- A Thorough Study on the Photoisomerization of Ferulic Acid Derivatives
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A thorough study on the (E) to (Z) photoisomerization of ferulic acid derivatives (esters, amides of all types, and ketones) was carried out. At the photostationary state, only aliphatic or benzylic tertiary amides reach a nearly complete conversion of (E) isomers into the (Z) ones, whereas for esters, primary and secondary amides or aromatic tertiary amides mixtures of (Z)/(E) ranging from 7 : 93 to 72 : 28 are observed. Ketones show rather limited photoisomerization. However, (Z) ketones may be obtained by the reaction of organometal compounds with an isomerized (Z) Weinreb amide.
- Moni, Lisa,Banfi, Luca,Basso, Andrea,Mori, Alessia,Risso, Federica,Riva, Renata,Lambruschini, Chiara
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p. 1737 - 1749
(2021/03/23)
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- Design, synthesis of Cinnamyl-paeonol derivatives with 1, 3-Dioxypropyl as link arm and screening of tyrosinase inhibition activity in vitro
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This study aimed to obtain tyrosinase inhibitors for treating hyperpigmentation. A series of cinnamyl ester analogues were designed and synthesized with cinnamic acid (CA) and peaonol compounds. The safety, melanin content and inhibitory effects of all ta
- Tang, Kai,Jiang, Yi,Zhang, Huawei,Huang, Wenli,Xie, Yundong,Deng, Chong,Xu, Hongbo,Song, Xiaomei,Xu, Hong
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supporting information
(2020/12/13)
-
- Oat polyphenol avenanthramide-2c confers protection from oxidative stress by regulating the Nrf2-ARE signaling pathway in PC12 cells
-
Accumulating evidence has demonstrated that cellular antioxidant systems play essential roles in retarding oxidative stress-related diseases, such as Parkinson's disease. Because nuclear factor erythroid 2-related factor 2 (Nrf2) is a chief regulator of c
- Hou, Yanan,Peng, Shoujiao,Song, Zilong,Bai, Feifei,Li, Xinming,Fang, Jianguo
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- Design, synthesis, and biological evaluation of novel tetramethyl-pyrazine-nitrone derivatives as antioxidants
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Background: Thrombolysis and endovascular thrombectomy are the two main therapeutic strategies for ischemic stroke in clinic. However, reperfusion injury causes oxidative stress leading to overproduction of reactive oxygen species, mitochondrial dysfuncti
- Chen, Haiyun,Yan, Chunyan,Cao, Jie,Liu, Zheng,Sun, Yewei,Wang, Yuqiang
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p. 499 - 508
(2021/10/02)
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- Quorum sensing and nf-κb inhibition of synthetic coumaperine derivatives from piper nigrum
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Bacterial communication, termed Quorum Sensing (QS), is a promising target for virulence attenuation and the treatment of bacterial infections. Infections cause inflammation, a process regulated by a number of cellular factors, including the transcription Nuclear Factor kappa B (NF-κB); this factor is found to be upregulated in many inflammatory diseases, including those induced by bacterial infection. In this study, we tested 32 synthetic derivatives of coumaperine (CP), a known natural compound found in pepper (Piper nigrum), for Quorum Sensing Inhibition (QSI) and NF-κB inhibitory activities. Of the compounds tested, seven were found to have high QSI activity, three inhibited bacterial growth and five inhibited NF-κB. In addition, some of the CP compounds were active in more than one test. For example, compounds CP-286, CP-215 and CP-158 were not cytotoxic, inhibited NF-κB activation and QS but did not show antibacterial activity. CP-154 inhibited QS, decreased NF-κB activation and inhibited bacterial growth. Our results indicate that these synthetic molecules may provide a basis for further development of novel therapeutic agents against bacterial infections.
- Baruch, Yifat,Gopas, Jacob,Kadosh, Yael,Kumar, Rajendran Saravana,Kushmaro, Ariel,Muthuraman, Subramani,Yaniv, Karin
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supporting information
(2021/05/28)
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- A Series of Ferulic Acid Amides Reveals Unexpected Peroxiredoxin 1 Inhibitory Activity with in vivo Antidiabetic and Hypolipidemic Effects
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Insulin resistance is a major pathophysiological feature in the development of type 2 diabetes (T2DM). Ferulic acid is known for attenuating the insulin resistance and reducing the blood glucose in T2DM rats. In this work, we designed and synthesized a library of new ferulic acid amides (FAA), which could be considered as ring opening derivatives of the antidiabetic PPARγ agonists Thiazolidinediones (TZDs). However, since these compounds displayed weak PPAR transactivation capacity, we employed a proteomics approach to unravel their molecular target(s) and identified the peroxiredoxin 1 (PRDX1) as a direct binding target of FAAs. Interestingly, PRDX1, a protein with antioxidant and chaperone activity, has been implied in the development of T2DM by inducing hepatic insulin resistance. SPR, mass spectrometry-based studies, docking experiments and in vitro inhibition assay confirmed that compounds VIe and VIf bound PRDX1 and induced a dose-dependent inhibition. Furthermore, VIe and VIf significantly improved hyperglycemia and hyperlipidemia in streptozotocin-nicotinamide (STZ-NA)-induced diabetic rats as confirmed by histopathological examinations. These results provide guidance for developing the current FAAs as new potential antidiabetic agents.
