Characterization of novel furan compounds on the basis of their radical scavenging activity and cytoprotective effects against glutamate- and lipopolysaccharide-induced insults.

Abstract:

:There is increasing evidence indicating that free radicals and oxygenases such as cyclooxygenase (COX) and lipoxygenase (LOX) are related to the onset and development of neurodegenerative diseases. In order to prevent and/or delay these diseases, the use of radical-scavenging antioxidants and inhibitors against oxygenases has received much attention. In the present study, we examined the radical-scavenging activity and cytoprotective effects of some novel furan compounds with potent inhibitory activity against oxygenases such as COX-1, COX-2, and 5-LOX. The radical-scavenging activity was assessed by studying the bleaching of beta-carotene by free radicals generated from an azo initiator. In this assay system, the rate constants for scavenging peroxyl radicals by furan S and furan L was estimated to be 2 x 10(4) and 3 x 10(4) M(-1) s(-1), respectively. We also investigated the cytoprotective effects of these compounds against cell death induced by several toxins. We found that the furan compounds exhibited cytoprotective effects against PC12 cell death induced by linoleic acid hydroperoxide, primary neuronal cell death induced by glutamate, and cell death induced by lipopolysaccharide. These results suggest the beneficial effects of the furan compounds against disorders related to glutamate and lipopolysaccharide.

journal_name

Bioorg Med Chem

authors

Nishio K,Fukuhara A,Omata Y,Saito Y,Yamaguchi S,Kato H,Yoshida Y,Niki E

doi

10.1016/j.bmc.2008.10.038

subject

Has Abstract

pub_date

2008-12-15 00:00:00

pages

10332-7

issue

24

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(08)00988-7

journal_volume

16

pub_type

杂志文章
  • 2,4-Disubstituted oxazoles and thiazoles as latent pharmacophores for diacylhydrazine of SC-51089, a potent PGE2 antagonist.

    abstract::8-Chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[1-oxo-3-(4-pyridinyl)propyl]hydrazide, monohydrochloride (1, SC-51089) is a functional PGE2 antagonist selective for the EP1 receptor subtype with antinociceptive activity. Analogues of SC-51089, in which the diacylhydrazine moiety has been replaced with 2,...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(00)00229-7

    authors: Hallinan EA,Hagen TJ,Tsymbalov S,Stapelfeld A,Savage MA

    更新日期:2001-01-01 00:00:00

  • Synthesis, biological assays and QSAR studies of N-(9-benzyl-2-phenyl-8-azapurin-6-yl)-amides as ligands for A1 adenosine receptors.

    abstract::2-Phenyl-9-benzyl-8-azapurines, bearing at the 6 position an amido group interposed between the 8-azapurine moiety and an alkyl or a substituted phenyl group, have been synthesised and assayed as ligands for adenosine receptors. All the compounds show high affinity for the A(1) adenosine receptor, and many of them als...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.01.060

    authors: Giorgi I,Leonardi M,Pietra D,Biagi G,Borghini A,Massarelli I,Ciampi O,Bianucci AM

    更新日期:2009-03-01 00:00:00

  • Synthesis and biological evaluation of pentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecane derivatives as potential therapeutic agents in Parkinson's disease.

    abstract::In previous studies, the polycyclic cage amine 8-benzylamino-8,11-oxapentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecane (NGP1-01) and a number of its derivatives showed positive effects in neuroprotection studies with MPTP, in vivo. In view of these findings, we examined these compounds for their effects on [(3)H]dopamin...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2003.12.045

    authors: Geldenhuys WJ,Malan SF,Murugesan T,Van der Schyf CJ,Bloomquist JR

    更新日期:2004-04-01 00:00:00

  • Scutione, a new bioactive norquinonemethide triterpene from Maytenus scutioides (Celastraceae).

    abstract::Scutione (1), a new norquinonemethide triterpene with a netzahualcoyene type skeleton, has been isolated from the root bark of Maytenus scutioides (Celastraceae) by bioactivity-directed fractionation. The structure of 1 has been elucidated by means of 1H and 13C NMR spectroscopic studies, including 1H-13C heteronuclea...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/0968-0896(96)00078-8

    authors: González AG,Alvarenga NL,Ravelo AG,Bazzocchi IL,Ferro EA,Navarro AG,Moujir LM

