New 3-methylquinoxaline-2-carboxamide 1,4-di-N-oxide derivatives as anti-Mycobacterium tuberculosis agents.

Abstract:

:Mycobacterium tuberculosis (M.Tb) is a bacillus capable of causing a chronic and fatal condition in humans known as tuberculosis (TB). It is estimated that there are 8 million new cases of TB per year and 3.1 million infected people die annually. Thirty-six new amide quinoxaline 1,4-di-N-oxide derivatives have been synthesized and evaluated as potential anti-tubercular agents, obtaining biological values similar to the reference compound, Rifampin (RIF).

journal_name

Bioorg Med Chem

authors

Ancizu S,Moreno E,Solano B,Villar R,Burguete A,Torres E,Pérez-Silanes S,Aldana I,Monge A

doi

10.1016/j.bmc.2010.02.024

subject

Has Abstract

pub_date

2010-04-01 00:00:00

pages

2713-9

issue

7

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(10)00145-8

journal_volume

18

pub_type

杂志文章
  • An altered zinc-binding site confers resistance to a covalent inactivator of New Delhi metallo-beta-lactamase-1 (NDM-1) discovered by high-throughput screening.

    abstract::Due to the global threat of antibiotic resistance mediated by New Delhi metallo-beta-lactamase-1 (NDM-1) and the lack of structurally diverse inhibitors reported for this enzyme, we developed screening and counter-screening assays for manual and automated formats. The manual assay is a trans-well absorbance-based endp...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.03.031

    authors: Thomas PW,Spicer T,Cammarata M,Brodbelt JS,Hodder P,Fast W

    更新日期:2013-06-01 00:00:00

  • Tools and methodologies capable of isolating and identifying a target molecule for a bioactive compound.

    abstract::Elucidating the mechanism of action of bioactive compounds, such as commonly used pharmaceutical drugs and biologically active natural products, in the cells and the living body is important in drug discovery research. To this end, isolation and identification of target protein(s) for the bioactive compound are essent...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.12.022

    authors: Sakamoto S,Hatakeyama M,Ito T,Handa H

    更新日期:2012-03-15 00:00:00

  • Effect of the complexation with cyclodextrins on the in vitro antiviral activity of ganciclovir against human cytomegalovirus.

    abstract::The toxicity of the molecules currently used in the treatment of human cytomegalovirus (HCMV) in immunocompromised hosts often causes interruption of the therapy. Cyclodextrins (Cds), oligosaccharides possessing a hydrophobic cavity, have the property of forming inclusion complexes with a great number of molecules, im...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(00)00247-9

    authors: Nicolazzi C,Abdou S,Collomb J,Marsura A,Finance C

    更新日期:2001-02-01 00:00:00

  • Design, synthesis, biological evaluation and docking studies of pterostilbene analogs inside PPARalpha.

    abstract::Pterostilbene, a naturally occurring analog of resveratrol, has previously shown PPARalpha activation in H4IIEC3 cells and was found to decrease cholesterol levels in animals. In this study, analogs of pterostilbene were synthesized and their ability to activate PPARalpha was investigated. Among analogs that was synth...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.01.051

    authors: Mizuno CS,Ma G,Khan S,Patny A,Avery MA,Rimando AM

    更新日期:2008-04-01 00:00:00

  • Evaluation of fosmidomycin analogs as inhibitors of the Synechocystis sp. PCC6803 1-deoxy-D-xylulose 5-phosphate reductoisomerase.

    abstract::Analogs of the antibiotic fosmidomycin, an inhibitor of the methylerythritol phosphate pathway to isoprenoids, were synthesized and evaluated against the recombinant Synechocystis sp. PCC6803 1-deoxy-d-xylulose 5-phosphate reductoisomerase (DXR). Fosfoxacin, the phosphate analog of fosmidomycin, and its acetyl congene...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.11.012

    authors: Woo YH,Fernandes RP,Proteau PJ

    更新日期:2006-04-01 00:00:00

  • Piperine analogs as potent Staphylococcus aureus NorA efflux pump inhibitors.

