- Design, synthesis, and biological evaluation of N-hydroxycinnamamide/ salicylic acid hybrids as histone deacetylase inhibitors
-
Novel histone deacetylase (HDAC) inhibitors 9a-l were designed and synthesized by coupling the carboxyl group of salicylic acid (SA) with N-hydroxycinnamamides through various alkylol amines, and their in vitro biological activities were evaluated. The N-hydroxycinnamamide/SA hybrids 9b-f and 9h showed good to moderate anti-tumor activities. Notably, compound 9e had a greater potency, comparable to vorinostat (SAHA), in human colon carcinoma cells, which was probably, or at least partially, attributable to the positive effects of the chain length noted in alkylol amines. Furthermore, the HDAC inhibitory activities of 9e against Hela cell nuclear were also similar to that of vorinostat (SAHA), while the tested compounds 9c-f did not exhibit any isoform selectivity in the inhibition of HDACs. In addition, compound 9e could selectively inhibit tumor cells, but not inhibit non-tumor cell proliferation in vitro. Our findings suggest that the N-hydroxycinnamamide/SA hybrids may hold significant promise as therapeutic agents for the intervention of human cancers.
- You, Tao,Chen, Ke,Wang, Fei-Hai,Li, Pi-Hong,Li, Li-Yi,Wu, Zhi-Hao,Ni, Kong-Hai,Zheng, Zhi-Qiang
-
-
Read Online
- Synthesis and cytotoxic activity of 4-O-β-D-galactopyranosyl derivatives of phenolic acids esters
-
The glycosylation of naturally occurring phenolic acids has a significant impact on their solubility, stability and physiochemical properties. D-Galactose residue was found to form a part of glycoconjugates in several tissues and involved in a variety of physiological process. To the best of our knowledge, we have noticed a little information about the glycosylation of the phenolic acids with galactose residue. In this work, we describe the glycosylation of methyl vanillate and methyl ferulate with peracetylated-β-D-galactopyranose in the presence of BF3·OEt2. The coupling reaction yielded efficiently and selectively only the acetylated β-D-galactopyranosides 3 and 6. Removal of the acetyl groups using sodium methoxide afforded the corresponding β-D-galactopyranosides 4 and 7 in good yields. Anticancer activity in vitro was evaluated against two human cancer cell lines (MCF-7 breast cancer cell lines and PC-3 prostate cancer cell lines). β-D-galactopyranosides 4 and 7 demonstrated improved cytotoxic activity compared to the parental esters.
- Al Bujuq, Nader,Arar, Sharif,Khalil, Raida
-
-
Read Online
- Optimization of the reaction conditions for the synthesis of dihydrobenzofuran neolignans
-
We have optimized the experimental conditions for the silver(I)-promoted oxidative coupling of methyl p-coumarate (I) and methyl ferulate (II), which is the most frequently used methodology to synthesize the bioactive dihydrobenzofuran neolignans 1 ((±)-trans-dehydrodicoumarate dimethyl ester) and 2 ((±)-trans-dehydrodiferulate dimethyl ester). Most of the tested conditions affected the conversion (i.e., the consumption of I and II) and the selectivity (i.e., the percentage of I and II that was converted into 1 and 2, respectively), so the optimized conditions were the ones that afforded the best balance between conversion and selectivity. Silver(I) oxide (0.5 equiv.) is the most efficient oxidant agent amongst the silver(I) reagents that were tested to convert methyl esters I and II into compounds 1 and 2, respectively. Acetonitrile, which has not yet been reported as a solvent for this reaction, provided the best balance between conversion and selectivity, besides being "greener" than other solvents that are more often employed (e.g., dichloromethane and benzene). Under the optimized conditions, the reaction time decreased from 20 to 4 h without significantly impacting the conversion and selectivity.
- Crotti, Ant?nio E. M.,Dias, Herbert J.,Rodrigues, Matheus L.
-
-
- Carboxylic Acid Reductase Can Catalyze Ester Synthesis in Aqueous Environments
-
Most of the well-known enzymes catalyzing esterification require the minimization of water or activated substrates for activity. This work reports a new reaction catalyzed by carboxylic acid reductase (CAR), an enzyme known to transform a broad spectrum of carboxylic acids into aldehydes, with the use of ATP, Mg2+, and NADPH as co-substrates. When NADPH was replaced by a nucleophilic alcohol, CAR from Mycobacterium marinum can catalyze esterification under aqueous conditions at room temperature. Addition of imidazole, especially at pH 10.0, significantly enhanced ester production. In comparison to other esterification enzymes such as acyltransferase and lipase, CAR gave higher esterification yields in direct esterification under aqueous conditions. The scalability of CAR catalyzed esterification was demonstrated for the synthesis of cinoxate, an active ingredient in sunscreen. The CAR esterification offers a new method for green esterification under high water content conditions.
