Synthesis and biology of bis-xylosylated dihydroxynaphthalenes.

Abstract:

:The 10 analogous bis-xylosylated dihydroxynaphthalenes have been synthesized and their chemical and biological properties investigated. The yield of the xylosylation reactions can be correlated to the electrostatic potential, and thus to the nucleophilicity, for the oxygen atoms of the dihydroxynaphthalenes. The bis-xylosylated compounds were more stable compared to the mono-xylosylated ones. They initiate priming of glycosaminoglycan chains to less extent but the priming proceeds in two directions. Contrary to the mono-xylosylated analogs, the tested compounds did not show any antiproliferative properties.

journal_name

Bioorg Med Chem

authors

Johnsson R,Mani K,Ellervik U

doi

10.1016/j.bmc.2007.02.020

subject

Has Abstract

pub_date

2007-04-15 00:00:00

pages

2868-77

issue

8

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(07)00122-8

journal_volume

15

pub_type

杂志文章
  • Anti-MRSA cephems. Part 2: C-7 cinnamic acid derivatives.

    abstract::Forty-five novel cephalosporin derivatives with activity against methicillin-resistant Staphylococcus aureus (MRSA) are described. The compounds contain novel cinnamic acid moieties at C-7 that were synthesized using a key Heck reaction followed by nucleophilic aromatic substitution reactions. The most active compound...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(02)00336-x

    authors: Springer DM,Luh BY,Goodrich J,Bronson JJ

    更新日期:2003-01-17 00:00:00

  • Biocatalytic combinatorial synthesis.

    abstract::Combinatorial biocatalysis, based on a principle of the combinatorial use of biosynthetic steps rather than the combinatorial use of reagents, offers a complementary approach to combinatorial chemistry, which, used individually or in connection with synthetic organic transformations, provides access to analogues not r...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(99)00145-5

    authors: Krstenansky JL,Khmelnitsky Y

    更新日期:1999-10-01 00:00:00

  • Synthesis of N-benzyl- and N-phenyl-2-amino-4,5-dihydrothiazoles and thioureas and evaluation as modulators of the isoforms of nitric oxide synthase.

    abstract::Inhibition of the isoforms of nitric oxide synthase (NOS) has important applications in therapy of several diseases, including cancer. Using 1400 W [N-(3-aminomethylbenzyl)acetamidine], thiocitrulline and N(delta)-(4,5-dihydrothiazol-2-yl)ornithine as lead compounds, series of N-benzyl- and N-phenyl-2-amino-4,5-dihydr...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(03)00451-6

    authors: Goodyer CL,Chinje EC,Jaffar M,Stratford IJ,Threadgill MD

    更新日期:2003-09-15 00:00:00

  • C-nucleoside analogues of furanfurin as ligands to A1 adenosine receptors.

    abstract::Furanfurin (2-beta-D-ribofuranosylfuran-4-carboxamide) derivatives and analogues were synthesized and their affinity for adenosine receptors was determined. The agonistic behavior of furanfurin against A1 receptors is preserved only when the furan ring is substituted with isosteric pentatomic ring systems such as oxaz...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(00)00167-x

    authors: Franchetti P,Cappellacci L,Marchetti S,Martini C,Costa B,Varani K,Borea PA,Grifantini M

    更新日期:2000-09-01 00:00:00

  • SAR studies of acidic dual γ-secretase/PPARγ modulators.

    abstract::A novel set of dual γ-secretase/PPARγ modulators characterized by a 2-benzyl hexanoic acid scaffold is presented. Synthetic efforts were focused on the variation of the substitution pattern of the central benzene. Finally, we obtained a new class of 2,5-disubstituted 2-benzylidene hexanoic acid derivatives, which act ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.08.003

    authors: Hieke M,Ness J,Steri R,Greiner C,Werz O,Schubert-Zsilavecz M,Weggen S,Zettl H

    更新日期:2011-09-15 00:00:00

  • Flavanones from the stem bark of Erythrina abyssinica.

    abstract::Twelve new flavanones bearing a 2,2-dimethylpyrano ring were isolated from a MeOH extract of the stem bark of Erythrina abyssinica. Their structures were determined on the basis of spectroscopic (UV, CD, 1D and 2D NMR, HRMS) and physico-chemical analyses. Compounds 1, 3, 5, 6, 8, and 9 exhibited inhibitory effects on ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.10.012

    authors: Cui L,Thuong PT,Lee HS,Ndinteh DT,Mbafor JT,Fomum ZT,Oh WK

    更新日期:2008-12-15 00:00:00

  • Inhibition studies of new ureido-substituted sulfonamides incorporating a GABA moiety against human carbonic anhydrase isoforms I-XIV.