    abstract::Based on our recent findings that piperine is a potent Staphylococcus aureus NorA efflux pump inhibitor (EPI), 38 piperine analogs were synthesized and bioevaluated for their EPI activity. Twenty-five of them were found active with potentiating activity equivalent or more than known EPIs like reserpine, carsonic acid ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.09.042

    authors: Sangwan PL,Koul JL,Koul S,Reddy MV,Thota N,Khan IA,Kumar A,Kalia NP,Qazi GN

    更新日期:2008-11-15 00:00:00

  • Synthesis and photodynamic activity of zinc(II) phthalocyanine derivatives bearing methoxy and trifluoromethylbenzyloxy substituents in homogeneous and biological media.

    abstract::Two zinc(II) phthalocyanines bearing either four methoxy (ZnPc 3) or trifluoromethylbenzyloxy (ZnPc 4) substituents have been synthesized by a two-step procedure starting from 4-nitrophthalonitrile. Absorption and fluorescence spectroscopic studies were analyzed in different media. These compounds are essentially non-...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.10.003

    authors: Yslas EI,Rivarola V,Durantini EN

    更新日期:2005-01-03 00:00:00

  • Discovery of thiochroman and chroman derivatives as pure antiestrogens and their structure-activity relationship.

    abstract::In order to develop pure antiestrogens, a series of 7-hydroxy-3-(4-hydroxyphenyl)-3-methylchroman and 7-hydroxy-3-(4-hydroxyphenyl)-3-methylthiochroman derivatives with sulfoxide containing side chains at the 4-position were designed, synthesized, and evaluated. Among them, compounds 14b and 24b functioned as pure ant...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.03.020

    authors: Kanbe Y,Kim MH,Nishimoto M,Ohtake Y,Kato N,Tsunenari T,Taniguchi K,Ohizumi I,Kaiho S,Morikawa K,Jo JC,Lim HS,Kim HY

    更新日期:2006-07-15 00:00:00

  • Enzyme-catalysed enantioselective hydrolysis of racemic naproxen nitrile.

    abstract::The bacterial strain Rhodococcus butanica (ATCC 21197), which exhibits nitrilase and nitrile hydratase/amidase activities, catalyses the enantioselective hydrolysis of racemic naproxen nitrile (R/S)-1 to furnish a moderate enantiomeric excess of (S)-naproxen (S)-3. Racemic naproxen amide (R/S)-2 is not a good substrat...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/0968-0896(94)85022-4

    authors: Effenberger F,Böhme J

    更新日期:1994-07-01 00:00:00

  • A novel fluorescent probe based on naphthalimide for imaging nitroreductase (NTR) in bacteria and cells.

    abstract::A nitroreductase (NTR) responsive fluorescent probe, Na-NO2, comprising p-nitrobenzyl as the unique recognition group and 1,8-naphthalimide as fluorophore, was synthesized. Na-NO2 showed remarkable fluorescence "turn-on" signal in the presence of NTR under DMSO/H2O (1:19, v/v) buffered with PBS (pH = 7) solution in th...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2019.115280

    authors: Zhang Z,Lv T,Tao B,Wen Z,Xu Y,Li H,Liu F,Sun S

    更新日期:2020-02-01 00:00:00

  • Synthesis and evaluation of symmetric acyclic nucleoside bisphosphonates as inhibitors of the Plasmodium falciparum, Plasmodium vivax and human 6-oxopurine phosphoribosyltransferases and the antimalarial activity of their prodrugs.

    abstract::Two new series of symmetric acyclic nucleoside bisphosphonates (ANbPs) have been synthesised as potential inhibitors of the Plasmodium falciparum (Pf) and vivax (Pv) 6-oxopurine phosphoribosyltransferases. The structural variability between these symmetric ANbPs lies in the number of atoms in the two acyclic linkers c...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.05.048

    authors: Špaček P,Keough DT,Chavchich M,Dračínský M,Janeba Z,Naesens L,Edstein MD,Guddat LW,Hocková D

