19319-32-5Relevant academic research and scientific papers
Antioxidant, anti-tyrosinase and anti-melanogenic effects of (E)-2,3-diphenylacrylic acid derivatives
Ullah, Sultan,Park, Yujin,Park, Chaeun,Lee, Sanggwon,Kang, Dongwan,Yang, Jungho,Akter, Jinia,Chun, Pusoon,Moon, Hyung Ryong
, p. 2192 - 2200 (2019/04/30)
During our continued search for strong skin whitening agents over the past ten years, we have investigated the efficacies of many tyrosinase inhibitors containing a common (E)-β-phenyl-α,β-unsaturated carbonyl scaffold, which we found to be essential for
Design, synthesis, and biological evaluation of compounds with a new scaffold as anti-neuroinflammatory agents for the treatment of Alzheimer's disease
Fang, Yuying,Xia, Wenjuan,Cheng, Bao,Hua, Pei,Zhou, Huihao,Gu, Qiong,Xu, Jun
, p. 129 - 138 (2018/03/06)
Twenty-eight compounds with a new scaffold were designed and synthesized by assembling fragments derived from known agents such as stilbenes and piperazinyl pyrimidines. Many strategies have been explored to improve the druggability of these series of compounds, such as increasing the distance between two benzene rings in the scaffold and introducing functional groups at designated positions. These compounds were validated for their anti-neuroinflammatory activity in BV2 cells. Experimental results reveal that the most active compound 8b can inhibit nitric oxide (NO), tumor necrosis factor-α (TNF-α), and interleukin-1β (IL-1β) production with IC50 values of 1.0, 2.6, and 0.5 μM, respectively. The compound can also significantly modulate the MAPK pathways through inhibiting the phosphorylation of JNK, ERK1/2, and p38 MAPK without disturbing NF-κB pathway. Parallel artificial membrane permeation assay demonstrated that the most active compound can overcome the blood-brain barrier (BBB). Therefore, this compound can be a promising lead for the treatment of Alzheimer's disease.
Surface enhanced Raman spectroscopic (SERS) behavior of substituted propenoic acids used in heterogeneous catalytic asymmetric hydrogenation
Firkala, Tams,Tlas, Emlia,Kristyn, Sndor,Sz?ll'si, Gy?rgy,Drotr, Eszter,Mink, Jnos,Mihly, Judith
, p. 1102 - 1109 (2016/01/26)
The strength and geometry of adsorption of substituted propenoic acids on silver surface were studied by means of surface enhanced Raman spectroscopy (SERS) using silver sol. Based on their SERS behavior, two classes of phenylpropenoic acids studied were distinguished. The first class of propenoic acids (atropic acid, (E)-2,3-diphenylpropenoic acid, (E)-2-(2-methoxyphenyl)-3-phenylpropenoic acid, (E)-2,3-di-(4-methoxyphenyl)phenylpropenoic acid and (E)-2-(2-methoxyphenyl)-3-(4-fluorophenyl)propenoic acid) has shown strong charge transfer (CT) effect. We suggest bidentate carboxyl bonded species based on the SERS enhanced bands of νCOO- around 1394 cm-1 and νC-C of the -C-COO- moiety at 951 cm-1. In these series the plane of the α-phenyl group (γCH out-of-plane vibrations at 850-700 cm-1) is almost parallel to the silver surface, while the β-phenyl group is in tilted position depending on the type and the position of substituent(s) showing strong SERS enhanced bands of νCC + βCH (in-plane mode) at 1075 cm-1, νCC (ring breathing mode, in-plane) at 1000 cm-1 and γCCC (out-of-plane mode) around 401 cm-1. The other class of propenoic acids (cinnamic acid, (E)-2-phenyl-3-(4-methoxyphenyl)propenoic acid) has shown weak electromagnetic (EM) enhancement (CC bands is enhanced in cinnamic acid). In this case no significant carboxyl enhancement was observed, so we suggest that adsorbed species lie parallel to the surface. The two types of adsorption can be related to the dissociation ability of the carboxylic group. In the first case the carboxylic H dissociates, while in the second case it does not, as indicated also by the characteristic νCO band at 1686 cm-1 in the FT-Raman spectra of methanolic solutions.
Palladium-catalyzed fluoride-free cross-coupling of intramolecularly activated alkenylsilanes and alkenylgermanes: Synthesis of tamoxifen as a synthetic application
Matsumoto, Kenji,Shindo, Mitsuru
supporting information; experimental part, p. 642 - 650 (2012/05/04)
We have demonstrated that intramolecular hypercoordination of a carboxylic acid is a powerful activation strategy for the palladium-catalyzed cross-coupling reaction of trialkyl(vinyl)silanes and trialkyl(vinyl)germanes under fluoride-free conditions. Z-β-Trialkylsilyl- and Z-β- trialkylgermylacrylic acids, synthesized stereoselectively by olefination with ynolates, are highly stable and useful reagents for cross-coupling with a variety of aryl iodides to provide tetrasubstituted olefins possessing different carbon substituents in a stereocontrolled and diversity-oriented manner. An application to a stereoselective synthesis of (Z)-tamoxifen is also reported. Copyright
Synthesis and biological evaluation of some stilbene derivatives
Karki, Subhas Somalingappa,Bhutle, Santosh Ramarao,Sahoo, Subhas,Reddy, Ratnakar,Balzarini, Jan,De Clercq, Erik,Darji, Satyanarayana Y.
experimental part, p. 1349 - 1356 (2012/05/05)
Several trans and cis stilbenes with substitution n the olefinic bridge were synthesized and characterized by IR, NMR and mass spectroscopy in an effort to obtain ubstances that could be more readily formulated. All the synthesized compounds were screened against Molt4/C8, CEM and L1210 cell lines. None of these compounds were ndowed with pronounced cytostatic activity. However,Schiff derivatives emerged as cytostatic agents (IC50: 0.77-10 μg/ml) that deserve further investigation. Springer Science+Business Media, LLC 2010.