    abstract::Reaction of γ-Boc-GABA, prepared by protecting the γ-amino moiety of the amino butyric acid with the tert-butyloxycarbonyl (Boc) protecting group, with 4-methyl/ethyl benzenesulfonamide, followed by removal of the Boc protecting group in 3 M HCl afforded the corresponding hydrochlorides, which were further derivatized...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.10.041

    authors: Ceruso M,Antel S,Vullo D,Scozzafava A,Supuran CT

    更新日期:2014-12-15 00:00:00

  • 3-Phenylalkyl-2H-chromenes and -chromans as novel rhinovirus infection inhibitors.

    abstract::Following our studies on structure-activity relationships of anti-rhinovirus chromene and chroman derivatives, we designed and synthesized new series of 3-phenylalkyl-2H-chromenes and -chromans bearing differently sized, aliphatic linker chains between the two cycles. The cytotoxicity and the antiviral activity of the...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.02.012

    authors: Conti C,Proietti Monaco L,Desideri N

    更新日期:2017-04-01 00:00:00

  • Amide conjugates of ketoprofen and indole as inhibitors of Gli1-mediated transcription in the Hedgehog pathway.

    abstract::We have previously reported small-molecule inhibitors of Gli1-mediated transcription, an essential down-stream element of the Hh pathway. We created new derivatives of the previous compounds aiming to improve the druggable properties. The new compounds, amide conjugates of ketoprofen and indole, showed inhibitory acti...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.05.001

    authors: Mahindroo N,Connelly MC,Punchihewa C,Yang L,Yan B,Fujii N

    更新日期:2010-07-01 00:00:00

  • Apoptosis-inducing effect of epolactaene derivatives on BALL-1 cells.

    abstract::Epolactaene, a neuritogenic compound in human neuroblastoma SH-SY5Y, induces apoptosis in a human leukemia B-cell line, BALL-1. The apoptosis-inducing activities of 34 epolactaene derivatives, including those of the newly synthesized alpha-alkyl-alpha,beta-epoxy-gamma-lactam derivative and cyclopropane derivatives, we...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.10.057

    authors: Kuramochi K,Matsui R,Matsubara Y,Nakai J,Sunoki T,Arai S,Nagata S,Nagahara Y,Mizushina Y,Ikekita M,Kobayashi S

    更新日期:2006-04-01 00:00:00

  • Cell surface biotinylation by azaelectrocyclization: easy-handling and versatile approach for living cell labeling.

    abstract::Versatile method for living cell labeling has been established. Cell surfaces are initially biotinylated by azaelectrocyclization, and then treated with the fluorescence-labeled avidin or the anti-biotin antibody. ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.12.043

    authors: Tanaka K,Yokoi S,Morimoto K,Iwata T,Nakamoto Y,Nakayama K,Koyama K,Fujiwara T,Fukase K

    更新日期:2012-03-15 00:00:00

  • The design and optimization of a series of 2-(pyridin-2-yl)-1H-benzimidazole compounds as allosteric glucokinase activators.

    abstract::The optimization of a series of benzimidazole glucokinase activators is described. We identified a novel and potent achiral benzimidazole derivative as an allosteric GK activator. This activator was designed and synthesized via removal of the chiral center of the lead compound, 6-(N-acylpyrrolidin-2-yl)benzimidazole. ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.05.037

    authors: Takahashi K,Hashimoto N,Nakama C,Kamata K,Sasaki K,Yoshimoto R,Ohyama S,Hosaka H,Maruki H,Nagata Y,Eiki J,Nishimura T

    更新日期:2009-10-01 00:00:00

  • Discovery of a novel activator of 5-lipoxygenase from an anacardic acid derived compound collection.

    abstract::Lipoxygenases (LOXs) and cyclooxygenases (COXs) metabolize poly-unsaturated fatty acids into inflammatory signaling molecules. Modulation of the activity of these enzymes may provide new approaches for therapy of inflammatory diseases. In this study, we screened novel anacardic acid derivatives as modulators of human ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.10.015

    authors: Wisastra R,Kok PA,Eleftheriadis N,Baumgartner MP,Camacho CJ,Haisma HJ,Dekker FJ

    更新日期:2013-12-15 00:00:00

  • Design, synthesis and biological evaluation of novel 3,4,5-trisubstituted aminothiophenes as inhibitors of p53-MDM2 interaction. Part 2.

    abstract::Five series of novel 3,4,5-trisubstituted aminothiophene derivatives and analogs were designed and synthesized based on our previous studies. All target compounds were evaluated for their p53-MDM2 binding inhibitory activities and anti-proliferation activities against A549 and PC3 tumor cell lines. Twelve compounds di...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.03.070

    authors: Wang W,Lv D,Qiu N,Zhang L,Hu C,Hu Y

    更新日期:2013-06-01 00:00:00

  • The effect of the length and flexibility of the side chain of basic amino acids on the binding of antimicrobial peptides to zwitterionic and anionic membrane model systems.

