- Synthesis of Novel Antiviral Ferulic Acid-Eugenol and Isoeugenol Hybrids Using Various Link Reactions
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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
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p. 13724 - 13733
(2021/11/23)
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- Structure?Activity Relationships of Cinnamate Ester Analogues as Potent Antiprotozoal Agents
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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.
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- Ferulic acid ester derivative containing quinazoline, as well as preparation method and purpose of ferulic acid ester derivative
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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.
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Paragraph 0013; 0025
(2016/10/09)
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- One-pot preparation of phenylpropanoid esters co-catalyzed by boric acid and piperidine
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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
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experimental part
p. 207 - 213
(2012/05/20)
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- Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer
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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
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p. 6085 - 6088
(2012/10/29)
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