- Pongpamorn, Pornkanok,Kiattisewee, Cholpisit,Kittipanukul, Narongyot,Jaroensuk, Juthamas,Trisrivirat, Duangthip,Maenpuen, Somchart,Chaiyen, Pimchai
-
supporting information
p. 5749 - 5753
(2021/02/01)
-
- Synthesis of Novel Antiviral Ferulic Acid-Eugenol and Isoeugenol Hybrids Using Various Link Reactions
-
To develop novel antiviral agents, some novel conjugates between ferulic acid and eugenol or isoeugenol were designed and synthesized by the link reaction. The antiviral activities of compounds were evaluated using the half leaf dead spot method. Bioassay results showed acceptable antiviral activities of some conjugates against the tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV). Compounds A9, A10, E1, and E4 showed remarkable curative, protective, and inactivating effects on TMV and CMV at 500 μg mL-1. Notably, these compounds exhibited excellent protective effects on TMV and CMV. The EC50 values of compounds A9, A10, E1, and E4 against TMV were 180.5, 169.5, 211.4, and 135.5 μg mL-1, respectively, and those against CMV were 210.5, 239.1, 218.4, and 178.6 μg mL-1, respectively, which were superior to those of ferulic acid (471.5 and 489.2 μg mL-1), eugenol (456.3 and 463.2 μg mL-1), isoeugenol (478.4 and 487.5 μg mL-1), and ningnanmycin (246.5 and 286.6 μg mL-1). Then, the antiviral mechanisms of compound E4 were investigated by determining defensive enzyme activities and multi-omics analysis. The results indicated that compound E4 resisted the virus infection by enhancing defensive responses via inducing the accumulation of secondary metabolites from the phenylpropanoid biosynthesis pathway in tobacco.
- Gan, Xiuhai,Wang, Zhengxing,Hu, Deyu
-
p. 13724 - 13733
(2021/11/23)
-
- METHOD FOR PRODUCING CINNAMIC ACID ESTER COMPOUND
-
A method for producing a cinnamic acid ester derivative includes reacting a cinnamic acid derivative compound represented by the formula (1), wherein the symbols are as defined in the description, with an alcohol compound represented by the formula: R6OH, wherein the symbol is as defined in the description, in the presence of a strong acid resin catalyst without using a solvent. As the cinnamic acid derivative compound, cinnamic acid, ferulic acid, and caffeic acid are preferred, and as the alcohol compound, methanol, ethanol, propanol, butanol, pentanol, hexanol, ethylene glycol, glycerol, phenethyl alcohol, and a monosaccharide are preferred.
- -
-
Paragraph 0066-0067; 0075
(2020/05/06)
-
- Structure?Activity Relationships of Cinnamate Ester Analogues as Potent Antiprotozoal Agents
-
Protozoal infections are still a global health problem, threatening the lives of millions of people around the world, mainly in impoverished tropical and sub-tropical regions. Thus, in view of the lack of efficient therapies and increasing resistances against existing drugs, this study describes the antiprotozoal potential of synthetic cinnamate ester analogues and their structure-activity relationships. In general, Leishmania donovani and Trypanosoma brucei were quite susceptible to the compounds in a structure-dependent manner. Detailed analysis revealed a key role of the substitution pattern on the aromatic ring and a marked effect of the side chain on the activity against these two parasites. The high antileishmanial potency and remarkable selectivity of the nitro-aromatic derivatives suggested them as promising candidates for further studies. On the other hand, the high in vitro potency of catechol-type compounds against T. brucei could not be extrapolated to an in vivo mouse model.
- Bernal, Freddy A.,Kaiser, Marcel,Wünsch, Bernhard,Schmidt, Thomas J.
-
-
- Study on the formation of antihypertensive twin drugs by caffeic acid and ferulic acid with telmisartan
-
Purpose: This study aimed to synthesize twin drugs from cinnamic acid compounds, caffeic acid (CFA) and ferulic acid (FLA), which can antagonize endothelin-1 (ET-1) with telmisartan through ester bonds. Moreover, the antihypertensive effect of telmisartan and its influence on blood pressure variability (BPV) were enhanced, and the bioavailability of caffeic acid and ferulic acid was improved. Methods: Six twin drugs, which were the target compounds, were synthesized. Hypertensive rats (SHR) and conscious sinoaortic-denervated (SAD) rats were spontaneously used as models for pharmacodynamic research to study the antihypertensive efficacy of these twin drugs. Wistar rats were employed as pharmacokinetic research models to investigate the pharmacokinetics of the target compounds via intragastric administration. Cellular pharmacodynamic research was also conducted on the antagonistic action on Ang II-AT1, ETA and ETB receptor. Results: Compound 1a was determined as the best antihypertensive twin drug and thus was further studied for its effect on BPV. Compared with that of telmisartan, the antihypertensive effect of compound 1a was improved (p50 of Lps-2 was still two orders of magnitude higher than that of the positive drug telmisartan. Hence, the twin drugs worked by metabolizing and regenerating telmisartan and caffeic acid or ferulic acid in the body. Conclusion: The synthesized twin drugs improved telmisartan’s antihypertensive effects, significantly decreased BPV in SAD rats and increased the bioavailability of caffeic acid and ferulic acid. This study serves as a basis for the development of new angiotensin receptor blocker (ARB) in the future and a reference for the development of new drugs to antagonize ET-1.
