当前位置： SCI文献检索 > EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY期刊下所有文献 > Synthesis and biological evaluation of a new series of 2-amino-3-aroyl thiophene derivatives as agonist allosteric modulators of the A1 adenosine receptor. A position-dependent effect study.

Synthesis and biological evaluation of a new series of 2-amino-3-aroyl thiophene derivatives as agonist allosteric modulators of the A1 adenosine receptor. A position-dependent effect study.

Abstract：

:The 2-amino-3-(p-chlorobenzoyl)thiophene scaffold has been widely employed as a pharmacophore for the identification of small molecules acting as allosteric modulators at the adenosine A1 receptor. A new series of 2-amino-3-(p-chlorobenzoyl)-4-benzyl-5-arylthiophene derivatives, characterized by the absence as well as the presence of electron-releasing or electron-withdrawing groups on the phenyl ring at the 4- and 5-positions of the thiophene ring, were identified as positive allosteric enhancers at the adenosine A1 receptor in binding (saturation, competition and dissociation kinetics) and functional assays. To better understand the positional requirements of substituents on the 2-amino-3-(p-chlorobenzoyl)thiophene core, the corresponding regioisomeric 4-aryl-5-benzylthiophene analogues were synthesized and found to possess reduced allosteric enhancer activity.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Romagnoli R,Baraldi PG,Lopez-Cara C,Cruz-Lopez O,Moorman AR,Massink A,IJzerman AP,Vincenzi F,Borea PA,Varani K

doi

10.1016/j.ejmech.2015.06.041

subject

Has Abstract

pub_date

2015-08-28 00:00:00

pages

185-204

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(15)30117-3

journal_volume

101

pub_type

杂志文章

相关文献

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY文献大全
  • Synthesis and antifungal activities of some aryl [3-(imidazol-1-yl/triazol-1-ylmethyl) benzofuran-2-yl] ketoximes.

    abstract：:In this study, some aryl [3-(imidazol-1-yl/triazol-1-ylmethyl)benzofuran-2-yl] ketones, aryl (3-methyl-benzofuran-2-yl) ketoximes and aryl [3-(imidazol-1-yl/triazol-1-ylmethyl)benzofuran-2-yl] ketoximes were synthesised starting from 2-aryloyl-3-methyl-benzofuranes. The structure elucidation of the compounds was perfo...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2005.12.013

    authors： Gündoğdu-Karaburun N,Benkli K,Tunali Y,Uçucu U,Demirayak S

    更新日期：2006-05-01 00:00:00

  • Tetrazole hybrids and their antifungal activities.

    abstract：:Fungi, which can cause serious infections, results in more than 1.35 million deaths annually throughout the world. Azole antifungal drugs which could inhibit the enzyme lanosterol 14α-demethylase, occupy an important position in the treatment of fungal infections. Tetrazoles, practically non-metabolized bioisosteric a...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.ejmech.2019.03.023

    authors： Wang SQ,Wang YF,Xu Z

    更新日期：2019-05-15 00:00:00

  • Synthesis of C- and O-prenylated tetrahydroxystilbenes and O-prenylated cinnamates and their action towards cancer cells.

    abstract：:Synthesis of the naturally occurred C- and O-prenylated tetrahydroxystilbenes and O-prenylated cinnamates was carried out by decarbonylative Heck reaction and selenium dioxide catalysed oxidation, respectively. In the decarbonylative Heck synthetic route, fusion of benzoyl chloride and styrene derivatives was catalyse...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2013.02.017

    authors： Koolaji N,Abu-Mellal A,Tran VH,Duke RK,Duke CC

    更新日期：2013-05-01 00:00:00

  • Design, synthesis and evaluation of diarylpiperazine derivatives as potent anti-tubercular agents.

    abstract：:Molecular hybridization is an emerging approach to design novel ligands by combination of two or more pharmacophoric subunits of known bioactive compounds. In the present study, we have designed a novel series of diarylpiperazine analogues, synthesized, characterized using FTIR, (1)H NMR, Mass, Elemental analysis and ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2015.10.024

    authors： Penta A,Franzblau S,Wan B,Murugesan S

    更新日期：2015-11-13 00:00:00

  • Design, synthesis and biological evaluation of vinyl selenone derivatives as novel microtubule polymerization inhibitors.

