New coumarin-based fluorescent melatonin ligands. Design, synthesis and pharmacological characterization.

Abstract:

:The design and synthesis of a series of new fluorescent coumarin-containing melatonin analogues is presented. The combination of high-binding affinities for human melatonergic receptors (h-MT₁R and h-MT₂R) and fluorescent properties, derived from the inclusion of melatonin pharmacophoric elements in the coumarin scaffold, yielded suitable candidates for the development of MT₁R and MT₂R fluorescent probes for imaging in biological media.

journal_name

Eur J Med Chem

authors

de la Fuente Revenga M,Herrera-Arozamena C,Fernández-Sáez N,Barco G,García-Orue I,Sugden D,Rivara S,Rodríguez-Franco MI

doi

10.1016/j.ejmech.2015.09.003

subject

Has Abstract

pub_date

2015-10-20 00:00:00

pages

370-3

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(15)30247-6

journal_volume

103

pub_type

杂志文章
  • Synthesis of polyfluoroalkyl sp2-iminosugar glycolipids and evaluation of their immunomodulatory properties towards anti-tumor, anti-leishmanial and anti-inflammatory therapies.

    abstract::Immunomodulatory glycolipids, among which α-galactosylceramide (KRN7000) is an iconic example, have shown strong therapeutic potential in a variety of conditions ranging from cancer and infection to autoimmune or neurodegenerative diseases. A main difficulty for those channels is that they often provoke a cytokine sto...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.111604

    authors: Sánchez-Fernández EM,García-Moreno MI,Arroba AI,Aguilar-Diosdado M,Padrón JM,García-Hernández R,Gamarro F,Fustero S,Sánchez-Aparicio JE,Masgrau L,García Fernández JM,Ortiz Mellet C

    更新日期:2019-11-15 00:00:00

  • PRODRUGS FOR NITROREDUCTASE BASED CANCER THERAPY- 2: Novel amide/Ntr combinations targeting PC3 cancer cells.

    abstract::The use of nitroreductases (NTR) that catalyze the reduction of nitro compounds by using NAD(P)H in GDEPT (Gene-directed enzyme prodrug therapy) studies which minimize toxicity at healthy cells and increases concentration of drugs at cancer cells is remarkable. Discovery of new prodrug/NTR combinations is necessary to...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.03.035

    authors: Güngör T,Önder FC,Tokay E,Gülhan ÜG,Hacıoğlu N,Tok TT,Çelik A,Köçkar F,Ay M

    更新日期:2019-06-01 00:00:00

  • Synthesis and biological activity of novel N6-substituted and 2,N6-disubstituted adenine ribo- and 3'-C-methyl-ribonucleosides as antitumor agents.

    abstract::A series of N6-aminopurine-9-β-D-ribonucleosides and ribose-modified 3'-C-methyl analogues substituted at N6-position with a small group like hydroxy, methoxy or amino group or at C2(N6) position have been synthesized and tested against a panel of human leukemia and carcinoma cell lines. N6-Hydrazino-9-β-D-ribofuranos...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.01.055

    authors: Cappellacci L,Petrelli R,Franchetti P,Vita P,Kusumanchi P,Kumar M,Jayaram HN,Zhou B,Yen Y,Grifantini M

    更新日期:2011-05-01 00:00:00

  • Synthesis and biological evaluation of α-santonin derivatives as anti-hepatoma agents.

    abstract::A series of α-santonin-derived compounds as potentially anti-hepatoma agents were designed and synthesized in an effort to find novel therapeutic agents. Among them, derivative 5h was more potent than the positive control 5-fluorouracil (5-Fu) on HepG-2, QGY-7703 and SMMC-7721 with IC50 values of 7.51, 3.06 and 4.08 μ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.02.073

    authors: Chen H,Yang X,Yu Z,Cheng Z,Yuan H,Zhao Z,Wu G,Xie N,Yuan X,Sun Q,Zhang W

    更新日期:2018-04-10 00:00:00

  • A convenient synthesis of 13N-labelled azo compounds: a new route for the preparation of amyloid imaging PET probes.