    更新日期:2017-08-01 00:00:00

  • Transdermal penetration behaviour of drugs: CART-clustering, QSPR and selection of model compounds.

    abstract::A set of 116 structurally very diverse compounds, mainly drugs, was characterized by 1630 molecular descriptors. The biological property modelled in this study was the transdermal permeability coefficient logK(p). The main objective was to find a limited set of suitable model compounds for skin penetration studies. Th...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.07.050

    authors: Baert B,Deconinck E,Van Gele M,Slodicka M,Stoppie P,Bodé S,Slegers G,Vander Heyden Y,Lambert J,Beetens J,De Spiegeleer B

    更新日期:2007-11-15 00:00:00

  • Discovery of melanin-concentrating hormone receptor R1 antagonists using high-throughput synthesis.

    abstract::A structure-activity study on benzylpiperidine 1 was accomplished by utilizing high-throughput synthesis. Three focused libraries were designed and synthesized to quickly develop SAR. Further optimization led to the discovery of compound 2, an MCH receptor R1 antagonist with over 400-fold improvement in biological act...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.11.046

    authors: Su J,McKittrick BA,Tang H,Czarniecki M,Greenlee WJ,Hawes BE,O'Neill K

    更新日期:2005-03-01 00:00:00

  • 2D QSAR and similarity studies on cruzain inhibitors aimed at improving selectivity over cathepsin L.

    abstract::Hologram quantitative structure-activity relationships (HQSAR) were applied to a data set of 41 cruzain inhibitors. The best HQSAR model (Q(2)=0.77; R(2)=0.90) employing Surflex-Sim, as training and test sets generator, was obtained using atoms, bonds, and connections as fragment distinctions and 4-7 as fragment size....

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.10.048

    authors: Freitas RF,Oprea TI,Montanari CA

    更新日期:2008-01-15 00:00:00

  • Molecular modifications on carboxylic acid derivatives as potent histone deacetylase inhibitors: Activity and docking studies.

    abstract::In the light of known HDAC inhibitors, 33 carboxylic acid derivatives were tested to understand the structural requirements for HDAC inhibition activity. Several modifications were applied to develop the structure-activity relationships of carboxylic acid HDAC inhibitors. HDAC inhibition activities were investigated i...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.05.042

    authors: Bora-Tatar G,Dayangaç-Erden D,Demir AS,Dalkara S,Yelekçi K,Erdem-Yurter H

    更新日期:2009-07-15 00:00:00

  • Design, synthesis and biological evaluation of aryl-substituted sialyl Lewis X mimetics prepared via cross-metathesis of C-fucopeptides.

    abstract::Several aryl substituted C-fucopeptides have been developed as sialyl Lewis X mimetics. Although the compounds have a much simpler structure compared to SLe(x), up to 3-times higher binding affinity toward E-selectin and > 1000 times toward P-selectin was observed. Furthermore, a convenient strategy for generating a n...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(98)00245-4

    authors: Huwe CM,Woltering TJ,Jiricek J,Weitz-Schmidt G,Wong CH

    更新日期:1999-05-01 00:00:00

  • Reaction of thymidine and ascorbic acid induced by UV in the presence of salicylic acid.

    abstract::When a neutral solution of thymidine and ascorbic acid was irradiated with UV light of wavelength longer than 300 nm in the presence of salicylic acid as a photosensitizer, six product peaks appeared in an HPLC chromatogram in addition to small amounts of thymidine dimers. The six products were identified as three pai...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2019.115046

    authors: Suzuki T,Kishida Y

    更新日期:2019-10-01 00:00:00

  • Tautomeric and non-tautomeric N-substituted 2-iminobenzimidazolines as new lead compounds for the design of anti-influenza drugs: An in vitro study.