    更新日期:1996-06-01 00:00:00

  • Synthesis and cytotoxic activity of novel C7-functionalized spongiane diterpenes.

    abstract::Based on two lead cytotoxic spongiane diterpenes, a new series of C7-oxygenated derivatives were synthesized and evaluated for their antitumor activity in vitro against the cancer cell lines HeLa and HEp-2. In general, introduction of either hydroxyl or acetoxy groups at C-7 did not improve the resultant cytotoxicity,...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(03)00230-x

    authors: Arnó M,Betancur-Galvis L,González MA,Sierra J,Zaragozá RJ

    更新日期:2003-07-17 00:00:00

  • Carbon-carbon-linked (pyrazolylphenyl)oxazolidinones with antibacterial activity against multiple drug resistant gram-positive and fastidious gram-negative bacteria.

    abstract::In an effort to expand the spectrum of activity of the oxazolidinone class of antibacterial agents to include Gram-negative bacteria, a series of new carbon-carbon linked pyrazolylphenyl analogues has been prepared. The alpha-N-substituted methyl pyrazole (10alpha) in the C3-linked series exhibited very good Gram-posi...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(01)00233-4

    authors: Lee CS,Allwine DA,Barbachyn MR,Grega KC,Dolak LA,Ford CW,Jensen RM,Seest EP,Hamel JC,Schaadt RD,Stapert D,Yagi BH,Zurenko GE,Genin MJ

    更新日期:2001-12-01 00:00:00

  • Structural insights into binding of inhibitors to soluble epoxide hydrolase gained by fragment screening and X-ray crystallography.

    abstract::Soluble epoxide hydrolase (sEH) is a component of the arachidonic acid cascade and is a candidate target for therapies for hypertension or inflammation. Although many sEH inhibitors are available, their scaffolds are not structurally diverse, and knowledge of their specific interactions with sEH is limited. To obtain ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.03.001

    authors: Amano Y,Yamaguchi T,Tanabe E

    更新日期:2014-04-15 00:00:00

  • 2-(2-Bromophenyl)-formononetin and 2-heptyl-formononetin are PPARγ partial agonists and reduce lipid accumulation in 3T3-L1 adipocytes.

    abstract::Isoflavones are bioactive compounds that have been shown to decrease lipid accumulation in vitro. However, the knowledge of the isoflavone formononetin is limited. The aim of the study was to assess the effects of formononetin and its two synthetic analogues, 2-(2-bromophenyl)-formononetin and 2-heptyl-formononetin, o...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.08.037

    authors: Andersen C,Kotowska D,Tortzen CG,Kristiansen K,Nielsen J,Petersen RK

    更新日期:2014-11-01 00:00:00

  • [1,2,4]Triazole derivatives as 5-HT(1A) serotonin receptor ligands.

    abstract::A series of new 4-amino-3-[3-[4-(2-methoxy or nitro phenyl)-1-piperazinyl] propyl]thio]-5-(substitutedphenyl)[1,2,4]triazoles 11a-t was synthesized in order to obtain compounds with high affinity and selectivity for 5-HT(1A) receptor over the alpha(1)-adrenoceptor. A series of isomeric 4-amino-2-[3-[4-(2-methoxy or ni...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(01)00281-4

    authors: Sarvà MC,Romeo G,Guerrera F,Siracusa M,Salerno L,Russo F,Cagnotto A,Goegan M,Mennini T

    更新日期:2002-02-01 00:00:00

  • QSAR models for Daphnia toxicity of pesticides based on combinations of topological parameters of molecular structures.

    abstract::A topological parameter is defined as an integer value of a given local or global invariant of a molecular graph. We examined three types of local graph invariants, the vertex degrees (0EC), the extended connectivity of first order (1EC), and the numbers of paths of length two (P2), as elementary invariants for constr...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.11.060

    authors: Toropov AA,Benfenati E

    更新日期:2006-04-15 00:00:00

  • Fine tuning of agonistic/antagonistic activity for vitamin D receptor by 22-alkyl chain length of ligands: 22S-Hexyl compound unexpectedly restored agonistic activity.

