Category: 16909-09-4

Ge, Weizhi published the artcileSynthesis and structure-activity relationship studies of parthenolide derivatives as potential anti-triple negative breast cancer agents, SDS of cas: 16909-09-4, the publication is European Journal of Medicinal Chemistry (2019), 445-469, database is CAplus and MEDLINE.

Triple-neg. breast cancer (TNBC) is the most aggressive cancers with a high recurrence rate and rapidly acquired drug resistance among various breast cancer subtypes. There is no specific drug for treatment of TNBC. Discovery of therapeutic agents with unique modes of actions is urgently needed. In this study, a series of seventy parthenolide derivatives was designed, synthesized, and evaluated for their anti-TNBC activities. Compound I exhibited the most potent activity against different breast cancer cells with IC₅₀ values ranging from 0.20 ¦ÌM to 0.27 ¦ÌM, which demonstrated 11.6- to 18.6-fold improvement comparing to that of the parent compound parthenolide with IC₅₀ values of 2.68-4.63 ¦ÌM. It is worth to note that I was more active than the pos. control drug ADR. Moreover, compound I could induce apoptosis of SUM-159 cells through mitochondria pathway and cause G1 phase arrest of SUM-159 cells. These findings indicate that compound I deserves further studies as a lead compound for ultimate discovery of effective anti-TNBC drug.

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

Popiol, Justyna published the artcileThe involvement of xanthone and (E)-cinnamoyl chromophores for the design and synthesis of novel sunscreening agents, Related Products of catalysis-chemistry, the publication is International Journal of Molecular Sciences (2021), 22(1), 34, database is CAplus and MEDLINE.

In this study, seventeen novel mols. I [R¹ = H, 6-MeO, 7-Cl; R² = ([3-(2-chlorophenyl)prop-2-enoyl]oxy)methyl, ([3-phenylprop-2-enoyl]oxy)methyl, (3-([3-(4-methoxyphenyl)prop-2-enoyl]oxy)propoxy)methyl, etc.] by combining in the structures two chromophores: xanthone and (E)-cinnamoyl moiety were designed and synthesized. The UV spectroscopic properties of the tested compounds I were confirmed in chloroform solutions They acted as UVB or UVA/UVB absorbers. The most promising compound I [R¹ = 6-MeO, R² = ([3-(2,4-dimethoxyphenyl)prop-2-enoyl]oxy)methyl] absorbed UV radiation in the range 290-369 nm. Its photoprotective activity and functional photostability were further evaluated after wet milling and incorporation in the cream base. This tested formulation with compound I [R¹ = 6-MeO, R² = ([3-(2,4-dimethoxyphenyl)prop-2-enoyl]oxy)methyl] possessed very beneficial UV protection parameters (SPFin vitro of 19.69 ¡À 0.46 and UVA PF of 12.64 ¡À 0.32) which were similar as broad-spectrum UV filter tris-biphenyl triazine. Addnl., compound I [R¹ = 6-MeO, R² = ([3-(2,4-dimethoxyphenyl)prop-2-enoyl]oxy)methyl] was characterized by high values of critical wavelength (381 nm) and UVA/UVB ratio (0.830) thus it was a good candidate for broad-spectrum UV filter and it might protect skin against UVA-induced photoaging. Compound I [R¹ = 6-MeO, R² = ([3-(2,4-dimethoxyphenyl)prop-2-enoyl]oxy)methyl] were also shown to be photostable, non-cytotoxic at concentrations up to 50¦ÌM when tested on five cell lines and non-mutagenic in Ames test. It also possessed no estrogenic activity, according to the results of MCF-7 breast cancer model. Addnl., its favorable lipophilicity (miLogP = 5.62) does not predispose it to penetrate across the skin after topical application.

International Journal of Molecular Sciences 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, Related Products of catalysis-chemistry.

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

Atmaram Upare, Abhay published the artcileDesign, synthesis and biological evaluation of (E)-5-styryl-1,2,4-oxadiazoles as anti-tubercular agents, Application In Synthesis of 16909-09-4, the publication is Bioorganic Chemistry (2019), 507-512, database is CAplus and MEDLINE.

The present study reports the synthesis of cinnamic acid derivatives via bioisosteric replacement of terminal carboxylic acid with “oxadiazole”. A series of cinnamic acid derivatives (styryl oxadiazoles) were designed and synthesized in good yields by reaction of substituted cinnamic acids with amidoximes. The synthesized styryl oxadiazoles were evaluated in vitro for anti-tubercular activity against Mycobacterium tuberculosis (Mtb) H37Ra strain. The structure-activity relationship (SAR) study has identified several compounds with mixed anti-tubercular profiles. The compound I displayed potent anti-tubercular activity (IC₅₀ = 0.045 ¦Ìg/mL). Mol. docking studies on mycobacterial enoyl-ACP reductase enzyme corroborated well with the exptl. findings providing a platform for structure based hit-to-lead development.