- Yasmin, Sabina,Cerchia, Carmen,Badavath, Vishnu Nayak,Laghezza, Antonio,Dal Piaz, Fabrizio,Mondal, Susanta K.,Atl?, ?zlem,Baysal, Merve,Vadivelan, Sankaran,Shankar,Siddique, Mohd Usman Mohd,Pattnaik, Ashok Kumar,Singh, Ravi Pratap,Loiodice, Fulvio,Jayaprakash, Venkatesan,Lavecchia, Antonio
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p. 484 - 498
(2020/11/02)
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- Ferulic acid amide derivative, and synthesis method and application thereof
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The invention provides a ferulic acid amide derivative represented by the following general formula IV, wherein R represents phenyl, p-methoxyphenyl, 4-aminodiphenyl ether, 4-trifluoromethoxyphenyl, 4-(trifluoromethyl)phenyl, 3-aminobenzene isopropyl ethe
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-
Paragraph 0022-0024
(2021/06/13)
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- Thiourea derivatives, and preparation method and application thereof
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The invention relates to thiourea derivatives represented by formula I, pharmaceutically acceptable salts thereof and a pharmaceutical composition thereof, and an application of the thiourea derivatives in the preparation of an influenza virus neuraminida
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Paragraph 0038-0041
(2020/06/05)
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- Synthesis and antiviral activity of novel myricetin derivatives containing ferulic acid amide scaffolds
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A variety of myricetin derivatives bearing ferulic acid amide scaffolds were designed and synthesized. The structures of all title compounds were determined by 1H NMR, 13C NMR, 19F NMR and HRMS. Preliminary bioassays suggested that some of the target compounds exhibited remarkable antiviral activities. In particular, compound 4l possessed significant protective activity against tobacco mosaic virus (TMV), with a half maximal effective concentration (EC50) value of 196.11 μg mL-1, which was better than that of commercial agent ningnanmycin (447.92 μg mL-1). Meanwhile, microscale thermophoresis (MST) indicated that compound 4l has strong binding capability to the tobacco mosaic virus coat protein (TMV-CP) with a dissociation constant (Kd) value of 0.34 μmol L-1, which was better than that of ningnanmycin (0.52 μmol L-1). These results suggested that novel myricetin derivatives bearing ferulic acid amide scaffolds may be considered as an activator for antiviral agents.
- Tang, Xu,Zhang, Cheng,Chen, Mei,Xue, Yining,Liu, Tingting,Xue, Wei
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p. 2374 - 2379
(2020/02/20)
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- Pyrazine derivative, and preparation method and medical use thereof
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The present invention relates to a pyrazine derivative, and preparation method and medical use thereof. The pyrazine derivative can remove free radicals and suppress calcium overload and has cytoprotective effects, and can be used for the prevention and t
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Paragraph 0098-0099
(2019/09/20)
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- Substituted cinnamic anhydrides act as selective inhibitors of acetylcholinesterase
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Cinnamic anhydrides have been shown to be more than reactive reagents, but they also act as inhibitors of the enzyme acetylcholinesterease (AChE). Thus, out of a set of 33 synthesised derivatives, several of them were mixed type inhibitors for AChE (from electric eel). Thus, (E)-3-(2,4-dimethoxyphenyl)acrylic anhydride (2c) showed Ki = 8.30 ± 0.94 μM and Ki′ = 9.54 ± 0.38 μM, and for (E)-3-(3-chlorophenyl)acrylic anhydride (2u) Ki = 8.23 ± 0.93 μM and Ki′ = 13.07 ± 0.46 μM were measured. While being not cytotoxic to many human cell lines, these compounds showed an unprecedented and noteworthy inhibitory effect for AChE but not for butyrylcholinesterase (BChE).
- Gie?el, Josephine M.,Serbian, Immo,Loesche, Anne,Csuk, René
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- Design, synthesis and biological evaluation of curcumin analogues as novel LSD1 inhibitors
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Histone lysine-specific demethylase 1 (LSD1) was the first discovered histone demethylase. Inactivating LSD1 or downregulating its expression inhibits cancer-cell development, and thus, it is an attractive molecular target for the development of novel cancer therapeutics. In this study, we worked on the structural optimization of natural products and identified 30 novel LSD1 inhibitors. Utilizing a structure-based drug design strategy, we designed and synthesized a series of curcumin analogues that were shown to be potent LSD1 inhibitors in the enzyme assay. Compound WB07 displayed the most potent LSD1 inhibitory activity, with an IC50 value of 0.8 μM. Moreover, WA20 showed an anticlonogenic effect on A549 cells with an IC50 value of 4.4 μM. Molecular docking simulations were also carried out, and the results indicated that the inhibitors bound to the protein active site located around the key residues of Asp555 and Asp556. These findings suggested that compounds WA20 and WB07 are the first curcumin analogue-based LSD1 inhibitors with remarkable A549 suppressive activity, providing a novel scaffold for the development of LSD1 inhibitors.
