- Novel α,β-unsaturated amide derivatives bearing α-amino phosphonate moiety as potential antiviral agents
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Based on flexible construction and broad bioactivity of ferulic acid, a series of novel α,β-unsaturated amide derivatives bearing α-aminophosphonate moiety were designed, synthesized and systematically evaluated for their antiviral activity. Bioassay results indicated that some compounds exhibited good antiviral activities against cucumber mosaic virus (CMV) and tobacco mosaic virus (TMV) in vivo. Especially, compound g18 showed excellent curative and protective activities against CMV, with half-maximal effective concentration (EC50) values of 284.67 μg/mL and 216.30 μg/mL, which were obviously superior to that of Ningnanmycin (352.08 μg/mL and 262.53 μg/mL). Preliminary structure-activity relationships (SARs) analysis revealed that the introduction of electron-withdrawing group at the 2-position or 4-position of the aromatic ring is favorable for antiviral activity. Present work provides a promising template for development of potential inhibitor of plant virus.
- Lan, Xianmin,Xie, Dandan,Yin, Limin,Wang, Zhenzhen,Chen, Jin,Zhang, Awei,Song, Baoan,Hu, Deyu
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- Novel Ferulic Amide Ac6c Derivatives: Design, Synthesis, and Their Antipest Activity
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Thirty-eight novel ferulic amide 1-aminocyclohexane carboxylic acid (Ac6c) derivativesD1-D19andE1-E19were designed and synthesized, and their antibacterial, antifungal, and insecticidal activities were tested. Most of the synthesized compounds displayed e
- Dai, Ali,Deng, Peng,Guo, Shengxin,Wang, Ya,Wu, Jian,Zhang, Renfeng
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p. 10082 - 10092
(2021/09/13)
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- Synthesis of 1,3,4-trisubstituted pyrrolidines as meropenem adjuvants targeting New Delhi metallo-β-lactamase
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The effective strategies to neutralize the New Delhi metallo-β-lactamase (NDM-1) activity offer unique opportunities to combination therapy because NDM-1 inactivates all classes of carbapenem antibiotics, which are widely regarded as the last resort of drugs for treating serious bacterial infections. Here we describe the efficient construction of a series of trans-1,3,4-trisubstituted pyrrolidines via boric acid-catalyzed 1,3-dipolar cycloaddition of N-benzylazomethine ylide with methyl ferulate for the biological evaluation of their cytotoxicity and synergistic activity in combination with meropenem towards NDM-1 positive carbapenem-resistant Enterobacteriaceae (CRE). The cell-based screens generated one promising hit, namely compound 10e, which exhibited low cytotoxicity (IC50 > 128 μM), moderate NDM-1 enzyme inhibition (IC50 = 51 μM), and potent synergistic activity against a panel of clinically isolated NDM-1 positive CRE with fractional inhibitory concentration indexes ranging from 0.01 to 0.25. Structure-activity relationship studies revealed that the zinc-chelating moiety of 2-(bis(pyridin-2-ylmethyl)-amino)acetyl group of compound 10e plays a pivotal role for potent activity. Regarding the inhibition mechanism, a series of biochemical assays revealed that compound 10e may inactivate NDM-1 activity by displacing both zinc ions from the active site of the enzyme. Altogether, our studies indicate that compound 10e represents an important pyrrolidine-type scaffold targeting NDM-1, providing a promising starting point to be further developed as carbapenem antibiotic adjuvants. This journal is
- Jin, Wen Bin,Xu, Chen,Qi, Xiao Lin,Zeng, Ping,Gao, Wei,Lai, Ki Hon,Chiou, Jiachi,Chan, Edward W. C.,Leung, Yun-Chung,Chan, Tak Hang,Wong, Kwok-Yin,Chen, Sheng,Chan, Kin-Fai
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supporting information
p. 3515 - 3534
(2021/03/03)
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- Ferulic acid derivative as well as preparation method and application thereof
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The invention relates to a ferulic acid derivative as well as a preparation method and application thereof. The ferulic acid derivative has any structural formula, the ferulic acid derivative takes gefitinib as a positive control, and the result shows that compared with gefitinib, the ferulic acid derivative has good activity. The ferulic acid derivative has high reference value for further modification of antitumor drugs and discovery of new antitumor drug candidates. The invention further provides a preparation method of the ferulic acid derivative and application of the ferulic acid derivative in preparation of anti-cancer drugs.
