Urea/thiourea derivatives of quinazolinone-lysine conjugates: synthesis and structure-activity relationships of a new series of antimicrobials.

Abstract:

:Synthesis of a series of urea/thiourea/acetamide/sulphonamide derivatives of quinazolinones conjugated lysine has been reported. Structures of the products have been determined by standard spectroscopical studies. All the compounds have been screened for their antibacterial studies and structure-activity relationship has been developed. The activity profile revealed that the compounds containing urea and thiourea functionalities along with fluoro group have exerted a highly potent activity. Thus, the title compounds represent a novel class of potent antimicrobial agents.

journal_name

Eur J Med Chem

authors

Suresha GP,Suhas R,Kapfo W,Gowda DC

doi

10.1016/j.ejmech.2011.03.041

subject

Has Abstract

pub_date

2011-06-01 00:00:00

pages

2530-40

issue

6

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(11)00256-X

journal_volume

46

pub_type

杂志文章
  • 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

  • Synthesis and in vitro stability of nucleoside 5'-phosphonate derivatives.

    abstract::Nucleoside derivatives are largely synthesized and tested to investigate their influence on platelet aggregation. It's well known that P2Y receptors play an important role in the regulation of platelet function and, as consequence, in controlling atherothrombotic events. The research of compounds that antagonize P2Y(1...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.04.045

    authors: Vertuani S,Baldisserotto A,Varani K,Borea PA,De Marcos Maria Cruz B,Ferraro L,Manfredini S,Dalpiaz A

    更新日期:2012-08-01 00:00:00

  • 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 scaff...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.09.003

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

    更新日期:2015-10-20 00:00:00

  • Structure-based virtual screening for identification of novel 11beta-HSD1 inhibitors.

    abstract::Structure-based pharmacophore models were built by using LigandScout and used for virtual screening of the SPECS database to identify new potential 11beta-HSD1 inhibitors. As a refinement of the results obtained from virtual 3D pharmacophore screening, the best fitting virtual hits were subjected to docking study. The...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.06.005

    authors: Yang H,Shen Y,Chen J,Jiang Q,Leng Y,Shen J

    更新日期:2009-03-01 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

    doi:10.1016/j.ejmech.2014.07.050

    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 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

  • Synthesis of [11C]FEDAA1106 as a new PET imaging probe of peripheral benzodiazepine receptor expression.

    abstract::Peripheral benzodiazepine receptor (PBR) is associated with neuroinflammation and tumor progression. [(11)C]DAA1106 and [(18)F]FEDAA1106 are two promising radioligands for positron emission tomography (PET) imaging of PBR. This study was designed to develop a new radiolabeled analog of [(11)C]DAA1106 and [(18)F]FEDAA1...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.08.001

    authors: Wang M,Gao M,Hutchins GD,Zheng QH

    更新日期:2009-06-01 00:00:00

  • Design, synthesis, and fungicidal evaluation of a series of novel 5-methyl-1H-1,2,3-trizole-4-carboxyl amide and ester analogues.

    abstract::Succinate dehydrogenase inhibitors (SDHIs) are efficient fungicides that are widely used to control plant diseases caused by phytopathogenic fungi, although their effectiveness is undermined by the development of resistance across a range of different fungi. One of the most common structural features of SDHIs is their...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.08.029

    authors: Wang ZJ,Gao Y,Hou YL,Zhang C,Yu SJ,Bian Q,Li ZM,Zhao WG

    更新日期:2014-10-30 00:00:00

  • Novel acylureidoindolin-2-one derivatives as dual Aurora B/FLT3 inhibitors for the treatment of acute myeloid leukemia.

    abstract::A series of 6-acylureido derivatives containing a 3-(pyrrol-2-ylmethylidene)indolin-2-one scaffold were synthesized as potential dual Aurora B/FLT3 inhibitors by replacing the 6-arylureido moiety in 6-arylureidoindolin-2-one-based multi-kinase inhibitors. (Z)-N-(2-(pyrrolidin-1-yl)ethyl)-5-((6-(3-(2-fluoro-4-methoxybe...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.07.108

    authors: Jagtap AD,Chang PT,Liu JR,Wang HC,Kondekar NB,Shen LJ,Tseng HW,Chen GS,Chern JW

    更新日期:2014-10-06 00:00:00

  • Structure-based modification of carbonyl-diphenylpyrimidines (Car-DPPYs) as a novel focal adhesion kinase (FAK) inhibitor against various stubborn cancer cells.

