Synthesis and biological evaluation of novel structural hybrids of benzofuroxan derivatives and fluoroquinolones.


:A series of novel hybrids based on benzofuroxan derivatives and fluoroquinolones (4a-d-6a-d) have been synthesized. Unexpectedly, the reactions have resulted in salt products formation during the hydrolysis of benzofuroxans by water molecules being present in the solvent instead of usual substitution products. All the compounds have been screened for antimicrobial and toxic activities. All resulting compounds retain high activity characteristic for fluoroquinolones. Many of the salts based on benzofuroxans and fluoroquinolones have higher activity than starting fluoroquinolones against Bacillus cereus 8035. Among the screened compounds, the compound 4d has shown the best antibacterial activity against B. cereus 8035, 8 times higher than the original Lomefloxacin (MBC value 1.5 μg/mL).


Eur J Med Chem


Chugunova E,Akylbekov N,Bulatova A,Gavrilov N,Voloshina A,Kulik N,Zobov V,Dobrynin A,Syakaev V,Burilov A




Has Abstract


2016-06-30 00:00:00












  • Design, synthesis and antitubercular evaluation of novel series of N-[4-(piperazin-1-yl)phenyl]cinnamamide derivatives.

    abstract::The analogs of N-[4-(piperazin-1-yl)phenyl]cinnamamide were designed and synthesized by molecular hybridization approach in which part C of the designed molecule was linked through amide and carbamate functionality that improves the physicochemical properties and govern the pharmacokinetic and pharmacodynamic behavior...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Patel KN,Telvekar VN

    更新日期:2014-03-21 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


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

    更新日期:2020-07-15 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


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

    更新日期:2010-11-01 00:00:00

  • The evaluation of 1,4-benzoquinones as inhibitors of human monoamine oxidase.

    abstract::The monoamine oxidase (MAO) enzymes are of considerable pharmacological interest and inhibitors are used in the clinic for the treatment of major depressive disorder and Parkinson's disease. A limited number of studies have shown that the quinone class of compounds possesses MAO inhibition properties. Most notable amo...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Mostert S,Petzer A,Petzer JP

    更新日期:2017-07-28 00:00:00

  • Selenium analogues of raloxifene as promising antiproliferative agents in treatment of breast cancer.

    abstract::Synthetic protocols for the preparation of selenium analogues of raloxifene were elaborated. General aim of the current research is to improve the positive impact of selenium atom introduction in drug design. Antiproliferative activity on CCL-8 (mouse sarcoma), MDA-MB-435s (human melanoma), MES-SA (human uterus sarcom...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Arsenyan P,Paegle E,Domracheva I,Gulbe A,Kanepe-Lapsa I,Shestakova I

    更新日期:2014-11-24 00:00:00

  • Synthesis, antitumor activity and molecular docking study of novel sulfonamide-Schiff's bases, thiazolidinones, benzothiazinones and their C-nucleoside derivatives.

    abstract::A series of sulfapyridine-polyhydroxyalkylidene (or arylidene)-imino derivatives (Schiff's bases) 2a-c and 4a-e were prepared by condensation of 4-amino-N-pyridin-2-ylbenzenesulfonamide (1) with different monosaccharides or with aromatic aldehydes. Treatment of 2a-c with thioglycolic acid led to the formation of the C...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Kamel MM,Ali HI,Anwar MM,Mohamed NA,Soliman AM

    更新日期:2010-02-01 00:00:00

  • Photoactivation provides a mechanistic explanation for pan-assay interference behaviour of 2-aminopyrroles in lipoxygenase inhibition.

    abstract::Human 15-lipoxygenase-1 (h-15-LOX-1) is a promising drug target in inflammation and cancer. In this study substitution-oriented screening (SOS) has been used to identify compounds with a 2-aminopyrrole scaffold as inhibitors for h-15-LOX-1. The observed structure activity relationships (SAR) proved to be relatively fl...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Guo H,Eleftheriadis N,Rohr-Udilova N,Dömling A,Dekker FJ

    更新日期:2017-10-20 00:00:00

  • Homology modeling in tandem with 3D-QSAR analyses: a computational approach to depict the agonist binding site of the human CB2 receptor.

