当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY期刊下所有文献 > 1,2,3-triazole-, arylamino- and thio-substituted 1,4-naphthoquinones: potent antitumor activity, electrochemical aspects, and bioisosteric replacement of C-ring-modified lapachones.

1,2,3-triazole-, arylamino- and thio-substituted 1,4-naphthoquinones: potent antitumor activity, electrochemical aspects, and bioisosteric replacement of C-ring-modified lapachones.

Abstract：

:1,2,3-Triazole-, arylamino- and thio-substituted naphthoquinones (24, 8, and 2 representatives, respectively) were synthesized in moderate yields and evaluated against several human cancer cell lines (blood, ovarian, breast, central nervous system, colon, and prostate cancers and melanoma), showing, for some of them, IC50 values below 2 μM. The cytotoxic potential of the tested naphthoquinones was also assayed on non-tumor cells such as human peripheral blood mononucluear cells (PBMC) and two murine fibroblast lines (L929 and V79 cells). α-Lapachone- and nor-α-lapachone-based 1,2,3-triazoles and arylamino-substituted naphthoquinones showed potent cytotoxicity against different cancer cell lines. The compounds may represent promising new lead derivatives for anticancer drug development. The electrochemical properties of selected compounds were evaluated in an attempt to correlate them with antitumor activity.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

da Cruz EH,Hussene CM,Dias GG,Diogo EB,de Melo IM,Rodrigues BL,da Silva MG,Valença WO,Camara CA,de Oliveira RN,de Paiva YG,Goulart MO,Cavalcanti BC,Pessoa C,da Silva Júnior EN

doi

10.1016/j.bmc.2014.01.033

subject

Has Abstract

pub_date

2014-03-01 00:00:00

pages

1608-19

issue

5

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(14)00061-3

journal_volume

22

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY文献大全
  • Secondary assembly of bile salts mediated by beta-cyclodextrin-terbium(III) complex.

    abstract：:A fluorescent cyclodextrin-Tb(III) complex is successfully synthesized and can include bile salts in its hydrophobic cavities. Therefore, it can efficiently induce the secondary assembly of small bile salt primary micelles to large micelle aggregates, and the aggregation process can be easily observed by transmission ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2006.06.002

    authors： Liu Y,Zhang N,Chen Y,Chen GS

    更新日期：2006-10-01 00:00:00

  • Controllable synthesis of polymerizable ester and amide prodrugs of acyclovir by enzyme in organic solvent.

    abstract：:A facile control of the acylation position at the primary hydroxyl and amino of acyclovir, respectively, was achieved and five polymerizable acyclovir prodrugs were synthesized. Various reaction conditions were studied in detail. Thus, lipase acrylic resin from Candida antarctica (CAL-B) in pyridine or acetone showed ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2005.12.050

    authors： Li X,Wu Q,Lv DS,Lin XF

    更新日期：2006-05-15 00:00:00

  • Pharmacodynamics and pharmacokinetics studies of phenoxazinium derivatives for antimalarial agent.

    abstract：:In vivo antimalarial drug candidates screening test was carried out on a series of water-soluble 3,7-bis(dialkylamino)phenoxazin-5-ium derivatives. Among them, 3-(diethylamino)-7-(piperidin-1-yl)phenoxazin-5-ium chloride (SSJ-206) showing highest efficacy was chosen for further pharmcodynamics and pharmacokinetics stu...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.01.021

    authors： Yang M,Ge JF,Arai C,Itoh I,Fu Q,Ihara M

    更新日期：2009-02-15 00:00:00

  • Novel quinolinequinone antitumor agents: structure-metabolism studies with NAD(P)H:quinone oxidoreductase (NQO1).

    abstract：:A series of quinolinequinones bearing various substituents has been synthesized, and the effects of substituents on the metabolism of the quinones by recombinant human NAD(P)H:quinone oxidoreductase (hNQO1) was studied. A range of quinolinequinones were selected for study, and were specifically designed to probe the e...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.01.021

    authors： Fryatt T,Pettersson HI,Gardipee WT,Bray KC,Green SJ,Slawin AM,Beall HD,Moody CJ

