Selective antiproliferative activity of hydroxynaphthyl-beta-D-xylosides.

Abstract:

:The antiproliferative activity of the 14 isomeric monoxylosylated dihydroxynaphthalenes has been tested in vitro toward normal HFL-1 and 3T3 A31 cells as well as transformed T24 and 3T3 SV40 cells. The antiproliferative effect toward HFL-1 cells was correlated with the polarity of the compounds. However, in the case of transformed T24 cells, some compounds showed a clearly different behavior resulting in a selective antiproliferative effect. No such correlation was found for normal 3T3 A31 or virus transformed 3T3 SV40 cells, nor for the free aglycon. These results suggest that the antiproliferative activity shown by naphthoxylosides is diverse in different cell lines and dependent on the nature of the aglycon. The antiproliferative effect of 2-(6-hydroxynaphthyl)-beta-D-xylopyranoside, in contrast to inactive 2-naphthyl-beta-D-xylopyranoside, on T24 cells was accompanied by increased apoptosis as indicated by a TUNEL assay.

journal_name

J Med Chem

authors

Jacobsson M,Ellervik U,Belting M,Mani K

doi

10.1021/jm0512488

keywords:

subject

Has Abstract

pub_date

2006-03-23 00:00:00

pages

1932-8

issue

6

eissn

0022-2623

issn

1520-4804

journal_volume

49

pub_type

杂志文章
  • Binding of sulfonyl-containing arylalkylamines at human 5-HT6 serotonin receptors.

    abstract::Various sulfonyl-containing compounds (e.g. sulfonamides, sulfones) bind at human 5-HT6 serotonin receptors, but it has been difficult relating the binding mode(s) of such agents to one another, even though many possess a common SO2 moiety, to identify a common pharmacophore model(s). On the basis of the hypothesis th...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm060469q

    authors: Sikazwe D,Bondarev ML,Dukat M,Rangisetty JB,Roth BL,Glennon RA

    更新日期:2006-08-24 00:00:00

  • Amide Bond Bioisosteres: Strategies, Synthesis, and Successes.

    abstract::The amide functional group plays a key role in the composition of biomolecules, including many clinically approved drugs. Bioisosterism is widely employed in the rational modification of lead compounds, being used to increase potency, enhance selectivity, improve pharmacokinetic properties, eliminate toxicity, and acq...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1021/acs.jmedchem.0c00530

    authors: Kumari S,Carmona AV,Tiwari AK,Trippier PC

    更新日期:2020-11-12 00:00:00

  • Direct NMR Probing of Hydration Shells of Protein Ligand Interfaces and Its Application to Drug Design.

    abstract::Fragment-based drug design exploits initial screening of low molecular weight compounds and their concomitant affinity improvement. The multitude of possible chemical modifications highlights the necessity to obtain structural information about the binding mode of a fragment. Herein we describe a novel NMR methodology...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/acs.jmedchem.7b00845

    authors: Geist L,Mayer M,Cockcroft XL,Wolkerstorfer B,Kessler D,Engelhardt H,McConnell DB,Konrat R

    更新日期:2017-11-09 00:00:00

  • Synthesis and antitumor activities of novel pyrimidine derivatives of 2,3-O,O-dibenzyl-6-deoxy-L-ascorbic acid and 4,5-didehydro-5,6- dideoxy-L-ascorbic acid.

    abstract::The new pyrimidine derivatives of 2,3-O, O-dibenzyl-6-deoxy-L-ascorbic acid (8-10) were synthesized by condensation of uracil and its 5-fluoro- and 5-trifluoromethyl-substituted derivatives with 4-(5,6-epoxypropyl)-2, 3-O,O-dibenzyl-L-ascorbic acid (7), while pyrimidine derivatives of 4,5-didehydro-5,6-dideoxy-L-ascor...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm0009540

    authors: Raić-Malić S,Svedruzić D,Gazivoda T,Marunović A,Hergold-Brundić A,Nagl A,Balzarini J,De Clercq E,Mintas M

    更新日期:2000-12-14 00:00:00

  • 5-Cyano-2'-deoxyuridine 5'-phosphate: a potent competitive inhibitor of thymidylate synthetase.