Bioorganic 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

Matos, M. A. R. published the artcileStandard molar enthalpies of combustion of five trans-dimethoxycinnamic acids, COA of Formula: C11H12O4, the publication is Journal of Chemical Thermodynamics (2001), 33(8), 899-904, database is CAplus.

The standard (p^o = 0.1 MPa) molar enthalpies of formation for 2,3-, 2,4-, 2,5-, 3,4- and 3,5- trans-dimethoxycinnamic acids in the gaseous phase were derived from the standard molar enthalpies of combustion in oxygen of the crystalline compounds determined by static bomb combustion calorimetry at T = 298.15 K and from the literature values for the resp. enthalpies of sublimation. (c) 2001 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, COA of Formula: C11H12O4.

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

Vitali, Alberto published the artcile¦Â-glucosyltransferase in cell cultures of Verbesina caracasana, Safety of (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, the publication is Heterocycles (1999), 50(2), 721-730, database is CAplus.

(E)-3,4-Dimethoxycinnamic acid, inoculated in cell cultures of Verbesina caracasana, was converted to the corresponding ¦Â-glucopyranoside ester, revealing the presence of an exoglucosyltransferase. An extensive study on other cinnamic acid derivatives showed that the aromatic ring must contain at least one methoxy substituent, but no hydroxy group, for the esterification to be performed. Moreover, the presence of the double bond was shown to have no influence. The glucosylation reaction may involve also the hydroxyl of benzyl alcs., with the same specificity towards the substitution of the aromatic ring as shown by the cinnamic acids.

Heterocycles 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 C23H20BN, Safety of (E)-3-(2,4-Dimethoxyphenyl)acrylic acid.

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

Chakravarti, Duhkhaharan published the artcileSynthesis of coumarins from ¦Ï-hydroxyaryl alkyl ketones. IV. Formation of ¦Ï-coumaric acids from ¦Ï-hydroxy aldehydes, Computed Properties of 16909-09-4, the publication is Journal of the Indian Chemical Society (1943), 338-40, database is CAplus.

cf. C. A. 34, 6252.7. Reformatski¨« reactions of some 2-methoxybenzaldehydes gave HO esters which on dehydration and hydrolysis yielded trans-¦Ï-coumaric acids. It was shown that 2-MeO aldehydes, always lead to trans-¦Ï-methoxycinnamic acids by Perkin’s reaction, by malonic acid condensation, and by the method of Chakravarti and Majumdar (Reformatski¨«) (cf. C. A. 34, 2348.9). A mixture of 8 g. 5,2-Me(MeO)C₆H₃CHO (I), 13.4 g. BrCH₂CO₂Et (II), 5.5 g. Zn wool and 75 cc. anhydrous benzene was heated at 100¡ã for 2.5 h. and poured into ice-cold dilute H₂SO₄. After washing and drying, the benzene layer was distilled, yielding 5.5 g. of Et ¦Â-hydroxy-¦Â-(2-methoxy-5-methylphenyl)propionate, b₁₂ 200¡ã, which was converted by treating with 3 g. SOCl₂ and 3 g. pyridine in 100 cc. anhydrous Et₂O into 3.8 g. Et 2-methoxy-5-methyl-trans-cinnamate (III), b₇ 165¡ã. Hydrolysis of III with alc. KOH gave the free trans acid (IV), m. 145-6¡ã, which was identical with the compound obtained in good yield by heating 1 g. I with 2 g. Ac₂O and 8 g. fused AcONa at 180¡ã for 10 h., extracting with alkali and acidifying with HCl. Similarly I was converted by Reformatski¨«’s reaction with Zn and MeCHBrCO₂Et (V) to the corresponding HO ester which was dehydrated with SOCl₂ and pyridine to Et ¦Á-methyl-2-methoxy-5-methylcinnamate (VI), b₅ 160¡ã. Alc. KOH hydrolysis of VI gave the trans acid, m. 109-10¡ã, identical with the acid obtained by heating I with EtCO₂Na and (EtCO)₂O. By the same series of reactions the following compounds were prepared: Et 2,4-dimethoxycinnamate, brown viscous liquid, b₆ 160¡ã (trans acid (VII), m. 184¡ã); Et ¦Á-methyl-2,4-dimethoxycinnamate, viscous brown liquid, b₆ 200¡ã (trans acid (VIII), m. 130¡ã); Et ¦Â-(2-methoxy-1-naphthyl)acrylate, b₄ 210-2¡ã; (free acid (IX), m. 153-4¡ã); Et ¦Á-methyl-¦Â-(2-methoxy-1-naphthyl)acrylate, viscous brown liquid, b₅, 220-5¡ã (free acid (X), m. 138-9¡ã). VII, VIII, IX, and X were also prepared by Perkin’s reaction and were compared with those compounds prepared above by mixed m. ps. In addition, condensation of 2,4-(MeO)₂C₆H₃CHO with malonic acid in the presence of piperidine also yielded the trans acid (VII). III or IV, heated with HI (d. 1.7) at 140¡ã for 2 h., yielded only a sticky precipitate which could not be crystallized No ring closure was effected.

