Category: 16909-09-4

Sehgal, C. K. published the artcileA novel ring opening of coumarins, Computed Properties of 16909-09-4, the publication is Synthetic Communications (1980), 10(1), 37-42, database is CAplus.

Treatment of coumarins I (R = H or Me; R¹, R² = H, OH or MeO; R³ = H or CH₂CH:CMe₂), furocoumarins II (R⁴ = R⁵ = H or Me; R⁶ = Me, OMe or OH) and dioxolocoumarin III with MeI, EtI or Me₂C:CHCH₂Br with NaH in anhydr. THF gave either a mixture of cis and trans o-alkoxycinnamic acids in which the cis isomer predominated or the cis isomer exclusively. When the coumarin or furocoumarin was substituted in the 4-position, conversion to the cis isomer was almost quant.

Synthetic Communications 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 C6H16OSi, Computed Properties of 16909-09-4.

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

Priyadarshini, S. published the artcileCopper catalyzed cross-coupling reactions of carboxylic acids: an expedient route to amides, 5-substituted ¦Ã-lactams and ¦Á-acyloxy esters, Safety of (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, the publication is RSC Advances (2013), 3(40), 18283-18287, database is CAplus.

A convenient and recyclable catalytic protocol for the synthesis of N,N-di-Me substituted amides, 5-substituted ¦Ã-lactams, and ¦Á-acyloxy ethers from carboxylic acids using CuO nanoparticles and TBHP is described.

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

Kim, Soon Ok published the artcileSynthesis of N-(disubstituted styryl) carboxamides, SDS of cas: 16909-09-4, the publication is Yakhak Hoechi (1992), 36(5), 433-9, database is CAplus.

For the synthesis of tuberin derivatives N-(disubstituted styryl)carboxamides, a series of cinnamic acids were transformed through chlorides and azides to isocyanates; then the isocyanates were reduced sep. by Dibal and Grignard reagent. As a result of antimicrobial susceptibility test, N-(3,4-dichlorostyryl)formamide and N-(3,4-dichlorostyrl)acetamide showed comparatively large activity against some bacteria i.e., MIC was resp. 50 ppm, 6.25?50 ppm. The MIC of other derivatives was similar to that of tuberin, about 100.

Yakhak Hoechi 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

Monte, Manuel J. S. published the artcileVapor pressures, enthalpies and entropies of sublimation of trans-cinnamic acid and of nine methoxy and dimethoxycinnamic acids, HPLC of Formula: 16909-09-4, the publication is Journal of Chemical Thermodynamics (1999), 31(11), 1443-1456, database is CAplus.

The Knudsen mass-loss effusion technique was used to measure the vapor pressure as a function of temperature for trans-cinnamic acid and nine substituted methoxy and dimethoxy cinnamic acids. From the temperature dependence of the vapor pressure, the standard molar enthalpies and entropies of sublimation at 298.15 K were calculated for all the studied compounds using the estimated value ¦¤_cr^gc_p,m^o = -50 J¡¤K^-1¡¤mol^-1. The results obtained for trans-cinnamic acid and for the trans-methoxy and trans-dimethoxy cinnamic acids together with literature results for benzoic acid and substituted methoxy and dimethoxy benzoic acids allowed us to derive the correlation: ¦¤_cr^gH_m^o{T(p = 0.5 Pa)}/(kJ¡¤mol^-1) = (0.623 ¡À 0.026)¡¤{T(p = 0.5 Pa)/K} + (-106.3 ¡À 9.4) where T(p = 0.5 Pa) is the temperature at which the equilibrium vapor pressure of each crystalline compound is 0.5 Pa. (c) 1999 Academic Press.

Journal of Chemical Thermodynamics 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, HPLC of Formula: 16909-09-4.

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

Estrada, Martin published the artcileNew cinnamic – N-benzylpiperidine and cinnamic – N,N-dibenzyl(N-methyl)amine hybrids as Alzheimer-directed multitarget drugs with antioxidant, cholinergic, neuroprotective and neurogenic properties, Safety of (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, the publication is European Journal of Medicinal Chemistry (2016), 376-386, database is CAplus and MEDLINE.