    abstract::The 5'-phosphate (1) of the antiviral nucleoside 5-cyano-2'-deoxyuridine was synthesized and evaluated for inhibition of thymidylate synthetase purified from methotrexate-resistant Lactobacillus casei. Compound 1 was a potent competitive inhibitor with a K1 of 0.55 microns. Irreversible enzyme inhibition by this compo...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm00195a028

    authors: Chang CT,Edwards MW,Torrence PF,Mertes MP

    更新日期:1979-09-01 00:00:00

  • Studies of cardiotonic agents. 8. Synthesis and biological activities of optically active 6-(4-(benzylamino)-7-quinazolinyl)-4,5-dihydro-5-methyl-3(2H)- pyridazinone (KF15232).

    abstract::We previously reported that (+/-)-6-(4-(benzylamino)-7-quinazolinyl)-4,5- dihydro-5-methyl-3(2H)-pyridazinone (+/-)-1, KF15232) showed potent cardiotonic activity with a strong myofibrillar Ca(2+)-sensitizing effect. As an extension of our work, we attempted to synthesize optically active 1. (+/-)-4-(4-(Benzylamino)-7...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm950197j

    authors: Nomoto Y,Takai H,Ohno T,Nagashima K,Yao K,Yamada K,Kubo K,Ichimura M,Mihara A,Kase H

    更新日期:1996-01-05 00:00:00

  • Antimicrobial and cytotoxic properties of 9,10-dihydrophenanthrenes: structure-activity studies on juncusol.

    abstract::The antimicrobial and cytotoxic properties of a series of 9,10-dihydrophenanthrenes structurally related to juncusol (1a), a postulated phytoalexin with confirmed cytotoxic properties, are detailed. Two simple 9,10-dihydrophenanthrenes, 2,7-dihydroxy-3,8-dimethyl-9,10-dihydrophenanthrene (2h, desvinyljuncusol) and 2-h...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm00148a031

    authors: Boger DL,Mitscher LA,Mullican MD,Drake SD,Kitos P

    更新日期:1985-10-01 00:00:00

  • Syntheses of potent, selective, and orally bioavailable indazole-pyridine series of protein kinase B/Akt inhibitors with reduced hypotension.

    abstract::Compound 7 was identified as a potent (IC50 = 14 nM), selective, and orally bioavailable (F = 70% in mouse) inhibitor of protein kinase B/Akt. While promising efficacy was observed in vivo, this compound showed effects on depolarization of Purkinje fibers in an in vitro assay and CV hypotension in vivo. Guided by an X...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm0701019

    authors: Zhu GD,Gandhi VB,Gong J,Thomas S,Woods KW,Song X,Li T,Diebold RB,Luo Y,Liu X,Guan R,Klinghofer V,Johnson EF,Bouska J,Olson A,Marsh KC,Stoll VS,Mamo M,Polakowski J,Campbell TJ,Martin RL,Gintant GA,Penning TD,

    更新日期:2007-06-28 00:00:00

  • Synthesis and antitumor activity of tropolone derivatives. 5.

    abstract::As part of a study on the structure-activity relationship of antitumor-active tropolone derivatives, a series of bistropone analogues, related to potently active bistropolone 1a, were synthesized and tested for their antitumor activity in in vitro (KB cell) and in vivo (leukemia P388 in mice) systems. The methoxytropo...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm00390a022

    authors: Yamato M,Hashigaki K,Sakai J,Takeuchi Y,Tsukagoshi S,Tashiro T,Tsuruo T

    更新日期:1987-07-01 00:00:00

  • Synthesis and sigma binding properties of 2'-substituted 5,9 alpha-dimethyl-6,7-benzomorphans.

    abstract::The synthesis and sigma 1 and sigma 2 binding properties of several (+)- and (-)-2-benzyl- and 2-dimethylallyl-2'-substituted-5,9 alpha-dimethyl-6,7-benzomorphans (3 and 4) are presented. In agreement with previously reported binding data for 2-substituted 5,9 alpha-dimethyl-2'-hydroxy-6,7-benzomorphans (N-substituted...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm00015a022

    authors: Danso-Danquah R,Bai X,Zhang X,Mascarella SW,Williams W,Sine B,Bowen WD,Carroll FI

    更新日期:1995-07-21 00:00:00

  • Development of potent and selective phosphinic peptide inhibitors of angiotensin-converting enzyme 2.

    abstract::Angiotensin-converting enzyme 2 (ACE2), a recently identified human homologue of angiotensin-converting enzyme, is a zinc metallocarboxypeptidase which may play a unique role in cardiovascular and renal function. Here we report the discovery of potent and selective inhibitors of ACE2, which have been identified by eva...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm701275z

    authors: Mores A,Matziari M,Beau F,Cuniasse P,Yiotakis A,Dive V

    更新日期:2008-04-10 00:00:00

  • Regulating bioactivity of Cu2+ bis-1,10-phenanthroline artificial metallonucleases with sterically functionalized pendant carboxylates.