- Li, Pengshou,Li, Ziyong,Ma, Qixiang,Peng, Yingying,Zhang, Xiaohua
-
p. 977 - 992
(2020/03/13)
-
- METHOD OF FORMING MONOMERS AND FURFURAL FROM LIGNOCELLULOSE
-
The present disclosure relates to a method of producing monophenolicmonomers and furfural from lignocellulosic biomass beating the biomass in a solvent together with a zeolite based catalyst.
- -
-
Page/Page column 17
(2020/06/05)
-
- Synthesis method of valerolactam alkaloid compound (by machine translation)
-
The invention discloses a synthesis method, of a valerolactam alkaloid compound. Comprising: 1) reacting thionyl chloride with methanol, then adding ferulic acid, synthesizing ferulic acid methyl ester; 2) reacting 2 -nitrogen hexanone with phosphorus pentachloride; 4) 3, 3 -dibromo -2 - azaltrexone reacts with hydrogen and sodium acetate under the action of potassium iodide to generate 3-bromo 3 -cyclohexanone; 3) reaction, and reacting with hydrogen -2 - and sodium acetate under the action of potassium iodide; and the like 3 -2 . 5) 4) The terpineol prepared in step 3 -) is reacted, with sodium hydroxide, with the terpineol prepared in step -2 2 -) to form a lactam alkaloid compound. The synthetic method has the advantages of accessible raw material sources, mild reaction conditions, and simple reaction process operation. (by machine translation)
- -
-
Paragraph 0029; 0042-0046
(2019/10/01)
-
- Design, synthesis and antitumor evaluation of novel celastrol derivatives
-
On the basis of the hybridization strategy of natural products, a total of 32 novel celastrol hybrids were designed, synthesized and evaluated for their antitumor activities. Most of these derivatives exihibited significant antiproliferative activities compared to celastrol, among which compound 29 displayed the strongest inhibitory capability [IC50 = 0.15 ± 0.03 μM (A549),0.17 ± 0.03 μM (MCF-7), 0.26 ± 0.02 μM (HepG2)], which exhibited equal or superior anti-cancer activities in comparison to 2-cyano-3,12-dioxoolean-1,9 (11)-dien-28-oic acid methyl ester (CDDO-Me). The mechanism of pharmacological research indicated that 29 possessed the ability to disrupt Hsp90-Cdc37 complex which was stronger than celastrol. Meanwhile, compound 29 could induce abnormal regulation of clients (p-Akt and Cdk4) of Hsp90 and cell cycle arrest at G0/G1 phase in a concentration-dependent manner. In addition, compound 29 could also induce cell apoptosis through the death receptor pathway on A549 cells. Taken together, our results demonstrated that 29 might be a promising novel candidate for further druggability research.
- Xu, Manyi,Li, Na,Zhao, Zihao,Shi, Zhixian,Sun, Jianbo,Chen, Li
-
p. 265 - 276
(2019/05/04)
-
- Antifungal activity of cinnamic acid and benzoic acid esters against Candida albicans strains
-
Candida albicans is an important opportunistic fungal pathogen capable of provoking infection in humans. In the present study, we evaluated the antifungal effect of 23 ester derivatives of the cinnamic and benzoic acids against 3 C. albicans strains (ATCC-76645, LM-106 and LM-23), as well as discuss their Structure–Activity Relationship (SAR). The antifungal assay results revealed that the screened compounds exhibited different levels of activity depending on structural variation. Among the ester analogues, methyl caffeate (5) and methyl 2-nitrocinnamate (10) were the analogues that presented the best antifungal effect against all C. albicans strains, presenting the same MIC values (MIC?=?128?μg/mL), followed by methyl biphenyl-2-carboxylate (21) (MIC?=?128, 128 and 256?μg/mL for C. albicans LM-106, LM-23, and ATCC-76645, respectively). Our results suggest that certain molecular characteristics are important for the antifungal action.
- Lima, Tamires C.,Ferreira, Alana R.,Silva, Daniele F.,Lima, Edeltrudes O.,de Sousa, Dami?o P.
-
p. 572 - 575
(2017/09/30)
-
- Palladium nanoparticles immobilized on amphiphilic and hyperbranched polymer-functionalized magnetic nanoparticles: An efficient semi-heterogeneous catalyst for Heck reaction
-
To address the obstacles facing the use of palladium-based homogeneous and heterogeneous catalysts in C─C cross-coupling reactions, a novel semi-heterogeneous support was developed based on hyperbranched poly(ethylene glycol)-block-poly(citric acid)-functionalized Fe3O4 magnetic nanoparticles (Fe3O4@PCA-b-PEG). Because of the surface modification of the Fe3O4 nanoparticles with amphiphilic and hyperbranched polymers (PCA-b-PEG), these hybrid materials are not only soluble in a wide range of solvents (e.g. water, ethanol and dimethylformamide) but also are able to trap Pd2+ ions via complex formation of free carboxyl groups of the PCA dendrimer with metal ions. The reduction of trapped palladium ions in the dendritic shell of Fe3O4@PCA-b-PEG leads to immobilized palladium nanoparticles. The morphology and structural features of the catalyst were characterized using various microscopic and spectroscopic techniques. The catalyst was effectively used in the palladium-catalysed Mizoroki–Heck coupling reaction in water as a green solvent. In addition, the catalyst can be easily recovered from the reaction mixture by applying an external magnetic field and reused for more than ten consecutive cycles without much loss in activity, exhibiting an example of a sustainable and green methodology.