    更新日期：2004-04-01 00:00:00

  • Synthesis of novel 7-oxo and 7-hydroxy trifluoroallocolchicinoids with cytotoxic effect.

    abstract：:The synthesis of 7-oxo and 7-hydroxy trifluoroallocolchicinoids was achieved through the intramolecular cyclization of o-phenyl-β-phenylalanines. The resulting compounds were evaluated for their cytotoxic activity against KB cells and their inhibitory effect towards the polymerization of tubulin. The results yielded s...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2012.02.043

    authors： Chosson E,Santoro F,Rochais C,Santos JS,Legay R,Thoret S,Cresteil T,Sinicropi MS,Besson T,Dallemagne P

    更新日期：2012-04-15 00:00:00

  • Kinetic controlled affinity labeling of target enzyme with thioester chemistry.

    abstract：:High specificity has been an important feature in affinity labeling for target profiling. Especially, to label targets via rapidly progressing reactions with consumption of ligand (probe), high specificity of reaction with common functional groups of target protein should be achieved without reactions with similar gro...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2016.05.059

    authors： Tomohiro T,Nakabayashi M,Sugita Y,Morimoto S

    更新日期：2016-08-01 00:00:00

  • Structure-activity correlations for beta-phenethylamines at human trace amine receptor 1.

    abstract：:A cell line in which RD-HGA16 cells were stably transfected with the hTAAR 1 receptor was created and utilized to carry out a systematic evaluation of a series of beta-phenethylamines. Fair agreement was observed with data obtained for aryl and ethylene chain substituted analogs in an AV12-664 cell line in which hemag...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.06.009

    authors： Lewin AH,Navarro HA,Mascarella SW

    更新日期：2008-08-01 00:00:00

  • Effective discrimination of antimalarial potency of artemisinin compounds based on quantum chemical calculations of their reaction mechanism.

    abstract：:The reaction mechanism of 12 antimalarial artemisinin compounds with two competitive pathways was studied by means of quantum chemical calculations using the IMOMO(B3LYP/6-31(d,p):HF/3-21G) method. The oxygen-centered radicals, carbon-centered radicals, and transition states (TS) in both pathways were geometrically op...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2005.07.003

    authors： Tonmunphean S,Parasuk V,Kokpol S

    更新日期：2006-04-01 00:00:00

  • A prenylbisabolane with NF-kappaB inhibiting properties from Cascarilla (Croton eluteria).

    abstract：:Investigation of the bark of Croton eluteria Bennett for biologically active compounds has led to the isolation of the new prenylbisabolane 3, whose structure was assessed by spectroscopic methods. The corresponding known enone 4 and the eudesmane sesquiterpene 2 were also obtained. Compound 3 proved active in selecti...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2005.04.025

    authors： Campagnuolo C,Fattorusso E,Petrucci F,Taglialatela-Scafati O,Appendino G,Marquez N,Muñoz E

    更新日期：2005-07-01 00:00:00

  • Optimization and determination of the absolute configuration of a series of potent inhibitors of human papillomavirus type-11 E1-E2 protein-protein interaction: a combined medicinal chemistry, NMR and computational chemistry approach.

    abstract：:We have previously reported the discovery and initial SAR optimization of the first series of inhibitors of the human papillomavirus type-11 (HPV11) E1-E2 protein-protein interaction. These inhibitors featured an indandione system spiro-fused onto an all syn substituted tetrahydrofuran ring. In this paper, we report n...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.01.036

    authors： Goudreau N,Cameron DR,Déziel R,Haché B,Jakalian A,Malenfant E,Naud J,Ogilvie WW,O'meara J,White PW,Yoakim C

    更新日期：2007-04-01 00:00:00

  • Hole filling and library optimization: application to commercially available fragment libraries.