Journal of the Indian 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 C11H12O4, Computed Properties of 16909-09-4.

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

Al-Horani, Rami A. published the artcilePotent direct inhibitors of factor Xa based on the tetrahydroisoquinoline scaffold, Application In Synthesis of 16909-09-4, the publication is European Journal of Medicinal Chemistry (2012), 771-783, database is CAplus and MEDLINE.

Direct inhibition of coagulation factor Xa (FXa) carries significant promise for developing effective and safe anticoagulants. Although a large number of FXa inhibitors have been studied, each can be classified as either possessing a highly flexible or a rigid core scaffold. The authors reasoned that an intermediate level of flexibility would provide high selectivity for FXa, considering that its active site is less constrained in comparison to thrombin and more constrained as compared to trypsin. They studied several core scaffolds including 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid for direct FXa inhibition. Using a genetic algorithm-based docking and scoring approach, a promising candidate I was identified, synthesized, and found to inhibit FXa with a K_i of 28 ¦ÌM. Optimization of derivative I resulted in the design of a potent dicarboxamide II, which displayed a K_i of 135 nM. Dicarboxamide II displayed at least 1852-fold selectivity for FXa inhibition over other coagulation enzymes and doubled PT and aPTT of human plasma at 17.1 ¦ÌM and 20.2 ¦ÌM, resp., which are comparable to those of clin. relevant agents. Dicarboxamide II is expected to serve as an excellent lead for further anticoagulant discovery.

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

Corradi, Silvia published the artcileSynthesis of Bromoundecyl Resorc[4]arenes and Applications of the Cone Stereoisomer as Selector for Liquid Chromatography, Recommanded Product: (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, the publication is Journal of Organic Chemistry (2018), 83(15), 7683-7693, database is CAplus and MEDLINE.

As an extension of the authors’ studies on the multifaceted properties of C-alkylated resorc[4]arenes, the authors planned to immobilize on a solid support resorc[4]arenes with C₁₁-long side chains in the lower rim. To this purpose, the authors synthesized two conformationally diverse resorc[4]arenes containing a bromoundecyl moiety in the four axial pendants. The cone stereoisomer 6a (30% yield) was selected for the reaction with an aminopropylated silica gel (APSG) obtained from spherical Kromasil Si 100, 5 ¦Ìm particles, to give the corresponding immobilized SP-C₁₁-resorc[4]arene system. The resulting polar-embedded stationary phase was fully characterized and studied in the HPLC discrimination of the E/Z stereoisomers of naturally occurring and semisynthetic combretastatins, a family of (Z)-stilbene anticancer drugs. The chair stereoisomer 6b (20% yield), when submitted to x-ray diffraction anal., showed a noteworthy self-assembly in the crystal lattice, with intercalated hydrophobic and polar layers as a result of intermol. Br¡¤¡¤¡¤O halogen bond interactions, according to a unique stacking motif. The potential and versatility of the SP-C₁₁-resorc[4]arene stationary phase were shown as well in the separation of highly polar natural products (namely, flavonoids), under reversed-phase (RP) conditions, and of fullerenes C60 and C70, by using apolar solvents as mobile phases.

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

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

Rajadurai, Maruthamuthu published the artcilePhytochemical profiling of medically significant crude extract using GC-MS analysis, Application of (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, the publication is International Journal of Current Pharmaceutical Research (2018), 10(6), 16-20, database is CAplus.

The objective of this research is to identify the phytochem. constitutions present in Natural crude extract which obtained from Thumlappati district. Kidney stone is one of the most clin. disorder arising nowadays. They are existing due to the depletion of the urine and disproportionate execration of the components such as oxalate, phosphate, uric, cysteine, and struvite. Many alopathy medicine are not effectively curable in the case of kidney stone, consequently people are in need of traditional medicine system. Thus there is a great demand for research on potential inhibitor from natural products for dissolving kidney stone. In present work deals with an unknown crude extract collected from G. Thumlappati, Battalagundu Dindugal district Tamil Nadu. The crude extract of phytochem. are analyzed by using GCMS method. Thus the sample has some bioactive compound to discharge the stone particles. So we subjected the crude extract sample to GC-MS process which reveals 210 compounds in 21 different peaks. This studies forms a basis for the biol. characterization and importance of bioactive compounds were identified.