Here we describe new families of multi-target directed ligands obtained by linking antioxidant cinnamic-related structures with N-benzylpiperidine (NBP) or N,N-dibenzyl(N-methyl)amine (DBMA) fragments. Resulting hybrids, in addition to their antioxidant and neuroprotective properties against mitochondrial oxidative stress, are active at relevant mol. targets in Alzheimer’s disease, such as cholinesterases (hAChE and hBuChE) and monoamine oxidases (hMAO-A and hMAO-B). Hybrids derived from umbellic – NBP (8), caffeic – NBP (9), and ferulic – DBMA (12) displayed balanced biol. profiles, with IC₅₀s in the low-micromolar and submicromolar range for hChEs and hMAOs, and an antioxidant potency comparable to vitamin E. Moreover, the caffeic – NBP hybrid 9 is able to improve the differentiation of adult SGZ-derived neural stem cells into a neuronal phenotype in vitro.

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, Safety of (E)-3-(2,4-Dimethoxyphenyl)acrylic acid.

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

Slotta, K. H. published the artcile¦Â-Phenylethylamines. I. Mescaline and mescaline-like substances, Name: (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, the publication is Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1930), 3029-44, database is CAplus.

In addition to the sympathomimetic action which is a general property of ¦Â-aryl-ethylamines and -ethanolamines, mescaline, 3,4,5-(MeO)₃C₆H₂CH₂CH₂NH₂ (I), possesses a peculiar narcotic action. For a pharmacol. and clinical investigation of I and a study of its relationships to other sympathomimetic drugs it was necessary to find a way by which it would be possible to prepare several hundred g. of I. The only method by which it had hitherto been synthesized (RCHO (+ MeNO₂) ¡ú RCH:CHNO₂ (+ H₂) ¡ú RCH₂CH:NOH (+ H₂) ¡ú RCH₂CH₂NH₂) serves to establish its structure rather than to prepare the compound The new method should also make it possible to prepare more easily the isomers of I, as well as mono- and dimethoxyphenylethylamines, in order to determine the influence of the position and number of the MeO groups on the physiol. action of the alkoxyphenylethylamines. An examination of 4 other possible methods of preparation indicated that the only feasible one was that based on the scheme RCHO (+ CH₂(CO₂H)₂) ¡ú RCH:CHCO₂H (+ H₂) ¡ú RCH₂CH₂CO₂H (+ SOCl₂) ¡ú RCH₂CH₂COCl (+ NH₃) ¡ú RCH₂CH₂CONH₂ (+ KOBr) ¡ú RCH₂CH₂NH₂. The m- and p-mono- and the 2,3-, 3,4-and 3,5-di-MeO compounds have already been prepared by this method but in all attempts to prepare I it had hitherto been impossible to carry out the last step. S. and H. have now found, however, that under certain conditions not only I but also its isomers can readily be obtained in very satisfactory yield by using concentrated NaOBr for the Hofmann degradation. The condensation of the aldehydes with CH₂(CO₂H)₂ was effected in 2-3 parts C₅H₅N (distilled over KOH) and 1-5 cc. piperidine per mol. of aldehyde; com. CH₂(CO₂H)₂ can be used directly and a 20% excess. is quite sufficient. The splitting off of CO₂ from the primary di-CO₂H acid is almost quant. on the H₂O bath and only in a few cases was it necessary to boil the C₅H₅N solution a short while. The yield of RCH:CHCO₂H was in general above 80%. The reduction of the unsaturated acid was in all cases easily carried out with an excess of Na-Hg, usually on the H₂O bath; a higher temperature was required only where the unsaturated acid was difficultly soluble in NaOH, and a toning down of the alkalinity with AcOH was necessary only with 3,4,5-(MeO)₃C₆H₂CH:CHCO₂H. The chlorides RCH₂CH₂COCl were obtained by heating the acids in CHCl₃ 4-5 hrs. on the H₂O bath with twice the calculated amount of SOCl₂; they were not isolated but the reaction mixtures were concentrated to about 0.5 volume in vacuo and added, with cooling, to concentrated NH₄OH containing