    abstract::CB2 receptor belongs to the large family of G-protein coupled receptors (GPCRs) controlling a wide variety of signal transduction. The recent crystallographic determination of human β2 adrenoreceptor and its high sequence similarity with human CB2 receptor (hCB2) prompted us to compute a theoretical model of hCB2 base...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Cichero E,Ligresti A,Allarà M,di Marzo V,Lazzati Z,D'Ursi P,Marabotti A,Milanesi L,Spallarossa A,Ranise A,Fossa P

    更新日期:2011-09-01 00:00:00

  • Design, synthesis and biological evaluation of monobactams as antibacterial agents against gram-negative bacteria.

    abstract::A series of monobactam derivatives were prepared and evaluated for their antibacterial activities against susceptible and resistant Gram-negative strains, taking Aztreonam and BAL30072 as the leads. Six conjugates (12a-f) bearing PIH-like siderophore moieties were created to enhance the bactericidal activities against...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Fu HG,Hu XX,Li CR,Li YH,Wang YX,Jiang JD,Bi CW,Tang S,You XF,Song DQ

    更新日期:2016-03-03 00:00:00

  • Novel 9'-substituted-noscapines: synthesis with Suzuki cross-coupling, structure elucidation and biological evaluation.

    abstract::Tubulin is a major molecular target for anticancer drugs. The dynamic process of microtubule assembly and disassembly can be blocked by various agents that bind to distinct sites on tubulin, usually its β-subunit. Among the antimitotic agents that perturb microtubule dynamics, noscapinoids represent an emerging class ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Porcù E,Sipos A,Basso G,Hamel E,Bai R,Stempfer V,Udvardy A,Bényei AC,Schmidhammer H,Antus S,Viola G

    更新日期:2014-09-12 00:00:00

  • Synthesis, molecular docking and biological evaluation of novel phthaloyl derivatives of 3-amino-3-aryl propionic acids as inhibitors of Trypanosoma cruzi trans-sialidase.

    abstract::In the last two decades, trans-sialidase of Trypanosoma cruzi (TcTS) has been an important pharmacological target for developing new anti-Chagas agents. In a continuous effort to discover new potential TcTS inhibitors, 3-amino-3-arylpropionic acid derivatives (series A) and novel phthaloyl derivatives (series B, C and...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Kashif M,Chacón-Vargas KF,López-Cedillo JC,Nogueda-Torres B,Paz-González AD,Ramírez-Moreno E,Agusti R,Uhrig ML,Reyes-Arellano A,Peralta-Cruz J,Ashfaq M,Rivera G

    更新日期:2018-08-05 00:00:00

  • Transferrin conjugates of antitubercular drug isoniazid: Synthesis and in vitro efficacy.

    abstract::Tuberculosis (TB) caused by Mycobacterium tuberculosis (Mtb) has become the world's leading killer disease due to a single infectious agent which survives in the host macrophage for the indefinite period. Hence, it is necessary to enhance the efficacy of the clinically existing antitubercular agents or to discover new...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Sutar YB,Mali JK,Telvekar VN,Rajmani RS,Singh A

    更新日期:2019-12-01 00:00:00

  • New naphthopyran analogues of LY290181 as potential tumor vascular-disrupting agents.

    abstract::A series of 19 analogues of the antiproliferative naphthopyran LY290181 were prepared for structure-activity relationship studies. We found the best activities for test compounds bearing small substituents at the meta position of the phenyl ring. The mode of action of LY290181 and eight new analogues was studied in de...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Schmitt F,Gold M,Rothemund M,Andronache I,Biersack B,Schobert R,Mueller T

    更新日期:2019-02-01 00:00:00

  • Polycyclic propargylamine and acetylene derivatives as multifunctional neuroprotective agents.

    abstract::The aim of this study was to design drug-like molecules with multiple neuroprotective mechanisms which would ultimately inhibit N-methyl-D-aspartate (NMDA) receptors, block L-type voltage gated calcium channels (VGCC) and inhibit apoptotic processes as well as the monoamine oxidase-B (MAO-B) enzyme in the central nerv...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Zindo FT,Barber QR,Joubert J,Bergh JJ,Petzer JP,Malan SF

    更新日期:2014-06-10 00:00:00

  • Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin.

    abstract::Inflammation and oxidative stress are common in many chronic diseases. Targeting signaling pathways that contribute to these conditions may have therapeutic potential. The transcription factor Nrf2 is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective g...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Deck LM,Hunsaker LA,Vander Jagt TA,Whalen LJ,Royer RE,Vander Jagt DL