- Tabatabaei Rezaei, Seyed Jamal,Shamseddin, Azin,Ramazani, Ali,Mashhadi Malekzadeh, Asemeh,Azimzadeh Asiabi, Pegah
-
-
- Synthesis of novel ester series and study of its mesomorphism dependence on terminal end group with lateral-OCH3 group
-
Novel liquid crystal (LC) materials of ester derivatives were synthesized and studied with a view to understanding and establishing the effects of molecular structure on LC properties. The novel molecules consist of two phenyl rings bonded through-COO-central group and a laterally substituted methoxy group with-OCnH2n+1 as well as-COOCH3 terminal end groups, and yielded 12 homologous members of an ester series. The C1 to C3 members are nonmesomorphic, the C4 to C12 members are enantiotropic nematic only, and the C14 to C16 members are enantiotropically smectogenic in addition to nematogenic. Transition temperatures and the textures of LC state were observed through an optical polarizing microscope (POM) equipped with a heating stage. The textures of nematic phase are threaded or Schlieren, and that of smectic phase are focal conic of the type A or C. Transition curves of a phase diagram behave in normal manner with the exhibition of an odd-even effect (only N-I). Analytical and spectral data support the molecular structures of the novel ester derivatives. The LC properties of the present series are compared with structurally similar other known series. The average thermal stability of the series is 93°C for smectic and 120.88°C for nematic and the mesogenic phase length ranges between 2°C and 46°C.
- Vadodaria,Ladva,Doshi,Travadi
-
-
- Ferulic acid ester derivative containing quinazoline, as well as preparation method and purpose of ferulic acid ester derivative
-
The invention discloses a ferulic acid ester derivative containing quinazoline, as well as a preparation method and a purpose of the ferulic acid ester. A structural general formula (I) of the ferulic acid ester derivative containing the quinazoline is as follows: R1 is methyl, ethyl, n-propyl, isopropyl and normal-butyl; R2 is hydrogen, 6,7-dimethoxy and 6,7-bis-methoxyethoxy. The ferulic acid ester derivative containing the quinazoline can resist the cucumber mosaic virus, the tobacco mosaic virus, the southern rice black-streaked dwarf virus and the rice stripe virus.The structural general formula (I) is shown in the specification.
- -
-
Paragraph 0013; 0031; 0035; 0039; 0043; 0047; 0051; 0053
(2016/10/09)
-
- Synthesis and anticancer activities of glycyrrhetinic acid derivatives
-
A total of forty novel glycyrrhetinic acid (GA) derivatives were designed and synthesized. The cytotoxic activity of the novel compounds was tested against two human breast cancer cell lines (MCF-7, MDA-MB-231) in vitro by the MTT method. The evaluation results revealed that, in comparison with GA, compound 42 shows the most promising anticancer activity (IC50 1.88 ± 0.20 and 1.37 ± 0.18 μM for MCF-7 and MDA-MB-231, respectively) and merits further exploration as a new anticancer agent.
- Li, Yang,Feng, Ling,Song, Zhi-Fang,Li, Hai-Bei,Huai, Qi-Yong
-
-
- Design, synthesis and "in vitro" anti-leukemic evaluation of ferulic acid analogues as BCR-Abl inhibitors
-
Semi-synthetic modification of ferulic acid isolated from Salicornia brachiata was performed and the derivatives showed gratifying in silico binding scores with the BCR-Abl protein, comparable with imatinib. Anti-proliferative activity against K562, U937 and Hep G2 cancer cell lines and the BCR-Abl kinase inhibitory activity using an ADP-Glo assay were investigated. Compounds 2i and 3j were potent BCR-Abl inhibitors and were also active against K562 cells.
- Rajendran, Narendran,Subramaniam, Shankar,Charan Raja, Mamilla R.,Venkata Subbarao, Himesh Makala,Raghunandan, Subhashree,Venkatasubramanian, Ulaganathan,Pemaiah, Brindha,Mahapatra, Santanu Kar,Sivasubramanian, Aravind
-
p. 70480 - 70484
(2016/08/06)
-
- Antiallergic activity of rosmarinic acid esters is modulated by hydrophobicity, and bulkiness of alkyl side chain
-
Methyl, propyl and hexyl esters of rosmarinic, caffeic and p-coumaric acids were tested for antiallergic activity, and rosmarinic acid propyl ester exhibited the greatest β-hexosaminidase release suppression (IC50, 23.7 μM). Quadratic correlations between pIC50 and cLogP (r2 = 0.94, 0.98, and 1.00, respectively) were observed in each acid ester series. The antiallergic activity is modulated by hydrophobicity, and alkyl chain bulkiness.