- Wang, Jiming,Zhang, Xiangyu,Yan, Jiangkun,Li, Wei,Jiang, Qinwen,Wang, Xinran,Zhao, Dongmei,Cheng, Maosheng
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supporting information
(2019/10/22)
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- Synthesis of N-hydroxycinnamoyl amide derivatives and evaluation of their anti-oxidative and anti-tyrosinase activities
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Twelve N-hydroxycinnamoyl amino acid amide ethyl esters (CAES) were synthesized by using L-amino acid ethyl ester hydrochloride and corresponding cinnamic acid (ferulic acid, acetylferulic acid and caffeic acid) as raw materials in the presence of a catal
- Wang, Dong,Zhu, Jun,Xu, Jin-Rong,Ji, Dan-Dan
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- Novel piperazine amides of cinnamic acid derivatives as tyrosinase inhibitors
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Background: A series of novel cinnamic acid piperazine amide derivatives has been designed and synthesized, and their biological activities were also evaluated as potential tyrosinase inhibitors. Methods: Compounds 9, 11 and 17 showed the most potent biological activity (IC50 = 66.5, 61.1 and 66 μM, respectively). In silico docking simulation was performed to position compound 11 into the Agaricus bisporus mushroom tyrosinase’s active site to determine the putative binding interactions. Results and Conclusion: The results indicated that compound 11 could serve as a promising lead compound for further development of potent tyrosinase inhibitors.
- Gür, Zehra Tu??e,?enol, Fatma Sezer,Shekfeh, Suhaib,Orhan, ?lkay Erdo?an,Bano?lu, Erden,?ali?kan, Burcu
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- Synthesis of a series of benzothiazole amide derivatives and their biological evaluation as potent hemostatic agents
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A series of benzothiazole amide derivatives were synthesized through a facile and efficient method via a nucleophilic acyl substitution reaction between 2-aminobenzothiazole and various cinnamic acid compounds. The obtained products exhibited good thermal stabilities. All compounds were evaluated for their in vitro hemostatic activities using the commercially available standard drug etamsylate as a positive control. The results showed that compound Q2 had a significant partial coagulation activity, reduced capillary permeability at 5, 10 and 50 μmol L-1, activated thrombin activity, and a more potent platelet aggregation activity than the positive control group (etamsylate, up to 1283.9 times in the nanomole range). A molecular modeling study revealed that compound Q2 was a competitive thrombin activator. Therefore, Q2 may be a potential lead for further biological screening and for the generation of drug molecules. Moreover, the structure-activity relationship of the prepared compounds is also discussed herein.
- Nong, Wenqian,Zhao, Anran,Wei, Jinrui,Cheng, Hui,Luo, Xuan,Lin, Cuiwu
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p. 6231 - 6241
(2018/02/19)
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- Preparation of ferulic acid dimer derivative and application of ferulic acid dimer derivative to treatment of Alzheimer's disease
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The invention discloses a ferulic acid dimer derivative and a preparation method thereof. Modification is carried out on the structural foundation of a natural lead compound ferulic acid; the preparedferulic acid derivative keeps the capability of elimina
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-
Paragraph 0020; 0021; 0022; 0023; 0024
(2018/07/30)
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- Regioselective synthesis of 7-O-esters of the flavonolignan silibinin and SARs lead to compounds with overadditive neuroprotective effects
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A series of neuroprotective hybrid compounds was synthesized by conjugation of the flavonolignan silibinin with natural phenolic acids, such as ferulic, cinnamic and syringic acid. Selective 7-O-esterfication without protection groups was achieved by appl
- Schramm, Simon,Huang, Guozheng,Gunesch, Sandra,Lang, Florian,Roa, Judit,H?gger, Petra,Sabaté, Raimon,Maher, Pamela,Decker, Michael
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supporting information
p. 93 - 107
(2018/02/15)
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- Dimeric cinnamoylamide analogues for regulation of tyrosinase activity in melanoma cells: A role of diamide-link chain length
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Dimeric cynnamoyl analogues (DCAs) with depigmenting activity have been developed. In this study, a role of diamide linkage chain length of DCAs as a tyrosinase inhibitor was investigated on tyrosinase inhibitory activity, antioxidative activity, hydropho
- Ha, Ji hoon,Park, Soo Nam
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p. 6015 - 6022
(2018/11/23)
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- Easy Access to Quinolin-2(1 H)-ones via a One-Pot Tandem Oxa-Michael-Aldol Sequence
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An efficient strategy for the synthesis of a variety of quinolin-2(1 H)-one derivatives has been developed. The reaction proceeded from cinnamide derivatives via a tandem reaction in the presence of NaOH to afford the corresponding 2- quinolin-2(1 H)-one derivatives in good to excellent yields.