    abstract::A series of 1,3-disubstituted 2-iminobenzimidazolines as well as a number of their tautomeric analogs were synthesized. The synthesized compounds were tested for their cytotoxicity against MDCK cells and for inhibiting activity against influenza virus A/California/07/09 (H1N1)pdm09. Based on the results obtained, 50% ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.09.036

    authors: Zarubaev VV,Morkovnik AS,Divaeva LN,Karpinskaya LA,Borodkin GS

    更新日期:2016-11-15 00:00:00

  • Discovery of novel quinoline-based mTOR inhibitors via introducing intra-molecular hydrogen bonding scaffold (iMHBS): The design, synthesis and biological evaluation.

    abstract::A series of quinoline derivatives featuring the novelty of introducing intra-molecular hydrogen bonding scaffold (iMHBS) were designed, synthesized and biologically evaluated for their mTOR inhibitory activity, as well as anti-proliferative efficacies against HCT-116, PC-3 and MCF-7 cell lines. As a result, six compou...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.11.003

    authors: Ma X,Lv X,Qiu N,Yang B,He Q,Hu Y

    更新日期:2015-12-15 00:00:00

  • Synthesis, tuberculosis inhibitory activity, and SAR study of N-substituted-phenyl-1,2,3-triazole derivatives.

    abstract::The aim of this work was to describe the synthesis, the in vitro anti-Mycobacterium tuberculosis profile, and the structure-activity relationship (SAR) study of new N-substituted-phenyl-1,2,3-triazole-4-carbaldehydes (3a-l). The reactions of aromatic amine hydrochlorides with diazomalonaldehyde (1) produced several N-...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.08.019

    authors: Costa MS,Boechat N,Rangel EA,da Silva Fde C,de Souza AM,Rodrigues CR,Castro HC,Junior IN,Lourenço MC,Wardell SM,Ferreira VF

    更新日期:2006-12-15 00:00:00

  • Synthesis and evaluation of 11β-(4-substituted phenyl) estradiol analogs: transition from estrogen receptor agonists to antagonists.

    abstract:INTRODUCTION:As part of our program to develop estrogen receptor (ER) targeted imaging and therapeutic agents we chose to evaluate 11β-substituted estradiol analogs as a representative scaffold. Previous synthetic studies provided an entry into this class of compounds and other work indicated that 11β-(substituted aryl...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.04.041

    authors: Hanson RN,Hua E,Hendricks JA,Labaree D,Hochberg RB

    更新日期:2012-06-15 00:00:00

  • Synthesis, anticoagulant and PIVKA-II induced by new 4-hydroxycoumarin derivatives.

    abstract::The action of the coumarin-type drugs and related compounds is reviewed to their VKOR antagonistic effects. In our study, twenty 3-pyridinyl, pyrimidinyl and pyrazolyl-4-hydroxycoumarin derivatives were synthesized. A comparative in vivo (CT, PT determination) and in vitro (measurement of PIVKA-II levels) anticoagulan...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.04.009

    authors: Abdelhafez OM,Amin KM,Batran RZ,Maher TJ,Nada SA,Sethumadhavan S

    更新日期:2010-05-15 00:00:00

  • Syntheses of ferulic acid derivatives and their suppressive effects on cyclooxygenase-2 promoter activity.

    abstract::Novel ferulic acid derivatives in which feruloyl groups were attached to the hydroxyl groups of myo-inositol 1,3,5-orthoformate derivatives were synthesized. These feruloyl-myo-inositols suppressed the cyclooxygenase-2 (COX-2) promoter activity in a concentration-dependent manner. Among the examined compounds, compoun...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(01)00386-8

    authors: Hosoda A,Ozaki Y,Kashiwada A,Mutoh M,Wakabayashi K,Mizuno K,Nomura E,Taniguchi H

    更新日期:2002-04-01 00:00:00

  • The search for potent, small molecule NNRTIs: A review.

