当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY期刊下所有文献 > Design, synthesis and biological evaluation of aryl-substituted sialyl Lewis X mimetics prepared via cross-metathesis of C-fucopeptides.

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 number of analogues from a SLe(x) mimetic template at a very late stage of the synthesis was introduced, using a ruthenium catalyzed cross olefin metathesis under benchtop conditions.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

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

doi

10.1016/s0968-0896(98)00245-4

subject

Has Abstract

pub_date

1999-05-01 00:00:00

pages

773-88

issue

5

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(98)00245-4

journal_volume

7

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY文献大全
  • Competitive antagonism of insect GABA receptors by 4-substituted 5-(4-piperidyl)-3-isothiazolols.

    abstract：:γ-Aminobutyric acid (GABA) receptors are important targets of parasiticides/insecticides. Several 4-substituted analogs of the partial GABAA receptor agonist 5-(4-piperidyl)-3-isothiazolol (Thio-4-PIOL) were synthesized and examined for their antagonism of insect GABA receptors expressed in Drosophila S2 cells or Xeno...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2014.07.021

    authors： Liu G,Furuta K,Nakajima H,Ozoe F,Ozoe Y

    更新日期：2014-09-01 00:00:00

  • Chemistry-driven glycoscience.

    abstract：:Carbohydrates are the most prominent features of the cell's exterior-they are the cell's "face" and serve as the cell's identification card. The features of cell surface glycans (e.g. glycoproteins, glycolipids, polysaccharides) can be read by proteins, other cells, or organisms. In all of these contexts, glycan-bindi...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 社论

    doi：10.1016/j.bmc.2018.09.024

    authors： Kiessling LL

    更新日期：2018-10-15 00:00:00

  • Polymer-bound reagents for the introduction of spacer-modified biotin labels.

    abstract：:We have developed a method for the chemoselective introduction of spacer modified biotin labels into unprotected multi-functional amines. A range of novel biotin spacer conjugates attached to a polymer-bound sulfonamide anchor was prepared using established amide bond forming procedures. After chemical transformation ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.03.038

    authors： Herforth C,Heidler P,Franke S,Link A

    更新日期：2004-06-01 00:00:00

  • Synthesis, biological evaluation and molecular modelling studies of methyleneimidazole substituted biaryls as inhibitors of human 17alpha-hydroxylase-17,20-lyase (CYP17). Part I: Heterocyclic modifications of the core structure.

    abstract：:Novel chemical entities were prepared via Suzuki and S(N) reaction as AC-ring substrate mimetics of CYP17. The synthesised compounds 1-31 were tested for activity using human CYP17 expressed in Escherichia coli. Promising compounds were tested for selectivity against hepatic CYP enzymes (3A4, 2D6, 1A2, 2C9, 2C19, 2B6)...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.10.094

    authors： Jagusch C,Negri M,Hille UE,Hu Q,Bartels M,Jahn-Hoffmann K,Pinto-Bazurco Mendieta MA,Rodenwaldt B,Müller-Vieira U,Schmidt D,Lauterbach T,Recanatini M,Cavalli A,Hartmann RW

    更新日期：2008-02-15 00:00:00

  • A novel sesquiterpenoid dimer parviflorene F induces apoptosis by up-regulating the expression of TRAIL-R2 and a caspase-dependent mechanism.

    abstract：:Parviflorene F (1), a novel sesquiterpenoid dimer isolated from Curcuma parviflora Wall, is a cytotoxic compound. In this study, we examined the mechanism of its cytotoxic effect in HeLa cells. Treatment with 1 enhanced the mRNA and protein expression of TRAIL-R2 (tumor necrosis factor alpha-related apoptosis inducing...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.11.022

    authors： Ohtsuki T,Tamaki M,Toume K,Ishibashi M

    更新日期：2008-02-15 00:00:00

  • Synthesis and cytotoxicity of methyl-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione derivatives.