- Zhu, Fengxian,Xu, Zhongming,Yonekura, Lina,Yang, Ronghua,Tamura, Hirotoshi
-
p. 1178 - 1182
(2015/10/05)
-
- The synthesis and analysis of advanced lignin model polymers
-
If the lignin-first biorefinery concept becomes a reality, high quality lignins close in structure to native lignins will become available in large quantities. One potential way to utilise this renewable material is through depolymerisation to aromatic chemicals. This will require the development of new chemical methods. Here, we report the synthesis and characterisation of advanced lignin model polymers to be used as tools to develop these methods. The controlled incorporation of the major linkages in lignin is demonstrated to give complex hardwood and softwood lignin model polymers. These polymers have been characterised by 2D HSQC NMR and GPC analysis and have been compared to isolated lignins.
- Lancefield,Westwood
-
supporting information
p. 4980 - 4990
(2015/11/16)
-
- Antioxidant properties and efficacies of synthesized alkyl caffeates, ferulates, and coumarates
-
Caffeic, ferulic, and coumaric acids were lipophilized with saturated fatty alcohols (C1-C20). The antioxidant properties of these hydroxycinnamic acids and their alkyl esters were evaluated in various assays. Furthermore, the antioxidant efficiency of the compounds was evaluated in a simple o/w microemulsion using the conjugated autoxidizable triene (CAT) assay. All evaluated phenolipids had radical scavenging, reducing power, and metal chelating properties. Only caffeic acid and caffeates were able to form a complex with iron via their catechol group in the phenolic ring. In the o/w emulsion, the medium chain phenolipids of the three homologues series were most efficient. The antioxidant properties and efficacies were dependent upon functional groups substituted to the ring structure and were in the following order: caffeic acid and caffeates > ferulic acid and ferulates > coumaric acid and coumarates. Moreover, the results demonstrated that the test system has an impact on the antioxidative properties measured.
- Sorensen, Ann-Dorit Moltke,Jacobsen, Charlotte,Durand, Erwann,Laguerre, Mickal,Bayrasy, Christelle,Lecomte, Jrme,Villeneuve, Pierre
-
p. 12553 - 12562
(2015/04/21)
-
- Structure-activity relationships of glycogen phosphorylase inhibitor FR258900 and its analogues: A combined synthetic, enzyme kinetics, and computational study
-
A series of O- or N-cinnamoylated, p-coumaroylated, feruloylated, phenyl, and substituted phenylpropiolated derivatives of lmalic, 3-hydroxypentanedioic, and l-glutamic acids were synthesized as analogues of the natural product glycogen phosphorylase (GP) inhibitor FR258900 (2,3-bis(4-hydroxycinnamoyloxy) glutaric acid). These compounds proved practically inactive against rabbit muscle glycogen phosphorylase b. A structure-activity study involving previously synthesized tartaric acid analogues of FR258900 revealed that two acyl moieties must be present in the compounds to make a good inhibitor. Molecular modeling methods (docking and quantitative structure-activity relationship (QSAR) calculations) were used to understand the nature of the binding affinities of these GP inhibitors. The generated 3D models for GP-inhibitor complexes showed that both the polar allosteric site pocket and the hydrophobic pocket at the interface of the homodimeric units of GP were important for effective binding of the acyl and aromatic moieties of the inhibitors. The predictive QSAR models consist of empirical and quantum mechanics descriptors and provide good explanatory and predictive abilities (prediction coefficient Q2=0.7-0.9 when cross-validation procedures were performed).
- Juhsz, Lszl,Varga, Gergely,Sztankovics, Andrea,Bke, Ferenc,Docsa, Tibor,Kiss-Szikszai, Attila,Gergely, Pl,Ka, Juraj,Tvaroka, Igor,Somsk, Lszl
-
p. 1558 - 1568
(2015/02/05)
-
- Synthesis and biological activity of nitric oxide-releasing derivatives of ferulic acid as potential agents for the treatment of chronic kidney diseases
-
In order to search for novel potential agents for the treatment of chronic kidney diseases (CKD), nitric oxide (NO)-releasing derivatives (5a-c) of ferulic acid were synthesized and characterized by MS, 1H NMR, and elementary analysis. They showed different NO-releasing rate in the absence or presence of L-cysteine in vitro. In the adenine induced CKD rats, these compounds revealed reno-protective effect via lowering blood urea nitrogen (BUN), creatinine (Cr) in serum and malondialdehyde (MDA) in kidney, increasing NO and superoxide dismutase (SOD) level in kidney. Among them, 3-methoxy-4-(nitrooxy)ethoxy cinnamic acid (5a) was confirmed to have a higher NO-releasing rate in vitro and better effect in ameliorating adenine-induced kidney damage in rats.
