Synthetic phenylethanoid glycoside derivatives as potent neuroprotective agents.

Abstract:

:Several phenylethanoid glycoside derivatives were designed and synthesized. Most of the synthetic compounds showed significant neuroprotective effects, including antioxidative and anti-apoptotic properties. Specifically, target compounds displayed potent effects against various toxicities such as H2O2 and 6-hydroxydopamine (6-OHDA) in PC12 cells. Among the synthetic derivatives, three compounds (5, 6, 8) exhibited much superior activities to the marketed drug Edaravone. The compounds were able to prevent the 6-OHDA-induced damage in PC12 cells in a dose-dependent manner. The anti-apoptotic effects could be observed via cell morphological changes. Moreover, the compounds significantly reduced the intracellular ROS increase resulting from 6-OHDA treatment. The preliminary structure-activity relationships were also explored. Compounds 5, 6, 8 may hold the potential as promising neuroprotective agents and new lead compounds for the treatment of neurodegenerative diseases or cerebral ischemia.

journal_name

Eur J Med Chem

authors

Liu YG,Li X,Xiong DC,Yu B,Pu X,Ye XS

doi

10.1016/j.ejmech.2015.03.038

subject

Has Abstract

pub_date

2015-05-05 00:00:00

pages

313-23

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(15)00205-6

journal_volume

95

pub_type

杂志文章
  • Synthesis of novel thiazole-based 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as potential antitumor and antifungal agents.

    abstract::A new series of novel thiazole-based 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines 6a-g and 7a-g were obtained with high regioselectivity from the reaction of triamino- or tetraaminopyrimidines 4 and 5 with α,β-unsaturated carbonyl compounds 3a-g based on 2,4-dichlorothiazol-5-carbaldehyde 1. Twelve of the synthesized...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.01.053

    authors: Ramírez J,Svetaz L,Quiroga J,Abonia R,Raimondi M,Zacchino S,Insuasty B

    更新日期:2015-03-06 00:00:00

  • Synthesis of isatin based N1-alkylated 3-β-C-glycoconjugated-oxopropylidene oxindoles as potent antiplasmodial agents.

    abstract::In an attempt to develop new antimalarial drugs, we have synthesized a new class of N-alkylated 3-glycoconjugated-oxopropylidene oxindoles starting from substituted isatins and glucopyranosyl propanone via a well-known cross-aldol reaction followed by dehydration. The newly synthesized compounds were screened for thei...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.11.008

    authors: Thakur RK,Joshi P,Upadhyaya K,Singh K,Sharma G,Shukla SK,Tripathi R,Tripathi RP

    更新日期:2019-01-15 00:00:00

  • Naphthyl quinoxaline thymidine conjugate is a potent anticancer agent post UVA activation and elicits marked inhibition of tumor growth through vaccination.

    abstract::Anticancer anthracyclines are cytotoxic drugs that can induce antitumor immune response as a secondary effect through immunogenic cell death (ICD) mechanism. However, the immunogenic potency is quite limited, possibly due to that these chemotherapeutic agents are not specifically developed as ICD inducers. Thus, new d...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.03.051

    authors: Yuan Y,Wang Z,Yang R,Qian T,Zhou Q

    更新日期:2019-06-01 00:00:00

  • Synthesis and pharmacological properties of a new hydrophilic and orally bioavailable 5-HT4 antagonist.

    abstract::5-HT4 receptor antagonists have been suggested to have clinical potential in treatment of atrial fibrillation, diarrhea-prone irritable bowel syndrome and urinary incontinence. Recently, the use of 5-HT4 antagonists has been suggested to have a therapeutic benefit in heart failure. Affinity for the hERG potassium ion ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.03.060

    authors: Brudeli B,Moltzau LR,Nguyen CH,Andressen KW,Nilsen NO,Levy FO,Klaveness J

    更新日期:2013-06-01 00:00:00

  • Stereospecific ligands and their complexes. Part VII. Synthesis, characterization and in vitro antitumoral activity of platinum(II) complexes with O,O'-dialkyl esters of (S,S)-ethylenediamine-N,N'-di-2-(4-methyl)pentanoic acid.