    abstract::In the present paper, a fast and automated method for the synthesis of (13)N-labelled azo compounds is reported for the first time. The labelling strategy is based on trapping [(13)N]NO(2)(-) in an anion exchange resin. The reaction with primary aromatic amines in acidic media led to the formation of the corresponding...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.08.053

    authors: Gómez-Vallejo V,Borrell JI,Llop J

    更新日期:2010-11-01 00:00:00

  • Anilides and quinolones with nitrogen-bearing substituents from benzothiophene and thienothiophene series: synthesis, photochemical synthesis, cytostatic evaluation, 3D-derived QSAR analysis and DNA-binding properties.

    abstract::A series of new anilides (2a-c, 4-7, 17a-c, 18) and quinolones (3a-b, 8a-b, 9a-b, 10-15, 19) with nitrogen-bearing substituents from benzo[b]thiophene and thieno[2,3-c]thiophene series are prepared. Benzo[b]thieno[2,3-c]- and thieno[3',2':4,5]thieno[2,3-c]quinolones (3a-b, 8a-b) are synthesized by the reaction of phot...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.11.010

    authors: Aleksić M,Bertoša B,Nhili R,Depauw S,Martin-Kleiner I,David-Cordonnier MH,Tomić S,Kralj M,Karminski-Zamola G

    更新日期:2014-01-01 00:00:00

  • New groups of antimycobacterial agents: 6-chloro-3-phenyl-4-thioxo-2H-1,3-benzoxazine-2(3H)-ones and 6-chloro-3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dithiones.

    abstract::A series of 6-chloro-3-phenyl-4-thioxo-2H-1,3-benzoxazine-2(3H)-ones 3 and a series of 6-chloro-3-phenyl-2H-1,3-benzoxazine-2, 4(3H)-dithiones 4 were synthesized by melting 6-chloro-3-phenyl-2H-1, 3-benzoxazine-2,4(3H)-dione and its derivatives substituted on the phenyl ring 2 with tetraphosphorus decasulfide. Compoun...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(00)00174-4

    authors: Waisser K,Gregor J,Kubicová L,Klimesová V,Kunes J,Machácek M,Kaustová J

    更新日期:2000-07-01 00:00:00

  • Oxo-heterocyclic fused naphthalimides as antitumor agents: synthesis and biological evaluation.

    abstract::Three series of novel oxo-heterocyclic fused naphthalimide derivatives (8a-8f, 13a-13d, 17a-17d) were prepared. The newly-synthesized compounds, and their thio-heterocyclic fused analogs (1a-1c, 2a-2d, 3a-3c) exhibited potent antiproliferative activity correlated well with their structure. Further research demonstrate...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.12.039

    authors: Tan S,Yin H,Chen Z,Qian X,Xu Y

    更新日期:2013-04-01 00:00:00

  • Chalcogen containing heterocyclic scaffolds: New hybrids with antitumoral activity.

    abstract::In this work, 27 novel hybrid derivatives containing diverse substituents with chalcogen atoms (selenium or sulfur) and several active heterocyclic scaffolds have been synthesized. Compounds were tested against two human cancer cells lines (MCF7 and PC-3) and a normal human mammary epithelial cell line (184B5) in orde...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.07.042

    authors: Alcolea V,Plano D,Encío I,Palop JA,Sharma AK,Sanmartín C

    更新日期:2016-11-10 00:00:00

  • Attenuation of Mycobacterium species through direct and macrophage mediated pathway by unsymmetrical diaryl urea.

    abstract::Tuberculosis is a major threat for mankind and the emergence of resistance strain of Mycobacterium tuberculosis (Mtb) against first line antibiotics makes it lethal for human civilization. In this study, we have synthesized different diaryl urea derivatives targeting the inhibition of mycolic acid biosynthesis. Among ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.09.083

    authors: Velappan AB,Charan Raja MR,Datta D,Tsai YT,Halloum I,Wan B,Kremer L,Gramajo H,Franzblau SG,Kar Mahapatra S,Debnath J

    更新日期:2017-01-05 00:00:00

  • Targeting different binding sites in the CFTR structures allows to synergistically potentiate channel activity.

    abstract::Recent evidence shows that combination of correctors and potentiators, such as the drug ivacaftor (VX-770), can significantly restore the functional expression of mutated Cystic Fibrosis Transmembrane conductance Regulator (CFTR), an anion channel which is mutated in cystic fibrosis (CF). The success of these combinat...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112116

    authors: Froux L,Elbahnsi A,Boucherle B,Billet A,Baatallah N,Hoffmann B,Alliot J,Zelli R,Zeinyeh W,Haudecoeur R,Chevalier B,Fortuné A,Mirval S,Simard C,Lehn P,Mornon JP,Hinzpeter A,Becq F,Callebaut I,Décout JL