    abstract::A family of carbonyl-substituted diphenylpyrimidine derivatives (Car-DPPYs) with strong activity against focal adhesion kinase (FAK), were described in this manuscript. Among them, compounds 7a (IC50 = 5.17 nM) and 7f (IC50 = 2.58 nM) displayed equal anti-FAK enzymatic activity to the lead compound TAE226 (6.79 nM). I...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.04.004

    authors: Wang L,Ai M,Yu J,Jin L,Wang C,Liu Z,Shu X,Tang Z,Liu K,Luo H,Guan W,Sun X,Ma X

    更新日期:2019-06-15 00:00:00

  • Synthesis of novel triazole derivatives as inhibitors of cytochrome P450 14alpha-demethylase (CYP51).

    abstract::A series of 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-[(4-substitutedphenyl)-piperazin-1-yl]-propan-2-ols have been designed and synthesized on the basis of the structure-activity relationships and antimycotic mechanism of azole antifungal agents. Their structures were confirmed by elemental analysis, IR, MS ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2007.01.006

    authors: Sun QY,Xu JM,Cao YB,Zhang WN,Wu QY,Zhang DZ,Zhang J,Zhao HQ,Jiang YY

    更新日期:2007-09-01 00:00:00

  • Single-molecule chemiluminescent photosensitizer for a self-activating and tumor-selective photodynamic therapy of cancer.

    abstract::While photodynamic therapy is known for significant advantages over conventional cancer therapies, its dependence on light has limited it to treating tumors on or just under the skin or on the outer lining of organs/cavities. Herein, we have developed a single-molecule photosensitizer capable of intracellular self-act...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.111683

    authors: Pinto da Silva L,Núnez-Montenegro A,Magalhães CM,Ferreira PJO,Duarte D,González-Berdullas P,Rodríguez-Borges JE,Vale N,Esteves da Silva JCG

    更新日期:2019-12-01 00:00:00

  • Synthesis and biological evaluation of novel aliphatic amido-quaternary ammonium salts for anticancer chemotherapy: part II.

    abstract::A series of novel aliphatic amido-quaternary ammonium salts were synthesized and evaluated for their anticancer effects involving induction of RhoB. Most of these compounds, featuring open-ring forms of aliphatic amido-quaternary ammonium salts, exhibited potent anti-proliferative activities in human cancer cell lines...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.12.063

    authors: Yang JS,Song D,Ko WJ,Kim B,Kim BK,Park SK,Won M,Lee K,Lee K,Kim HM,Han G

    更新日期:2013-05-01 00:00:00

  • 4-Indolyl-N-hydroxyphenylacrylamides as potent HDAC class I and IIB inhibitors in vitro and in vivo.

    abstract::A series of 4,5-indolyl-N-hydroxyphenylacrylamides, as HDAC inhibitors, has been synthesized and evaluated in vitro and in vivo. 4-Indolyl compounds 13 and 17 functions as potent inhibitors of HDAC1 (IC50 1.28 nM and 1.34 nM) and HDAC 2 (IC50 0.90 and 0.53 nM). N-Hydroxy-3-{4-[2-(1H-indol-4-yl)-ethylsulfamoyl]-phenyl}...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.03.079

    authors: Mehndiratta S,Wang RS,Huang HL,Su CJ,Hsu CM,Wu YW,Pan SL,Liou JP

    更新日期:2017-07-07 00:00:00

  • Synthesis of a new series of heterocyclic scaffolds for medicinal purposes.

    abstract::A new series of substituted 8-fluro-4H-pyrimido[2,1-b] [1,3]benzothiazole-4-ones () substituted 7-methyl-4H-isoxazolo[2,3-a]pyrimidin-4-ones, and substituted 2-methyl-5,6,7,8-tetrahydro-9H-isoxazolo[2,3-a]pyridopyrimidin-9-ones, compounds I-VII, have been prepared via condensation of beta-keto esters with 2-aminopyrid...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2006.03.025

    authors: Hilal HS,Ali-Shtayeh MS,Arafat R,Al-Tel T,Voelter W,Barakat A

    更新日期:2006-08-01 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

  • Design, synthesis and biological evaluation of piperazinyl-β-carbolinederivatives as anti-leishmanial agents.

