molecular formula is C11H12O4, Recommanded Product: (E)-3-(2,4-Dimethoxyphenyl)acrylic acid.

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

Thiemann, Thies published the artcileFacile, direct reaction of benzaldehydes to 3-arylprop-2-enoic acids and 3-arylprop-2-ynoic acids in aqueous medium, Recommanded Product: (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, the publication is International Journal of Organic Chemistry (2016), 6(2), 126-141, database is CAplus.

Wittig reactions of benzaldehydes, alkanals, and cycloalkanals as well as of acetophenones are carried out with alkoxycarbonyl methylidenetriphenylphosphoranes in 10 w% aqueous NaOH, where the cinnamates and alkenoates produced are hydrolyzed in situ and the corresponding acids are obtained after mostly simple extractive work-up, often without employing organic solvents. Under the same conditions, benzaldehydes are reacted with alkoxycarbonyl bromomethylidenephosphorane to produce 3-arylprop-2-ynoic acids (arylpropiolic acids).

International Journal of Organic Chemistry published new progress about 16909-09-4. 16909-09-4 belongs to catalysis-chemistry, auxiliary class Alkenyl,Carboxylic acid,Benzene,Ether, name is (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, and the molecular formula is C25H34N4O2S, Recommanded Product: (E)-3-(2,4-Dimethoxyphenyl)acrylic acid.

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

Guo, Ju published the artcileSynthesis and cytotoxicity of 3-aryl acrylic amide derivatives of the simplified saframycin-ecteinascidin skeleton prepared from L-dopa, SDS of cas: 16909-09-4, the publication is European Journal of Medicinal Chemistry (2013), 670-676, database is CAplus and MEDLINE.

Twenty four compounds with diversified 3-arylacrylic amide side chains of the simplified saframycin-ecteinascidin pentacyclic skeleton were synthesized via a 14-step stereospecific route starting from L-dopa. The cytotoxicities of these compounds were tested against eight human tumor cell lines including HCT-8, BEL-7402, BGC-803, A549, A2780, MCF-7, MX-1, and MDA-MB-231. Most of these compounds exhibited potent antitumor activity, and a preliminary structure-activity relationship (SAR) was discussed. Compound I with 3-thiophenyl acrylic amide side chain exhibited selective cytotoxicity against MDA-MB-231 cell line with the IC₅₀ value of 50 nM.

European Journal of Medicinal Chemistry published new progress about 16909-09-4. 16909-09-4 belongs to catalysis-chemistry, auxiliary class Alkenyl,Carboxylic acid,Benzene,Ether, name is (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, and the molecular formula is C11H12O4, SDS of cas: 16909-09-4.

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

Peterson, John R. published the artcileCerium(IV)-induced nitration of cinnamic acids. Novel remote electrophilic substitution, Quality Control of 16909-09-4, the publication is Canadian Journal of Chemistry (1988), 66(7), 1670-4, database is CAplus.

The treatment of (E)-3,4-(MeO)₂C₆H₃CH:CHCO₂H with (NH₄)Ce(NO₃)₆ in CF₃CO₂H afforded 79% (E)-4,5,2-(MeO)₂(O₂N)C₆H₂CH:CHNO₂ (I). The unusual ipso substitution of the CO₂H moiety by NO₂ illustrated a new reaction manifold of Ce(IV). Four cinnamic acids were similarly nitrated to give products analogous to I, though in only 3-39% yields. The bidentate nitrato structure of the metal salt is believed to account for the nitrating ability of this system.

Canadian Journal of Chemistry published new progress about 16909-09-4. 16909-09-4 belongs to catalysis-chemistry, auxiliary class Alkenyl,Carboxylic acid,Benzene,Ether, name is (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, and the molecular formula is C11H12O4, Quality Control of 16909-09-4.

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

Botta, Bruno published the artcileSynthesis of C-Alkylcalix[4]arenes. 4. Design, Synthesis, and Computational Studies of Novel Chiral Amido[4]resorcinarenes, Safety of (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, the publication is Journal of Organic Chemistry (1997), 62(4), 932-938, database is CAplus.

In extending our studies involving BF₃¡¤Et₂O-catalyzed reaction of cinnamic acid analogs, we have shown that amido derivatives also can afford [4]resorcinarene octamethyl ethers. Subsequently, chiral monomeric amides, derived from the mixed anhydride of cinnamic acid and L– or D-valine, upon treatment with BF₃¡¤Et₂O, yielded for the first time chiral amido[4]resorcinarenes in enantiomerically pure forms. Four stereoisomers were isolated, and three of them were assigned the flattened-cone, chair, and 1,2-alternate conformations. The major product was assigned a novel chairlike structure, namely, flattened partial cone 1. The flattened-cone stereoisomer, which was indicated by mol. modeling studies to be the most stable, became the major product under more drastic exptl. conditions. Chromatog. studies on chiral phases revealed that the above tetramers could be used for the enantiodiscrimination of racemic mols.