about 10% NaOH (only 2,4-(MeO)₂C₆H₃CH₂CH₂CONH₂ could not be obtained in this way). For the successful degradation of the amides to the amines, it is necessary to have a very pure amide. The statement in the literature that NaOCl gives better yields than NaOBr was confirmed for only some of the amides (the best results were obtained with a solution prepared by passing 5.5 g. Cl into 10 g. NaOH in 100 cc. H₂O). The behavior of the amides in the Hofmann degradation depends greatly on the position and nature of the nucleus substituents. The products are best worked up by distillation in vacuo. The physiol. action of the amines prepared will be described later by Hesse and Lange. o-MeOC₆H₄CH:CHCO₂H, m. 183¡ã (80% from o-MeOC₆H₄CHO), gave 99% MeOC₆H₄CH₂CO₂H, m. 92¡ã (literature, 85-6¡ã); the amide, m. 111¡ã (86.3% yield), gave with NaOCl 35.2% o-MeOC₆H₄CH₂CH₂NH₂, b. 115-20¡ã in the vacuum of a H₂O pump (HCl salt, m. 143¡ã; sulfate, m. 230¡ã). m-HOC₆H₄CHO, m. 106¡ã (69% by diazotization of m-H₂NC₆H₄CHO, prepared from the NO₂ compound with FeSO₄), yielded 80% of the MeOC₆H₄CHO which gave 69% MeOC₆H₄CH: CHCO₂H, m. 177¡ã; the saturated acid, m. 50¡ã (80% yield) gave 27.5% of the amide, b₁₂ 222-5¡ã, m. 56¡ã, which yielded with NaOBr 61% (with NaOCl 19%) of m-MeOC₆H₄CH₂CH₂NH₂, b₁₂ 128¡ã. p-MeOC₆H₄CH₂CH₂NH₂. HCl, m. 210¡ã, was obtained in 43% yield with NaOCl from the amide which itself was obtained in 75% yield through the MeOC₆H₄CH:CHCO₂H (92.5%) and the saturated acid (81%). p-iso-PrC₆H₄CH:CHCO₂H, m. 165¡ã (64%); saturated acid, m. 73¡ã (98%); amide, m. 142¡ã (81.5%), boils explosively with NaOCl at 80¡ã and at 65¡ã gives only a little a ¦Â-(p-isopropylphenyl)ethylamine, b. 150¡ã in the vacuum of a H₂O pump (HCl salt, m. 270¡ã). Vanillin Et ether, m. 63¡ã (85% from vanillin and alk. Et₂SO₄), gave 89% 3-methoxy-4-ethoxycinnamic acid, m. 205¡ã; propionic acid, m. 130¡ã (79%); amide, m. 124¡ã (33.9%), gave with NaOCl the ethylamine, b_15-8 165¡ã (HCl salt, m. 120¡ã). m-C₆H₄(OMe)₂, b₁₂: 117-8¡ã (90% from m-C₆H₄(OH)₂ with alk. Me₂SO₄), gave in Et₂O with HCN, HCl and ZnCl₂: 76% of 2,4-(MeO)₂C₆H₃CHO; 2,4-(MeO)₂C₆H₃CH:CHCO₂H, m. 138¡ã (99%); propionic acid, m. 105¡ã (94%); attempts to prepare the amide through the chloride gave a red-brown oil which decomposed on distillation, in vacuo. 3,4-CH₂O₂C₆H₃CH:CHCO₂H, m. 232¡ã (94%); propionic acid (92%); amide (83.5%), gave with NaOCl 37% of the ethylamine-HCl, m. 206¡ã, 1,2,3-C₆H₃(OMe)₃, b₁₂ 140¡ã (65% with alk. Me₂SO₄), gives with HCN and AlCl₃ in C₆H₆ 53% 2,3,4-(MeO)₃C₆H₂CHO, b₁₂ 170¡ã. 2,3,4-Trimethoxycinnamic acid, m. 172¡ã (94%); propionic acid, m. 76¡ã (65%); amide, m. 171¡ã (63.5%), gives with NaOBr 71.5% ¦Â-(2,3,4-trimethoxyphenyl)ethylamine, b₁₂ 167¡ã, quickly forms the carbonate in the air. 3,4,5-(MeO)₃C₆H₂CO₂H (86% from (HO)₃C₆H₂CO₂H with alk. Me₂SO₄); chloride (86% with PCl₅) in boiling xylene (distilled from Na) with Pd-BaSO₄ and H gave in 30 hrs. 80% 3,4,5-(MeO)₃C₆H₂-CHO, m. 74¡ã; cinnamic acid, m. 124¡ã (80%); ¦Â-(3,4,5-trimethoxyphenyl) propionic acid, m. 98¡ã (88% yield); amide, m. 106¡ã (60%), gave with NaOBr (52g. Br and 150g. NaOH in 375 cc. H₂O) 66% I, b₁₂, 180¡ã (HCl salt, m. 181¡ã). p-BrC₆H₄OMe, b₁₂ 120¡ã (82.9% from PhOMe in AcOH with Br vapors) gave in Et₂O with Mg (activated with I) and ethylene oxide and subsequent decomposition with HCl 31.1% of p-MeOC₆H₄CH₂-CH₂OH, b. 145-60¡ã in the vacuum of the H₂O pump, and this with boiling 47.5% HBr yielded 45% of the bromide, b_12.6 140-50¡ã, from which, when refluxed with a mixture of C₆H₄(CO)₂NH and 0.5 mol. K₂CO₃ until no liquid condensed in the condenser tube, then treated in alc. with N₂H₄.H₂O and finally with HCl gas, was obtained 11.8% p-MeOC₆H₄CH₂CH₂NH₂.HCl, m. 211¡ã. 4-Bromoveratrole, p-BrC₆H₄OH, p-BrC₆-H₄OAc, o- and p-BrC₆H₄NO₂ and o-C₆H₄Cl₂ could not be made to react with Mg in either Et₂O, (iso-Am)₂O or otherwise.

Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen 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 C7H13NO2, Name: (E)-3-(2,4-Dimethoxyphenyl)acrylic acid.

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

Bai, Yajun published the artcilePolygala tenuifolia-Acori tatarinowii herbal pair as an inspiration for substituted cinnamic ¦Á-asaronol esters: Design, synthesis, anticonvulsant activity, and inhibition of lactate dehydrogenase study, Synthetic Route of 16909-09-4, the publication is European Journal of Medicinal Chemistry (2019), 111650, database is CAplus and MEDLINE.

Inspired by the traditional Chinese herbal pair of Polygala tenuifolia-Acori Tatarinowii for treating epilepsy, 33 novel substituted cinnamic ¦Á-asaronol esters and analogs, I [R = 2-, 3-, 4-OMe, 2,3-(MeO)₂, 2,3,5-(MeO)₃, 2,3,4,5,6-(MeO)₅, 4-Br, 3-CF₃, etc.], II, III, and IV, were designed by Combination of Traditional Chinese Medicine Mol. Chem. (CTCMMC) strategy, synthesized and tested systematically not only for anticonvulsant activity in three mouse models but also for lactate dehydrogenase (LDH) inhibitory activity. Thus, compounds I [R = 3,4,5-(MeO)₃, 2,3,4,5-(MeO)₄, 2,3,4,6-(MeO)₄, 4-F] (V) displayed excellent and broad spectra of anticonvulsant activities with modest ability in preventing neuropathic pain, as well as low neurotoxicity. The protective indexes of these four compounds compared favorably with stiripentol, lacosamide, carbamazepine and valproic acid. 68-70 exhibited good LDH1 and LDH5 inhibitory activities with noncompetitive inhibition type, and were more potent than stiripentol. Compounds V exhibited good LDH1 and LDH5 inhibitory activities with noncompetitive inhibition type, and were more potent than stiripentol. Notably, I [R = 2,3,4,6-(MeO)₄], as a representative agent, was also shown as a moderately pos. allosteric modulator at human ¦Á1¦Â2¦Ã2 GABA_A receptors (EC₅₀ 46.3 ¡À 7.3 ¦ÌM). Thus, I [R = 3,4,5-(MeO)₃, 2,3,4,5-(MeO)₄, 2,3,4,6-(MeO)₄] were promising candidates for developing into anti-epileptic drugs, especially for treatment of refractory epilepsies such as Dravet syndrome.