    abstract::The synthetic chemical nuclease, [Cu(1,10-phenanthroline)2](2+), has stimulated research within metallonuclease development and in the area of cytotoxic metallodrug design. Our analysis reveals, however, that this agent is "promiscuous" as it binds both dsDNA and protein biomolecules, without specificity, and induces ...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm401465m

    authors: Prisecaru A,McKee V,Howe O,Rochford G,McCann M,Colleran J,Pour M,Barron N,Gathergood N,Kellett A

    更新日期:2013-11-14 00:00:00

  • Energy aspects of oil/water partition leading to the novel hydrophobic parameters for the analysis of quantitative structure-activity relationships.

    abstract::Partition properties, that is partition coefficients and enthalpies (delta Hp degree) and entropies (delta Sp degree) of partition, have been measured for 50 benzoic acids in the 1-octanol/water system, and their role in QSAR (quantitative structure-activity relationship) analysis examined. The novel hydrophobic param...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm00096a014

    authors: Da YZ,Ito K,Fujiwara H

    更新日期:1992-09-04 00:00:00

  • Antiviral activity of C-alkylated purine nucleosides obtained by cross-coupling with tetraalkyltin reagents.

    abstract::2-, 6-, And 8-alkylated (methyl, ethyl, and vinyl) adenosine analogues were synthesized by a palladium-catalyzed cross-coupling of a tetraalkyltin with the halogenated purine nucleosides. The synthesis of the 8-substituted analogues was accomplished using a transient protection procedure. The 6-alkylated-9-beta-D-ribo...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm00072a013

    authors: Van Aerschot AA,Mamos P,Weyns NJ,Ikeda S,De Clercq E,Herdewijn PA

    更新日期:1993-10-01 00:00:00

  • NMR-Based screening with competition water-ligand observed via gradient spectroscopy experiments: detection of high-affinity ligands.

    abstract::Water-ligand observed via gradient spectroscopy (WaterLOGSY) represents a powerful method for primary NMR screening in the identification of compounds interacting with macromolecules, including proteins and DNA or RNA fragments. The method is useful for the detection of compounds binding to a receptor with binding aff...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm011122k

    authors: Dalvit C,Fasolini M,Flocco M,Knapp S,Pevarello P,Veronesi M

    更新日期:2002-06-06 00:00:00

  • Solid phase synthesis and biological activity of tuftsin conjugates.

    abstract::New tuftsin/retro-tuftsin conjugates were designed and synthesized using a classical fluorenylmethoxycarbonyl (Fmoc) solid phase procedure. All the peptide conjugates were divided into three series: 1,4-dihydroxyanthraquinone (type A), 1-nitroacridine (type B), and 4-carboxyacridone (type C) derivatives. In type A con...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm200002s

    authors: Kukowska-Kaszuba M,Dzierzbicka K,Serocki M,Skladanowski A

    更新日期:2011-04-14 00:00:00

  • Antioxidant-Inspired Drug Discovery: Antitumor Metabolite Is Formed in Situ from a Hydroxycinnamic Acid Derivative upon Free-Radical Scavenging.

    abstract::Cancer cells generally possess higher levels of reactive oxygen species than normal cells, and this can serve as a possible therapeutic target. In this proof-of-concept study, an antioxidant-inspired drug discovery strategy was evaluated using a hydroxycinnamic acid derivative. The processing of oxidized mixtures of p...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/acs.jmedchem.8b01994

    authors: Fási L,Di Meo F,Kuo CY,Stojkovic Buric S,Martins A,Kúsz N,Béni Z,Dékány M,Balogh GT,Pesic M,Wang HC,Trouillas P,Hunyadi A

    更新日期:2019-02-14 00:00:00

  • 7-[3-(1-piperidinyl)propoxy]chromenones as potential atypical antipsychotics.

    abstract::Compound 1 (1-benzyl-3-methyl-4-[4-(4-fluorophenyl)-4-oxobutyl]piperazine), a synthetic intermediate identified as a potential atypical antipsychotic, was selected as the starting point for pharmacological improvement. From 1, sequential structural variations were conducted in order to improve its potency and oral bio...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm950894b

    authors: Bolós J,Gubert S,Anglada L,Planas JM,Burgarolas C,Castelló JM,Sacristán A,Ortiz JA