    abstract::Platinum(II) complexes (1-4) with bidentate N,N'-ligands, O,O'-dialkyl esters (alkyl = ethyl, n-propyl, n-butyl and n-pentyl), of (S,S)-ethylenediamine-N,N'-di-2-(4-methyl)pentanoic acid were synthesized and characterized by IR, (1)H NMR and (13)C NMR spectroscopy and elemental analysis. DFT calculations were performe...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.07.034

    authors: Vujić JM,Kaluđerović GN,Milovanović M,Zmejkovski BB,Volarević V,Živić D,Đurđeviće P,Arsenijević N,Trifunović SR

    更新日期:2011-09-01 00:00:00

  • An exhaustive perspective on structural insights of SGLT2 inhibitors: A novel class of antidiabetic agent.

    abstract::Diabetes mellitus is the global health issue and become an alarming threat in the modern era where human lifestyle gets compromised with modernization. According to the latest statistical report 2020, USA has 9.47% (31 million among 32.72 cr), China has 8.3% (116.4 million among 139.27 cr) and India has 5.6% (77 milli...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2020.112523

    authors: Bhattacharya S,Rathore A,Parwani D,Mallick C,Asati V,Agarwal S,Rajoriya V,Das R,Kashaw SK

    更新日期:2020-10-15 00:00:00

  • New imidazolidineiminothione derivatives: Synthesis, spectral characterization and evaluation of antitumor, antiviral, antibacterial and antifungal activities.

    abstract::A series of new imidazolidineiminothione derivatives with various halogenated and alkylated aromatic substituents at N-(1) and at N-(3) was synthesized through the reaction of N-arylcyanothioformamides with arylisocyanate derivatives. Structure of imidazolidineiminothione derivatives were established based on spectros...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.06.051

    authors: Moussa Z,El-Sharief MAMS,Abbas SY

    更新日期:2016-10-21 00:00:00

  • Synthesis and antimicrobial activities of novel 1,5-diaryl pyrazoles.

    abstract::Novel 1,5-diaryl pyrazole derivatives viz. 5-(4-chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazole-3-carboxamides (2a-e, 3, 3a-f), 2-(5-(4-chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazole-3-yl)thiazoles (6a-c,7, 8, 9a-c, 10, 11) were synthesized by varying the active part (amide group) of pyrazole, characterized using IR, (1)H ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2009.12.042

    authors: Ragavan RV,Vijayakumar V,Kumari NS

    更新日期:2010-03-01 00:00:00

  • Synthesis and antiamoebic activity of new 1-N-substituted thiocarbamoyl-3,5-diphenyl-2-pyrazoline derivatives and their Pd(II) complexes.

    abstract::Some 1-N-substituted thiocarbamoyl-3,5-diphenyl-2-pyrazoline derivatives (L), 1-8 were synthesized by a base-catalyzed Claisen-Schmidt condensation of benzaldehyde with acetophenone followed by cyclization with various N-4 substituted thiosemicarbazides. The palladium(II) complexes [PdLCl2], 1a-8a of these ligands wer...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2005.06.013

    authors: Budakoti A,Abid M,Azam A

    更新日期:2006-01-01 00:00:00

  • Design, synthesis and docking studies of quinoline-oxazolidinone hybrid molecules and their antitubercular properties.

    abstract::New series of quinoline-oxazolidinone hybrid molecules were synthesized based on the preliminary docking studies. All the newly synthesized compounds were characterized by spectral analyses. The newly synthesized compounds were screened for their antimycobacterial properties based on the promising preliminary antibact...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.07.049

    authors: Thomas KD,Adhikari AV,Chowdhury IH,Sandeep T,Mahmood R,Bhattacharya B,Sumesh E

    更新日期:2011-10-01 00:00:00

  • pH and DNA luminescence switching, DNA photocleavage and cytotoxic properties of two thiophene-containing ruthenium(II) complexes.

    abstract::Two new Ru(II) complexes, [Ru(Htip)3]Cl2 (1) and [Ru(Htip)2(dppz)]Cl2 (2), were synthesised and were characterised. The ground- and excited-state acid-base properties of 1 and 2 were studied and demonstrated that 1 acted as a pH-induced "on-off-on" luminescence switch. The binding behaviours of 1 and 2 to calf thymus ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.09.041

    authors: Zhao XL,Li ZS,Zhang AG,Liu P,Song XM,Wang KZ

    更新日期:2014-11-24 00:00:00

  • Synthesis and biological evaluation of novel ferrocene-naphthoquinones as antiplasmodial agents.