- Liu, Hao-Ran,Liu, Ying,Li, Yan-Lai,Qi, Min-You,Liu, Wu-Kun
-
p. 875 - 880
(2013/09/23)
-
- Renewable benzoxazine monomers from Lignin-like naturally occurring phenolic derivatives
-
The benzoxazines of three naturally occurring phenylpropanoid phenols: ferulic, coumaric, and phloretic acids, and their esters are described. Benzoxazines with conjugated unsaturated chains exhibit unusual poor thermal stability and degrade partially at the polymerization temperature making necessary the use of a catalyst (BF3.Et2O) to low the polymerization temperature and prevent degradation. Polybenzoxazines are prepared thermally and characterized by DSC and TGA techniques. The resulting materials have superior Tgs when compared with those prepared from an unsubstituted monofuctional benzoxazine due to the additional crosslinking through the ester and carboxylic moieties.
- Comí, Marc,Lligadas, Gerard,Ronda, Juan C.,Galià, Marina,Cádiz, Virginia
-
p. 4894 - 4903
(2013/11/06)
-
- Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer
-
The anticancer activities of alkyl esters and NO-donors of ferulic acid (FA) and caffeic acid (CA) were assessed by a high-throughout screening (HTS) method, and the structure-activity relationships were described. CA alkyl esters had better anticancer activities than FA alkyl esters with the same alkyl substituent. Mono-nitrates and phenylfuroxan nitrates were more potent than the dual nitrates. Phenylsulfonylfuroxan nitrates of FA, especially compounds 8b-8d, exhibited more potent activities in anticancer.
- Li, Weixia,Li, Nianguang,Tang, Yuping,Li, Baoquan,Liu, Li,Zhang, Xu,Fu, Haian,Duan, Jin-Ao
-
p. 6085 - 6088
(2012/10/29)
-
- Chemical interaction between polyphenols and a cysteinyl thiol under radical oxidation conditions
-
Chemical interaction between polyphenols and thiols was investigated under radical oxidation conditions using a model cysteinyl thiol derivative, N-benzoylcysteine methyl ester. The radical oxidation was carried out with a stoichiometric amount of 2,2-diphenyl-1-picrylhydrazyl (DPPH), and the decreases in the amounts of polyphenols and the thiol were measured by HPLC analysis. Cross-coupling products between various polyphenols and the thiol were examined by LC-MS in reactions that showed decreases in both the polyphenols and the thiol. The LC-MS results indicated that three phenolic acid esters (methyl caffeate, methyl dihydrocaffeate, and methyl protocatechuate) and six flavonoids (kaempferol, myricetin, luteolin, morin, taxifolin, and catechin) gave corresponding thiol adducts, whereas three polyphenols (methyl ferulate, methyl sinapate, and quercetin) gave only dimers or simple oxidation products without thiol substituents. Thiol adducts of the structurally related compounds methyl caffeate and methyl dihydrocaffeate were isolated, and their chemical structures were determined by NMR analysis. The mechanism for the thiol addition was discussed on the basis of the structures of the products.
- Fujimoto, Aya,Masuda, Toshiya
-
experimental part
p. 5142 - 5151
(2012/10/07)
-
- In vitro analysis of the monolignol coupling mechanism using dehydrogenative polymerization in the presence of peroxidases and controlled feeding ratios of coniferyl and sinapyl alcohol
-
In this study, dehydrogenative polymers (DHP) were synthesized in vitro through dehydrogenative polymerization using different ratios of coniferyl alcohol (CA) and sinapyl alcohol (SA) (10:0, 8:2, 6:4, 2:8, 0:10), in order to investigate the monolignol coupling mechanism in the presence of horseradish peroxidase (HRP), Coprinus cinereus peroxidase (CiP) or soybean peroxidase (SBP) with H2O2, respectively. The turnover capacities of HRP, CiP and SBP were also measured for coniferyl alcohol (CA) and sinapyl alcohol (SA), and CiP and SBP were found to have the highest turnover capacity for CA and SA, respectively. The yields of HRP-catalyzed DHP (DHP-H) and CiP-catalyzed DHP (DHP-C) were estimated between ca. 7% and 72% based on the original weights of CA/SA in these synthetic conditions. However, a much lower yield of SBP-catalyzed DHP (DHP-S) was produced compared to that of DHP-H and DHP-C. In general, the DHP yields gradually increased as the ratio of CA/SA increased. The average molecular weight of DHP-H also increased with increasing CA/SA ratios, while those of DHP-C and DHP-S were not influenced by the ratios of monolignols. The frequency of β-O-4 linkages in the DHPs decreased with increasing CA/SA ratios, indicating that the formation of β-O-4 linkages during DHP synthesis was influenced by peroxidase type.
- Moon, Sun-Joo,Kwon, Mi,Choi, Donha,Won, Keehoon,Kim, Yong Hwan,Choi, In-Gyu,Choi, Joon Weon
-
-
- One-pot preparation of phenylpropanoid esters co-catalyzed by boric acid and piperidine
-
Phenylpropanoid esters, especially those with hydroxyl and/or methoxy groups on the benzene ring, are important medicinal chemicals or intermediates. They are usually prepared by esterification of their corresponding substituted cinnamic acids with various alcohols. However, the esterification procedures often suffer from environmentally hazardous problems when sulfuric acid is used as a catalyst or suffer from unsatisfactory yields and expensive raw material when enzyme is applied as a catalyst. In this paper, a convenient one-pot process for preparing various phenylpropanoid esters from substituted benzaldehydes bearing hydroxyl and/or methoxyl groups has been developed. The alcohols react first with malonic acid catalyzed by boric acid to form monomalonate, then without separation, let the resultant mixture immediately react with the injected various substituted benzaldehydes in the presence of piperidine to afford the desired esters with moderate to good yields. Springer Science+Business Media B.V. 2011.