    abstract：:Compound libraries comprise an integral component of drug discovery in the pharmaceutical and biotechnology industries. While in-house libraries often contain millions of molecules, this number pales in comparison to the accessible space of drug-like molecules. Therefore, care must be taken when adding new compounds t...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2012.03.037

    authors： An Y,Sherman W,Dixon SL

    更新日期：2012-09-15 00:00:00

  • Peptide T-araC conjugates: solid-phase synthesis and biological activity of N4-(acylpeptidyl)-araC.

    abstract：:Due to the capability of peptidyl derivatives of araC to behave as prodrugs of this antimetabolite, and because of the well known biological properties of peptide T and its analogues (in particular that of targeting CD4+ cells), new peptide T-araC conjugates were prepared and tested in vitro for antiproliferative acti...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(99)00317-x

    authors： Manfredini S,Marastoni-M,Tomatis R,Durini E,Spisani S,Pani A,Marceddu T,Musiu C,Marongiu ME,La Colla P

    更新日期：2000-03-01 00:00:00

  • A class of sulfonamide carbonic anhydrase inhibitors with neuropathic pain modulating effects.

    abstract：:A series of benzene sulfonamide carbonic anhydrase (CA, EC 4.2.1.1) inhibitors which incorporate lipophilic 4-alkoxy- and 4-aryloxy moieties, together with several derivatives of ethoxzolamide and sulfanilamide are reported. These derivatives were investigated as inhibitors of the metalloenzyme carbonic anhydrase (CA,...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.02.027

    authors： Carta F,Di Cesare Mannelli L,Pinard M,Ghelardini C,Scozzafava A,McKenna R,Supuran CT

    更新日期：2015-04-15 00:00:00

  • Polycyclic aromatic compounds as anticancer agents: synthesis and biological evaluation of dibenzofluorene derivatives.

    abstract：:Highly regioselective electrophilic substitution of dibenzofluorene was achieved and the nitro derivative was transformed to a variety of new anticancer agents. ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(00)00213-3

    authors： Becker FF,Mukhopadhyay C,Hackfeld L,Banik I,Banik BK

    更新日期：2000-12-01 00:00:00

  • 1,2,4-Triazole and 1,3,4-oxadiazole analogues: Synthesis, MO studies, in silico molecular docking studies, antimalarial as DHFR inhibitor and antimicrobial activities.

    abstract：:1,2,4-Triazole and 1,3,4-oxadiazole analogues are of interest due to their potential activity against microbial and malarial infections. In search of suitable antimicrobial and antimalarial compounds, we report here the synthesis, characterization and biological activities of 1,2,4-triazole and 1,3,4-oxadiazole analog...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.05.054

    authors： Thakkar SS,Thakor P,Doshi H,Ray A

    更新日期：2017-08-01 00:00:00

  • 1,3,7-Triethyl-substituted xanthines--possess nanomolar affinity for the adenosine A1 receptor.

    abstract：:Adenosine A1 receptors are attracting great interest as drug targets for their role in cognitive deficits. Antagonism of the adenosine A1 receptor may offer therapeutic benefits in complex neurological diseases, such as Alzheimer's and Parkinson's disease. The aim of this study was to discover potential selective aden...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.09.012

    authors： Van der Walt MM,Terre'Blanche G

    更新日期：2015-10-15 00:00:00

  • Stereostructure-based differences in the interactions of cardiotoxic local anesthetics with cholesterol-containing biomimetic membranes.

    abstract：:Amide-type pipecoloxylidide local anesthetics, bupivacaine, and ropivacaine, show cardiotoxic effects with the potency depending on stereostructures. Cardiotoxic drugs not only bind to cardiomyocyte membrane channels to block them but also modify the physicochemical property of membrane lipid bilayers in which channel...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2011.04.030

    authors： Tsuchiya H,Ueno T,Mizogami M

    更新日期：2011-06-01 00:00:00

  • Piperidine variations in search for non-imidazole histamine H(3) receptor ligands.