    abstract::This work deals with the synthesis and evaluation of new compounds designed by combination of 1,4-naphthoquinone and ferrocene fragments in a 3-ferrocenylmethyl-2-hydroxy-1,4-naphthoquinone arrangement. A practical coupling reaction between 2-hydroxy-1,4-naphthoquinone and ferrocenemethanol derivatives has been develo...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.10.011

    authors: García-Barrantes PM,Lamoureux GV,Pérez AL,García-Sánchez RN,Martínez AR,San Feliciano A

    更新日期:2013-01-01 00:00:00

  • Dual-acidity-labile polysaccharide-di-drugs conjugate for targeted cancer chemotherapy.

    abstract::Polymer-drug conjugates synthesized by binding therapeutic agents to functional polymers have long been a mainstay of prodrugs, while the slow drug release, insufficient efficacy of a single drug, and low selectivity hamper the clinical translation. By rational prodrug design, a targeted dual-acidity-labile polysaccha...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112367

    authors: Li D,Su T,Ma L,Yin F,Xu W,Ding J,Li Z

    更新日期:2020-08-01 00:00:00

  • Studies on quinones. Part 46. Synthesis and in vitro antitumor evaluation of aminopyrimidoisoquinolinequinones.

    abstract::In the search of structure-activity relationship studies and to explore the antitumor effect associated with the pyrimidoisoquinolinequinone scaffold, several diversily substituted 8-aminopyrimido[4,5-c]isoquinolinequinones were regioselectively synthesized. Variation in the structure of the nitrogen substituent bonde...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.08.040

    authors: Vásquez D,Rodríguez JA,Theoduloz C,Calderon PB,Valderrama JA

    更新日期:2010-11-01 00:00:00

  • Novel pyrazolopyridine derivatives as potential angiogenesis inhibitors: Synthesis, biological evaluation and transcriptome-based mechanistic analysis.

    abstract::Modified purine derivatives exemplified by pyrazolopyrimidines have emerged as highly selective inhibitors of several angiogenic receptor tyrosine kinases. Herein, we designed and synthesized a new series of substituted pyrazolopyridines and explored their ability to influence crucial pro-angiogenic attributes of endo...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.05.035

    authors: Michailidou M,Giannouli V,Kotsikoris V,Papadodima O,Kontogianni G,Kostakis IK,Lougiakis N,Chatziioannou A,Kolisis FN,Marakos P,Pouli N,Loutrari H

    更新日期:2016-10-04 00:00:00

  • 6-Amino-2,4,5-trimethylpyridin-3-ols: a new general synthetic route and antiangiogenic activity.

    abstract::A new synthetic strategy for preparation of a wide range of 6-amino-2,4,5-trimethylpyridin-3-ols from pyridoxine·HCl via a six-step sequence has been developed. This approach features an introduction of various amino groups to C(6)-position of 3-benzyloxy-6-bromo-2,4,5-trimethylpyridine (13), a key intermediate, by a ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.03.045

    authors: Kim DG,Kang Y,Lee H,Lee EK,Nam TG,Kim JA,Jeong BS

    更新日期:2014-05-06 00:00:00

  • Design, synthesis, and structure-activity relationships of novel benzothiazole derivatives bearing the ortho-hydroxy N-carbamoylhydrazone moiety as potent antitumor agents.

    abstract::A series of novel benzothiazole derivatives bearing the ortho-hydroxy N-carbamoylhydrazone moiety were designed and synthesized and their cytotoxic activities against five cancer cell lines (NCI-H226, SK-N-SH, HT29, MKN45, and MDA-MB-231) were screened in vitro. Most of them showed moderate to excellent activity again...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.08.058

    authors: Ma J,Chen D,Lu K,Wang L,Han X,Zhao Y,Gong P

    更新日期:2014-10-30 00:00:00

  • Synthesis, biological evaluation, and molecular docking investigation of 3-amidoindoles as potent tubulin polymerization inhibitors.