    abstract::The intent of this investigation was to determine the effect of varying the side chain length of the basic amino acids residues on the binding of a series of antimicrobial peptides (AMPs) to zwitterionic and anionic LUVs, SUVs and micelles. These AMPs are based on the incorporation of three dipeptide units consisting ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.01.015

    authors: Russell AL,Williams BC,Spuches A,Klapper D,Srouji AH,Hicks RP

    更新日期:2012-03-01 00:00:00

  • Design, synthesis and pharmacological evaluation of (E)-3,4-dihydroxy styryl sulfonamides derivatives as multifunctional neuroprotective agents against oxidative and inflammatory injury.

    abstract::A novel class of (E)-3,4-dihydroxy styryl sulfonamides and their 3,4-diacetylated derivatives as caffeic acid phenethyl ester (CAPE) analogs was designed and prepared for improving stability and solubility of the lead compound. Their neuroprotective properties were assessed by several models. The results showed that t...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.05.043

    authors: Ning X,Guo Y,Ma X,Zhu R,Tian C,Zhang Z,Wang X,Ma Z,Liu J

    更新日期:2013-09-01 00:00:00

  • In vitro activity of novel dual action MDR anthranilamide modulators with inhibitory activity on CYP-450 (Part 2).

    abstract::Synthesis and in vitro cytotoxicity assays of new anthranilamide MDR modulators have been performed to assess their inhibition potency on the P-glycoprotein (P-gp) transporter. Previous studies showed that the replacement of the aromatic spacer group between nitrogen atoms (N(1) and N(2)) in the P-gp inhibitor XR9576 ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.03.014

    authors: Labrie P,Maddaford SP,Lacroix J,Catalano C,Lee DK,Rakhit S,Gaudreault RC

    更新日期:2007-06-01 00:00:00

  • Amide and alpha-keto carbonyl inhibitors of thrombin based on arginine and lysine: synthesis, stability and biological characterization.

    abstract::We report structure-activity investigations in a series of tripeptide amide inhibitors of thrombin, and the development of a series of highly potent active site directed alpha-keto carbonyl inhibitors having the side chain of lysine at P1. Compounds of this class are unstable by virtue of reactivity at the electrophil...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/0968-0896(95)00105-p

    authors: Brady SF,Sisko JT,Stauffer KJ,Colton CD,Qiu H,Lewis SD,Ng AS,Shafer JA,Bogusky MJ,Veber DF

    更新日期:1995-08-01 00:00:00

  • Total synthesis and a systematic structure-activity relationship study of WAP-8294A2.

    abstract::WAP-8294A2 is a cyclic peptide antibiotic with novel structure and excellent activity against Gram-positive pathogens. Herein, we report the total synthesis of complex macrocyclic peptide WAP-8294A2 (W1), ent-analogue W2, deoxy analogue W3 and de-methyl analogue W4 using a solid-phase synthetic route followed by a fin...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2020.115677

    authors: Chen D,Tian L,Po KHL,Chen S,Li X

    更新日期:2020-09-15 00:00:00

  • Retinoic acid signaling pathways in development and diseases.

    abstract::Retinoids comprise a group of compounds each composed of three basic parts: a trimethylated cyclohexene ring that is a bulky hydrophobic group, a conjugated tetraene side chain that functions as a linker unit, and a polar carbon-oxygen functional group. Biochemical conversion of carotenoid or other retinoids to retino...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.bmc.2013.11.025

    authors: Das BC,Thapa P,Karki R,Das S,Mahapatra S,Liu TC,Torregroza I,Wallace DP,Kambhampati S,Van Veldhuizen P,Verma A,Ray SK,Evans T

    更新日期:2014-01-15 00:00:00

  • Discovery of pyridine-based agrochemicals by using Intermediate Derivatization Methods.

    abstract::Pyridine-based compounds have been playing a crucial role as agrochemicals or pesticides including fungicides, insecticides/acaricides and herbicides, etc. Since most of the agrochemicals listed in the Pesticide Manual were discovered through screening programs that relied on trial-and-error testing and new agrochemic...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.bmc.2015.09.031

    authors: Guan AY,Liu CL,Sun XF,Xie Y,Wang MA

    更新日期:2016-02-01 00:00:00

  • Active core structure of terfestatin A, a new specific inhibitor of auxin signaling.

    abstract::The auxins, plant hormones, regulate many aspects of the growth and development of plants. Terfestatin A (TrfA), a novel auxin signaling inhibitor, was identified in a screen of Streptomyces sp. F40 extracts for inhibition of the expression of an auxin-inducible gene. However, the mode of action of TrfA has not been e...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.02.085

    authors: Hayashi K,Yamazoe A,Ishibashi Y,Kusaka N,Oono Y,Nozaki H

    更新日期:2008-05-01 00:00:00

  • Hybrid stereoisomers of a compact molecular probe based on a jasmonic acid glucoside: syntheses and biological evaluations.