    abstract：:Synthesis and biological evaluation of the novel histamine H(3) receptor ligands is described. Two series of ethers (aliphatic and aromatic) have been prepared by four different methods. Compounds were evaluated for their affinities at recombinant human H(3) receptor stably expressed in CHO cells. The ethers show from...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.07.071

    authors： Łazewska D,Kuder K,Ligneau X,Schwartz JC,Schunack W,Stark H,Kieć-Kononowicz K

    更新日期：2008-09-15 00:00:00

  • Optimization of thiazole analogues of resveratrol for induction of NAD(P)H:quinone reductase 1 (QR1).

    abstract：:NAD(P)H:quinone reductase 1 (QR1) belongs to a class of enzymes called cytoprotective enzymes. It exhibits its cancer protective activity mainly by inhibiting the formation of intracellular semiquinone radicals, and by generating α-tocopherolhydroquinone, which acts as a free radical scavenger. It is therefore believe...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2012.10.006

    authors： Mayhoub AS,Marler L,Kondratyuk TP,Park EJ,Pezzuto JM,Cushman M

    更新日期：2012-12-15 00:00:00

  • Identification of sortase substrates by specificity profiling.

    abstract：:Sortases catalyze the attachment of surface proteins to the peptidoglycan layer of gram-positive bacteria and further represent powerful tools of protein chemistry. During catalysis sortases cleave a donor substrate containing the LPxTG (x=any amino acid) sorting motif under formation of an enzyme-bound thioester and ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.06.033

    authors： Schmohl L,Bierlmeier J,von Kügelgen N,Kurz L,Reis P,Barthels F,Mach P,Schutkowski M,Freund C,Schwarzer D

    更新日期：2017-09-15 00:00:00

  • Further optimization of sulfonamide analogs as EP1 receptor antagonists: synthesis and evaluation of bioisosteres for the carboxylic acid group.

    abstract：:4-{[2-[(2-Furylsulfonyl)(isobutyl)amino]-5-(trifluoromethyl)phenoxy]methyl}benzoic acid analogs 2a and b and a series of the acid analogs, in which the carboxylic acid residue of 2b was replaced with various kinds of carboxylic acid bioisosteres, were synthesized and evaluated as EP1 receptor antagonists. Compound 2b ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2006.06.067

    authors： Naganawa A,Matsui T,Ima M,Saito T,Murota M,Aratani Y,Kijima H,Yamamoto H,Maruyama T,Ohuchida S,Nakai H,Toda M

    更新日期：2006-11-01 00:00:00

  • 4-Fluoro-N-butylphenylacetamide (H6) inhibits cell growth via cell-cycle arrest and apoptosis in human cervical cancer cells.

    abstract：:Phenylacetate induced tumor cytostasis and differentiation. The chemotherapeutic function of the compound in lung cancer has been previously reported, however, whether or not phenylacetate performs other activities is not known. In this study, the potential usage of synthetic phenylacetate derivatives, 4-fluoro-N-buty...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.11.028

    authors： Liu CH,Huang LJ,Kuo SC,Lee TH,Tsai KJ,Chan HC

    更新日期：2009-01-01 00:00:00

  • Synthesis and SAR studies of benzyl ether derivatives as potent orally active S1P₁ agonists.

    abstract：:We report herein the synthesis and structure-activity relationships (SAR) of a series of benzyl ether compounds as an S1P₁ receptor modulator. From our SAR studies, the installation of substituents onto the central benzene ring of 2a was revealed to potently influence the S1P₁ and S1P₃ agonistic activities, in particu...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2014.05.035

    authors： Tsuji T,Suzuki K,Nakamura T,Goto T,Sekiguchi Y,Ikeda T,Fukuda T,Takemoto T,Mizuno Y,Kimura T,Kawase Y,Nara F,Kagari T,Shimozato T,Yahara C,Inaba S,Honda T,Izumi T,Tamura M,Nishi T

    更新日期：2014-08-01 00:00:00

  • Aurine tricarboxylic acid, a potent metal-chelating inhibitor of NFkappaB-DNA binding.