    abstract::Molecular hybridization is a ligand based drug design approach is well known recent medicinal chemistry to design anti-parasitic agents. In the present study, we have designed a series of (1-phenyl-9H-pyrido [3,4-b]indol-3-yl) (4-phenylpiperazin-1-yl)methanone derivatives using molecular hybridization approach. Design...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.03.022

    authors: Ashok P,Chander S,Smith TK,Sankaranarayanan M

    更新日期:2018-04-25 00:00:00

  • An orally available inverse agonist of estrogen-related receptor gamma showed expanded efficacy for the radioiodine therapy of poorly differentiated thyroid cancer.

    abstract::Estrogen-related receptor gamma (ERRγ) is the NR3B subgroup of associated transcription factors. In this report, a new generation of a potent and selective ERRγ inverse agonist (25) with good biocompatibility was proposed. We also explored the potential of the newly developed compound 25 in the PDTC model to expand th...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112501

    authors: Kim J,Hwang H,Yoon H,Lee JE,Oh JM,An H,Ji HD,Lee S,Cha E,Ma MJ,Kim DS,Lee SJ,Kadayat TM,Song J,Lee SW,Jeon JH,Park KG,Lee IK,Jeon YH,Chin J,Cho SJ

    更新日期:2020-11-01 00:00:00

  • QSAR study for a novel series of ortho disubstituted phenoxy analogues of alpha1-adrenoceptor antagonist WB4101.

    abstract::On the basis of the affinities at the alpha1a-, alpha1b- and alpha1d-adrenoceptors and the 5-HT1A receptor of a previous series of sixteen 2-[(2-phenoxyethyl)aminomethyl]-1,4-benzodioxanes ortho monosubstituted at the phenoxy moiety, a number of ortho disubstituted analogues were designed, synthesized in both the enan...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2006.04.004

    authors: Pallavicini M,Fumagalli L,Gobbi M,Bolchi C,Colleoni S,Moroni B,Pedretti A,Rusconi C,Vistoli G,Valoti E

    更新日期:2006-09-01 00:00:00

  • Discovery and optimization of adamantane carboxylic acid derivatives as potent diacylglycerol acyltransferase 1 inhibitors for the potential treatment of obesity and diabetes.

    abstract::We have developed a series of adamantane carboxylic acid derivatives exhibiting potent diacylglycerol acyltransferase 1 (DGAT1) inhibitory activities. Optimization of the series led to the discovery of E-adamantane carboxylic acid compound 43c, which showed excellent in vitro activity with an IC50 value of 5 nM agains...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.06.043

    authors: Pagire SH,Pagire HS,Lee GB,Han SJ,Kwak HJ,Kim JY,Kim KY,Rhee SD,Ryu JI,Song JS,Bae MA,Park MJ,Kim D,Lee DH,Ahn JH

    更新日期:2015-08-28 00:00:00

  • Novel cross-link breaker based on zwitterion structure: synthesis, structure and druggability studies.

    abstract::It has been universally acknowledged that the increase in cardiac and vascular stiffness is due to the formation of advanced glycosylation end-products (AGEs). Research on the stable form of 3-(carboxymethyl)-4-methylthiazol bromide sodium salt (C6H7BrNNaO2S) showed that it had a notable effect on breaking the AGEs. T...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.07.033

    authors: Cao S,Zhou XB,Zhang H,Li S,Zhong W

    更新日期:2013-10-01 00:00:00

  • Synthesis and in vitro antiproliferative activity of new 1,3,4-oxadiazole derivatives possessing sulfonamide moiety.

    abstract::Synthesis of a new series of 1,3,4-oxadiazole derivatives possessing sulfonamide moiety is described. Their in vitro antiproliferative activities against NCI-58 human cancer cell lines of nine different cancer types were tested. Compound 1k with p-methoxybenzenesulfonamido moiety showed the highest mean %inhibition va...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.11.011

    authors: Gamal El-Din MM,El-Gamal MI,Abdel-Maksoud MS,Yoo KH,Oh CH

    更新日期:2015-01-27 00:00:00

  • N1-Alkylated 3,4-dihydropyrimidine-2(1H)-ones: Convenient one-pot selective synthesis and evaluation of their calcium channel blocking activity.