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Paragraph 0048; 0053-0055
(2020/11/01)
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- A New Series of Salicylic Acid Derivatives as Non-saccharide α-Glucosidase Inhibitors and Antioxidants
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In this study, a series of salicylic acid derivatives were designed and synthesized as novel non-saccharide α-glucosidase inhibitors. Biological evaluation indicated that when compared to acarbose, compounds T9, T10, and T32 exhibited a higher potency of α-glucosidase inhibitory activity with IC50 values of 0.15±0.01, 0.086±0.01 and 0.32±0.02mM, respectively. Evaluation of the inhibition kinetics indicated that T9, T10, T32, and acarbose interacted with α-glucosidase in a mixed non-competitive inhibitory manner. Moreover, T9, T10, and T32 statically quenched the fluorescence of α-glucosidase by formation of an inhibitor-α-glucosidase complex. The docking results showed that hydrogen bonds were generated between the test compounds and α-glucosidase. The antioxidant study revealed that compound T10 exhibited a higher antioxidant activity via scavenging 1,1-diphenyl-2-picrylhydrazyl free radical (DPPH), thereby inhibiting lipid peroxidation and the total reduction capacity. In brief, the salicylic acid derivatives identified in this study were promising candidates for development as novel non-saccharide α-glucosidase inhibitors.
- Chen, Jiangang,Lu, Wenfang,Chen, Hao,Bian, Xiaoli,Yang, Guangde
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p. 231 - 246
(2019/02/19)
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- Pharmacokinetic alteration of paclitaxel by ferulic acid derivative
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P-glycoprotein (P-gp) is known to be involved in multidrug resistance (MDR) and modulation of pharmacokinetic (PK) profiles of substrate drugs. Here, we studied the effects of synthesized ferulic acid (FA) derivatives on P-gp function in vitro and examined PK alteration of paclitaxel (PTX), a well-known P-gp substrate drug by the derivative. Compound 5c, the FA derivative chosen as a significant P-gp inhibitor among eight FA candidates by in vitro results, increased PTX AUCinf as much as twofold versus the control by reducing PTX elimination in rats. These results suggest that FA derivative can increase PTX bioavailability by inhibiting P-gp existing in eliminating organs.
- Lee, Jaeok,Chae, Song Wha,Ma, Lianji,Lim, So Yeon,Alnajjar, Sarah,Choo, Hea-Young Park,Lee, Hwa Jeong,Rhie, Sandy Jeong
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- Synthesis of lignin model compound containing a β-O-4 linkage
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Development of catalysts for efficient conversion of lignin polymer to value-added materials requires appropriately-functionalized lignin model compounds. The predominant structural feature of lignin biopolymer is an extensive network of β-O-4 linkages. A
- Mukhtar, Asma,Zaheer, Muhammad,Saeed, Muhammad,Voelter, Wolfgang
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p. 119 - 124
(2017/12/26)
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- Compositions for the prevention or treatment of neurodegenerative disease containing alkoxyphenylpropenone derivatives or pharmaceutically acceptable salts thereof as an active ingredient
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PURPOSE: An alkoxyphenylpropenone derivative is provided to efficiently use as a pharmaceutical composition for preventing or treating a degenerative brain disease; or pharmaceutical composition for protecting a brain cell by having an excellent protecting effect of the brain cell. CONSTITUTION: An alkoxyphenylpropenone derivative or a pharmaceutically acceptable salt thereof is indicated as below chemical formula 1; and R^1 is hydrogen or O-R^4; R^2 is hydrogen or O-R^5; R^3 is hydroxy, O-R^6 or -NR^7R^8; R^4, R^5 and R^6 are C_1-C_12 straight chain or a side chain alkyl, C_2-C_12 straight chain or a side chain alkenyl, and unsubstituted or C_5-C_6 aryl which is substituted as C_1-C_4 straight chain, or a side chain alkoxy, C_5-C_6 aryl C_1-C_4 alkyl; R^7 is hydrogen, C_1-C_4 straight chain, or a side chain alkyl; R^8 is hydrogen, the C_1-C_4 straight chain or the side chain alkyl, and the C5-C6 aryl which is unsubstituted or hydroxy-substituted, the C1-C4 alkyl or the C5-C6.