    更新日期:2020-03-15 00:00:00

  • Computational methods-guided design of modulators targeting protein-protein interactions (PPIs).

    abstract::Protein-protein interactions (PPIs) play a pivotal role in extensive biological processes and are thus crucial to human health and the development of disease states. Due to their critical implications, PPIs have been spotlighted as promising drug targets of broad-spectrum therapeutic interests. However, owing to the g...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2020.112764

    authors: Qiu Y,Li X,He X,Pu J,Zhang J,Lu S

    更新日期:2020-12-01 00:00:00

  • Potent naphthoquinones against antimony-sensitive and -resistant Leishmania parasites: synthesis of novel α- and nor-α-lapachone-based 1,2,3-triazoles by copper-catalyzed azide-alkyne cycloaddition.

    abstract::Continuing our screening program for novel anti-parasite compounds, we synthesized seven 1,4-naphthoquinones coupled to 1,2,3-triazoles, five nor-β-lapachone-based 1,2,3-triazoles and ten α-lapachone-based 1,2,3-triazoles. These and other naphthoquinonoid compounds were evaluated for their activity against promastigot...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.02.038

    authors: Guimarães TT,Pinto Mdo C,Lanza JS,Melo MN,do Monte-Neto RL,de Melo IM,Diogo EB,Ferreira VF,Camara CA,Valença WO,de Oliveira RN,Frézard F,da Silva EN Jr

    更新日期:2013-05-01 00:00:00

  • Structure-activity relationships of new Organotin(IV) anticancer agents and their cytotoxicity profile on HL-60, MCF-7 and HeLa human cancer cell lines.

    abstract::There is a growing interest in the cancer cell growth inhibitory effects of organotin (IV) compounds and, accordingly, a new series of dimethyl-, di-(n-butyl)-, diphenyl- and chloro-phenyl tin(IV) complexes with a Schiff base core were prepared. Their binding to DNA was assessed by UV thermal denaturation showing no i...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.07.047

    authors: Ullah H,Previtali V,Mihigo HB,Twamley B,Rauf MK,Javed F,Waseem A,Baker RJ,Rozas I

    更新日期:2019-11-01 00:00:00

  • Acylated sulfonamide adenosines as potent inhibitors of the adenylate-forming enzyme superfamily.

    abstract::The superfamily of adenylate-forming enzymes all share a common chemistry. They activate a carboxylate group, on a specific substrate, by catalyzing the formation of a high energy mixed phosphoanhydride-linked nucleoside intermediate. Members of this diverse enzymatic family play key roles in a variety of metabolic pa...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.04.045

    authors: De Ruysscher D,Pang L,De Graef S,Nautiyal M,De Borggraeve WM,Rozenski J,Strelkov SV,Weeks SD,Van Aerschot A

    更新日期:2019-07-15 00:00:00

  • Comparative study of microtubule inhibitors--estramustine and natural podophyllotoxin conjugated PAMAM dendrimer on glioma cell proliferation.

    abstract::The synthetic estramustine (EM) and natural podophyllotoxin (PODO) anti-mitotic agents that inhibit tubulin polymerization are known anticancer agents. As low bioavailability limits their anticancer properties, we investigated whether conjugation with PAMAM dendrimer (D) could enhance the activity of D-EM and D-PODO b...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.07.007

    authors: Sk UH,Dixit D,Sen E

    更新日期:2013-10-01 00:00:00

  • Structure-activity relationship studies of lipophilic teicoplanin pseudoaglycon derivatives as new anti-influenza virus agents.

    abstract::Six series of semisynthetic lipophilic glycopeptide antibiotic derivatives were evaluated for in vitro activity against influenza A and B viruses. The new teicoplanin pseudoaglycon-derived lipoglycopeptides were prepared by coupling one or two side chains to the N-terminus of the glycopeptide core, using various conju...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.08.058

    authors: Szűcs Z,Kelemen V,Le Thai S,Csávás M,Rőth E,Batta G,Stevaert A,Vanderlinden E,Naesens L,Herczegh P,Borbás A

