当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY LETTERS期刊下所有文献 > Stereoselective synthesis of a novel 2-aza-7-oxabicyclo[3.3.0]octane as neurokinin-1 receptor antagonist.

Stereoselective synthesis of a novel 2-aza-7-oxabicyclo[3.3.0]octane as neurokinin-1 receptor antagonist.

Abstract：

:A novel neurokinin-1 receptor antagonist, (+/-)-(1R( *),3S( *),4S( *),5S( *))-4-[(N-(2-methoxy-5-trifluoromethoxybenzyl)amino]-3-phenyl-2-aza-7-oxabicyclo[3.3.0]octane (1), was synthesized stereoselectively using Padwa's intramolecular 1,3-dipolar cycloaddition methodology as the key step. Compound (+/-)-1 showed high affinity for the NK-1 receptors in human IM-9 cells with an IC(50) value of 0.22 nM. This new structural scaffold demonstrated significant in vivo antagonistic activity in the guinea pig ureter capsaicin-induced plasma extravasation model with an ED(50) value of 1-10mg/kg, po.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Shishido Y,Ito F,Morita H,Ikunaka M

doi

10.1016/j.bmcl.2007.10.010

subject

Has Abstract

pub_date

2007-12-15 00:00:00

pages

6887-90

issue

24

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(07)01179-1

journal_volume

17

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS文献大全
  • Tanzawaic acid derivatives from a marine isolate of Penicillium sp. (SF-6013) with anti-inflammatory and PTP1B inhibitory activities.

    abstract：:Chemical investigation of a marine-derived fungus Penicillium sp. SF-6013 resulted in the discovery of a new tanzawaic acid derivative, 2E,4Z-tanzawaic acid D (1), together with four known analogues, tanzawaic acids A (2) and D (3), a salt form of tanzawaic acid E (4), and tanzawaic acid B (5). Their structures were m...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2014.10.035

    authors： Quang TH,Ngan NTT,Ko W,Kim DC,Yoon CS,Sohn JH,Yim JH,Kim YC,Oh H

    更新日期：2014-12-15 00:00:00

  • A quantitative assessment of hERG liability as a function of lipophilicity.

    abstract：:The impact of lipophilicity as a factor contributing to hERG potency is assessed for a large dataset of compounds of differing ionisation type. This dataset is derived from compounds tested in the IonWorks-based in vitro electrophysiology hERG assay at AstraZeneca. Using logistic regression, a quantification of the ri...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2006.12.061

    authors： Waring MJ,Johnstone C

    更新日期：2007-03-15 00:00:00

  • Discovery of dual orexin receptor antagonists with rat sleep efficacy enabled by expansion of the acetonitrile-assisted/diphosgene-mediated 2,4-dichloropyrimidine synthesis.

    abstract：:Recent clinical studies have demonstrated that dual orexin receptor antagonists (OX1R and OX2R antagonists or DORAs) represent a novel treatment option for insomnia patients. Previously we have disclosed several compounds in the diazepane amide DORA series with excellent potency and both preclinical and clinical sleep...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2014.03.052

    authors： Roecker AJ,Mercer SP,Harrell CM,Garson SL,Fox SV,Gotter AL,Prueksaritanont T,Cabalu TD,Cui D,Lemaire W,Winrow CJ,Renger JJ,Coleman PJ

    更新日期：2014-05-01 00:00:00

  • Synthesis of sub-micromolar inhibitors of MraY by exploring the region originally occupied by the diazepanone ring in the liposidomycin structure.

    abstract：:The synthesis and inhibitory activity against MraY of a series of simplified analogues of liposidomycins are described. These compounds were mainly obtained by performing parallel synthesis in the 6'-position of a scaffold that gathers key features found necessary for the binding to MraY. Thus, inhibitory activity was...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(02)00109-9

    authors： Dini C,Didier-Laurent S,Drochon N,Feteanu S,Guillot JC,Monti F,Uridat E,Zhang J,Aszodi J

    更新日期：2002-04-22 00:00:00

  • Synthesis of novel multivalent fluorescent inhibitors with high affinity to prostate cancer and their biological evaluation.

    abstract：:Prostate-specific membrane antigen (PSMA) is an important biological target for therapy and diagnosis of prostate cancer. In this study, novel multivalent PSMA inhibitors with glutamate-urea-lysine structures were designed to improve inhibition characteristics. Precursors of the novel inhibitors were prepared from glu...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2018.01.047

    authors： Kwon YD,Chung HJ,Lee SJ,Lee SH,Jeong BH,Kim HK

    更新日期：2018-02-15 00:00:00

  • 3-cyanoindole-based inhibitors of inosine monophosphate dehydrogenase: synthesis and initial structure-activity relationships.