- Jarrige, Lucie,Merad, Jeremy,Zaied, Siwar,Blanchard, Florent,Masson, Géraldine
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p. 1724 - 1728
(2017/10/06)
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- Synthesis and biological evaluation of a new series of cinnamic acid amide derivatives as potent haemostatic agents containing a 2-aminothiazole substructure
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Ten new cinnamic acid derivatives containing a 2-aminothiazole substructure were designed and synthesized. This series of compounds exhibited good thermostabilities as demonstrated by thermogravimetric analysis. In coagulation assays (prothrombin time, activated partial thromboplastin time and thrombin time) in vitro, most compounds demonstrated excellent activities to promote blood coagulation. Among the studied series, compounds N1, N4, N5 and W5 exhibited a significant coagulation activity. Further studies indicated that compound N5 (IC50 = 1.87 μmol/L) displayed the most suitable efficacy of promoting platelet aggregation than the clinically used haemostatic drug etamsylate (IC50 = 46.22 μmol/L). Furthermore, the relationship between the functional groups of the compounds and the corresponding blood coagulant activity was explored in this study.
- Nong, Wenqian,Zhao, Anran,Wei, Jinrui,Lin, Xiao,Wang, Lisheng,Lin, Cuiwu
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supporting information
p. 4506 - 4511
(2017/09/12)
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- Enantioselective Organocatalytic Intramolecular Aza-Diels–Alder Reaction
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A highly efficient catalytic enantioselective intramolecular Povarov reaction was developed with primary anilines as 2-azadiene precursors. A wide variety of angularly fused azacycles were obtained without column chromatography in high to excellent yields and with excellent diastereo- and enantioselectivity (d.r.>99:1 and up to e.r. 99:1). Furthermore, the catalyst loading could be lowered to 1 mol %, and the obtained azacycles could be used as key intermediates for further transformations to generate additional molecular diversity.
- Jarrige, Lucie,Blanchard, Florent,Masson, Géraldine
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p. 10573 - 10576
(2017/08/22)
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- Novel ferulic amide derivatives with tertiary amine side chain as acetylcholinesterase and butyrylcholinesterase inhibitors: The influence of carbon spacer length, alkylamine and aromatic group
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Based on our recent investigations on chalcone derivatives as AChE inhibitors, a series of ferulic acid (FA) tertiary amine derivatives similar to chalcone compounds were designed and synthesized. The results of bioactivity evaluation revealed that most of new synthesized compounds had comparable or more potent AChE inhibitory activity than the control drug Rivastigmine. The alteration of carbon chain linking tertiary amine groups and ferulic acid scaffold markedly influenced the inhibition activity against AChE. Among them the inhibitory activity of compound 6d (IC50: 0.71 ± 0.09 μmol/L) and 6e (IC50: 1.11 ± 0.17 μmol/L) was equal to 15-fold and 9-fold than that of Rivastigmine against AChE (IC50: 10.54 ± 0.86 μmol/L), respectively. Moreover, compound 6d shows the highest selectivity for AChE over butyrylcholinesterase(BuChE) (ratio: 18.3). The kinetic study suggested that compound 6d revealed a mixed-type inhibition against AChE. The result of molecular docking showed that compound 6d combines to AChE with three amino acid sites(Trp84, Tyr334 and Trp279), while combines to BuChE with two amino acid sites (Tyr67 and Gly66) in enzyme domains, respectively. Compound 6d might act as a potential agent for the treatment of Alzheimer's diseases (AD).
- Liu, Haoran,Liu, Linbo,Gao, Xiaohui,Liu, Yingzi,Xu, Wanjun,He, Wei,Jiang, Hong,Tang, Jingjing,Fan, Haoqun,Xia, Xinhua
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p. 810 - 822
(2016/12/18)
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- Tetrahydroisoquinoline compound, preparation method and anti-tumor use
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The invention relates to the field of medicinal chemistry, and in particular relates to a tetrahydroisoquinoline compound with a general formula I or II, a preparation method as well as a pharmaceutical composition and an application thereof. Pharmacodyna
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Paragraph 0036; 0037; 0046; 0047
(2017/10/22)
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- COMPOUND APPLICABLE TO PHOTOALIGNMENT METHOD AND ITS PHOTOSENSITIVE POLYMER
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PURPOSE: A photosensitive polymer prepared by polymerizing a compound which is proper for photoalignment is provided to prevent static electricity and to manufacture liquid crystal alignment film with high optical uniformity. CONSTITUTION: A compound which is proper to photoalignment is denoted by chemical formula 1. A photosensitive polymer is used by polymerizing the compound of chemical formula 1. A liquid crystal alignment film is manufactured using the photoalignment agent. A liquid crystal display device is manufactured using the photoalignment agent.
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Paragraph 0243-0245; 0248-0249
(2017/09/29)
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- Study on the anticoagulant or procoagulant activities of type II phenolic acid derivatives
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In this study, three type II phenolic acids (caffeic acid, p-hydroxycinnamic acid, and ferulic acid) were used to synthesize a total of 18 phenolic acid derivatives. With molecular docking for molecule design and target protein (factors) screening, in combination with the confirmation of target proteins (factors) by surface plasmon resonance, and the evaluation of haemostatic and anticoagulant activities with five blood assays (plasma recalcification time, prothrombin time, activated partial thromboplastin time, fibrinogen, and thrombin time), the data indicated that caffeic acid derivatives showed certain anticoagulant or procoagulant activities and that two other series contained compounds with the best anticoagulant activities. Using Materials Studio analysis, particular functional groups that affect anticoagulant or procoagulant activities were revealed, and these conclusions can guide the discovery of compounds with better activities.
