59831-93-5Relevant academic research and scientific papers
Synthesis of Novel Antiviral Ferulic Acid-Eugenol and Isoeugenol Hybrids Using Various Link Reactions
Gan, Xiuhai,Wang, Zhengxing,Hu, Deyu
, p. 13724 - 13733 (2021/11/23)
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.
Br?nsted Acid Catalyzed Tandem Defunctionalization of Biorenewable Ferulic acid and Derivates into Bio-Catechol
Bal, Mathias,Bomon, Jeroen,Liao, Yuhe,Maes, Bert U. W.,Sels, Bert F.,Sergeyev, Sergey,Van Den Broeck, Elias,Van Speybroeck, Veronique
supporting information, p. 3063 - 3068 (2020/02/05)
An efficient conversion of biorenewable ferulic acid into bio-catechol has been developed. The transformation comprises two consecutive defunctionalizations of the substrate, that is, C?O (demethylation) and C?C (de-2-carboxyvinylation) bond cleavage, occurring in one step. The process only requires heating of ferulic acid with HCl (or H2SO4) as catalyst in pressurized hot water (250 °C, 50 bar N2). The versatility is shown on a variety of other (biorenewable) substrates yielding up to 84 % di- (catechol, resorcinol, hydroquinone) and trihydroxybenzenes (pyrogallol, hydroxyquinol), in most cases just requiring simple extraction as work-up.
Novel trans-Ferulic Acid Derivatives Containing a Chalcone Moiety as Potential Activator for Plant Resistance Induction
Gan, Xiuhai,Hu, Deyu,Wang, Yanjiao,Yu, Lu,Song, Baoan
, p. 4367 - 4377 (2017/06/13)
A series of novel trans-ferulic acid derivatives containing a chalcone moiety were designed and synthesized to induce plant resistance. Antiviral activities of the compounds were evaluated. Bioassay results demonstrated that compounds F3, F6, F17, and F27 showed remarkable curative, protective, and inactivating activities against tobacco mosaic virus (TMV). With a 50% effective concentration (EC50) value of 98.78 μg mL-1, compound F27 exhibited the best protective activity compared with trans-ferulic acid (328.6 μg mL-1), dufulin (385.6 μg mL-1), and ningnanmycin (241.3 μg mL-1). This protective ability was associated with potentiation of defense-related enzyme activity and activation of photosynthesis of tobacco at an early stage. This notion was confirmed by up-regulated expression of stress responses and photosynthesis regulating proteins. This work revealed that F27 can induce resistance and enhance plant tolerance to TMV infection. Hence, F27 can be considered as a novel activator for inducing plant resistance.
Ferulic acid ester derivative containing quinazoline, as well as preparation method and purpose of ferulic acid ester derivative
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Paragraph 0013; 0021, (2016/10/09)
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.
Dependence of Mesomorphism on Molecular Rigidity with Reference to Lateral Substitution and Central Bridge
Travadi,Vadodaria,Ladva,Doshi
, p. 58 - 67 (2016/04/05)
A novel mesogenic ester homologous series is synthesized and studied with a view to understanding and establishing the effect of laterally substituted-OCH3 on mesomorphic behavior. The series consists of twelve members. C1 to C4 members are nonmesogenic, C6 to C12 are smectogenic in addition to nematogenic, and C14 to C16 are only smectogenic. The textures of smectic and nematic phases are A or C type and threaded or Schlieren, respectively. The transition curves in a phase diagram exhibit an odd-even effect and behave in normal manner except for the C14 and C16 derivatives in Sm-I transitions. Thermometric data were determined by an optical polarizing microscope equippedwith a heating stage. Average thermal stability for smectic and nematic are 107.7°C and 121.0°C, respectively. Smectogenic and nematogenicmesophase length ranges from 11.0 to 44.0°C and 12.0°C to 39.0°C, respectively. The mesomorphic properties of present series are comparedwith structurally similar other known series. Thus, present series is predominantly smectogenic and partly nematogenic ofmiddle ordered melting type.
COMPOUNDS AND METHODS FOR THE TREATMENT OF MICROBIAL INFECTION(S)
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Page/Page column 30; 31;32, (2016/02/29)
The present invention relates to compounds useful in methods of treating at least one microbial infection, such methods and uses of said compounds, pharmaceutical formulations comprising said compounds, and/or synthetic processes. The compounds have the general formula (I) wherein R1 is H, N02, Br, I, NHC2H4OH, NHC(=NH)NH2; NH2; R2 is H, CH(CH3)2) S02-4-C6H4F or SO2-4-C6H4-OCH3; R3 is H or NO2; and R4 is CHO or CH=CHC(0)OR5, wherein R5 is CH2CH2CH2CH3, or more preferably H, CH3, CH2CH3 or CH2CH2CH3.
Antiallergic activity of rosmarinic acid esters is modulated by hydrophobicity, and bulkiness of alkyl side chain
Zhu, Fengxian,Xu, Zhongming,Yonekura, Lina,Yang, Ronghua,Tamura, Hirotoshi
, p. 1178 - 1182 (2015/10/05)
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.
Design, synthesis, and in vitro antiplatelet aggregation activities of ferulic acid derivatives
Zhang, Peng-Xuan,Lin, Hang,Qu, Cheng,Tang, Yu-Ping,Li, Nian-Guang,Kai, Jun,Shang, Guanxiong,Li, Baoquan,Zhang, Li,Yan, Hui,Liu, Pei,Duan, Jin-Ao
, (2015/05/05)
In order to discover new compounds with antiplatelet aggregation activities, some ferulic acid (FA) derivatives were designed and synthesized. The in vitro antiplatelet aggregation activities of these compounds were assessed by turbidimetric test. The results showed that the target compound 7f had potent antiplatelet aggregation activity with its IC50 27.6 μmol/L, and 7f can be regarded as a novel potent antiplatelet aggregation candidate.
Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer
Li, Weixia,Li, Nianguang,Tang, Yuping,Li, Baoquan,Liu, Li,Zhang, Xu,Fu, Haian,Duan, Jin-Ao
, p. 6085 - 6088 (2012/10/29)
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.
Laccase-catalyzed oxidative phenolic coupling of vanillidene derivatives
Constantin, Mihaela-Anca,Conrad, Juergen,Beifuss, Uwe
, p. 2375 - 2379 (2013/02/21)
The laccase-catalyzed oxidative phenolic coupling of vanillidene derivatives using aerial oxygen as the oxidant has been developed. Depending on the substitution pattern of the vanillidene double bond of the substrate, either dilactones, dihydrobenzo[b]furans or biphenyls are formed.
