14897-78-0Relevant articles and documents
Design and biological evaluation of cinnamic and phenylpropionic amide derivatives as novel dual inhibitors of HIV-1 protease and reverse transcriptase
Zhu, Mei,Shan, Qi,Ma, Ling,Wen, Jiajia,Dong, Biao,Zhang, Guoning,Wang, Minghua,Wang, Juxian,Zhou, Jinming,Cen, Shan,Wang, Yucheng
, (2021/05/04)
Upon the basis of both possible ligand-binding site interactions and the uniformity of key residues in active sites, a novel class of HIV-1 PR/RT dual inhibitors was designed and evaluated. Cinnamic acids or phenylpropionic acids with more flexible chain and smaller steric hindrance were introduced into the inhibitors, giving rise to significant improvement in HIV-1 RT inhibitory activity by one or two orders of magnitude, with comparable or even improved potency against PR at the same time, compared with coumarin anologues in our previous studies. Among these inhibitors, 38d displayed a 19-fold improvement in anti-PR activity with IC50 value of 0.081 nM compared to the control DRV. In addition, inhibitor 38c exhibited an excellent anti-RT IC50 value of 0.43 μM, only a 4.7-fold less potent activity than the control EFV. More significantly, the disparate ratio between HIV-1 PR and RT inhibition became more reasonable with ratio of 1: 10.4, just as 37b. Furthermore, the assays on HIV-1 late stage and early stage supported the rationality of designing dual inhibitors. The SAR data as well as molecular modeling studies provided new insight for further optimization of more potent HIV-1 PR/RT dual inhibitors.
Semi-aromatic biobased polyesters derived from lignin and cyclic carbonates
Horn, Jessica,Locklin, Jason,Ring, John,White, Evan M.,Winfield, Demichael
supporting information, p. 9658 - 9668 (2021/12/09)
The synthesis of biobased aromatic polyesters from lignin-derived monomers has become well described in the literature, but robust extrusion, thermomechanical, tensile and degradation studies of these materials is lacking. In this work, we have systematically investigated the mechanical and biodegradation properties of semi-aromatic polyesters that can potentially be derived from lignin. AB monomers were synthesized from reduced analogues of coumaric, ferulic, and sinapic acids along with cyclic carbonates, where the synthetic methodology was assessed using E-Factor and EcoScale. Polymerization yielded both semi-crystalline and amorphous polyesters with mechanical properties varying over three orders of magnitude. Detailed characterization revealed a wide array of properties including a highly ductile thermoplastic, a strong and rigid thermoplastic, and an elastomer. Composting biodegradation tests showed both degradable and nondegradable polymers can be achieved in this class. This work demonstrates the versatility of this class of polymers and illustrates their potential to replace non-sustainably derived plastics. This journal is
Synthesis of Lactams via Ir-Catalyzed C-H Amidation Involving Ir-Nitrene Intermediates
Li, Xiaoxun,Liu, Jitian,Tang, Weiping,Wang, Shuojin,Ye, Wenjing,Zheng, Junrong
, (2020/03/19)
x-membered lactams were synthesized via either an amidation of sp3 C-H bonds or an electrophilic substitution of arenes via Ir-nitrene intermediates. With the employment of a readily available iridium catalyst in dichloromethane or hexafluoro-2-propanol, a wide range of lactams were synthesized in good to excellent yields with high selectivity.
Preparation method for 3,5-dimethoxy-4-hydroxyphenylpropionic acid
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Paragraph 0014; 0015; 0016, (2016/11/09)
The invention discloses a preparation method for 3,5-dimethoxy-4-hydroxyphenylpropionic acid. The method comprises the following steps: dissolving a compound 3,5-dimethoxy-4-hydroxyphenyl ethylene acid in methanol, adding palladium carbon, carrying out stirring at room temperature, and carrying out hydrogen spheroidizing reaction overnight, wherein it is found that raw materials are completely reacted according to results of plate-dotting the next day; and carrying out filtration under the aid of diatomite, and subjecting methanol to spinning drying so as to obtain the compound 3,5-dimethoxy-4-hydroxyphenylpropionic acid. According to the invention, the raw materials like 3,5-dimethoxy-4-hydroxyphenyl ethylene acid, methanol and palladium carbon are used to synthesize the compound 3,5-dimethoxy-4-hydroxyphenylpropionic acid with a complex structure. The produced 3,5-dimethoxy-4-hydroxyphenylpropionic acid has the following advantages: a yield is up to 79%; meanwhile, good crystallization effect and high purity are realized; and high-purity standard samples or sample products are provided for subsequent chemical and biological experiments.