- Luo, Xuan,Du, Chuanrong,Cheng, Hui,Chen, Jian-hua,Lin, Cuiwu
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- Polymerizable compound, the photopolymerizable composition and the optical anisotropic
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PURPOSE: A polymerizable naphthoic acid phenyl compound is provided to have high reflection anisotropy and high storage stability and high orientation. CONSTITUTION: A polymerizable naphthoic acid phenyl compound is represented by chemical formula 1. In chemical formula 1, one of M^1-M4 is a fluorine atom, a chlorine atom, a cyno group, a nitro group, a C1-7 alkyl group, a C1-7 alkoxy group, or a C1-7 alkanoyl group. L^1-L^6 is hydrogen, fluorine or chloride. A polymerizable liquid composition comprises the polymerizable compound. The polymer is obtained by polymerizing the polymerizable liquid compositions. An optical anisotropic object uses the polymer.
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Paragraph 0175; 0176
(2017/07/26)
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- Microwave (MW) promoted high yield expedient synthesis of steryl ferulates - A class of novel biologically active compounds: A comparative study of their antioxidant activity with that of naturally occurring γ-oryzanol
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Synthetic steryl ferulates [3-O-(trans-4-feruloyl)-sterols] are currently gaining considerable importance in recent years to be used as nutraceuticals and food additives as well as in pharmaceutical applications substituting γ-oryzanol - a class of natura
- Begum, Ashma,Borah, Preetismita,Chowdhury, Pritish
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- Discovery of novel hybrids of diaryl-1,2,4-triazoles and caffeic acid as dual inhibitors of cyclooxygenase-2 and 5-lipoxygenase for cancer therapy
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Inflammation plays a key role in cancer initiation and propagation. Cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX), two important enzymes in inflammatory responses are up-regulated in various tumor types. Dual inhibition of COX-2 and 5-LOX constitutes a rational concept for the design of more efficacious anti-tumor agents with an improved safety profile. We have previously reported a series of diaryl-1,2,4-triazole derivatives as selective COX-2 inhibitors. Herein, we hybridized the diaryl-1,2,4-triazoles with caffeic acid (CA) which was reported to display 5-LOX inhibitory and anti-tumor activities, affording a novel class of COX-2/5-LOX dual inhibitors as anti-tumor drug candidates. Most of these compounds exhibited potent COX-2/5-LOX inhibitory and antiproliferative activities in vitro. And the most potent compound 22b could significantly inhibit tumor growth in vivo. Furthermore, mechanistic investigation showed that the representative compound 15c blocked cell cycle in G2 phase and induced apoptosis in human non-small cell lung cancer A549 cells in a dose-dependent manner. Our preliminary investigation results would provide new clues for the cancer theatment with COX-2/5-LOX dual inhibitors.
- Cai, Hao,Huang, Xiaojing,Xu, Shengtao,Shen, Hao,Zhang, Pengfei,Huang, Yue,Jiang, Jieyun,Sun, Yijun,Jiang, Bo,Wu, Xiaoming,Yao, Hequan,Xu, Jingyi
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supporting information
p. 89 - 103
(2015/12/04)
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- Design, synthesis, and biological evaluation of novel Tempol derivatives as effective antitumor agents
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Two series of novel Tempol derivatives T1–T6 based on the piperidine nitroxide Tempol and phenolic acids were designed and synthesized, and their biological evaluation is also described. The chemical structure was verified by HRMS, IR, and EPR analysis. The antitumor activity was tested against two tumor cell lines (A549 and Hela cells). Simultaneously, HK-2 cells were selected to investigate cytotoxicity and selectivity of synthetic compounds to the normal cells. The antioxidant property was also studied by DPPH radical scavenging assay and hydrogen peroxide-induced cell injury assay. The results demonstrated that most of the Tempol derivatives exhibited more active antioxidant activity than Tempol, and all synthesized Tempol derivatives exhibited more potent antitumor activity than Tempol. Among them, compound T6 displayed the highest antitumor activity (IC50?=?29.4?μg/mL for A549 cells; IC50?=?16.2?μg/mL for Hela cells). The results indicated that T6 exhibited efficient antitumor performance, having the potential of being excellent antitumor agents for cancer treatment.
- Sun, Xiao-Liang,Wang, Shi-Yu,Qi, Zhi-Min,Wan, Ning,Zhang, Bang-Le,He, Wei
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p. 7659 - 7673
(2016/09/20)
-
- ARYLOYL(OXY OR AMINO)PENTAFLUOROSULFANYLBENZENE COMPOUND, PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PRODRUGS THEREOF
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An aryloyl(oxy or amino)pentafluorosulfanylbenzene compound having pharmacological action. The aryloyl(oxy or amino)pentafluorosulfanylbenzene compound is represented by general formula (A-I), a pharmaceutically acceptable salt thereof, and a prodrug ther
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-
Paragraph 0386-0389
(2016/09/26)
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- A selective and mild glycosylation method of natural phenolic alcohols
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Several bioactive natural p-hydroxyphenylalkyl β-D-glucopyranosides, such as vanillyl β-D-glucopyranoside, salidroside and isoconiferin, and their glycosyl analogues were prepared by a simple reaction sequence. The highly efficient synthetic approach was achieved by utilizing acetylated glycosyl bromides as well as aromatic moieties and mild glycosylation promoters. The aglycones, p-O-acetylated arylalkyl alcohols, were prepared by the reduction of the corresponding acetylated aldehydes or acids. Various stereoselective 1,2-trans-O-glycosylation methods were studied, including the DDQ-iodine or ZnO-ZnCl2 catalyst combination. Among them, ZnO-iodine has been identified as a new glycosylation promoter and successfully applied to the stereoselective glycoside synthesis. The final products were obtained by conventional Zemplén deacetylation.