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, Synthetic Route of 16909-09-4.

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

Laufer, Stefan published the artcileTri- and tetra-substituted imidazoles as p38¦Á mitogen-activated protein kinase inhibitors, Application of (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2010), 20(22), 6671-6675, database is CAplus and MEDLINE.

The synthesis of 2,4,5-tri-substituted and 1,2,4,5-tetra-substituted imidazoles, e.g. I, as potent p38¦Á mitogen-activated protein kinase inhibitors is described. The tri-substituted imidazole series was found to be more potent than the tetra-substituted imidazole series. Many of these compounds show low-nanomolar activities in the isolated p38¦Á MAP kinase inhibition assay. The structure-activity relationships between these two series are different and not comparable.

Bioorganic & Medicinal Chemistry Letters 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 of (E)-3-(2,4-Dimethoxyphenyl)acrylic acid.

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

Dai, Yumin published the artcileIsolation of antiplasmodial anthraquinones from Kniphofia ensifolia, and synthesis and structure-activity relationships of related compounds, Recommanded Product: (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, the publication is Bioorganic & Medicinal Chemistry (2014), 22(1), 269-276, database is CAplus and MEDLINE.

Bioassay-guided separation of the South African plant Kniphofia ensifolia for antiplasmodial activity led to the isolation of two new anthraquinones, named kniphofiones A and B, I [R = COC₆H₄OH-4, (E)-COCH:CHC₆H₄OH-4, resp.], together with three known bioactive anthraquinone monomers, and four known bisanthraquinones. The structures of the two new compounds were elucidated based on analyses of their 1D and 2D NMR spectra and mass spectrometric data. The dimeric compounds II (R¹ = H, OH) displayed the strongest antiplasmodial activity among all the isolated compounds, with IC₅₀ values of 0.4 ¡À 0.1 and 0.2 ¡À 0.1 ¦ÌM, resp. The two new compounds displayed modest activities, with IC₅₀ values of 26 ¡À 4 and 9 ¡À 1 ¦ÌM, resp. Due to the synthetic accessibility of the new compounds and the increased activity shown by the dimeric compounds, a structure-activity relationship study was conducted. As a result, one analog of kniphofione B, the caffeic acid derivative of aloe-emodin, I [R = (E)-COCH:CHC₆H₃(OMe)₂-3,4], was found to have the highest activity among all the aloe-emodin derivatives, with an IC₅₀ value of 1.3 ¡À 0.2 ¦ÌM.

Bioorganic & 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, Recommanded Product: (E)-3-(2,4-Dimethoxyphenyl)acrylic acid.

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

Shie, Jiun-Jie published the artcileInhibition of the severe acute respiratory syndrome 3CL protease by peptidomimetic ¦Á,¦Â-unsaturated esters, Computed Properties of 16909-09-4, the publication is Bioorganic & Medicinal Chemistry (2005), 13(17), 5240-5252, database is CAplus and MEDLINE.

The proteolytic processing of polyproteins by the 3CL protease of severe acute respiratory syndrome coronavirus is essential for the viral propagation. A series of tripeptide ¦Á,¦Â-unsaturated esters and ketomethylene isosteres, including AG7088, are synthesized and assayed to target the 3CL protease. Though AG7088 is inactive (IC₅₀ > 100 ¦ÌM), the ketomethylene isosteres and tripeptide ¦Á,¦Â-unsaturated esters containing both P1 and P2 phenylalanine residues show modest inhibitory activity (IC₅₀ = 11-39 ¦ÌM). The Phe-Phe dipeptide inhibitors are designed on the basis of computer modeling of the enzyme-inhibitor complex. The most potent inhibitor (I) with an inhibition constant of 0.52 ¦ÌM is obtained by condensation of the Phe-Phe dipeptide ¦Á,¦Â-unsaturated ester with 4-(dimethylamino)cinnamic acid. The cell-based assays also indicate that I is a nontoxic anti-SARS agent with an EC₅₀ value of 0.18 ¦ÌM.

Bioorganic & 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 C8H6ClN, Computed Properties of 16909-09-4.

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