    abstract：:A series of novel vinyl selenone derivatives were designed, synthesized and evaluated as the tubulin polymerization inhibitors using a bioisosteric strategy. Among them, the representative compound 11k exhibited satisfactory anti-proliferative activities with IC50 values ranging from 0.287 to 0.621 μM against a panel ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2020.112716

    authors： Zhu H,Sun H,Liu Y,Duan Y,Liu J,Yang X,Li W,Qin S,Xu S,Zhu Z,Xu J

    更新日期：2020-12-01 00:00:00

  • The chemical diversity and structure-based evolution of non-peptide CXCR4 antagonists with diverse therapeutic potential.

    abstract：:The CXC chemokine receptor 4 (CXCR4) is a highly reserved G-protein coupled 7-transmembrane (TM) chemokine receptor which consists of 352 amino acids. CXCR4 has only one endogenous chemokine ligand of CXCL12, besides several other natural nonchemokine ligands such as extracellular ubiquitin and noncognate ligand of MI...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.ejmech.2018.02.043

    authors： Peng D,Cao B,Zhou YJ,Long YQ

    更新日期：2018-04-10 00:00:00

  • Design and synthesis of novel quinacrine-[1,3]-thiazinan-4-one hybrids for their anti-breast cancer activity.

    abstract：:In an attempt to develop effective and safe anticancer agents, we designed, synthesized and examined 23 novel quinacrine (QC) derivatives by combining the 9-aminoacridine scaffold and the [1,3]thiazinan-4-ones group. Most of these hybrids showed strong anticancer activities, among which 3-(3-(6-chloro-2-methoxyacridin...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2017.11.097

    authors： Solomon VR,Pundir S,Le HT,Lee H

    更新日期：2018-01-01 00:00:00

  • Synthesis of new chalcone derivatives containing a rhodanine-3-acetic acid moiety with potential anti-bacterial activity.

    abstract：:With an intention to synergize the anti-bacterial activity of chalcones and rhodanine-3-acetic acid, several hybrid compounds possessing chalcone and rhodanine-3-acetic acid moieties were synthesized and tested for their anti-bacterial activity. Some compounds presented great anti-microbial activities against Gram-pos...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2010.09.031

    authors： Chen ZH,Zheng CJ,Sun LP,Piao HR

    更新日期：2010-12-01 00:00:00

  • In silico design of novel 2H-chromen-2-one derivatives as potent and selective MAO-B inhibitors.

    abstract：:Inhibition data on rat monoamine oxidase B isoform of a large number of 7-metahalobenzyloxy-2H-chromen-2-one derivatives (67 compounds) carrying at position 4 a variety of substituents differing in steric, electrostatic, lipophilic and H-bonding properties, were modeled by Gaussian field-based 3D-QSAR and docking simu...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2014.10.029

    authors： Pisani L,Farina R,Nicolotti O,Gadaleta D,Soto-Otero R,Catto M,Di Braccio M,Mendez-Alvarez E,Carotti A

    更新日期：2015-01-07 00:00:00

  • Discovery of novel series of 2-substituted benzo[d]oxazol-5-amine derivatives as multi-target directed ligands for the treatment of Alzheimer's disease.

    abstract：:Alzheimer's disease (AD) is associated with multifactorial neuropathological conditions, which include cholinergic deficit, amyloid-beta plaques formation, loss of neuronal plasticity and neuronal death. Treating such multifactorial conditions with a single target directed approach is considered to be inadequate. Acco...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2019.111613

    authors： Gutti G,Kakarla R,Kumar D,Beohar M,Ganeshpurkar A,Kumar A,Krishnamurthy S,Singh SK

    更新日期：2019-11-15 00:00:00

  • Discovery of target based novel pyrrolyl phenoxy derivatives as antimycobacterial agents: an in silico approach.

    abstract：:A new series of pyrrolyl phenoxy derivatives bearing alkoxy linker were synthesized and evaluated for anti-tubercular activity (anti-TB) against Mycobacterium tuberculosis. Molecular modeling, pharmacophore constructed using GALAHAD to produce an effective alignment of data set and evaluated by Pareto ranking. The pha...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2015.03.013

    authors： More UA,Joshi SD,Aminabhavi TM,Kulkarni VH,Badiger AM,Lherbet C

    更新日期：2015-04-13 00:00:00

  • Peptidyl 3-substituted 1-hydroxyureas as isosteric analogues of succinylhydroxamate MMP inhibitors.