- Mastihubová, Mária,Poláková, Monika
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supporting information
p. 524 - 530
(2016/04/08)
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- α-Glucosidase inhibitory activities of phenolic acid amides with l-amino acid moiety
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α-Glucosidase inhibitors can effectively control postprandial hyperglycemia. In this study, a series of phenolic acids with the l-amino acid moiety were synthesized and their inhibitory activities against α-glucosidase from Saccharomyces cerevisiae (EC 3.
- Liu, Bin,Ma, Ji-Mei,Chen, Hang-Wei,Li, Zi-Long,Sun, Lin-Hao,Zeng, Zhen,Jiang, Hong
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p. 50837 - 50845
(2016/06/09)
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- Compound formed by combining ferulic acid with asarone analogue as well as preparation method and application of compound
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The invention belongs to the technical field of medicines and discloses a compound formed by combining ferulic acid with an asarone analogue as well as a preparation method and an application of the compound. The structure of the compound is shown in the
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-
Paragraph 0047; 0048
(2017/04/08)
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- Preparation method of ferulic acid derivative feed additive and application thereof
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The invention discloses a preparation method of a ferulic acid derivative feed additive and application thereof, and relates to the technical field of feed additives. The preparation method comprises the steps that ferulic acid is adopted as raw materials
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Paragraph 0032
(2017/07/04)
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- Monoamine Oxidase Inhibitory Activity of Ferulic Acid Amides: Curcumin-Based Design and Synthesis
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Ferulic acid has structural similarity with curcumin which is being reported for its monoamine oxidase (MAO) inhibitory activity. Based on this similarity, we designed a series of ferulic acid amides 6a-m and tested for their inhibitory activity on human MAO (hMAO) isoforms. All the compounds were found to inhibit the hMAO isoforms either selectively or non-selectively. Nine compounds (6a, 6b, 6g-m) were found to inhibit hMAO-B selectively, whereas the other four (6c-f) were found to be non-selective. There is a gradual shift from hMAO-B selectivity (6a,b) to non-selectivity (6c-f) as there is an increase in chain length at the amino terminus. In case of compounds having an aromatic nucleus at the amino terminus, increasing the carbon number between N and the aromatic ring increases the potency as well as selectivity toward hMAO-B. Compounds 6f, 6j, and 6k were subjected to membrane permeability and metabolic stability studies by in vitro assay methods. They were found to have a better pharmacokinetic profile than curcumin, ferulic acid, and selegiline. In order to understand the structural features responsible for the potency and selectivity of 6k, we carried out a molecular docking simulation study.
- Badavath, Vishnu N.,Baysal, Ipek,Uar, Gülberk,Mondal, Susanta K.,Sinha, Barij N.,Jayaprakash, Venkatesan
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-
- Design, Synthesis and Pharmacological Evaluation of Novel Piperlongumine derivatives as Potential Antiplatelet Aggregation Candidate
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A series of novel piperlongumine derivatives (4a-i, 6a-i) were designed and synthesized. The inhibitory activities of platelet aggregation induced by ADP and AA in vitro have been evaluated by bron turbidimetry and liver microsomal incubated assay. The assay results show that compounds 4e and 6e exhibited remarkable potency to that of the positive control piplartine and aspirin.
- Wang, Yujun,Wang, Jie,Li, Jiaming,Zhang, Yanchun,Huang, Weijun,Zuo, Jian,Liu, Huicai,Xie, Di,Zhu, Panhu
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p. 833 - 840
(2016/05/19)
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- Design, synthesis and "in vitro" anti-leukemic evaluation of ferulic acid analogues as BCR-Abl inhibitors
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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
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p. 70480 - 70484
(2016/08/06)
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- Oxyphytosterols as active ingredients in wheat bran suppress human colon cancer cell growth: Identification, chemical synthesis, and biological evaluation
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Consumption of whole grains has been reported to be associated with a lower risk of colorectal cancer. Recent studies illustrated that phytochemicals in wheat bran (WB) may protect against colorectal cancer. There is a growing interest in the phytosterol contents of foods as either intrinsic or added components due to their beneficial health effects. However, little is known whether phytosterols in WB contribute the observed chemopreventative activity of the grain. In the present study, we directly purified and identified four oxyphytosterols 1-4 from sterol-enriched fraction of WB, and also successfully synthesized five sterol oxides 5-8 and 13. Using these nine compounds as references, we outlined a comprehensive profile of steroids in WB using tandem liquid chromatography mass spectrometry with electrospray ionization (LC-ESI/MSn, n = 2-3) techniques for the first time. Among them, three sterol oxides 13, 14, and 18 are novel compounds, and 14 compounds 3, 4, 6-11, 13, 14, 16, and 18-20 were reported in WB for the first time. Our results on the inhibitory effects of available sterol oxides 1-8 and 13 against the growth of human colon cancer cells HCT-116 and HT-29 showed that compounds 2-8 exerted significant antiproliferative effects, with oxysterol 8 being the most active one in both cells. We further demonstrated that four most active sterol oxides 5-8 could induce cell death through the apoptosis pathway. Our results showed that phytosterols, particularly oxyphytosterols, in WB possess significant antiproliferative properties, and thereby may greatly contribute the observed chemoprevention of the whole grain wheat.