Journal of Organic Chemistry published new progress about 16909-09-4. 16909-09-4 belongs to catalysis-chemistry, auxiliary class Alkenyl,Carboxylic acid,Benzene,Ether, name is (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, and the molecular formula is C11H12O4, Safety of (E)-3-(2,4-Dimethoxyphenyl)acrylic acid.

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

Vermeulen, Nicolaas A. published the artcileSynthesis of Complex Allylic Esters via C-H Oxidation vs C-C Bond Formation, Product Details of C11H12O4, the publication is Journal of the American Chemical Society (2010), 132(32), 11323-11328, database is CAplus and MEDLINE.

A highly general, predictably selective C-H oxidation method for the direct, catalytic synthesis of complex allylic esters is introduced. This Pd(II)/sulfoxide-catalyzed method allows a wide range of complex aryl and alkyl carboxylic acids R¹CO₂H [R¹ = Me, Ph, (E)-2,4-(MeO)₂C₆H₃CH:CH, 3,4-F₂C₆H₃CH₂, BocNHCH₂CH₂, etc.] to couple directly with terminal olefins R²CH₂CH:CH₂ (R² = Ph, benzodioxolan-5-yl, t-BuSiMe₂CH₂CH₂, etc.) to furnish (E)-allylic esters R²CH:CHCH₂OCOR¹ in synthetically useful yields and selectivities (16 examples, E/Z ¡Ý 10:1) and without the use of stoichiometric coupling reagents or unstable intermediates. Strategic advantages of constructing allylic esters via C-H oxidation vs C-C bond-forming methods are evaluated and discussed in four “case studies”.

Journal of the American Chemical Society published new progress about 16909-09-4. 16909-09-4 belongs to catalysis-chemistry, auxiliary class Alkenyl,Carboxylic acid,Benzene,Ether, name is (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, and the molecular formula is C15H21BO2, Product Details of C11H12O4.

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

Chao, Rebecca R. published the artcileThe efficient and selective catalytic oxidation of para-substituted cinnamic acid derivatives by the cytochrome P450 monooxygenase, CYP199A4, Safety of (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, the publication is RSC Advances (2016), 6(60), 55286-55297, database is CAplus.

The oxidation of cinnamic acid derivatives, e.g., 3-(2H-1,3-benzodioxol-5-yl)prop-2-enoic acid, was investigated in order to determine the potential of CYP199A4 to act as a biocatalyst for this important class of biol. mols. The compounds such as 4-methoxy- and 4-methyl-cinnamic acids bound tightly to CYP199A4 and were better substrates for CYP199A4 than cinnamic acid itself. The oxidations of both 4-methoxy- and 4-methyl-cinnamic acids was 100% selective for attack at the para substituent. Certain dimethoxy substituted cinnamic acids were demethylated more efficiently than 4-methoxycinnamic acid and retained the selectivity for the para-methoxy substituent. Only very low product turnover was observed with 3,5-dimethoxycinnamic acid. The compound, 4-isopropylcinnamic acid was hydroxylated and desatd. by CYP199A4 at the iso-Pr group. Cinnamic acids with a para-substituted alkyl- and alkyloxy-cinnamic acid framework were a good fit for the active site of the CYP199A4 enzyme and as a consequence were efficiently and selectively oxidized. Whole-cell oxidations resulted in high yields of product and CYP199A4 could be developed for applications in the biocatalytic oxidation of cinnamic acid derivatives and related phenylpropanoids.

RSC Advances published new progress about 16909-09-4. 16909-09-4 belongs to catalysis-chemistry, auxiliary class Alkenyl,Carboxylic acid,Benzene,Ether, name is (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, and the molecular formula is C11H12O4, Safety of (E)-3-(2,4-Dimethoxyphenyl)acrylic acid.

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

Ghirga, Francesca published the artcileUndecenyl resorc[4]arene in the chair conformation as preorganized synthon for olefin metathesis, Category: catalysis-chemistry, the publication is RSC Advances (2013), 3(38), 17567-17576, database is CAplus.