    abstract::1α,25-Dihydroxyvitamin D3 exerts its actions by binding to vitamin D receptor (VDR). We are continuing the study related to the alteration of pocket structure of VDR by 22-alkyl substituent of ligands and the relationships between the alteration and agonistic/antagonistic activity. Previously we reported that compound...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.10.026

    authors: Anami Y,Sakamaki Y,Itoh T,Inaba Y,Nakabayashi M,Ikura T,Ito N,Yamamoto K

    更新日期:2015-11-15 00:00:00

  • Synthesis and screening of a cyclic peptide library: discovery of small-molecule ligands against human prolactin receptor.

    abstract::Prolactin receptor is involved in normal lactation and reproduction; however, excessive prolactin levels can cause various reproductive disorders such as prolactinomas. Small-molecule antagonists against the human prolactin receptor (hPRLr) thus have potential clinical applications and may serve as useful molecular pr...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.01.015

    authors: Liu T,Joo SH,Voorhees JL,Brooks CL,Pei D

    更新日期:2009-02-01 00:00:00

  • Synthesis and properties of triplex-forming oligonucleotides containing 2'-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine.

    abstract::2'-O-(2-Methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine phosphoramidite (MEPU) has been synthesized from d-ribose and 5-iodouracil and incorporated into triplex-forming oligonucleotides (TFOs) by automated solid-phase oligonucleotide synthesis. The TFOs gave very high triplex stability with their target duplexes as measu...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.07.005

    authors: Lou C,Xiao Q,Brennan L,Light ME,Vergara-Irigaray N,Atkinson EM,Holden-Dye LM,Fox KR,Brown T

    更新日期:2010-09-01 00:00:00

  • Analogs of iso-azepinomycin as potential transition-state analog inhibitors of guanase: synthesis, biochemical screening, and structure-activity correlations of various selectively substituted imidazo[4,5-e][1,4]diazepines.

    abstract::Guanase is an important enzyme of the purine salvage pathway of nucleic acid metabolism and its inhibition has beneficial implications in viral, bacterial, and cancer therapy. The work described herein is based on a hypothesis that azepinomycin, a heterocyclic natural product and a purported transition state analog in...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.06.069

    authors: Tantravedi S,Chakraborty S,Shah NH,Fishbein JC,Hosmane RS

    更新日期:2013-09-01 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 pyrimidine derivatives as novel human Pin1 inhibitors.

    abstract::Pin1 (Protein interacting with NIMA1) is a cis-trans isomerase and promotes the amide bond rotation of phosphoSer/Thr-Pro motifs in its substrates. Inhibition of Pin1 might be a novel strategy for developing anticancer agents. Herein, a series of pyrimidine derivatives were synthesized and their Pin1 inhibitory activi...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2018.03.024

    authors: Cui G,Jin J,Chen H,Cao R,Chen X,Xu B

    更新日期:2018-05-01 00:00:00

  • Design, synthesis and evaluation of retinoids with novel bulky hydrophobic partial structures.

    abstract::Many synthetic retinoids contain an aromatic structure with a bulky hydrophobic fragment. In order to obtain retinoids with therapeutic potential that do not bind to or activate retinoic acid X receptors (RXRs), we focused on the introduction of novel hydrophobic moieties, that is, metacyclophane, phenalene and benzoh...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.04.053

    authors: Amano Y,Noguchi M,Nakagomi M,Muratake H,Fukasawa H,Shudo K

    更新日期:2013-07-15 00:00:00

  • Pyrrolomycins as antimicrobial agents. Microwave-assisted organic synthesis and insights into their antimicrobial mechanism of action.

    abstract::New compounds able to counteract staphylococcal biofilm formation are needed. In this study we investigate the mechanism of action of pyrrolomycins, whose potential as antimicrobial agents has been demonstrated. We performed a new efficient and easy method to use microwave organic synthesis suitable for obtaining pyrr...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2019.01.010

    authors: Raimondi MV,Listro R,Cusimano MG,La Franca M,Faddetta T,Gallo G,Schillaci D,Collina S,Leonchiks A,Barone G