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Paragraph 0166; 0171-0173; 0230-0235
(2021/05/28)
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- Antioxidant and antimicrobial activity evaluation of polyhydroxycinnamic acid ester derivatives
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Polyhydroxycinnamic acid esters 5a-p have been synthesized starting from the appropriately substituted benzaldehydes. The antioxidant activity of these esters has been determined by superoxide free radical scavenging activity and DPPH free radical scavenging activity. The SAR studies reveal that pyrogallol, catechol moieties are essential for good antioxidant activity and an increase in the length of alkyl chain of the ester decreases the activity. Butyl hydroxycinnamates exhibit higher antibacterial activity among the synthesized hydroxycinnamates 5a-p, but, none of these show significant antifungal activity.
- Venkateswarlu, Somepalli,Ramachandra, Mareullapudi S.,Krishnaraju, Alluri V.,Trimurtulu, Golakoti,Subbaraju, Gottumukkala V.
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p. 252 - 257
(2007/10/03)
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- Synthesis and identification of 2,5-bis-(4-hydroxy-3-methoxyphenyl)- tetrahydrofuran-3,4-dicarboxylic acid, an unanticipated ferulate 8-8-coupling product acylating cereal plant cell walls
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A new product implicated in cereal grain polysaccharide cross-linking has been authenticated by independent synthesis. Saponification of cereal grain fiber releases the RRRS/SSSR-isomer of 2,5-bis-(4-hydroxy-3-methoxyphenyl)- tetrahydrofuran-3,4-dicarboxylic acid. The parent ester logically derives from 8-8-coupling of ferulate followed by water addition to one of the incipient quinone methide moieties and internal trapping of the other. The finding adds complexity to the analysis of plant cell wall cross-linking, but provides clues to important polysaccharide cross-linking pathways occurring in planta. The Royal Society of Chemistry 2006.
- Schatz, Paul F.,Ralph, John,Lu, Fachuang,Guzei, Ilia A.,Bunzel, Mirko
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p. 2801 - 2806
(2008/03/14)
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- Very short and efficient syntheses of the spermine alkaloid kukoamine A and analogs using isolable succinimidyl cinnamates
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Direct selective acylation of the primary amino functions of spermine and spermidine with a variety of isolable succinimidyl cinnamates, followed by catalytic hydrogenation, gave high yields of the spermine alkaloid kukoamine A and analogs suitable for structure-activity relationship studies. Suitable succinimidyl cinnamates were readily obtained through Wittig reaction of aromatic aldehydes with the ylides Ph3P=CRCO2Me, followed by saponification and activation with N-hydroxysuccinimide in the presence of N,N'-dicyclohexylcarbodiimide. Copyright
- Garnelis, Thomas,Athanassopoulos, Constantinos M.,Papaioannou, Dionissios,Eggleston, Ian M.,Fairlamb, Alan H.
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p. 264 - 265
(2007/10/03)
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- A highly stereospecific synthesis of (E)-α,β-unsaturated esters
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CrCl2-induced olefination of aldehydes using methyl dichloroacetate exclusively generates (E)-α,β-unsaturated esters in excellent yields. The intermediate α-chloro-β-hydroxy adducts could also be isolated in good yields under conditions of limited reagent.