    abstract：:To evaluate N-hydroxyurea as zinc binding group in the design of MMP inhibitors, two peptidyl 1-hydroxyureas were prepared by N-hydroxycarbamoylation of the diastereomeric dipeptides H-Leu-Phe-NHMe and H-D-Leu-Phe-NHMe. Peptidyl 1-hydroxyureas were more potent than the parent peptides, but dramatically weaker (4-5 ord...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2007.07.002

    authors： Campestre C,Tortorella P,Agamennone M,Preziuso S,Biasone A,Nuti E,Rossello A,Gallina C

    更新日期：2008-05-01 00:00:00

  • Design, synthesis, and biological evaluation of dual targeting inhibitors of histone deacetylase 6/8 and bromodomain BRPF1.

    abstract：:Histone modifying proteins, specifically histone deacetylases (HDACs) and bromodomains, have emerged as novel promising targets for anticancer therapy. In the current work, based on available crystal structures and docking studies, we designed dual inhibitors of both HDAC6/8 and the bromodomain and PHD finger containi...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2020.112338

    authors： Ghazy E,Zeyen P,Herp D,Hügle M,Schmidtkunz K,Erdmann F,Robaa D,Schmidt M,Morales ER,Romier C,Günther S,Jung M,Sippl W

    更新日期：2020-08-15 00:00:00

  • Synthesis, biological investigation and molecular docking study of N-malonyl-1,2-dihydroisoquinoline derivatives as brain specific and shelf-stable MAO inhibitors.

    abstract：:A group of N-malonyl-1,2-dihydroisoquinoline derivatives were synthesized and investigated as brain specific and shelf-stable MAO inhibitors. N-malonyl-1,2-dihydroisoquinoline redox carrier system was linked through amidic bond to 4-chloro and 4-nitrobenzylidenehydrazines (9a-b), as monoamine oxidase inhibitors (MAOIs...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2015.02.039

    authors： Abd El-Gaber MK,Hassan HY,Mahfouz NM,Farag HH,Bekhit AA

    更新日期：2015-03-26 00:00:00

  • Antihyperglycemic and antihyperlipidemic activities of 2-(4-[(2-hydroxybenzyl) amino]-phenyl amino-methyl)-phenol in STZ induced diabetic rats.

    abstract：:Oral administration of 2-(4-[(2-hydroxybenzyl) amino]-phenyl amino-methyl)-phenol (HBPMP) (30 mg/kg) to Streptozotocin (STZ) rats produced significant antidiabetic activity after 6 h of HBPMP administration. Treatment of the STZ rats with HBPMP (30 mg/kg/day) for 30 days resulted in a significant decrease in their Fas...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2013.05.014

    authors： Sirasanagandla S,Kasetti RB,Shaik AN,Natava R,Surtineni VP,Cirradur SR,Chippada A

    更新日期：2013-08-01 00:00:00

  • New isoxazolidinone and 3,4-dehydro-β-proline derivatives as antibacterial agents and MAO-inhibitors: A complex balance between two activities.

    abstract：:Among the different classes of antibiotics, oxazolidinone derivatives represent important drugs, since their unique mechanism of action overcomes commonly diffused multidrug-resistant bacteria. Anyway, the structural similarity of these molecules to monoamino oxidase (MAO) inhibitors, like toloxatone and blefoxatone, ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2016.09.007

    authors： Ferrazzano L,Viola A,Lonati E,Bulbarelli A,Musumeci R,Cocuzza C,Lombardo M,Tolomelli A

    更新日期：2016-11-29 00:00:00

  • Benzofuran-isatin hybrids and their in vitro anti-mycobacterial activities against multi-drug resistant Mycobacterium tuberculosis.

    abstract：:A series of benzofuran-isatin hybrids 6a-n and 7a-g linked by alkyl linkers were designed and synthesized. Among them, hybrids 6a-l and 7a-g were assessed for their in vitro anti-mycobacterial activities against two multi-drug resistant Mycobacterium tuberculosis (MDR-MTB) strains and the cytotoxicity towards CHO cell...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2019.111678

    authors： Gao F,Ye L,Wang Y,Kong F,Zhao S,Xiao J,Huang G

    更新日期：2019-12-01 00:00:00

  • Novel pleuromutilin derivatives with substituted 6-methylpyrimidine: Design, synthesis and antibacterial evaluation.