    更新日期:2019-03-01 00:00:00

  • Design and synthesis of thiazolylhydrazone derivatives as inhibitors of chitinolytic N-acetyl-β-d-hexosaminidase.

    abstract::N-acetyl-β-d-hexosaminidase (Hex) is potential target for pesticide design. Here, a series of thiazolylhydrazone derivatives were designed, synthesized and evaluated as competitive inhibitors of OfHex1, a Hex from the agricultural pest Ostrinia furnacalis. The derivative 3k, with a (benzyloxy)methyl group at the N3 at...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2018.09.014

    authors: Yang H,Liu T,Qi H,Huang Z,Hao Z,Ying J,Yang Q,Qian X

    更新日期:2018-11-01 00:00:00

  • Synthesis and evaluation of novel amide amino-β-lactam derivatives as cholesterol absorption inhibitors.

    abstract::The β-lactam cholesterol absorption inhibitor ezetimibe is so far the only representative of this class of compounds on the market today. The goal of this work was to synthesize new amide ezetimibe analogs from trans-3-amino-(3R,4R)-β-lactam and to test their cytotoxicity and activity as cholesterol absorption inhibit...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.03.067

    authors: Dražić T,Sachdev V,Leopold C,Patankar JV,Malnar M,Hećimović S,Levak-Frank S,Habuš I,Kratky D

    更新日期:2015-05-15 00:00:00

  • Optimizing phenylethylphosphonamidates for the inhibition of prostate-specific membrane antigen.

    abstract::A series of eight N-2-phenylethylphosphonyl derivatives of glutamic acid was prepared to determine if the inhibitory potency of a phenylethylphosphonyl derivative of glutamic acid against prostate-specific membrane antigen (PSMA) could be improved through rational substitutions on the phenyl ring. The design of these ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.07.056

    authors: Wone DW,Rowley JA,Garofalo AW,Berkman CE

    更新日期:2006-01-01 00:00:00

  • Cytotoxicity mechanisms of pyrazino[1,2-b]isoquinoline-4-ones and SAR studies.

    abstract::The cytotoxicity showed by 1b, an interesting representant of the title compounds, for HT-29 human colon cancer cells (CI(50) value of 1.95 x 10(-7)M) has been related to the induced cell death at the G2 phase and not to DNA damage. This compound promotes the degradation of components of the G2/M checkpoint machinery,...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.10.007

    authors: Ortín I,González JF,Cuesta Ede L,Manguan-García C,Perona R,Avendaño C

    更新日期:2009-12-01 00:00:00

  • Design and pharmacophore modeling of biaryl methyl eugenol analogs as breast cancer invasion inhibitors.

    abstract::Cell invasion and migration are required for the parent solid tumor cells to metastasize to distant organs. Microtubules form a polarized network, enabling organelle and protein movement throughout the cell. Cytoskeletal elements coordinately regulate cell's motility, adhesion, migration, exocytosis, endocytosis, and ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.12.019

    authors: Abdel Bar FM,Khanfar MA,Elnagar AY,Badria FA,Zaghloul AM,Ahmad KF,Sylvester PW,El Sayed KA

    更新日期:2010-01-15 00:00:00

  • Benzoic acid derivatives with improved antifungal activity: Design, synthesis, structure-activity relationship (SAR) and CYP53 docking studies.

    abstract::Previously, we identified CYP53 as a fungal-specific target of natural phenolic antifungal compounds and discovered several inhibitors with antifungal properties. In this study, we performed similarity-based virtual screening and synthesis to obtain benzoic acid-derived compounds and assessed their antifungal activity...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.06.042

    authors: Berne S,Kovačič L,Sova M,Kraševec N,Gobec S,Križaj I,Komel R

    更新日期:2015-08-01 00:00:00

  • Selective inhibition of β-N-acetylhexosaminidases by thioglycosyl-naphthalimide hybrid molecules.