    更新日期:2018-01-01 00:00:00

  • Ferrocene-based guanidine derivatives: in vitro antimicrobial, DNA binding and docking supported urease inhibition studies.

    abstract::Some novel ferrocenyl guanidines 1-8 were synthesized and characterized by different spectroscopic methods, elemental analysis and single crystal X-rays diffraction techniques. The crystallographic studies revealed that the existence of the strong non-bonding interactions facilitate these molecules to interact with bi...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Gul R,Rauf MK,Badshah A,Azam SS,Tahir MN,Khan A

    更新日期:2014-10-06 00:00:00

  • Synthesis and biological evaluation of a novel betulinic acid derivative as an inducer of apoptosis in human colon carcinoma cells (HT-29).

    abstract::A novel family of betulinic acid analogues, carrying a triazole unit at C-3 attached through a linker, was synthesized by the application of azide-alkyne "Click reaction". These were screened for their anticancer activity against different cancer cells and normal human PBMC by MTT assay. Compound 2c [(3S)-3-{2-(4-(hyd...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Chakraborty B,Dutta D,Mukherjee S,Das S,Maiti NC,Das P,Chowdhury C

    更新日期:2015-09-18 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


    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

  • Synthesis and preliminary mechanistic evaluation of 5-(p-tolyl)-1-(quinolin-2-yl)pyrazole-3-carboxylic acid amides with potent antiproliferative activity on human cancer cell lines.

    abstract::We synthesized a series of novel amide derivatives of 5-(p-tolyl)-1-(quinolin-2-yl)pyrazole-3-carboxylic acid and assessed their antiproliferative activities against three human cancer cell lines (Huh7, human liver; MCF7, breast and HCT116, colon carcinoma cell lines) with the sulforhodamine B assay. Compound 4j with ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Cankara Pirol Ş,Çalışkan B,Durmaz I,Atalay R,Banoglu E

    更新日期:2014-11-24 00:00:00

  • The 4-N-acyl and 4-N-alkyl gemcitabine analogues with silicon-fluoride-acceptor: Application to 18F-Radiolabeling.

    abstract::The coupling of gemcitabine with functionalized carboxylic acids using peptide coupling conditions afforded 4-N-alkanoyl analogues with a terminal alkyne or azido moiety. Reaction of 4-N-tosylgemcitabine with azidoalkyl amine provided 4-N-alkyl gemcitabine with a terminal azido group. Click reaction with silane buildi...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Gonzalez C,Sanchez A,Collins J,Lisova K,Lee JT,Michael van Dam R,Alejandro Barbieri M,Ramachandran C,Wnuk SF

    更新日期:2018-03-25 00:00:00

  • Design, synthesis and antitumour evaluation of pyrrolo[1,2-f]-phenanthridine and dibenzo[f,h]pyrrolo[1,2-b]isoquinoline derivatives.

    abstract::A series of 1,2-bis(hydroxymethyl)pyrrolo[1,2-f]phenanthridine derivatives and their alkyl (ethyl and isopropyl) carbamates and 12,13-bis(hydroxymethyl)-9,14-dihydro-dibenzo[f,h]pyrrolo[1,2-b]isoquinoline derivatives were synthesized for antiproliferative evaluation. The preliminary antitumour studies revealed that th...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Patel AS,Jain V,Rao VN,Lin YW,Shah A,Lai KC,Su TL,Lee TC

    更新日期:2020-09-15 00:00:00

  • The enhancement of neutron irradiation of HeLa-S cervix carcinoma cells by cell-nucleus-addressed deca-p-boronophenylalanine.

    abstract::Boron neutron capture therapy (BNCT) is an experimental treatment modality which depends on a sufficient cellular uptake of Boron ((10)B) followed by an exposure to a thermal neutron beam from a nuclear reactor. High energetic particles (4He and 7Li) are created during the neutron capture reaction and produce DNA dama...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Braun K,Wolber G,Waldeck W,Pipkorn R,Jenne J,Rastert R,Ehemann V,Eisenmenger A,Corban-Wilhelm H,Braun I,Heckl S,Debus J

    更新日期:2003-06-01 00:00:00

  • Recent advances of analogues of curcumin for treatment of cancer.