Tetramerization of (E)-2,4-dimethoxycinnamic acid ¦Ø-undecenyl ester with ethereal BF₃ gave three stereoisomers 1a, 1b, and 1c, which were assigned as the chair, cone, and 1,2-alternate conformations, resp. The chair conformation of 1a was confirmed by X-ray diffraction anal., which also showed a peculiar self-assembly behavior in the crystal lattice, forming intercalated hydrophilic and hydrophobic layers (6-7 ? thickness) as a consequence of strong CH-¦Ð interactions. Undecenyl resorc[4]arene 1a, which featured the simplest pattern of substituents, was submitted to olefin metathesis using the second-generation Grubbs complex as the catalyst. Depending on the reaction conditions, different products were isolated: a bicyclic alkene 2a (46%), a linear dimer 3a (5%), and a cross-linked homopolymer P1a (44%).

RSC Advances published new progress about 16909-09-4. 16909-09-4 belongs to catalysis-chemistry, auxiliary class Alkenyl,Carboxylic acid,Benzene,Ether, name is (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, and the molecular formula is C11H12O4, Category: catalysis-chemistry.

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

Go, Maybelle Kho published the artcileEstablishing a Toolkit for Precursor-Directed Polyketide Biosynthesis: Exploring Substrate Promiscuities of Acid-CoA Ligases, SDS of cas: 16909-09-4, the publication is Biochemistry (2012), 51(22), 4568-4579, database is CAplus and MEDLINE.

Polyketides are chem. diverse and medicinally important biochems. that are biosynthesized from acyl-CoA precursors by polyketide synthases. One of the limitations to combinatorial biosynthesis of polyketides has been the lack of a toolkit that describes the means of delivering novel acyl-CoA precursors necessary for polyketide biosynthesis. Using five acid-CoA ligases obtained from various plants and microorganisms, we biosynthesized an initial library of 79 acyl-CoA thioesters by screening each of the acid-CoA ligases against a library of 123 carboxylic acids. The library of acyl-CoA thioesters includes derivatives of cinnamyl-CoA, 3-phenylpropanoyl-CoA, benzoyl-CoA, phenylacetyl-CoA, malonyl-CoA, saturated and unsaturated aliphatic CoA thioesters, and bicyclic aromatic CoA thioesters. In our search for the biosynthetic routes of novel acyl-CoA precursors, we discovered two previously unreported malonyl-CoA derivatives (3-thiophenemalonyl-CoA and phenylmalonyl-CoA) that cannot be produced by canonical malonyl-CoA synthetases. This report highlights the utility and importance of determining substrate promiscuities beyond conventional substrate pools and describes novel enzymic routes for the establishment of precursor-directed combinatorial polyketide biosynthesis.

Biochemistry published new progress about 16909-09-4. 16909-09-4 belongs to catalysis-chemistry, auxiliary class Alkenyl,Carboxylic acid,Benzene,Ether, name is (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, and the molecular formula is C11H12O4, SDS of cas: 16909-09-4.

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

Qian, Jianchang published the artcileDesign and synthesis novel di-carbonyl analogs of curcumin (DACs) act as potent anti-inflammatory agents against LPS-induced acute lung injury (ALI), Application In Synthesis of 16909-09-4, the publication is European Journal of Medicinal Chemistry (2019), 414-425, database is CAplus and MEDLINE.

A novel series of di-carbonyl analogs of curcumin (DACs) were prepared and evaluated for their anti-inflammatory properties. Preliminary results showed that a vast majority of compounds tested in this study could effectively suppress LPS-induced production of tumor necrosis factor (TNF)-¦Á and interleukin (IL)-6. Structure-activity relationships of the compounds were discussed. Compounds I and II showed the most potent anti-inflammatory activities and had higher structural stability and orally bioavailability than curcumin in vitro. Mechanistically, they inhibited the activation of macrophages via the blockade of mitogen-activated protein kinase (MAPK) signaling and nuclear translocation of NF-¦ÊB. In vivo, I and II markedly alleviated lipopolysaccharides (LPS)-induced acute lung injury (ALI). The wet/dry ratio of lungs was significantly normalized by the active compounds, which was consistent with the suppression of neutrophil infiltration and production of proinflammatory cytokines. Collectively, these results present a new series of curcumin analogs as promising anti-inflammatory agents for treatment of ALI.

European Journal of Medicinal Chemistry published new progress about 16909-09-4. 16909-09-4 belongs to catalysis-chemistry, auxiliary class Alkenyl,Carboxylic acid,Benzene,Ether, name is (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, and the molecular formula is C11H12O4, Application In Synthesis of 16909-09-4.

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