    更新日期:2018-09-05 00:00:00

  • 2-Amino-thiophene derivatives present antileishmanial activity mediated by apoptosis and immunomodulation in vitro.

    abstract::This study evaluated the effects of 2-amino-thiophene derivatives on the promastigote and amastigote forms of Leishmania (Leishmania) amazonensis and their possible mechanisms of action. Initially, we evaluated the antileishmanial activity of ten 2-amino-thiophene derivatives on promastigote and axenic amastigote form...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.10.011

    authors: Rodrigues KA,Dias CN,Néris PL,Rocha Jda C,Scotti MT,Scotti L,Mascarenhas SR,Veras RC,de Medeiros IA,Keesen Tde S,de Oliveira TB,de Lima Mdo C,Balliano TL,de Aquino TM,de Moura RO,Mendonça Junior FJ,de Oliveira MR

    更新日期:2015-12-01 00:00:00

  • Indole chalcones: Design, synthesis, in vitro and in silico evaluation against Mycobacterium tuberculosis.

    abstract::Indole chalcones were designed and synthesized as a promising set of compounds against H37Rv strain of Mycobacterium tuberculosis. Within this library of compounds, (E)-1-(furan-3-yl)-3-(1H-indol-3-yl)prop-2-en-1-one (18), (E)-3-(1H-indol-3-yl)-1-(thiophen-2-yl)prop-2-en-1-one (20) and (E)-2-((1H-indol-2-yl)methylene)...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112358

    authors: Ramesh D,Joji A,Vijayakumar BG,Sethumadhavan A,Mani M,Kannan T

    更新日期:2020-07-15 00:00:00

  • Benzo[d]thiazol-2(3H)-ones as new potent selective CB2 agonists with anti-inflammatory properties.

    abstract::The high distribution of CB2 receptors in immune cells suggests their important role in the control of inflammation. Growing evidence offers this receptor as an attractive therapeutic target: selective CB2 agonists are able to modulate inflammation without triggering psychotropic effects. In this work, we report a new...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.12.008

    authors: Leleu-Chavain N,Baudelet D,Heloire VM,Rocha DE,Renault N,Barczyk A,Djouina M,Body-Malapel M,Carato P,Millet R

    更新日期:2019-03-01 00:00:00

  • Discovery and structure-activity relationship of novel diphenylthiazole derivatives as BTK inhibitor with potent activity against B cell lymphoma cell lines.

    abstract::By the analysis of different binding modes with Bruton's tyrosine kinase (BTK), series of novel diphenylthiazole derivatives were rationally designed, synthesized and characterized. Biologically evaluation in biochemistry and cellular assay indicated that, compounds 5m, 5o, 6b, 6c, 6g, 6i, 7h, 7i, 7k, 7m, 7n, 7o and 7...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.06.035

    authors: Guo X,Yang D,Fan Z,Zhang N,Zhao B,Huang C,Wang F,Ma R,Meng M,Deng Y

    更新日期:2019-09-15 00:00:00

  • Agonist and antagonist ligands of toll-like receptors 7 and 8: Ingenious tools for therapeutic purposes.

    abstract::The discovery of the TLRs family and more precisely its functions opened a variety of gates to modulate immunological host responses. TLRs 7/8 are located in the endosomal compartment and activate a specific signaling pathway in a MyD88-dependant manner. According to their involvement into various autoimmune, inflamma...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2020.112238

    authors: Patinote C,Karroum NB,Moarbess G,Cirnat N,Kassab I,Bonnet PA,Deleuze-Masquéfa C

    更新日期:2020-05-01 00:00:00

  • Dependence of fungistatic activity of 2, 4-dihydroxythiobenzanilideson the structure and lipophilic nature of the compounds.

    abstract::The quantitative dependencies of in vitro fungistatic action on the physico-chemical parameters connected with the structure of 2, 4-dihydroxythiobenzanilides were investigated. It was stated that the action of these compounds depends on lipophilicity determined by substitution of the N-aryl moiety and on electron pro...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(00)00136-7

    authors: Matysiak J,Niewiadomy A,Macik-Niewiadomy G,Kornillowicz T

    更新日期:2000-04-01 00:00:00

  • Design, synthesis and anti-mycobacterial activity of 1,2,3,5-tetrasubstituted pyrrolyl-N-acetic acid derivatives.