    abstract::AIDS has become the leading pandemic disease, and is the cause of death worldwide. Presently, HAART treatment, a combination of reverse transcriptase (RT) and protease inhibitors is also unsuccessful due to the virus getting resistant to the drugs because of mutational changes. Two types of RT inhibitors exist namely ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.bmc.2009.06.060

    authors: Prajapati DG,Ramajayam R,Yadav MR,Giridhar R

    更新日期:2009-08-15 00:00:00

  • A new metabotropic glutamate receptor agonist with in vivo anti-allodynic activity.

    abstract::As part of the vital search towards improved therapeutic agents for the treatment of neuropathic pain, the central nervous system glutamate receptors have become a major focus of research. Outlined herein are the syntheses of two new biologically active 3'-cycloalkyl-substituted carboxycyclopropylglycines, utilizing n...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.06.051

    authors: Stanley NJ,Hutchinson MR,Kvist T,Nielsen B,Mathiesen JM,Bräuner-Osborne H,Avery TD,Tiekink ER,Pedersen DS,Irvine RJ,Abell AD,Taylor DK

    更新日期:2010-08-15 00:00:00

  • Astersedifolioside A-C, three new oleane-type saponins with antiproliferative activity.

    abstract::A phytochemical analysis of Aster sedifolius has led to the isolation of three novel triterpenoid saponins, based on an oleane-type skeleton and named astersedifolioside A (1), B (2) and C (3). On the basis of chemical, and 2D NMR and mass spectrometry data, the structures of the new compounds were elucidated as 3-O-[...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.06.042

    authors: Corea G,Iorizzi M,Lanzotti V,Cammareri M,Conicella C,Laezza C,Bifulco M

    更新日期:2004-09-15 00:00:00

  • Synthesis and biological relationships of 3',6-substituted 2-phenyl-4-quinolone-3-carboxylic acid derivatives as antimitotic agents.

    abstract::As part of a continuing search for potential anticancer drug candidates in the 2-phenyl-4-quinolone series, 3',6-substituted 2-phenyl-4-quinolone-3-carboxylic acid derivatives and their salts were synthesized and evaluated. Preliminary screening showed that carboxylic acid analogs containing a m-fluoro substituted 2-p...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.09.041

    authors: Lai YY,Huang LJ,Lee KH,Xiao Z,Bastow KF,Yamori T,Kuo SC

    更新日期:2005-01-03 00:00:00

  • Synthesis and biological evaluation of nonpeptide mimetics of omega-conotoxin GVIA.

    abstract::A benzothiazole-derived compound (4a) designed to mimic the C(alpha)-C(beta) bond vectors and terminal functionalities of Lys2, Tyr13 and Arg17 in omega-conotoxin GVIA was synthesised, together with analogues (4b-d), which had each side-chain mimic systematically truncated or eliminated. The affinity of these compound...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.05.040

    authors: Baell JB,Duggan PJ,Forsyth SA,Lewis RJ,Lok YP,Schroeder CI

    更新日期:2004-08-01 00:00:00

  • Search for alpha-helical propensity in the receptor-bound conformation of glucagon-like peptide-1.

    abstract::To elucidate the receptor-bound conformation of glucagon-like peptide-1 (GLP-1), a series of conformationally constrained GLP-1 analogues were synthesized by introducing lactam bridges between Lys(i) and Glu(i)(+4) to form alpha-helices at various positions. The activity and affinity of these analogues to GLP-1 recept...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.10.006

    authors: Murage EN,Schroeder JC,Beinborn M,Ahn JM

    更新日期:2008-12-01 00:00:00

  • Synthesis and elastase-inhibiting activity of 2-pyridinyl-isothiazol-3(2H)-one 1,1-dioxides.

    abstract::The synthesis of a series of new isothiazol-3(2H)-one 1,1-dioxides with halogenated (mostly fluorinated) pyridinyl and pentafluorophenyl substituents at 2-position is reported. These compounds (18-24) became easily accessible from 2-thiocyanato-1-carboxaldehydes and aminopyridines, pentafluoroaniline, respectively, by...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.07.049

    authors: Eilfeld A,González Tanarro CM,Frizler M,Sieler J,Schulze B,Gütschow M

    更新日期:2008-09-01 00:00:00