Phenyl Esters Are Potent Inhibitors of Caseinolytic Protease P and Reveal a Stereogenic Switch for Deoligomerization
Hackl, Mathias W.,Lakemeyer, Markus,Dahmen, Maria,Glaser, Manuel,Pahl, Axel,Lorenz-Baath, Katrin,Menzel, Thomas,Sievers, Sonja,B?ttcher, Thomas,Antes, Iris,Waldmann, Herbert,Sieber, Stephan A.
supporting information, p. 8475 - 8483 (2015/07/15)
Caseinolytic protease P (ClpP) represents a central bacterial degradation machinery that is involved in cell homeostasis and pathogenicity. The functional role of ClpP has been studied by genetic knockouts and through the use of beta-lactones, which remain the only specific inhibitors of ClpP discovered to date. Beta-lactones have served as chemical tools to manipulate ClpP in several organisms; however, their potency, selectivity and stability is limited. Despite detailed structural insights into the composition and conformational flexibility of the ClpP active site, no rational efforts to design specific non-beta-lactone inhibitors have been reported to date. In this work, an unbiased screen of more than 137000 compounds was used to identify five phenyl ester compounds as highly potent ClpP inhibitors that were selective for bacterial, but not human ClpP. The potency of phenyl esters largely exceeded that of beta-lactones in ClpP peptidase and protease inhibition assays and displayed unique target selectivity in living S. aureus cells. Analytical studies revealed that while phenyl esters are cleaved like native peptide substrates, they remain covalently trapped as acyl-enzyme intermediates in the active site. The synthesis of 36 derivatives and subsequent structure-activity relationship (SAR) studies provided insights into conserved structural elements that are important for inhibition potency and acylation reactivity. Moreover, the stereochemistry of a methyl-substituent at the alpha position to the ester, resembling amino acid side chains in peptide substrates, impacted ClpP complex stability, causing either dissociation into heptamers or retention of the tetradecameric state. Mechanistic insights into this intriguing stereo switch and the phenyl ester binding mode were obtained by molecular docking experiments.
NOVEL DERIVATIVES OF SINAPINIC ACID AND THE COSMETIC OR PHARMACEUTICAL USES THEREOF
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Paragraph 0176-0177, (2015/12/23)
The present invention relates to a compound of general formula (I) below: in which: R1, R2 and R3 independently of one another represent a hydrogen atom; a C1-12 alkyl group; a C2-12 alkenyl group; a C2-12 alkynyl group; a C3-12 cycloalkyl group; a C1-12 acyl group; a sulfonyl group or a phosphonate group; represents a CH2—CH2 group or a CH═CH group; n is an integer between 1 and 3; or a salt thereof. The invention further relates to a process for synthesizing this compound or salt, to a composition comprising it, to its cosmetic use, more particularly as a depigmenting agent and/or as a radical scavenger, to a cosmetic care process, and to its use as a drug, advantageously intended for preventing and/or treating pathological hyperpigmentation and/or inflammation.
Tyrosinase inhibitory activities of cinnamic acid analogues
Takahashi,Miyazawa, Mitsuo
experimental part, p. 913 - 918 (2011/08/06)
The aim of this study was to show how tyrosinase inhibitory activity is correlated with the structure of cinnamic acid derivatives. We synthesized cinnamic acid derivatives, and investigated their tyrosinase inhibitory and DPPH radical scavenging activities. The results show that reduction of C=C double bonds and the substituent group of cinnamic acid derivatives have an effect on antioxidant activity and tyrosinase inhibitory activity. Among these compounds, compounds 2, 6 and 6a showed a potent tyrosinase inhibitory activity with IC50 (50% inhibitory concentration) values of 115.6 μM, 114.9 μM and 195.7 μM, respectively. The results obtained provide a useful clue for the design and development of new tyrosinase inhibitors.
Cosmetic use of derivatives of 3-Phenylpropionic acid
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Page/Page column 11, (2008/06/13)
The use of a compound having formula I wherein Y is selected from the group consisting of H, an alkyl group, a phenyl group, Na, K or NH4, and wherein R1, R2, R3, R4 and R5 are independently selected from the group consisting of H and -O-R6, wherein R6 is selected from the group consisting of H and a linear or branched, saturated or unsaturated alkyl group comprising 1 to 6 carbon atoms, and wherein at least one of the substituents R1, R2, R3, R4 and R5 is not H, for the manufacture of a composition for the cosmetic treatment of human skin, scalp or hair and for the cosmetic treatment of human skin, scalp or hair.
Antioxidative properties of phenolic antioxidants isolated from corn steep liquor
Niwa, Toshio,Dpi, Umeyuki,Kato, Yoji,Osawa, Toshihiko
, p. 177 - 182 (2007/10/03)
With the immersion of corn into dilute sulfur oxide during starch-manufacturing processes, corn steep liquor (CSL) remains as leftover material. CSL is often used for fermentation, but its components are not fully understood. To determine the properties of CSL, 12 p-coumaric acid-related compounds were isolated from an ethyl acetate extract of CSL with the guidance of antioxidative activity on the rabbit erythrocyte membrane ghost system. The activity of these compounds was compared against oxidative damages, and it was elucidated that the activity of p-coumaric acid derivatives was mainly affected by their functional groups at the 3-position and less, by the conjugated side chain. Moreover, p-coumaric acid derivatives exhibited inhibitory activity stronger than that of tocopherols and ascorbic acid on peroxynitrite-mediated lipoprotein nitration. These findings that p-coumaric acid derivatives, which might play a beneficial role against oxidative damage, exist in CSL suggest this byproduct might be a useful resource of phenolic antioxidants.