    abstract：:2- and 3-Methyl-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione and related derivatives were synthesized and evaluated in vitro by NCI against eight cancer types. Compounds 12-15 showed significant activity against melanoma, NCI-H23 non-small cell lung cancer, and MDA-MB-435 and MDA-N breast cancer cell lines; 2-h...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(98)00241-7

    authors： Chao YH,Kuo SC,Ku K,Chiu IP,Wu CH,Mauger A,Wang HK,Lee KH

    更新日期：1999-06-01 00:00:00

  • Switchable MRI contrast agents based on morphological changes of pH-responsive polymers.

    abstract：:Magnetic resonance imaging (MRI) contrast agents are effective tools in both medical diagnosis and life science research. Various smart contrast agents have been developed for the visualization of biological phenomena. These contrast agents have molecular switches that increase or reduce MRI signal intensity in respon...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2011.12.005

    authors： Okada S,Mizukami S,Kikuchi K

    更新日期：2012-01-15 00:00:00

  • Quantitative structure-activity relationships of 1,3,4-thiadiazol-2(3H)-ones and 1,3,4-oxadiazol-2(3H)-ones as human protoporphyrinogen oxidase inhibitors.

    abstract：:Protoporphyrinogen oxidase (Protox, EC 1.3.3.4) has attracted great interest during the last decades due to its unique biochemical characteristics and biomedical significance. As a continuation of our research work on the development of new PPO inhibitors, 23 new 1,3,4-thiadiazol-2(3H)-ones bearing benzothiazole subst...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2011.10.079

    authors： Zuo Y,Yang SG,Jiang LL,Hao GF,Wang ZF,Wu QY,Xi Z,Yang GF

    更新日期：2012-01-01 00:00:00

  • Synthesis of benzopolycyclic cage amines: NMDA receptor antagonist, trypanocidal and antiviral activities.

    abstract：:The synthesis of several 6,7,8,9,10,11-hexahydro-9-methyl-5,7:9,11-dimethano-5H-benzocyclononen-7-amines is reported. Several of them display low micromolar NMDA receptor antagonist and/or trypanocidal activities. Two compounds are endowed with micromolar anti vesicular stomatitis virus activity, while only one compou...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2011.11.050

    authors： Torres E,Duque MD,López-Querol M,Taylor MC,Naesens L,Ma C,Pinto LH,Sureda FX,Kelly JM,Vázquez S

    更新日期：2012-01-15 00:00:00

  • Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.

    abstract：:Tryprostatin A is an inhibitor of breast cancer resistance protein, consequently a series of structure-activity studies on the cell cycle inhibitory effects of tryprostatin A analogues as potential antitumor antimitotic agents have been carried out. These analogues were assayed for their growth inhibition properties a...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.02.050

    authors： Jain HD,Zhang C,Zhou S,Zhou H,Ma J,Liu X,Liao X,Deveau AM,Dieckhaus CM,Johnson MA,Smith KS,Macdonald TL,Kakeya H,Osada H,Cook JM

    更新日期：2008-04-15 00:00:00

  • Identification of a novel hormone sensitive lipase inhibitor with a reduced potential of reactive metabolites formation.

    abstract：:Hormone sensitive lipase (HSL) has emerged as an attractive target for the treatment of dyslipidemia. We previously reported compound 1 as a potent and orally active HSL inhibitor. Although an attractive profile was demonstrated, subsequent studies revealed that compound 1 has a bioactivation liability. The oxygen-car...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.02.045

    authors： Ogiyama T,Yamaguchi M,Kurikawa N,Honzumi S,Yamamoto Y,Sugiyama D,Takakusa H,Inoue SI

    更新日期：2017-04-01 00:00:00

  • Intestinal absorption of fluorescence-derivatized cationic peptide 001-C8-NBD via adsorptive-mediated transcytosis.

    abstract：:The intestinal absorption of an intact oligopeptide was investigated in rats using a synthetic cationic peptide, 001-C8 (H-MeTyr-Arg-MeArg-D-Leu-NH(CH2)8NH2). The peptide was coupled with 4-nitrobenzo-2-oxa-1,3-diazole (NBD) to prepare a fluorescence-labeled derivative 001-C8-NBD (H-MeTyr-Arg-MeArg-D-Leu-NH(CH2)8NH-NB...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(98)00031-5

    authors： Sai Y,Kajita M,Tamai I,Kamata M,Wakama J,Wakamiya T,Tsuji A

    更新日期：1998-06-01 00:00:00

  • Phenylimidazole derivatives as specific inhibitors of bacterial enoyl-acyl carrier protein reductase FabK.