    abstract：:A series of novel pleuromutilin derivatives with substituted 6-methylpyrimidine moieties was designed, synthesized, and evaluated for their antibacterial activities. Most of the tested compounds exhibited potent antibacterial activities against Staphylococcus aureus ATCC 25923 (S. aureus-25923), methicillin-resistant ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2020.112735

    authors： Fan Y,Liu Y,Wang H,Shi T,Cheng F,Hao B,Yi Y,Shang R

    更新日期：2020-12-01 00:00:00

  • Synthesis, colon-targeted studies and pharmacological evaluation of an anti-ulcerative colitis drug 4-Aminosalicylic acid-β-O-glucoside.

    abstract：:A glycoside prodrug of 4-aminosalicylic acid (4-ASA) with d-glucose was synthesized for targeted drug delivery to inflammatory bowel. The in vitro assessment of 4-aminosalicylic acid-β-O-glucoside (4-ASA-Glu) as a colon-specific prodrug was studied using colitis rat with the healthy one as control. The stability studi...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2015.12.021

    authors： Li F,Wu G,Zheng H,Wang L,Zhao Z

    更新日期：2016-01-27 00:00:00

  • Structure and biological properties of mixed-ligand Cu(II) Schiff base complexes as potential anticancer agents.

    abstract：:We synthesized two mixed-ligand Cu(II) complexes containing different aroylhydrazone ligands and a pyridine co-ligand, namely, [Cu(L1)(Py)] (C1) and [Cu(L2)(Py)(Br)] (C2) (L1 = (E)-2-hydroxy-N'-((2-hydroxynaphthalen-1-yl)methylene)benzohydrazide, Py = pyridine, L2 = (E)-2-hydroxy-N'-(phenyl(pyridin-2-yl)methylene)benz...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2017.04.026

    authors： Gou Y,Li J,Fan B,Xu B,Zhou M,Yang F

    更新日期：2017-07-07 00:00:00

  • Discovery of fast-acting dual-stage antimalarial agents by profiling pyridylvinylquinoline chemical space via copper catalyzed azide-alkyne cycloadditions.

    abstract：:To identity fast-acting, multistage antimalarial agents, a series of pyridylvinylquinoline-triazole analogues have been synthesized via CuAAC. Most of the compounds display significant inhibitory effect on the drug-resistant malarial Dd2 strain at low submicromolar concentrations. Among the tested analogues, compound ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2020.112889

    authors： Huang G,Solano CM,Melendez J,Yu-Alfonzo S,Boonhok R,Min H,Miao J,Chakrabarti D,Yuan Y

    更新日期：2021-01-01 00:00:00

  • Guanidine-modified cyclometalated iridium(III) complexes for mitochondria-targeted imaging and photodynamic therapy.

    abstract：:PDT is a well-established therapeutic modality for many types of cancer. Photoluminescent cyclometalated iridium(III) complexes are one of the most commonly used classes of organometallic compounds with potential beneficial applications in bioimaging and as promising anticancer agents. In the present study, three new ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2019.06.045

    authors： Song XD,Chen BB,He SF,Pan NL,Liao JX,Chen JX,Wang GH,Sun J

    更新日期：2019-10-01 00:00:00

  • Heterocyclic pharmacochemistry of new rhinovirus antiviral agents: A combined computational and experimental study.

    abstract：:Rhinovirus (RV), member of the Enterovirus genus, is known to be involved in more than half of the common colds. Through advances in molecular biology, rhinoviruses have also been associated with exacerbations of chronic pulmonary diseases (e.g. asthma, chronic obstructive pulmonary disease (COPD) and cystic fibrosis)...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2017.09.036

    authors： Da Costa L,Scheers E,Coluccia A,Rosetti A,Roche M,Neyts J,Terme T,Cirilli R,Mirabelli C,Silvestri R,Vanelle P

    更新日期：2017-11-10 00:00:00

  • Structural variations of piritrexim, a lipophilic inhibitor of human dihydrofolate reductase: synthesis, antitumor activity and molecular modeling investigations.