- Zhu, Yingdong,Soroka, Dominique,Sang, Shengmin
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p. 2267 - 2276
(2015/03/14)
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- Synergistic Photobactericidal Activity Based on Ultraviolet-A Irradiation and Ferulic Acid Derivatives
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Ultraviolet-A (UV-A)-mediated bactericidal activity was enhanced by combined treatment with trans-ferulic acid (trans-FA, compound 1) or its derivatives. Derivative compounds 4 and 10 contain a phenyl group or an l-tyrosine HCl tert-butyl ester, respectiv
- Shirai, Akihiro,Kajiura, Masato,Omasa, Takeshi
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p. 1422 - 1428
(2015/11/10)
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- Synthesis of Actinomycetes natural products JBIR-94, JBIR-125, and related analogues
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The synthesis of the natural products JBIR-94, DCP, DFP, and CFP is reported. A strategy for the coupling of ferulic or coumaric acid to putrescine is described. We determined that EDCI was the most effective coupling agent for this synthesis. In addition amide coupling with saturated cinnamic acids derivatives provided the best yield. The synthesis of JBIR-125 is accomplished through a novel synthesis of differentially protected spermidine. Preliminary bioassay data demonstrated that all five compounds were active against Pseudomonas aeruginosa.
- Taj, Rafiq,Sorensen, John L.
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supporting information
p. 7108 - 7111
(2015/12/01)
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- Novel 9H-carbazole ester derivative, the preparation thereof and composition containing the same for preventing or treating vascular disease
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The present invention relates to a novel 9H-carbazole ester derivative, a method for preparing the same, and a composition containing the same for preventing or treating vascular disease. The novel 9H-carbazole ester derivative has very excellent platelet
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Paragraph 0273; 0361-0362
(2021/05/16)
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- METHOD OF PRODUCING BENZOIC ACID
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PROBLEM TO BE SOLVED: To provide a novel synthesis method in the production of a benzoic acid, which is an important compound for the synthesis of an organic compound, and an industrially suitable production method using main materials derived from nonfossil resources. SOLUTION: This invention provides a method of producing a benzoic acid with a substituted hydroxyl group, methoxy group, or acetoxy group, comprising the step of the ozonation of a compound represented by formula (I), where R1 is H, a methyl group or an acetyl group; R2 is H or an acetoxy group; R3 is an alkyl group, a carboxy group, a formyl group, an alkoxycarbonyl group, an amide group, an acid chloride group, a halogenation alkyl group, or a hydroxyalkyl group. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0141-0143
(2016/10/08)
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- Synthesis and biological activity of isoflavone derivatives from chickpea as potent anti-diabetic agents
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A set of novel isoflavone derivatives from chickpea were synthesized. The structures of derivatives were identified by proton nuclear magnetic resonance (1H-NMR), carbon-13 (13C)-NMR and mass spectrometry (MS) spectral analyses. Thei
- Li, Pengshou,Shi, Xiaojuan,Wei, Ying,Qin, Lingling,Sun, Wen,Xu, Guangyuan,Xu, Tunhai,Liu, Tonghua
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p. 17016 - 17040
(2015/12/01)
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- (S)-allyl cysteine derivatives as a new-type cholinesterase inhibitor
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Even though cholinesterase (ChE) inhibitors and N-methyl-D-aspartate (NMDA) receptor antagonist are clinically approved to treat Alzheimer's disease (AD) patients, new therapeutic compounds still need to be developed. Therefore, many new targets and novel
- Kim, Beom-Cheol,Lee, Seung-Hwan,Jang, Mi,Won, Moo-Ho,Park, And Jeong Ho
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- Synthesis and antitumor activity of feruloyl and caffeoyl derivatives This paper is dedicated to Prof. Wei-xiao Hu for his lifelong commitment to mentoring graduate students
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We developed two efficient protocols for the synthesis of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde. Pharmacological activities were assessed against a panel of human cancer cell lines in vitro. Most synthesized compounds demonstrated attractive cytotoxicity. Several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. In particular, 5-nitro caffeic adamantyl ester showed broad spectrum of tumor inhibition in 10 cell lines, and reduced tumor weight by 36.7% in vivo when administered at a dose of 40 mg kg-1.