    abstract：:Bacterial enoyl-acyl carrier protein (ACP) reductases (FabI and FabK) catalyze the final step in each cycle of bacterial fatty acid biosynthesis and are attractive targets for the development of new antibacterial agents. Here, we report the development of novel FabK inhibitors with antibacterial activity against Strep...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.08.050

    authors： Ozawa T,Kitagawa H,Yamamoto Y,Takahata S,Iida M,Osaki Y,Yamada K

    更新日期：2007-12-01 00:00:00

  • Structural requirements of flavonoids for nitric oxide production inhibitory activity and mechanism of action.

    abstract：:To clarify the structure-activity relationships of flavonoids for nitric oxide (NO) production inhibitory activity, we examined the inhibitory effects of 73 flavonoids on NO production in lipopolysaccharide-activated mouse peritoneal macrophages. Among those flavonoids, apigenin (IC(50)=7.7 microM), diosmetin (8.9 mic...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(03)00067-1

    authors： Matsuda H,Morikawa T,Ando S,Toguchida I,Yoshikawa M

    更新日期：2003-05-01 00:00:00

  • Actin-binding doliculide causes premature senescence in p53 wild type cells.

    abstract：:Addressing the actin cytoskeleton as future anticancer target can be an innovative chemotherapeutic approach to combat malignancies. Doliculide is a potent stabilizer of actin filaments and can be used as tool and therapeutic lead in cancer research. Though a variety of molecules are known to bind to actin and lead to...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.11.042

    authors： Foerster F,Chen T,Altmann KH,Vollmar AM

    更新日期：2016-01-15 00:00:00

  • Design, chemical synthesis and biological evaluation of 3-spiromorpholinone/3-spirocarbamate androsterone derivatives as inhibitors of 17β-hydroxysteroid dehydrogenase type 3.

    abstract：:17β-Hydroxysteroid dehydrogenase type 3 (17β-HSD3) is a key enzyme involved in the biosynthesis of testosterone and dihydrotestosterone. These hormones are known to stimulate androgen-dependent prostate cancer. In order to generate effective inhibitors of androgen biosynthesis without androgenic effect, we synthesized...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.07.049

    authors： Djigoué GB,Kenmogne LC,Roy J,Maltais R,Poirier D

    更新日期：2015-09-01 00:00:00

  • Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship study of 2-phenyl- or hydroxylated 2-phenyl-4-aryl-5H-indeno[1,2-b]pyridines.

    abstract：:A series of novel twenty-eight rigid 2-phenyl- or hydroxylated 2-phenyl-4-aryl-5H-indeno[1,2-b]pyridines were synthesized and evaluated for their topoisomerase inhibitory activity as well as their cytotoxicity against several human cancer cell lines. Generally, hydroxylated compounds (16-18, 22-25, and 29-31) containi...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.04.031

    authors： Kadayat TM,Song C,Shin S,Magar TB,Bist G,Shrestha A,Thapa P,Na Y,Kwon Y,Lee ES

    更新日期：2015-07-01 00:00:00

  • Synthesis and antihistaminic activity of 2-guanadino-3-cyanopyridines and pyrido[2,3-d]-pyrimidines.

    abstract：:2-Guanadino-3-cyanopyridines 8-33 and pyrido[2,3-d]-pyrimidines 35-52 were synthesized by nucleophilic displacement and cyclization of the chloroamidines 6a-d easily obtained by reaction of 2-aminocyanopyridines 5a-d with phosgene iminium chloride and their action on the release of histamine by mast cells examined und...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(97)00108-9

    authors： Quintela JM,Peinador C,Botana L,Estévez M,Riguera R

    更新日期：1997-08-01 00:00:00

  • A novel library of saccharin and acesulfame derivatives as potent and selective inhibitors of carbonic anhydrase IX and XII isoforms.