    更新日期:1996-07-19 00:00:00

  • Structure-activity relationships at the 5-position of thiolactomycin: an intact (5R)-isoprene unit is required for activity against the condensing enzymes from Mycobacterium tuberculosis and Escherichia coli.

    abstract::Thiolactomycin inhibits bacterial cell growth through inhibition of the beta-ketoacyl-ACP synthase activity of type II fatty acid synthases. The effect of modifications of the 5-position isoprenoid side chain on both IC(50) and MIC were determined. Synthesis and screening of a structurally diverse set of 5-position an...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm050825p

    authors: Kim P,Zhang YM,Shenoy G,Nguyen QA,Boshoff HI,Manjunatha UH,Goodwin MB,Lonsdale J,Price AC,Miller DJ,Duncan K,White SW,Rock CO,Barry CE 3rd,Dowd CS

    更新日期:2006-01-12 00:00:00

  • Synthesis, resolution, absolute stereochemistry, and enantioselectivity of 3',4'-dihydroxynomifensine.

    abstract::3',4'-Dihydroxynomifensine, 8-amino-1,2,3,4-tetrahydro-4-(3,4-dihydroxyphenyl)-2-methylisoquinoli ne (1a), is an agonist of dopamine receptors in central and peripheral systems. Since this dopamine receptor agonist bears an asymmetric center at position 4, its synthesis and resolution were undertaken as part of a stud...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm00367a006

    authors: Dandridge PA,Kaiser C,Brenner M,Gaitanopoulos D,Davis LD,Webb RL,Foley JJ,Sarau HM

    更新日期:1984-01-01 00:00:00

  • Synthesis and biological evaluation of a new series of hexahydro-2H-pyrano[3,2-c]quinolines as novel selective σ1 receptor ligands.

    abstract::The synthesis and pharmacological activity of a new series of hexahydro-2H-pyrano[3,2-c]quinoline derivatives as potent σ1 receptor (σ1R) ligands are reported. This family, which does not contain the highly basic amino group usually present in other σ1R ligands, showed high selectivity over the σ2 receptor (σ2R). The ...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm400181k

    authors: Díaz JL,Christmann U,Fernández A,Luengo M,Bordas M,Enrech R,Carro M,Pascual R,Burgueño J,Merlos M,Benet-Buchholz J,Cerón-Bertran J,Ramírez J,Reinoso RF,Fernández de Henestrosa AR,Vela JM,Almansa C

    更新日期:2013-05-09 00:00:00

  • Interaction of noncompetitive inhibitors with the alpha3beta2 nicotinic acetylcholine receptor investigated by affinity chromatography and molecular docking.

    abstract::A molecular model of the alpha3beta2 nAChR lumen channel was constructed and hydrophobic clefts were observed near the receptor gate. Docking simulations indicated that ligand-nAChR complexes were formed by hydrophobic interactions with the cleft and hydrogen bond interactions. The equilibrium constants and associatio...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm070784s

    authors: Jozwiak K,Ravichandran S,Collins JR,Moaddel R,Wainer IW

    更新日期:2007-11-29 00:00:00

  • General synthesis of β-alanine-containing spider polyamine toxins and discovery of nephila polyamine toxins 1 and 8 as highly potent inhibitors of ionotropic glutamate receptors.

    abstract::Certain spiders contain large pools of polyamine toxins, which are putative pharmacological tools awaiting further discovery. Here we present a general synthesis strategy for this class of toxins and prepare five structurally varied polyamine toxins. Electrophysiological testing at three ionotropic glutamate receptor ...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm301255m

    authors: Lucas S,Poulsen MH,Nørager NG,Barslund AF,Bach TB,Kristensen AS,Strømgaard K

    更新日期:2012-11-26 00:00:00

  • Cyclopropane-based conformational restriction of histamine. (1S,2S)-2-(2-aminoethyl)-1-(1H-imidazol-4-yl)cyclopropane, a highly selective agonist for the histamine H3 receptor, having a cis-cyclopropane structure.

    abstract::A series of cyclopropane-based conformationally restricted analogues of histamine, the "folded" cis-analogues, i.e., (1S,2R)-2-(aminomethyl)-1-(1H-imidazol-4-yl)cyclopropane (11), (1S,2S)-2-(2-aminoethyl)-1-(1H-imidazol-4-yl)cyclopropane (13), and their enantiomers ent-11 and ent-13, and the "extended" trans-analogues...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm020415q

    authors: Kazuta Y,Hirano K,Natsume K,Yamada S,Kimura R,Matsumoto S,Furuichi K,Matsuda A,Shuto S