International Journal of Current Pharmaceutical Research 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

Chakravarti, Duhkhaharan published the artcileSynthesis of coumarins from o-hydroxyaryl alkyl ketones. II. Formation of o-coumaric acids from o-hydroxyaldehydes, Formula: C11H12O4, the publication is Journal of the Indian Chemical Society (1939), 389-92, database is CAplus.

cf. C. A. 32, 7026.9; 33, 549.4. The Me ethers of the o-HO aldehydes condense with EtO₂CCH₂Br (I) and EtO₂CCHBrMe (II) to form trans-cinnamic esters, which do not yield coumarins on heating with HI or on standing with cold H₂SO₄ as do the esters obtained from o-hydroxyaryl alkyl ketones. A mixture of 11 g. o-MeOC₆H₄CHO in 50 cc. anhydrous benzene, 6 g. Zn wool and 16 g. I was heated at 100¡ã for 2 h. and poured into ice-cold dilute H₂SO₄. The washed and dried benzene layer was evaporated down and distilled, yielding 11 g. of o-MeOC₆H₄CH(OH)CH₂CO₂Et, b₁₀ 150-4¡ã, which was converted by heating with 6 g. SOCl₂ and 9 g. pyridine in ether into 10 g. Et 2-methoxy-trans-cinnamate, C₁₂H₁₄O₃, b₈ 150¡ã, hydrolyzed to 2-methoxy-trans-cinnamic acid, m. 182¡ã, identical with a specimen prepared from o-coumaric acid by methylation with Me₂SO₄ and hydrolysis. Similarly, o-MeOC₆H₄CHO was converted by Reformatski¨«’s reaction with Zn and II to o-MeC₆H₄CH(OH)CHMeCO₂Et, b₄ 155¡ã, transformed by SOCl₂ in the presence of pyridine to Et 2-methoxy-¦Á-methyl-trans-cinnamate, C₁₃H₁₆O₃, b₄ 150-5¡ã, hydrolyzed by alc. KOH to the corresponding acid, m. 102¡ã. Condensation of 2,4-(MeO)₂C₆H₃CHO with I gave 2,4-(MeO)₂C₆H₃CH(OH)CH₂CO₂Et, b₈ 180-4¡ã, dehydrated to the cinnamic ester, b₈ 180-4¡ã, hydrolyzed to 2,4-dimethoxy-trans-cinnamic acid, m. 184¡ã. To study the influence of a Ph substituent on the formation of trans-cinnamic esters, 8.5 g. of 5,2-Cl(MeO)C₆H₃CHO was condensed with 8.5 g. I to the propionate (8 g.) which, on dehydration with SOCl₂, gave 6 g. of Et 2-methoxy-5-chloro-trans-cinnamate, C₁₂H₁₃ClO₃, b₆ 170¡ã, hydrolyzed to the corresponding acid (III), m. 191¡ã. A sample of authentic III was prepared by treating 6-chlorocoumarin with HgO, methylating and hydrolyzing with alc. KOH. Thus it is shown that if there are no ¦Â-alkyl groups in the resulting cinnamic ester, the latter has the trans configuration. Otherwise the esters have the cis configuration and readily form coumarins. The 2-MeO aldehydes are useful starting materials for the preparation of o-coumaric acid derivatives in satisfactory yields. Condensation of 10 g. of 2,4-(MeO)₂C₆H₃Ac (IV) with 9 g. II and distillation of the product yielded 8.5 g. of Et 2,4-dimethoxy-¦Á,¦Â-dimethyl-cinnamate (V), b₆ 180-2¡ã, converted by standing overnight in cold H₂SO₄ (d. 1.84) to 3,4-dimethyl-7-methoxycoumarin, m. 140¡ã. Heating V (1 g.) with 7 cc. HI (d. 1.7) at 140¡ã for 2 h. gave colorless needles of 3,4-dimethyl-7-hydroxycoumarin, m. 256¡ã, on recrystallization from alc. Similarly, condensation of 10 g. IV with I gave an unsaturated ester, b₆ 174¡ã, on vacuum distillation No ring closure was effected by heating with HI or on treatment with cold H₂SO₄. Hydrolysis gave the known 2,4-dimethoxy-¦Â-methylcinnamic acid, m. 145¡ã.

Journal of the Indian 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 C11H12O4, Formula: C11H12O4.

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