    abstract::Curcumin (CU), an edible natural pigment from Curcuma Longa, has demonstrated extensive anti-tumor effect in vivo and in vitro. With the property of reversing drug resistance and low toxicity, CU has been considered to develop a new adjuvant chemotherapy protocol of cancer. However, the poor stability, solubility, in ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审


    authors: Zhao S,Pi C,Ye Y,Zhao L,Wei Y

    更新日期:2019-10-15 00:00:00

  • LUMO energy of model compounds of bispyridinium compounds as an index for the inhibition of choline kinase.

    abstract::Eleven derivatives of 1,1'-[1,2-ethylenebis(benzene-1,4-diylmethylene)]bis(4-pyridinium) dibromides bearing various groups at C-4 of the pyridinium moiety were synthesized and examined for their inhibition of choline kinase (ChoK) and antiproliferative activities. The C-4 substituents include electron-releasing, neutr...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Campos J,del Carmen Núñez M,Rodríguez V,Entrena A,Hernández-Alcoceba R,Fernández F,Lacal JC,Gallo MA,Espinosa A

    更新日期:2001-03-01 00:00:00

  • N-alkyl-hydroxybenzoyl anilide hydroxamates as dual inhibitors of HDAC and HSP90, downregulating IFN-γ induced PD-L1 expression.

    abstract::Novel dual inhibitors of histone deacetylase (HDAC) and heat-shock protein 90 (HSP90) are synthesized and evaluated. These compounds are endowed with potent HDAC and HSP90 inhibitory activities with IC50 values in nanomolar range with Compound 20 (HDAC IC50 = 194 nM; HSP90α IC50 = 153 nM) and compound 26 (HDAC IC50 = ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Mehndiratta S,Lin MH,Wu YW,Chen CH,Wu TY,Chuang KH,Chao MW,Chen YY,Pan SL,Chen MC,Liou JP

    更新日期:2020-01-01 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


    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

  • α-D-mannose derivatives as models designed for selective inhibition of Golgi α-mannosidase II.

    abstract::Human Golgi α-mannosidase II (hGM) is a pharmaceutical target for the design of inhibitors with anti-tumor activity. Nanomolar inhibitors of hGM exhibit unwanted co-inhibition of the human lysosomal α-mannosidase (hLM). Hence, improving specificity of the inhibitors directed toward hGM is desired in order to use them ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Poláková M,Šesták S,Lattová E,Petruš L,Mucha J,Tvaroška I,Kóňa J

    更新日期:2011-03-01 00:00:00

  • Recent advance of peptide-based molecules and nonpeptidic small-molecules modulating PD-1/PD-L1 protein-protein interaction or targeting PD-L1 protein degradation.

    abstract::Tumor immunotherapy has made great progress in recent years. In the tumor microenvironment, the binding of PD-1 and its ligand PD-L1 can promote tumor immune escape and tumor survival. Clinical studies have indicated that antibodies blocking PD-1 and PD-L1 have reliable effects on many advanced malignant tumors. Howev...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审


    authors: Pan C,Yang H,Lu Y,Hu S,Wu Y,He Q,Dong X

    更新日期:2021-01-09 00:00:00

  • Indexing molecules for their hERG liability.

    abstract::The human Ether-a-go-go-Related-Gene (hERG) potassium (K(+)) channel is liable to drug-inducing blockage that prolongs the QT interval of the cardiac action potential, triggers arrhythmia and possibly causes sudden cardiac death. Early prediction of drug liability to hERG K(+) channel is therefore highly important and...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Rayan A,Falah M,Raiyn J,Da'adoosh B,Kadan S,Zaid H,Goldblum A

    更新日期:2013-07-01 00:00:00

  • Conjugation of substituted ferrocenyl to thiadiazine as apoptosis-inducing agents targeting the Bax/Bcl-2 pathway.

    abstract::Ferrocene compounds are a class of biologically active compounds that has antitumour and antifungal properties. This study investigated the induction of apoptosis in human fibrosarcoma cells (HT1080) after treatment with a series of 6-ferrocenyl-3-subsituted7H-1,2,4-triazolo[3,4-b]- 1,3,4-thiadiazine (FTFs). We found ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章


    authors: Miao R,Wei J,Lv M,Cai Y,Du Y,Hui X,Wang Q

    更新日期:2011-10-01 00:00:00