    abstract::A novel synthesis of highly substituted pyrrole-N-acetic derivatives is described through the coupling of 1,4-diketones with amino acids following Paal-Knorr's approach. These pyrrole-N-acetic acid derivatives are found to exhibit potent anti-mycobacterial activity against Mycobacterium smegmatis and Mycobacterium tub...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.06.075

    authors: Pagadala LR,Mukkara LD,Singireddi S,Singh A,Thummaluru VR,Jagarlamudi PS,Guttala RS,Perumal Y,Dharmarajan S,Upadhyayula SM,Ummanni R,Basireddy VS,Ravirala N

    更新日期:2014-09-12 00:00:00

  • Optimisation of correlation weights of SMILES invariants for modelling oral quail toxicity.

    abstract::The SMILES (simplified molecular input line entry system) nomenclature was used to elucidate the molecular structure in constructing the quantitative structure-property/activity relationships (QSPR/QSAR) for predicting quail toxicity after oral exposure. The presence of chemical elements in different electronic states...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2006.11.018

    authors: Toropov AA,Benfenati E

    更新日期:2007-05-01 00:00:00

  • An insight into the biological activities of heterocyclic-fatty acid hybrid molecules.

    abstract::Heterocyclic compounds are the interesting core structures for the development of new bioactive compounds. Fatty acids are derived from renewable raw materials and exhibit various biological activities. Several researchers are amalgamating these two bioactive components to yield bioactive hybrid molecules with some de...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2017.09.069

    authors: Venepally V,Reddy Jala RC

    更新日期:2017-12-01 00:00:00

  • Synthesis and biological evaluation of dialkylsubstituted maleic anhydrides as novel inhibitors of Cdc25 dual specificity phosphatases.

    abstract::An efficient synthesis of dialkylsubstituted maleic anhydrides 1a-j is described. The inhibitory potential of these original anhydride derivatives was tested toward the three human isoforms A, B and C of dual specific phosphatases Cdc25. A micromolar range inhibition of Cdc25s was observed with the maleic anhydrides b...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2006.09.014

    authors: Brault L,Denancé M,Banaszak E,El Maadidi S,Battaglia E,Bagrel D,Samadi M

    更新日期:2007-02-01 00:00:00

  • A novel NAE/UAE dual inhibitor LP0040 blocks neddylation and ubiquitination leading to growth inhibition and apoptosis of cancer cells.

    abstract::NEDD8 activating enzyme (NAE) plays an important role in regulating intracellular proteins with key parts in a broad array of cellular functions. On the basis of previously work, a series of 2H-chromen-2-one based NAE inhibitors were designed and synthesized. Through enzyme-based and cell-based assays, LP0040 was iden...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.05.027

    authors: Lu P,Guo Y,Zhu L,Xia Y,Zhong Y,Wang Y

    更新日期:2018-06-25 00:00:00

  • Pyrazolo[4,3-b]pyrimido[4,5-e][1,4]diazepine derivatives as new multi-targeted inhibitors of Aurora A/B and KDR.

    abstract::Aurora A, Aurora B and Kinase Insert Domain-containing Receptor (KDR) play essential roles in sustained cancer growth. In the present study, eighteen pyrazolo[4,3-b]pyrimido[4,5-e][1,4]diazepine derivatives were designed and synthesized. Most of the prepared compounds exhibited obviously enzymatic (Aurora A/B and KDR)...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.09.032

    authors: Zhang Q,Shen Q,Gao L,Tong L,Li J,Chen Y,Lu W

    更新日期:2018-10-05 00:00:00

  • New quinoxalinecarbonitrile 1,4-di-N-oxide derivatives as hypoxic-cytotoxic agents.

    abstract::We report the synthesis and biological in vitro activities of 16 new 2-quinoxalinecarbonitrile 1,4-di-N-oxides. These compounds present new basic lateral chains (piperazines and anilines) in the 3 position as well as different substituents in the 6 and/or 7 positions of the quinoxaline ring. Among piperazine derivativ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(00)00112-4

    authors: Ortega MA,Morancho MJ,Martínez-Crespo FJ,Sainz Y,Montoya ME,López de Ceráin A,Monge A

    更新日期:2000-01-01 00:00:00