    abstract：:Small libraries of N-substituted saccharin and N-/O-substituted acesulfame derivatives were synthesized and tested as atypical and selective inhibitors of four different isoforms of human carbonic anhydrase (hCA I, II, IX and XII, EC 4.2.1.1). Most of them inhibited hCA XII in the low nanomolar range, hCA IX with KIs ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2016.01.038

    authors： Carradori S,Secci D,De Monte C,Mollica A,Ceruso M,Akdemir A,Sobolev AP,Codispoti R,De Cosmi F,Guglielmi P,Supuran CT

    更新日期：2016-03-01 00:00:00

  • Design, synthesis, and biological evaluation of callophycin A and analogues as potential chemopreventive and anticancer agents.

    abstract：:Callophycin A was originally isolated from the red algae Callophycus oppositifolius and shown to mediate anticancer and cytotoxic effects. In our collaborative effort to identify potential chemopreventive and anticancer agents with enhanced potency and selectivity, we employed a tetrahydro-β-carboline-based template i...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2011.09.020

    authors： Shen L,Park EJ,Kondratyuk TP,Guendisch D,Marler L,Pezzuto JM,Wright AD,Sun D

    更新日期：2011-11-01 00:00:00

  • Synthesis and structure-activity relationship of new 1,5-dialkyl-1,5-benzodiazepines as cholecystokinin-2 receptor antagonists.

    abstract：:This article deals with the synthesis and the activities of some 1,5-dialkyl-3-arylureido-1,5-benzodiazepin-2,4-diones which were prepared as potential CCK2 antagonists, with the intention to find a possible follow up of our lead compound GV150013, showing an improved pharmacokinetic profile. The phenyl ring at N-5 wa...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2011.05.057

    authors： Roberts K,Ursini A,Barnaby R,Cassarà PG,Corsi M,Curotto G,Donati D,Feriani A,Finizia G,Marchioro C,Niccolai D,Oliosi B,Polinelli S,Ratti E,Reggiani A,Tedesco G,Tranquillini ME,Trist DG,van Amsterdam FT

    更新日期：2011-07-15 00:00:00

  • Modulation of remote DNA oxidation by hybridization with peptide nucleic acids (PNA).

    abstract：:We have examined the efficiency of DNA photooxidation in DNA/PNA duplex and DNA/(PNA)(2) triplex for the first time. DNA/PNA duplex was cleaved at GG steps by external riboflavin with high efficiency like specific GG cleavage in DNA/DNA duplex. However, the 5'G selectivity of the GG oxidation in DNA/PNA duplex was muc...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(01)00320-0

    authors： Okamoto A,Tanabe K,Dohno C,Saito I

    更新日期：2002-03-01 00:00:00

  • Anthranilic diamides derivatives as potential ryanodine receptor modulators: Synthesis, biological evaluation and structure activity relationship.

    abstract：:A series of novel anthranilic diamides derivatives (7a-s) containing halogen, trifluoromethyl group and cyano group were designed, synthesized, and characterized by melting point, 1H NMR, 13C NMR and elemental analyses. The bioactivity revealed that most of them showed moderate to excellent activities against oriental...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2018.05.028

    authors： Liu JB,Li FY,Dong JY,Li YX,Zhang XL,Wang YH,Xiong LX,Li ZM

    更新日期：2018-07-23 00:00:00

  • Novel pyridyl nitrofuranyl isoxazolines show antibacterial activity against multiple drug resistant Staphylococcus species.

    abstract：:A novel series of pyridyl nitrofuranyl isoxazolines were synthesized and evaluated for their antibacterial activity against multiple drug resistant (MDR) Staphylococcus strains. Compounds with piperazine linker between the pyridyl group and isoxazoline ring showed better activity when compared to compounds without the...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.05.037

    authors： Picconi P,Prabaharan P,Auer JL,Sandiford S,Cascio F,Chowdhury M,Hind C,Wand ME,Sutton JM,Rahman KM

    更新日期：2017-08-01 00:00:00

  • Solution-phase microwave assisted parallel synthesis, biological evaluation and in silico docking studies of N,N'-disubstituted thioureas derived from 3-chlorobenzoic acid.