    abstract::12-O-β-D-glucopyranosyl jasmonic acid (JAG) shows unique biological activities, including leaf-closing of Samanea saman. It is expected that the mode of action for such regulation is distinct from that of other jasmonates. We developed high-performance compact molecular probes (CMPs) based on JAG that can be used for ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.08.003

    authors: Ueda M,Yang G,Ishimaru Y,Itabashi T,Tamura S,Kiyota H,Kuwahara S,Inomata S,Shoji M,Sugai T

    更新日期:2012-10-01 00:00:00

  • Synthesis and structure activity relationships of novel non-peptidic metallo-aminopeptidase inhibitors.

    abstract::Racemic derivatives of 3-amino-2-tetralone were synthesised and evaluated for their ability to inhibit metallo-aminopeptidase activities. New compounds substituted in position 2 by methyl ketone, substituted oximes or hydroxamic acids as well as heterocyclic derivatives were evaluated against representative members of...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.06.050

    authors: Albrecht S,Defoin A,Salomon E,Tarnus C,Wetterholm A,Haeggström JZ

    更新日期:2006-11-01 00:00:00

  • A quantitative structure-activity relationship study on some HIV-1 protease inhibitors using molecular connectivity index.

    abstract::A quantitative structure-activity relationship (QSAR) study has been made on two different series of tetrahydropyrimidinones acting as HIV-1 protease inhibitors. A structural parameter, the first order valence molecular connectivity index ((1)chi(v)), has been used to account for the variation in the activity. The pro...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(01)00210-3

    authors: Gayathri P,Pande V,Sivakumar R,Gupta SP

    更新日期:2001-11-01 00:00:00

  • QSAR by LFER model of HIV protease inhibitor mannitol derivatives using FA-MLR, PCRA, and PLS techniques.

    abstract::The present quantitative structure-activity relationship (QSAR) study attempts to explore the structural and physicochemical requirements of mannitol derivatives for HIV protease inhibitory activity using linear free energy related model of Hansch. QSAR models have been developed using electronic (Hammett sigma), hydr...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.09.022

    authors: Leonard JT,Roy K

    更新日期:2006-02-15 00:00:00

  • Screening helix-threading peptides for RNA binding using a thiazole orange displacement assay.

    abstract::The fluorescent intercalator displacement assay using thiazole orange has been adapted to the study of RNA-binding helix-threading peptides (HTPs). This assay is highly sensitive with HTP-binding RNAs and provides binding affinity data in good agreement with quantitative ribonuclease footprinting without the need for ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.08.066

    authors: Krishnamurthy M,Schirle NT,Beal PA

    更新日期:2008-10-01 00:00:00

  • Selective activity against Mycobacteriumtuberculosis of new quinoxaline 1,4-di-N-oxides.

    abstract::New series of 3-phenylquinoxaline 1,4-di-N-oxide with selective activity against Mycobacterium tuberculosis have been prepared and evaluated. Thirty-four of the seventy tested compounds showed an MIC value less than 0.2 microg/mL, a value on the order of the MIC of rifampicin. Furthermore, 45% of the evaluated derivat...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.10.086

    authors: Vicente E,Pérez-Silanes S,Lima LM,Ancizu S,Burguete A,Solano B,Villar R,Aldana I,Monge A

    更新日期:2009-01-01 00:00:00

  • Synthesis and biological evaluation of novel quinazoline-derived human Pin1 inhibitors.

    abstract::A series of novel 2,4-disubstituted quinazoline derivatives were prepared and their inhibitory activities on hPin1 were evaluated. Of all the synthesized compounds, eight compounds displayed inhibitory activities with IC(50) value at the level of 10(-6)mol/L. Preliminary structure-activity relationships were analyzed ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.03.058

    authors: Zhu L,Jin J,Liu C,Zhang C,Sun Y,Guo Y,Fu D,Chen X,Xu B

    更新日期:2011-05-01 00:00:00

  • In vitro cytotoxicity of 5-aminosubstituted 20(S)-camptothecins. Part 1.

    abstract::A number of 5-aminosubstituted 20(S)-camptothecin analogues were prepared via semi-synthesis starting from 20(S)-camptothecin and 9-methoxy 20(S)-camptothecin. In vitro anti-cancer activity of these analogues was determined using 60 human tumor cell line assay. Although water solubility of most of these compounds was ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(99)00130-3

    authors: Subrahmanyam D,Sarma VM,Venkateswarlu A,Sastry TV,Kulakarni AP,Rao DS,Reddy KV

    更新日期:1999-09-01 00:00:00