- Wang, Huan,Wei, Qing-Yi,Jiang, Hong,Jiang, Zhen-Hua
-
experimental part
p. 207 - 213
(2012/05/20)
-
- Horseradish peroxidase catalyzed oxidative cross-coupling reactions: The synthesis of 'unnatural' dihydrobenzofuran lignans
-
The possibility to afford by a biomimetic reaction 'unnatural' products, which could offer a better bioactivity profile than natural analogues, is outlined and the first applications to the synthesis of lignans and related compounds have been reported. Here we describe the synthesis of new heterodimers, having a phenylcoumaran skeleton, by horseradish peroxidase catalyzed cross-coupling reactions of methyl esters of substituted hydroxycinnamic acids.
- Saliu, Francesco,Tolppa, Eeva-Liisa,Zoia, Luca,Orlandi, Marco
-
body text
p. 3856 - 3860
(2011/08/06)
-
- Crotonionosides A-G: Megastigmane glycosides from leaves of Croton cascarilloides R?uschel
-
From the 1-BuOH-soluble fraction of a MeOH extract of leaves of Croton cascarilloides, collected in Okinawa, Japan, seven megastigmane glycosides, named crotonionosides A-G, were isolated together with three known megastigmane glucosides, dendranthemosides A and B, and citroside A. This structures were elucidated by a combination of spectroscopic analyses, HPLC analyses, and application of the modified Mosher's method.
- Kawakami, Susumu,Matsunami, Katsuyoshi,Otsuka, Hideaki,Shinzato, Takakazu,Takeda, Yoshio
-
experimental part
p. 147 - 153
(2011/10/08)
-
- Derivatives of 8-epiblechnic Acid and their Effects on Down-Regulation of Endothelin (ETA) receptor mRNA
-
The present application discloses derivatives of 8-epiblechnic acid and use thereof in treating a disease related to endothelin receptor A or endothelin-1 (ET-1) over-expression, such as hypertension, cancer, atherosclerosis, and myocardial infarction.
- -
-
Page/Page column 4-5
(2010/03/31)
-
- Low molecular weight MPEG-assisted organic synthesis
-
A toolkit of low molecular weight MPEG-supported coupling agents ( MIIDQ, MEDCI), reagents for the Mitsunobu reaction ( MDEAD, MTPP), an alternative to diazomethane, and scavengers can be used in the solution-phase synthesis of amides, esters and ureas and are easily removed after use by solid-phase extraction (MSPE) using normal silica.
- Figlus, Marek,Tarruella, Albert C.,Messer, Anastasia,Sollis, Steven L.,Hartley, Richard C.
-
supporting information; experimental part
p. 4405 - 4407
(2010/09/15)
-
- Antileukotrienic phenethylamido derivatives of arylalkanoic acids in the treatment of ulcerative colitis
-
A series of arylalkanoic acid derivatives bearing methyl(phenethyl)amino groups were prepared and their inhibition of LTB4 biosynthesis was evaluated. Regression analysis showed the slightly different parabolic dependences of this activity on lipophilicity of α-methyl and α-unsubstituted alkanoic acid derivatives. The relationship derived for α-unsubstituted alkanoic acids was extended by previously prepared group of similar derivatives of arylacetic acids without any change of regression coefficients and statistical criteria. It was concluded that the most active compounds belong to 2-arylpropanoic acid derivatives with lipophilicity close to log Popt (=6.97). But generally, the structural changes in the acidic part of compounds under study did not yield the substantial improvement of LTB4 biosynthesis inhibition in comparison with the previously prepared series of derivatives IV. The anti-inflammatory effect of the compounds under study was evaluated in three animal models of inflammation and their possible utilization in the treatment of ulcerative colitis (UC) was followed. From 12 evaluated compounds, 4 compounds are more active in UC inhibition than the standard sulfasalazine but it can be stated that the change of connecting chain between aromatic ring and carboxyl did not bring about the important improvement of this activity in comparison with previous derivatives of arylacetic acids. Possible relation between LTB4 biosynthesis inhibition and ulcerative colitis is seriously broken by the compound 8a with carbonyl as the additional functional group on the connecting chain between carboxyl and aromatic ring.