Synthesis and biological evaluation of cytotoxic properties of stilbene-based resveratrol analogs
de Lima, Denis Pires,Rotta, Rodrigo,Beatriz, Adilson,Marques, Maria Rita,Montenegro, Raquel C.,Vasconcellos, Marne C.,Pessoa, Claudia,de Moraes, Manoel O.,Costa-Lotufo, Leticia V.,Frankland Sawaya, Alexandra Christine Helena,Eberlin, Marcos Nogueira
experimental part, p. 701 - 707 (2009/09/08)
This work deals with the preparation of stilbene-based resveratrol analogs by employing the Perkin reaction, aiming at synthesizing potential antitumor lead compounds and evaluating their pharmacological activities. The proliferation inhibitor test against tumor cell lines identified analogs 9 and 11 as the most active among all synthesized derivatives, presenting IC50 in micromolar range for certain cell lines. For study on the embryonic development, compounds 8 and 9 at the lowest tested concentration (41.7 μM) that inhibited sea urchin egg development, but only after third cleavage were used. Both the compounds inhibited 100% of normal development since first cleavage. These data partially corroborated the results obtained with MTT assay using tumor cell lines. None of the tested compounds revealed hemolytic action in assay with mouse erythrocytes.
Up to 96% enantioselectivities in the hydrogenation of fluorine substituted (E)-2,3-diphenylpropenoic acids over cinchonidine-modified palladium catalyst
Szollosi, Gyoergy,Herman, Beata,Felfoeldi, Karoly,Fueloep, Ferenc,Bartok, Mihaly
supporting information; experimental part, p. 2804 - 2814 (2009/10/20)
The enantioselective hydrogenation of methoxy-and fluorine-substituted (E)-2,3-diphenylpropenoic acid derivatives was studied over cinchonidine- modified, supported palladium catalysts in the absence and presence of benzylamine as additive. The fluorine substituent in the appropriate position was even more efficient than the methoxy group in increasing the optical purity of the saturated product. High enantioselectivities, up to 96%, were obtained in the hydrogenation of some disubstituted derivatives, unprecedented in the hydrogenation of prochiral unsaturated carboxylic acids over modified heterogeneous catalyst. The best optical purities were reached in the hydrogenation of derivates bearing a para-substituent on the β phenyl and an ortho-substituent on the a phenyl ring, respectively. The influence of the substituent on the β phenyl ring was attributed to the increase in the efficiency of the modifier-substrate interaction by electronic effects or to a decrease in the adsorption strength of the substituted acid over modified surface sites. The beneficial effect of the ortho-substituent on the a phenyl ring was assumed to be due to the additional interaction of this substituent with the modifier on the surface, its steric hindrance contributing only in a small part to the observed effect. These suggestions were supported by results obtained in the hydrogenations of some methyl-substituted derivatives.
Pathways for the solvent-free condensation between schiff bases and methylenic compounds
Razus, Alexandra C.,Nitu, Carmen,Tecuceanu, Victorita,Birzan, Liviu
, p. 729 - 736 (2007/10/03)
Pathways for the solvent-free condensation between Schiff Bases and methylenic compounds are discussed taking into account the reported mechanistic purposes and new experimental data.
Intramolecularly activated vinylsilanes: Fluoride-free cross-coupling of (Z)-β-(trialkylsilyl)acrylic acids
Shindo, Mitsuru,Matsumoto, Kenji,Shishido, Kozo
, p. 176 - 178 (2007/10/03)
The fluoride-free palladium-catalyzed cross-coupling reaction of trialkyl(vinyl)silanes activated by the intramolecular pentacoordination of carboxylic acid at the Z-β-position is described.
Design and synthesis of some new α-phenyl cinnamoyl derivatives for selective protection of purine nucleosides
Tripathi, Snehlata,Misra, Krishna,Sanghvi, Yogesh
, p. 3069 - 3081 (2007/10/03)
Three new α-phenylcinnamic acid derivatives [4-methoxy-α- phenylcinnamic acid, α-(4-methoxyphenyl)-cinnamic acid, and 4,4′-bismethoxy-α-phenylcinnamic acid] were synthesized, characterized, and selectively used for protecting the exocyclic amino function of purine nucleosides (2′-deoxyadenosine and 2′-deoxyguanosine) via active ester generation. The acids were first activated using p -nitrophenol, and these activated esters were used subsequently for the selective protection of amino groups. The N -protected derivatives of 2′-deoxyguanosine and 2′-deoxyadenosine have been found to be sufficiently stable toward acids, thus minimizing depurination under oligodeoxyribonucleotide synthesis protocol. The ease of syntheses of N -protected purine nucleosides, their stability under an acidic environment, and mild deprotection conditions are the key advantages of the new protecting groups. Copyright Taylor & Francis, Inc.