    abstract：:A facile and robust microwave-assisted solution phase parallel synthesis protocol was exercised for the development of a 38-member library of N,N'-disubstituted thiourea analogues (1-38) by using an identical set of conditions. The reaction time for synthesis of N,N'-disubstituted thiourea analogues was drastically re...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2016.07.042

    authors： Rauf MK,Zaib S,Talib A,Ebihara M,Badshah A,Bolte M,Iqbal J

    更新日期：2016-09-15 00:00:00

  • Novel 5-(2-hydroxyphenyl)-3-substituted-2,3-dihydro-1,3,4-oxadiazole-2-thione derivatives: promising anticancer agents.

    abstract：:A series of 5-(2-hydroxyphenyl)-3-substituted-2,3-dihydro-1,3,4-oxadiazole-2-thione derivatives was synthesized and 13 of them were selected by the National Cancer Institute (NCI) and evaluated for their in vitro anticancer activity. Seven of the investigated compounds, 3i, 3j, 3k, 3o, 3p, 3q, and 3r, displayed high a...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2005.09.053

    authors： Aboraia AS,Abdel-Rahman HM,Mahfouz NM,El-Gendy MA

    更新日期：2006-02-15 00:00:00

  • Synthesis and studies of 3'-C-trifluoromethyl nucleoside analogues bearing adenine or cytosine as the base.

    abstract：:3'-Deoxy-3'-C-CF3, 2',3'-dideoxy-3'-C-CF3 and 2',3'-unsaturated-3'-C-CF3 nucleoside derivatives of adenosine and cytidine have been synthesized. All these derivatives were prepared by glycosylation of adenine and uracil with a suitable peracylated 3-trifluoromethyl sugar precursor. The resulting protected nucleosides ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(02)00216-x

    authors： Jeannot F,Gosselin G,Standring D,Bryant M,Sommadossi JP,Giulia Loi A,La Colla P,Mathé C

    更新日期：2002-10-01 00:00:00

  • Development of novel bisubstrate-type inhibitors of histone methyltransferase SET7/9.

    abstract：:Histone modification, for example, by histone deacetylase (HDAC) and histone lysine methyltransferase (HMT), plays an important role in regulating gene expression. To obtain novel inhibitors as tools for investigating the physiological function of members of the HMT family, we designed and synthesized novel inhibitors...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.10.022

    authors： Mori S,Iwase K,Iwanami N,Tanaka Y,Kagechika H,Hirano T

    更新日期：2010-12-01 00:00:00

  • Multivalent presentation of a hydrolytically stable GM(3) lactone mimetic as modulator of melanoma cells motility and adhesion.

    abstract：:A hydrolytically stable mimetic of the tumour antigen GM(3) lactone is used to decorate multivalent scaffolds. Two of them positively interfere on melanoma cell adhesion, migration and resistance to apoptosis (anoikis). Notably, their ability to hamper melanoma-cells adhesion and reduce the metastatic potential is enh...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2013.03.021

    authors： Richichi B,Comito G,Cerofolini L,Gabrielli G,Marra A,Moni L,Pace A,Pasquato L,Chiarugi P,Dondoni A,Toma L,Nativi C

    更新日期：2013-05-15 00:00:00

  • The novel GABA adamantane derivative (AdGABA): design, synthesis, and activity relationship with gabapentin.

    abstract：:A facile preparation of 2-aminomethyl-2-tricyclo[3.3.1.1(1,7)]decaneacetic acid hydrochloride 5 (AdGABA) is described. The synthesis of AdGABA involves the hydrogenation of 2-cyano-2-tricyclo[3.3.1.1(1,7)]decaneacetic acid 11, which was synthesized by two different synthetic routes. AdGABA was found to antagonize the ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2005.02.030

    authors： Zoidis G,Papanastasiou I,Dotsikas I,Sandoval A,Dos Santos RG,Papadopoulou-Daifoti Z,Vamvakides A,Kolocouris N,Felix R

    更新日期：2005-04-15 00:00:00