    abstract：:Piritrexim (PTX) (1), a lipophilic inhibitor of the human dihydrofolate reductase, has been evaluated as an anticancer agent. The synthesis of four structural variations (2-5) of PTX is reported. The PTX analogues 2-5 were obtained by reaction of suitable C3-building blocks with pyrimidine-2,4,6-triamine (14) or with ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2004.09.001

    authors： Zink M,Lanig H,Troschütz R

    更新日期：2004-12-01 00:00:00

  • Structure-activity relationship and properties optimization of a series of quinazoline-2,4-diones as inhibitors of the canonical Wnt pathway.

    abstract：:Wnt signaling pathway plays a critical role in numerous cellular processes, including tumor initiation, proliferation, invasion/infiltration, metastasis formation and resistance to chemotherapy. In a drug discovery project aimed at the identification of inhibitors of the canonical Wnt pathway, we selected a series of ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2015.03.055

    authors： Nencini A,Pratelli C,Quinn JM,Salerno M,Tunici P,De Robertis A,Valensin S,Mennillo F,Rossi M,Bakker A,Benicchi T,Cappelli F,Turlizzi E,Nibbio M,Caradonna NP,Zanelli U,Andreini M,Magnani M,Varrone M

    更新日期：2015-05-05 00:00:00

  • Covalent allosteric modulation: An emerging strategy for GPCRs drug discovery.

    abstract：:Designing covalent allosteric modulators brings new opportunities to the field of drug discovery towards G-protein-coupled receptors (GPCRs). Targeting an allosteric binding pocket can allow a modulator to have protein subtype selectivity and low drug resistance. Utilizing covalent warheads further enables the modulat...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.ejmech.2020.112690

    authors： Bian Y,Jun JJ,Cuyler J,Xie XQ

    更新日期：2020-11-15 00:00:00

  • Evaluation of the local anaesthetic activity of 3-aminobenzo[d]isothiazole derivatives using the rat sciatic nerve model.

    abstract：:On the basis of computer prediction of biological activity by PASS and toxicity by DEREK, the most promising 32-alkylaminoacyl derivatives of 3-aminobenzo[d]isothiazole were selected for possible local anaesthetic action. This action was evaluated using an in vitro preparation of the isolated sciatic nerve of the rat ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2008.04.006

    authors： Geronikaki A,Vicini P,Dabarakis N,Lagunin A,Poroikov V,Dearden J,Modarresi H,Hewitt M,Theophilidis G

    更新日期：2009-02-01 00:00:00

  • 2-Methyl-4/5-nitroimidazole derivatives potentiated against sexually transmitted Trichomonas: Design, synthesis, biology and 3D-QSAR study.

    abstract：:Trichomoniasis is the most prevalent, non-viral sexually transmitted diseases (STD) caused by amitochondriate protozoan Trichomonas vaginalis. Increased resistance of T. vaginalis to the marketed drug Metronidazole necessitates the development of newer chemical entities. A library of sixty 2-methyl-4/5-nitroimidazole ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2016.09.006

    authors： Mandalapu D,Kushwaha B,Gupta S,Singh N,Shukla M,Kumar J,Tanpula DK,Sankhwar SN,Maikhuri JP,Siddiqi MI,Lal J,Gupta G,Sharma VL

    更新日期：2016-11-29 00:00:00

  • Diverse chemical space of indoleamine-2,3-dioxygenase 1 (Ido1) inhibitors.

    abstract：:Indoleamine-2,3-dioxygenase 1 (IDO1) catalyses the first and rate limiting step of kynurenine pathway accounting for the major contributor of L-Tryptophan degradation. The Kynurenine metabolites are identified as essential cofactors, antagonists, neurotoxins, immunomodulators, antioxidants as well as carcinogens. The ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.ejmech.2020.113071

    authors： Singh R,Salunke DB

    更新日期：2021-02-05 00:00:00

  • 5-Substituted [1]pyrindine derivatives with antiproliferative activity.

    abstract：:We report herein the synthesis of 5-substituted [1]pyrindine derivatives and the evaluation of their antiproliferative properties on HeLa cells, a cervical carcinoma tumor cell line, and on the melanoma A2058 cell line. The most efficient compounds display cytotoxicity against tumor cells in the micromolar range but h...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2009.11.028

    authors： Kolb S,Goddard ML,Loukaci A,Mondésert O,Ducommun B,Braud E,Garbay C

    更新日期：2010-03-01 00:00:00