- Barma, Deb K.,Kundu, Asish,Bandyopadhyay, Anish,Kundu, Abhijit,Sangras, Bhavani,Briot, Anne,Mioskowski, Charles,Falck
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p. 5917 - 5920
(2007/10/03)
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- A new approach for synthesis of erythro 8-0-4′ neolignans
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Erythro- 1-(4-hydroxy-3-methoxyphenyl)-2- (4-formyl-2-methoxy-phenoxy)-propane-1,3-diol, a 8-0-4′ norneolignan, has been stereoselectively synthesized in eight steps from ferulic acid. In this new route to prepare erythro 8-0-4′ neolignans the cis addition of mCPBA to a double bond with high regioselectivity was a key step, and its mechanism is discussed.
- Chen, XiaoChuan,Gu, WenXin,Jing, XiaoBi,Pan, XinFu
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p. 557 - 564
(2007/10/03)
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- First asymmetric synthesis of chiral 1,4-benzodioxane lignans
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An asymmetric and regioselective total synthesis approach to 1,4-benzodioxane lignans was reported in which (2R,3R)- and (2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodi oxan-6-carbaldehyde were synthesized firstly. A natural 1,4-benzodioxane neolignan was synthesized firstly by the synthesis approach. (C) 2000 Elsevier Science Ltd.
- Gu,Jing,Pan,Chan,Yang
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p. 6079 - 6082
(2007/10/03)
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- First enantioselective syntheses of (2R,3R)- and (2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxan-6-carbaldehyde
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An enantioselective and regioselective total synthesis approach to chiral 1,4-benzodioxane lignans (2R,3R)- and (2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-benzodioxan-6-carbaldehyde is reported. Copyright (C) 2000 Elsevier Science Ltd.
- Gu, Wenxin,Chen, Xiaochuan,Pan, Xinfu,Chan, Albert S. C.,Yang, Teng-Kuei
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p. 2801 - 2807
(2007/10/03)
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- Enantioselective synthesis of phenylpropanetriols
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The four stereomer 1-(4-hydroxy-3-methoxy)-phenyl-1,2,3-propanetriols were obtained in about 30% yields starting from ferulic acid by synthesis based on osmium catalyzed asymmetric dihydroxylation.
- DellaGreca, Marina,Fiorentino, Antonio,Monaco, Pietro,Previtera, Lucio
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p. 3693 - 3700
(2007/10/03)
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- Intramolecular regioselective insertion into unactivated prochiral carbon-hydrogen bonds with diazoacetates of primary alcohols catalyzed by chiral dirhodium(II) carboxamidates. Highly enantioselective total synthesis of natural lignan lactones
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Intramolecular insertion into unactivated prochiral C-H bonds of 3-aryl-1-propyl diazoacetates catalyzed by dirhodium(II) tetrakis[methyl 1-(3-phenyl propanoyl)imidazolidin-2-one-4(R or S)-carboxylate], Rh2(4R-MPPIM)4 or Rh2(4S-MPPIM)4, occurs in 91-96% ee and with virtually complete regiocontrol for the formation of β-benzyl-γ-butyrolactones. This methodology has been applied to the total synthesis of dibenzylbutyrolactone lignans (-)- and (+)-enterolactone, (-)- and (+)-hinokinin, and (+)-arctigenin from substituted cinnamic acids in 19-27% overall yields. Aryltetralin lignan (+)-isodeoxypodophyllotoxin was prepared from the reactant 3,4-(methylenedioxy)cinnamic acid in 36% yield overall, and the lactone precursor to (+)-isolauricerisinol was formed in 96.5% ee and 23% yield overall. Applications of the chiral Rh2(MPPIM)4 catalysts to fully aliphatic systems resulting in the formation of β-substituted-γ-butyrolactones with high regiocontrol and with 93-96% ee have demonstrated the generality of this methodology. A model that provides accurate predictions of β-substituted-γ-butyrolactone absolute configurations in these asymmetric metal carbene transformations is described.
- Bode,Doyle,Protopopova,Zhou
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p. 9146 - 9155
(2007/10/03)
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