    abstract::It has been found that selective N1-alkylation of 3,4-dihydropyrimidine-2(1H)-ones can be achieved under solvent-less, mild phase transfer catalytic (PTC) conditions with tetrabutylammonium hydrogen sulfate and 50% aqueous NaOH as the catalyst and base, respectively. The procedure is tolerant to substitutional variati...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.10.002

    authors: Singh K,Arora D,Poremsky E,Lowery J,Moreland RS

    更新日期:2009-05-01 00:00:00

  • Novel hydrazone moiety-bearing aminopyrimidines as selective inhibitors of epidermal growth factor receptor T790M mutant.

    abstract::The epidermal growth factor receptor (EGFR) T790M mutant is found in approximately 50% of clinically acquired resistance to gefitinib among patients with non-small cell lung cancer (NSCLC). Here, a series of novel aminopyrimidines bearing a hydrazone moiety were identified as potent and selective EGFR inhibitors. Comp...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.09.031

    authors: Qin M,Wang T,Xu B,Ma Z,Jiang N,Xie H,Gong P,Zhao Y

    更新日期:2015-11-02 00:00:00

  • Synthesis, evaluation against Leishmania amazonensis and cytotoxicity assays in macrophages of sixteen new congeners Morita-Baylis-Hillman adducts.

    abstract::We report the design, synthesis, in vitro evaluation against Leishmania amazonensis (IC(50)), cytotoxicity assays in macrophages (CC(50)), and selectivity index (SICC(50)/IC(50)) of sixteen new congeners aromatic Morita-Baylis-Hillman adducts 1-16. The 1-16 were prepared in good to excellent yields (58%-97%) from the ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.06.036

    authors: Silva FP,de Assis PA,Junior CG,de Andrade NG,da Cunha SM,Oliveira MR,Vasconcellos ML

    更新日期:2011-09-01 00:00:00

  • Second-generation sulfonamide inhibitors of D-glutamic acid-adding enzyme: activity optimisation with conformationally rigid analogues of D-glutamic acid.

    abstract::D-Glutamic acid-adding enzyme (MurD) catalyses the essential addition of d-glutamic acid to the cytoplasmic peptidoglycan precursor UDP-N-acetylmuramoyl-l-alanine, and as such it represents an important antibacterial drug-discovery target enzyme. Based on a series of naphthalene-N-sulfonyl-d-Glu derivatives synthesise...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.04.011

    authors: Sosič I,Barreteau H,Simčič M,Sink R,Cesar J,Zega A,Grdadolnik SG,Contreras-Martel C,Dessen A,Amoroso A,Joris B,Blanot D,Gobec S

    更新日期:2011-07-01 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 of new isoxazoline-based acidic amino acids and investigation of their affinity and selectivity profile at ionotropic glutamate receptors.

    abstract::The synthesis of four new isoxazoline-based amino acids being analogues of previously described glutamate receptor ligands is reported and their affinity for ionotropic glutamate receptors is analyzed in comparison with that of selected model compounds. Molecular modelling investigations have been carried out to ratio...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.12.020

    authors: Pinto A,Conti P,Grazioso G,Tamborini L,Madsen U,Nielsen B,De Micheli C

    更新日期:2011-02-01 00:00:00

  • Synthesis by microwave irradiation and binding properties of novel 5-HT(1A) receptor ligands.

    abstract::This work reports the synthesis by microwave irradiation and the binding tests on the 5-HT(1A), 5-HT(2A) and 5-HT(2C) receptors of new substituted piperazines in order to identify selective ligands for 5-HT(1A) subtype receptor. Conventional heating and microwave irradiation of the reactions was compared. Synthesis by...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:

    authors: Caliendo G,Fiorino F,Perissutti E,Severino B,Gessi S,Cattabriga E,Borea PA,Santagada V

    更新日期:2001-11-01 00:00:00

  • 2-hydroxyisoquinoline-1,3(2H,4H)-diones as inhibitors of HIV-1 integrase and reverse transcriptase RNase H domain: influence of the alkylation of position 4.

    abstract::We report herein the synthesis of a series of fifteen 2-hydroxyisoquinoline-1,3(2H,4H)-dione derivatives. Alkyl and arylalkyl groups were introduced on position 4 of the basis scaffold. All the compounds presented poor inhibitory properties against HIV-1 reverse transcriptase ribonuclease H (RNase H). Four compounds i...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.11.033

    authors: Billamboz M,Bailly F,Lion C,Calmels C,Andréola ML,Witvrouw M,Christ F,Debyser Z,De Luca L,Chimirri A,Cotelle P

    更新日期:2011-02-01 00:00:00