    abstract::A series of novel 3-amidoindole derivatives possessing 3,4,5-trimethoxylphenyl groups were synthesized and evaluated for their antiproliferative and tubulin polymerization inhibitory activities. Some of them demonstrated moderate to potent activities in vitro against six cancer cell lines including MCF-7, MDA-MB-231, ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.11.038

    authors: Chen P,Zhuang YX,Diao PC,Yang F,Wu SY,Lv L,You WW,Zhao PL

    更新日期:2019-01-15 00:00:00

  • Use of copper(I) catalyzed azide alkyne cycloaddition (CuAAC) for the preparation of conjugated pyrrolo[2,3-a]carbazole Pim kinase inhibitors.

    abstract::We have previously demonstrated that pyrrolo[2,3-a]carbazole-3-carbaldehydes are potent Pim kinase inhibitors with in vitro antiproliferative activities. In the present study, we report the synthesis of new pyrrolocarbazoles substituted at the N-10 position. When their ability to inhibit Pim kinase activities were eva...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.02.009

    authors: Letribot B,Akué-Gédu R,Santio NM,El-Ghozzi M,Avignant D,Cisnetti F,Koskinen PJ,Gautier A,Anizon F,Moreau P

    更新日期:2012-04-01 00:00:00

  • Identification of putative steroid-binding sites in human ABCB1 and ABCG2.

    abstract::Homology modelling was used to generate three-dimensional structures of the nucleotide-binding domains (NBDs) of human ABCB1 and ABCG2. Interactions between a series of steroidal ligands and transporter NBDs were investigated using an in silico docking approach. C-terminal ABCB1 NBD (ABCB1 NBD2) was predicted to bind ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2009.02.027

    authors: Mares-Sámano S,Badhan R,Penny J

    更新日期:2009-09-01 00:00:00

  • The novel phosphoramidate derivatives of NSAID 3-hydroxypropylamides: synthesis, cytostatic and antiviral activity evaluations.

    abstract::The target phosphoramidates 5a-e were prepared in one step from 3-hydroxypropyl derivatives 3a-e of nonsteroidal anti-inflammatory drugs (fenoprofen, ketoprofen, ibuprofen, indomethacin, diclofenac). The products 3a-e and 5a-e were evaluated for their cytostatic and antiviral activity against malignant tumour cell lin...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.03.037

    authors: Wittine K,Benci K,Rajić Z,Zorc B,Kralj M,Marjanović M,Pavelić K,De Clercq E,Andrei G,Snoeck R,Balzarini J,Mintas M

    更新日期:2009-01-01 00:00:00

  • Antitumor platinum(II) complexes of N-monoalkyl 1R,2R-diamino-cyclohexanes with 3-(nitrooxy)cyclobutane-1,1-dicarboxylate as a leaving group.

    abstract::A series of platinum(II) complexes of N-monoalkyl-1R,2R-diaminocylclohexanes with 3-(nitrooxy)cyclobutane-1,1-dicarboxylate as a leaving group were synthesized and characterized by elemental analysis, IR, (1)H, (13)C and (195)Pt NMR spectroscopy together with ESI-MS spectrometer. In vitro cytotoxicity study on these c...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.08.007

    authors: Zhao J,Gou S,Xu G,Cheng L

    更新日期:2014-10-06 00:00:00

  • Synthetic tumor-specific antigenic peptides with a strong affinity to HLA-A2 elicit anti-breast cancer immune response through activating CD8+ T cells.

    abstract::Researches on tumor-associated antigen have become a hot target in immunotherapy, but it stagnated in the pre-clinical/clinical stages. Here, we developed a series of MAGE-A1-restricted antigenic peptides, which exhibited prominent inhibiting effect on specific breast cancer. Peptides were synthesized by Fmoc solid ph...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112051

    authors: Shi W,Qiu Q,Tong Z,Guo W,Zou F,Feng Z,Wang Y,Huang W,Qian H

    更新日期:2020-03-01 00:00:00

  • New amphiphilic neamine conjugates bearing a metal binding motif active against MDR E. aerogenes Gram-negative bacteria.