    abstract：:The metal-interaction of aurine tricarboxylic acid (ATA) and its inhibitory effect on the DNA binding of NFkappaB were studied. Chemical speciation and spectroscopic studies have shown the strong interaction of ATA with metal ions present in the biological systems. EPR, FTIR and electronic spectral studies indicated t...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(00)00109-7

    authors： Sharma RK,Garg BS,Kurosaki H,Goto M,Otsuka M,Yamamoto T,Inoue J

    更新日期：2000-07-01 00:00:00

  • Toward the development of chemoprevention agents (III): synthesis and anti-inflammatory activities of a new class of 5-glycylamino-2-substituted-phenyl-1,3-dioxacycloalkanes.

    abstract：:A new series of 5-glycylamino-2-substituted-phenyl-1,3-dioxacycloalkanes were designed and synthesized. The anti-inflammatory activities of these compounds were tested using the xylene-induced mouse ear edema model. Sixteen of these new compounds exhibited comparable or better anti-inflammatory activities than aspirin...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.11.017

    authors： Bi L,Zhao M,Gu K,Wang C,Ju J,Peng S

    更新日期：2008-02-15 00:00:00

  • The phytoalexins brassilexin and camalexin inhibit cyclobrassinin hydrolase, a unique enzyme from the fungal pathogen Alternaria brassicicola.

    abstract：:Alternaria brassicicola is a fungal pathogen of many agriculturally important cruciferous crops. Cyclobrassinin hydrolase (CH) is an enzyme produced by A. brassicicola that catalyzes the transformation of the cruciferous phytoalexin cyclobrassinin into S-methyl[(2-sulfanyl-1H-indolyl-3)methyl]carbamothioate. The purif...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2013.11.005

    authors： Pedras MS,Minic Z

    更新日期：2014-01-01 00:00:00

  • Photodynamic inactivation of Candida albicans using bridged polysilsesquioxane films doped with porphyrin.

    abstract：:Novel photoactive bridged polysilsesquioxane films were prepared by doped with a porphyrin derivative. The films were formed by acid-catalyzed polycondensation reaction of a precursor of a bridged silsesquioxane, based on the reaction product of (glycidoxypropyl)trimethoxysilane with n-dodecylamine in the presence of ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2012.05.012

    authors： Alvarez MG,Gómez ML,Mora SJ,Milanesio ME,Durantini EN

    更新日期：2012-07-01 00:00:00

  • Novel steroidal vinyl fluorides as inhibitors of steroid C17(20) lyase.

    abstract：:20-fluoro-17(20)-pregnenolone derivatives were designed as enol mimics of pregnenolone. All of the targeted, novel fluoroolefins were potent inhibitors of C17(20) lyase. ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(01)00354-6

    authors： Burkhart JP,Weintraub PM,Gates CA,Resvick RJ,Vaz RJ,Friedrich D,Angelastro MR,Bey P,Peet NP

    更新日期：2002-04-01 00:00:00

  • Synthesis and receptor binding affinity of new selective GluR5 ligands.

    abstract：:Two hybrid analogues of the kainic acid receptor agonists, 2-amino-3-(5-tert-butyl-3-hydroxy-4-isoxazolyl)propionic acid (ATPA) and (2S,4R)-4-methylglutamic acid ((2S,4R)-4-Me-Glu), were designed, synthesized, and characterized in radioligand binding assays using cloned ionotropic and metabotropic glutamic acid recept...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(00)00304-7

    authors： Bunch L,Johansen TH,Bräuner-Osborne H,Stensbøl TB,Johansen TN,Krogsgaard-Larsen P,Madsen U

    更新日期：2001-04-01 00:00:00

  • A novel assay revealed that ribonucleotide reductase is functionally important for interstrand DNA crosslink repair.

    abstract：:Cells have evolved complex biochemical pathways for DNA interstrand crosslink (ICL) removal. Despite the chemotherapeutic importance of ICL repair, there have been few attempts to identify which mechanistic DNA repair inhibitor actually inhibits ICL repair. To identify such compounds, a new and robust ICL repair assay...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.09.045

    authors： Fujii N,Evison BJ,Actis ML,Inoue A

    更新日期：2015-11-01 00:00:00