    abstract::To develop selective inhibitors for β-N-acetylhexosaminidases which are involved in a myriad of physiological processes, a series of novel thioglycosyl-naphthalimide hybrid inhibitors were designed, synthesized and evaluated for inhibition activity against glycosyl hydrolase family 20 and 84 (GH20 and GH84) β-N-acetyl...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.11.042

    authors: Chen W,Shen S,Dong L,Zhang J,Yang Q

    更新日期:2018-01-15 00:00:00

  • Substituted thiophene-anthranilamides as potent inhibitors of human factor Xa.

    abstract::A series of thiophene-containing non-amidine factor Xa inhibitors is described. Simple methyl-substituted thiophene analogs were relatively weak inhibitors. However, introduction of hydrophilic substituents at C-4 or C-5 of the thiophene afforded inhibitors with low nanomolar potency. Optimization of the thiophene sub...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.12.019

    authors: Kochanny MJ,Adler M,Ewing J,Griedel BD,Ho E,Karanjawala R,Lee W,Lentz D,Liang AM,Morrissey MM,Phillips GB,Post J,Sacchi KL,Sakata ST,Subramanyam B,Vergona R,Walters J,White KA,Whitlow M,Ye B,Zhao Z,Shaw KJ

    更新日期:2007-03-01 00:00:00

  • Structure-activity relationship and conformational analysis of monoglycosylceramides on the syngeneic mixed leukocyte reaction.

    abstract::We examined effects of alpha-, beta-galactosylceramides (CalCers) and alpha-, beta-glucosylceramides (GlcCers) on the syngeneic mixed leukocyte reaction (MLR) using spleen cells (responder cells) and dendritic cells (DC, stimulator cells). The DC pretreated with these alpha-monoglycosylceramides markedly stimulated th...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(98)00112-6

    authors: Iijima H,Kimura K,Sakai T,Uchimura A,Shimizu T,Ueno H,Natori T,Koezuka Y

    更新日期:1998-10-01 00:00:00

  • Improving metabolic stability and removing aldehyde oxidase liability in a 5-azaquinazoline series of IRAK4 inhibitors.

    abstract::In this article, we report our efforts towards improving in vitro human clearance in a series of 5-azaquinazolines through a series of C4 truncations and C2 expansions. Extensive DMPK studies enabled us to tackle high Aldehyde Oxidase (AO) metabolism and unexpected discrepancies in human hepatocyte and liver microsoma...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2020.115815

    authors: Degorce SL,Aagaard A,Anjum R,Cumming IA,Diène CR,Fallan C,Johnson T,Leuchowius KJ,Orton AL,Pearson S,Robb GR,Rosen A,Scarfe GB,Scott JS,Smith JM,Steward OR,Terstiege I,Tucker MJ,Turner P,Wilkinson SD,Wrigley GL,

    更新日期:2020-12-01 00:00:00

  • Novel trans-2-aryl-cyclopropylamine analogues as potent and selective dipeptidyl peptidase IV inhibitors.

    abstract::A series of trans-2-aryl-cyclopropylamine derived compounds were synthesized and evaluated their biological activities against DPP-IV. The structure-activity relationships (SAR) led to the discovery of novel series of DPP-IV inhibitors, having IC(50) values of <100 nM with excellent selectivity over the closely relate...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.02.020

    authors: Tsai TY,Hsu T,Chen CT,Cheng JH,Yeh TK,Chen X,Huang CY,Chang CN,Yeh KC,Hsieh SH,Chien CH,Chang YW,Huang CH,Huang YW,Huang CL,Wu SH,Wang MH,Lu CT,Chao YS,Jiaang WT

    更新日期:2009-03-15 00:00:00

  • Transition state analogue inhibitors of protozoan nucleoside hydrolases.

    abstract::Protozoan parasites are unable to synthesize purines de novo and must rely on purine salvage pathways for their requirements. Nucleoside hydrolases, which are not found in mammals, function as key enzymes in purine salvage in protozoa. Inhibition of these enzymes may disrupt purine supply and specific inhibitors are p...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(99)00210-2

    authors: Furneaux RH,Schramm VL,Tyler PC

    更新日期:1999-11-01 00:00:00