    abstract::Structure of bacterial envelope is one of the major factors contributing to Gram negative bacterial resistance. To develop new agents that target the bacterial membranes, we synthesized, by analogy with our previous peptide conjugates, new amphiphilic 3',4',6-trinaphthylmethylene neamines functionalized at position 5 ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.10.054

    authors: Allam A,Maigre L,Alves de Sousa R,Dumont E,Vergalli J,Pagès JM,Artaud I

    更新日期:2017-02-15 00:00:00

  • Potential cytotoxic and anti-metastatic effects of berberine on gynaecological cancers with drug-associated resistance.

    abstract::Gynaecological disorders, such as cervical, ovarian, and endometrial cancers are the second most prevalent cancer types in women worldwide. Therapeutic approaches for gynaecological cancers involve chemotherapy, radiation, and surgery. However, lifespan is not improved, and novel medications are required. Among variou...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2019.111951

    authors: Mortazavi H,Nikfar B,Esmaeili SA,Rafieenia F,Saburi E,Chaichian S,Heidari Gorji MA,Momtazi-Borojeni AA

    更新日期:2020-02-01 00:00:00

  • Synthesis of amphiphilic galactopyranosyl diamines and amino alcohols as antitubercular agents.

    abstract::Mono- and diacylated derivatives of galactopyranosyl amines were obtained from d-galactose, via aminated intermediates prepared by reaction of 6-deoxy-6-iodo-1,2:3,4-di-O-isopropylidene-alpha-d-galactopyranose with 1,3-propanediamine, 1,2-ethanediamine or ethanolamine. Monoacylated derivatives displayed antitubercular...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2007.01.009

    authors: de Almeida MV,Le Hyaric M,Amarante GW,Silva Lourenço MC,Lima Brandão ML

    更新日期:2007-08-01 00:00:00

  • Synthesis and structure guided evaluation of estrogen agonist and antagonist activities of some new tetrazolyl indole derivatives.

    abstract::Several regioisomeric tetrazolyl indole derivatives with structurally modified alkyl substituents at the tetracyclic indole nitrogen containing N-ethyl amino tetrazole moiety have been synthesized and screened for their ER binding affinity, agonist (estrogenic), antagonist (antiestrogenic) and anti-implantation activi...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2007.10.035

    authors: Singh US,Shankar R,Yadav GP,Kharkwal G,Dwivedi A,Keshri G,Singh MM,Moulik PR,Hajela K

    更新日期:2008-10-01 00:00:00

  • Synthesis of stilbene derivatives with inhibition of SARS coronavirus replication.

    abstract::Stilbene derivatives have wide range of activities. In an effort to find other potential activities of this kind of compounds, 17 derivatives, including resveratrol, were synthesized. Twelve of them were evaluated for their antiviral potential against severe acute respiratory syndrome (SARS)-CoV-induced cytopathicity ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2006.03.024

    authors: Li YQ,Li ZL,Zhao WJ,Wen RX,Meng QW,Zeng Y

    更新日期:2006-09-01 00:00:00

  • Polyamine-based analogs and conjugates as antikinetoplastid agents.

    abstract::Naturally occurring polyamines: putrescine, spermidine and spermine are crucial for Kinetoplastid growth and persistence. These aliphatic polycations are either biosynthesized or internalized into Kinetoplastid by active transport. Impairing the polyamine metabolism using polyamine derivatives is an interesting path i...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2017.08.014

    authors: Jagu E,Pomel S,Pethe S,Loiseau PM,Labruère R

    更新日期:2017-10-20 00:00:00

  • New 5-substituted thiazolo[3,2-b][1,2,4]triazol-6-ones: synthesis and anticancer evaluation.

    abstract::Following [2+3]-cyclocondensation reaction of 1,2,4-triazole-3(5)-thiol with N-arylmaleimides or with monochloroacetic acid and oxocompounds, N-(R-phenyl)-(6-oxo-5,6-dihydro[1,3]thiazol[3,2-b][1,2,4]triazol-5-yl)acetamides (1-5) and 5-ylidene-[1,3]thiazolo[3,2-b][1,2,4]triazol-6-ones (6-11) were synthesized as possibl...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2006.12.006

    authors: Lesyk R,Vladzimirska O,Holota S,Zaprutko L,Gzella A

    更新日期:2007-05-01 00:00:00