- Chen, Hui-Zhen,Chen, You-Bao,Lv, Ya-Ping,Zeng, Fang,Zhang, Juan,Zhou, Yong-Lie,Li, Han-Bing,Chen, Li-Fei,Zhou, Bin-Jie,Gao, Jian-Rong,Xia, Chun-Nian
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supporting information
p. 4367 - 4371
(2015/02/06)
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- Synthesis of steryl ferulates with various sterol structures and comparison of their antioxidant activity
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Steryl ferulates synthesised from commercial sterols as well as commercial oryzanol were used to better understand how structural features affect antioxidant activity in vitro by the ABTS+radical decolorization assay, by oxidative stability ind
- Winkler-Moser, Jill K.,Hwang, Hong-Sik,Bakota, Erica L.,Palmquist, Debra A.
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- A biocompatible alkene hydrogenation merges organic synthesis with microbial metabolism
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Organic chemists and metabolic engineers use orthogonal technologies to construct essential small molecules such as pharmaceuticals and commodity chemicals. While chemists have leveraged the unique capabilities of biological catalysts for small-molecule production, metabolic engineers have not likewise integrated reactions from organic synthesis with the metabolism of living organisms. Reported herein is a method for alkene hydrogenation which utilizes a palladium catalyst and hydrogen gas generated directly by a living microorganism. This biocompatible transformation, which requires both catalyst and microbe, and can be used on a preparative scale, represents a new strategy for chemical synthesis that combines organic chemistry and metabolic engineering. Reduction to practice: A hydrogenation reaction has been developed that employs hydrogen generated in situ by a microorganism and a biocompatible palladium catalyst to reduce alkenes on a synthetically useful scale. This type of transformation, which directly combines tools from organic chemistry with the metabolism of a living organism for small-molecule production, represents a new strategy for chemical synthesis.
- Sirasani, Gopal,Tong, Liuchuan,Balskus, Emily P.
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supporting information
p. 7785 - 7788
(2014/08/05)
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- Synthesis and in vitro biological evaluation of hybrids from tetrahydro-β-carboline and hydroxylcinnamic acid as antitumor carcinoma agents
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Novel hybrids 8a-j and 9a-j were designed and synthesized by coupling the carboxyl group of hydroxylcinnamic acids with tetrahydro-β-carboline alkaloids which were linked with different substituted nitrogen-containing heterocycles at the positions-N9, and
- Lin, Ying,Xia, Xuanping,Yao, Rongxin,Ni, Li,Hu, Jie,Guo, Wenjian,Zhu, Baoling
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p. 343 - 349
(2014/04/17)
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- Synthesis and biological evaluation of novel curcuminoid derivatives
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Curcuminoids have been reported to possess multiple bioactivities, such as antioxidant, anticancer and anti-inflammatory properties. Three novel series of curcuminoid derivatives (11a-h, 15a-h and 19a-d) with enhanced bioactivity have been synthesized. Among the synthesized compounds, 11b exhibited the most significant activity with an MIC of 0.5 μ M /mL against selected medically important Gram-positive cocci (S aureus and S viridans) and Gram-negative bacilli (E. coli and E. cloacae). The derivatives exhibited remarkable results in an antioxidant test with an IC50 2.4- to 9.3-folder smaller than curcuminoids. With respect to antiproliferative activity against Hep-G2, LX-2, SMMC7221 and MDA-MB-231, the derivatives exhibited an effect stronger than curcuminoids with an IC50 ranging from 0.18 to 4.25 μ M.
- Cao, Ya-Kun,Li, Hui-Jing,Song, Zhi-Fang,Li, Yang,Huai, Qi-Yong
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p. 16349 - 16372
(2015/01/08)
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- Synthesis, cytotoxicity and molecular modelling studies of new phenylcinnamide derivatives as potent inhibitors of cholinesterases
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The present study reports the synthesis of cinnamide derivatives and their biological activity as inhibitors of both cholinesterases and anticancer agents. Controlled inhibition of brain acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) may slow neurodegeneration in Alzheimer's diseases (AD). The anticholinesterase activity of phenylcinnamide derivatives was determined against Electric Eel acetylcholinesterase (EeAChE) and horse serum butyrylcholinesterase (hBChE) and some of the compounds appeared as moderately potent inhibitors of EeAChE and hBChE. The compound 3-(2-(Benzyloxy)phenyl)-N- (3,4,5-trimethoxyphenyl)acrylamide (3i) showed maximum activity against EeAChE with an IC50 0.29 ± 0.21 μM whereas 3-(2-chloro-6- nitrophenyl)-N-(3,4,5-trimethoxyphenyl)acrylamide (3k) was proved to be the most potent inhibitor of hBChE having IC50 1.18 ± 1.31 μM. To better understand the enzyme-inhibitor interaction of the most active compounds toward cholinesterases, molecular modelling studies were carried out on high-resolution crystallographic structures. The anticancer effects of synthesized compounds were also evaluated against cancer cell line (lung carcinoma). The compounds may be useful leads for the design of a new class of anticancer drugs for the treatment of cancer and cholinesterase inhibitors for Alzheimer's disease (AD).
- Saeed, Aamer,Mahesar, Parvez Ali,Zaib, Sumera,Khan, Muhammad Siraj,Matin, Abdul,Shahid, Mohammad,Iqbal, Jamshed
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