- Junek, Richard,Kverka, Miloslav,Jandera, Antonin,Panajotova, Vladimira,Satinsky, Dalibor,Machacek, Milos,Kuchar, Miroslav
-
experimental part
p. 332 - 344
(2009/04/06)
-
- A selective de-O-methylation of guaiacyl lignans to corresponding catechol derivatives by 2-iodoxybenzoic acid (IBX). the role of the catechol moiety on the toxicity of lignans
-
We report here the first selective de-O-methylation of a large panel of guaiacyl lignans to the corresponding catechol derivatives by using IBX as primary oxidant under green conditions (dimethyl carbonate-H2O solvent) through an in situ reduction procedure. The influence of the catechol moiety on the cytotoxicity and genotoxicity of new lignan derivatives has been investigated. The results obtained indicated that the presence of the catechol moiety sharply enhances the clastogenic potential (e.g. induction of chromosomal aberrations), the cytotoxicity and the modulation of cell cycle progression with respect to the parent compounds. Thus, despite the in vitro antioxidant activity usually described for catechol derivatives, our results show for the first time the generation of a clastogenic potential, highly indicative of a long-term genetic and cancer risk. The Royal Society of Chemistry 2009.
- Bernini, Roberta,Barontini, Maurizio,Mosesso, Pasquale,Pepe, Gaetano,Willfoer, Stefan M.,Sjoeholm, Rainer E.,Eklund, Patrik C.,Saladino, Raffaele
-
scheme or table
p. 2367 - 2377
(2009/09/26)
-
- Nitrification inhibitors from the root tissues of Brachiaria humidicola, a tropical grass
-
Nitrification inhibitory activity was found in root tissue extracts of Brachiaria humidicola, a tropical pasture grass. Two active inhibitory compounds were isolated by activity-guided fractionation, using recombinant Nitrosomonas europaea containing luxAB genes derived from the bioluminescent marine gram-negative bacterium Vibrio harveyi. The compounds were identified as methyl-p-coumarate and methyl ferulate, respectively. Their nitrification inhibitory properties were confirmed in chemically synthesized preparations of each. The IC50 values of chemically synthesized preparations were 19.5 and 4.4 μM, respectively. The ethyl, propyl, and butyl esters of p-coumaric and ferulic acids inhibited nitrification, whereas the free acid forms did not show inhibitory activity.
- Gopalakrishnan, Subramaniam,Subbarao, Guntur V.,Nakahara, Kazuhiko,Yoshihashi, Tadashi,Ito, Osamu,Maeda, Ikuko,Ono, Hiroshi,Yoshida, Mitsuru
-
experimental part
p. 1385 - 1388
(2009/10/01)
-
- A mild, efficient and selective deprotection of t-butyldimethylsilyl-protected phenols using cesium carbonate
-
A mild and efficient method for the deprotection of aryl t-butyldimethysilyl (TBS) ethers is described. The protecting group TBS could be cleaved from aryl silyl ethers using cesium carbonate in DMF-H2O at room temperature to give the corresponding phenols in excellent yields. The reaction conditions allowed selective deprotection of aryl TBS-protected phenols in the presence of TBS, phenyloxycarbonyl or tetrahydropyranyl-protected alcohols.
- Jiang, Zhi-Yong,Wang, Yan-Guang
-
p. 3859 - 3861
(2007/10/03)
-
- Microwave promoted facile synthesis of methyl and ethyl carboxylates
-
Microwave irradiation of carboxylic acids with trialkyl orthoacetate in solvent-free conditions afforded an efficient method for alkylation of carboxylic acids to corresponding alkyl carboxylates.
- Lee, Jong Chan,Song, In-Goul,Park, Jin Young
-
p. 2209 - 2213
(2007/10/03)
-
- β-fluoro-coniferyl alcohol does not inhibit lignin biosynthesis in suspension cultures of Picea abies (L.) Karst.
-
A fluorinated analogue of coniferyl alcohol has been reported to be a specific inhibitor of oxidases involved in the biosynthesis of lignin. The Z isomer of β-fluoro-coniferyl alcohol was synthesized and used for the preparation of dehydrogenation polymers (DHPs) and was also tested on lignin producing suspension cultures of spruce (Picea abies (L.) Karst.). The growth of the cells or the production of lignin by the suspension cultures was not significantly affected by the addition of fluoroconiferyl alcohol. This analogue did not form polymers quite as easily as did coniferyl alcohol in oxidation with hydrogen peroxide and horseradish peroxidase. In both cases the β-fluoroconiferyl alcohol became incorporated in the polymeric product. We were unable to detect any specific inhibition of peroxidase activity, which is at variance with earlier reports of pronounced inhibition of lignin biosynthesis in poplar plantlets by fluoroconiferin, a potential inhibitor of oxidases involved in lignin biosynthesis.
- Gustafsson, Mikaela,Kaerkoenen, Anna,Simola, Liisa K,Teeri, Teemu H,Sipilae, Jussi,Kilpelaeinen, Ilkka,Brunow, Goesta
-
p. 243 - 248
(2007/10/03)
-
- PHENOLIC CONSTITUENTS OF PHELLODENDRON AMURENSE BARK
-
Glycosides of (+/-)-5,5'-dimethoxyariciresinol, 2-(p-hydroxy-phenyl)-ethanol and N-methylhigenamine were isolated from the dried bark of Phellodendron amurense, together with nine phenolic compounds.
- Ida, Yoshiteru,Satih, Yohko,Ohtsuka, Masumi,Nagasao, Miki,Shoji, Junzo
-
p. 209 - 216
(2007/10/02)
-