    更新日期:2003-05-08 00:00:00

  • Design, synthesis, and characterization of a dual modality positron emission tomography and fluorescence imaging agent for monoclonal antibody tumor-targeted imaging.

    abstract::A novel lysine-based trifunctional chelate 3 was designed, synthesized, and characterized and bears both a chelating moiety (CHX-A' ') for sequestering radiometals (86Y or 111In) and the near-infrared dye Cy5.5 for dual modality PET (or SPECT) and fluorescence imaging, respectively. Successful conjugation of 3 to the ...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm070657w

    authors: Xu H,Baidoo K,Gunn AJ,Boswell CA,Milenic DE,Choyke PL,Brechbiel MW

    更新日期:2007-09-20 00:00:00

  • 5'-Substituted Amiloride Derivatives as Allosteric Modulators Binding in the Sodium Ion Pocket of the Adenosine A2A Receptor.

    abstract::The sodium ion site is an allosteric site conserved among many G protein-coupled receptors (GPCRs). Amiloride 1 and 5-(N,N-hexamethylene)amiloride 2 (HMA) supposedly bind in this sodium ion site and can influence orthosteric ligand binding. The availability of a high-resolution X-ray crystal structure of the human ade...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/acs.jmedchem.6b00142

    authors: Massink A,Louvel J,Adlere I,van Veen C,Huisman BJ,Dijksteel GS,Guo D,Lenselink EB,Buckley BJ,Matthews H,Ranson M,Kelso M,IJzerman AP

    更新日期:2016-05-26 00:00:00

  • Ligand-Based Design of Allosteric Retinoic Acid Receptor-Related Orphan Receptor γt (RORγt) Inverse Agonists.

    abstract::Retinoic acid receptor-related orphan receptor γt (RORγt) is a nuclear receptor associated with the pathogenesis of autoimmune diseases. Allosteric inhibition of RORγt is conceptually new, unique for this specific nuclear receptor, and offers advantages over traditional orthosteric inhibition. Here, we report a highly...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/acs.jmedchem.9b01372

    authors: Meijer FA,Doveston RG,de Vries RMJM,Vos GM,Vos AAA,Leysen S,Scheepstra M,Ottmann C,Milroy LG,Brunsveld L

    更新日期:2020-01-09 00:00:00

  • Synthesis and antitumor activity of 7- and 9-(6'-deoxy-alpha-L-talofuranosyl) hypoxanthine and 9-(6'-deoxy-alpha-L-talofuranosyl)-6-thiopurine.

    abstract::Reaction of 6-deoxy-2,3,5-tris-O-(p-nitrobenzoyl)-L-talofuranosyl bromide (1) with the trimethylsilyl derivative of hypoxanthine, followed by removal of blocking groups, afforded 9- (6) and 7-(6'-deoxy-alpha-L-talofuranosyl)hypoxanthine (7). A study of the published optical rotations and circular dichroic (CD) spectra...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm00364a032

    authors: Nelson V,El Khadem HS

    更新日期:1983-10-01 00:00:00

  • Design of novel, potent, noncovalent inhibitors of thrombin with nonbasic P-1 substructures: rapid structure-activity studies by solid-phase synthesis.

    abstract::Study of surface representations of the inhibitor-bound thrombin P-1 pocket revealed a lipophilic recess in this pocket which is not occupied by any known inhibitor. Solid-phase synthesis was used to generate benzylamides of D-diphenylAlaPro by aminolysis of Boc dipeptide Kaiser resin. The resulting amides inhibited t...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm9706933

    authors: Lumma WC Jr,Witherup KM,Tucker TJ,Brady SF,Sisko JT,Naylor-Olsen AM,Lewis SD,Lucas BJ,Vacca JP

    更新日期:1998-03-26 00:00:00

  • S-adenosylmethionine decarboxylase inhibitors: new aryl and heteroaryl analogues of methylglyoxal bis(guanylhydrazone).

    abstract::A series of 3-acylbenzamidine (amidino)hydrazones 7a-h, the corresponding (hetero)aromatic congeners 7i-p, and 3,3'-bis-amidino-biaryls 25a-e were synthesized. The hydrazones 7a-p were prepared by conversion of the corresponding acyl nitriles 1a,c-d,i,n-p to the imido esters 3a,c-d,i and the amidines 5a,c-d,h-i, follo...

    journal_title:Journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1021/jm00053a007

    authors: Stanek J,Caravatti G,Capraro HG,Furet P,Mett H,Schneider P,Regenass U

    更新日期:1993-01-08 00:00:00