    abstract：:A series of novel small molecule inhibitors of inosine monophosphate dehydrogenase (IMPDH), based upon a 3-cyanoindole core, were explored. IMPDH catalyzes the rate determining step in guanine nucleotide biosynthesis and is a target for anticancer, immunosuppressive and antiviral therapy. The synthesis and the structu...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(03)00757-1

    authors： Dhar TG,Shen Z,Gu HH,Chen P,Norris D,Watterson SH,Ballentine SK,Fleener CA,Rouleau KA,Barrish JC,Townsend R,Hollenbaugh DL,Iwanowicz EJ

    更新日期：2003-10-20 00:00:00

  • Design and synthesis of novel substituted quinazoline derivatives as antileishmanial agents.

    abstract：:4-(Substituted-benzylidine)-2-substituted-5,6-dihydrobenzo[h]quinazoline (5a-p) and 4-(substituted-benzylidine)-2-substituted-3, 4, 5, 6-tetrahydrobenzo[h]quinazoline (6a-p) have been synthesized from 2-(substituted-benzylidine)tetralone-1(3a-d) and several substituted guanidine sulfates(4a-d).These compounds were tes...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2009.07.081

    authors： Agarwal KC,Sharma V,Shakya N,Gupta S

    更新日期：2009-09-15 00:00:00

  • Synthesis and haemolytic activity of novel salts made of nicotine alkaloids and bile acids.

    abstract：:A series of novel salts made of nicotine alkaloids and bile acids were synthesized and their haemolytic activity was examined in vitro using human erythrocytes. All compounds were characterized by spectroscopic methods. The novel salts show membrane-perturbing properties inducing the erythrocyte shape alterations and ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2014.01.005

    authors： Jasiewicz B,Mrówczyńska L,Malczewska-Jaskóła K

    更新日期：2014-02-15 00:00:00

  • Synthesis of novel 5,6-dehydrokawain analogs as osteogenic inducers and their action mechanisms.

    abstract：:An imbalance between bone resorption by osteoclasts and bone formation by osteoblasts can cause bone loss and bone-related disease. In a previous search for natural products that increase osteogenic activity, we found that 5,6-dehydrokawain (1) from Alpinia zerumbet promotes osteoblastogenesis. In this study, we synth...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2017.04.016

    authors： Kumagai M,Nishikawa K,Mishima T,Yoshida I,Ide M,Koizumi K,Nakamura M,Morimoto Y

    更新日期：2017-06-01 00:00:00

  • Structure-activity relationships in 2-aminodiphenylsulfides against trypanothione reductase from Trypanosoma cruzi.

    abstract：:In order to establish structural elements responsible for inhibition of trypanothione reductase (TR) from Trypanosoma cruzi by 2-aminodiphenylsulfides, a series of dissymmetrical derivatives, corresponding to the replacement of one aromatic moiety by different amines, was synthesized. TR inhibition studies revealed th...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(98)00180-2

    authors： Girault S,Davioud-Charvet E,Salmon L,Berecibar A,Debreu MA,Sergheraert C

    更新日期：1998-05-19 00:00:00

  • Synthesis and preliminary evaluation steroidal antiestrogen-geldanamycin conjugates.

    abstract：:Three novel steroidal antiestrogen-geldanamycin conjugates were prepared using a convergent strategy. The antiestrogenic component utilized the 11β-(4-functionalized-oxyphenyl) estradiol scaffold, while the geldanamycin component was derived by replacement of the 17-methoxy group with an appropriately functionalized a...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 信件

    doi：10.1016/j.bmcl.2013.03.116

    authors： Adam Hendricks J,Hanson RN,Amolins M,Mihelcic JM,Blagg BS

    更新日期：2013-06-15 00:00:00

  • Ligand binding cooperativity: Bioisosteric replacement of CO with SO2 among thrombin inhibitors.

    abstract：:Ligand-protein binding is a complex process that involves the formation of number of non-covalent interactions, e.g. H-bonds and hydrophobic interactions, between the ligand and the protein host. Upon binding, ligand functional groups can act synergistically (positive cooperativity) to improve the overall ligand bindi...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2016.07.024

    authors： Said AM,Hangauer DG

    更新日期：2016-08-15 00:00:00

  • Spirocyclic nonpeptide glycoprotein IIb-IIIa antagonists. Part 2: design of potent antagonists containing the 3-azaspiro[5.5]undecanes.

    abstract：:The synthesis and biological activity of novel glycoprotein IIb-IlIa anatagonists containing 3-azaspiro[5.5]undec-9-yl nucleus are described. The potent activity of these compounds as platelet aggregation inhibitors demonstrates the utility of the monoazaspirocyclic structure as central template for nonpeptide RGD mim...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(01)00216-5

    authors： Pandey A,Seroogy J,Volkots D,Smyth MS,Rose J,Mehrotra MM,Heath J,Ruhter G,Schotten T,Scarborough RM

    更新日期：2001-05-21 00:00:00

  • Nonpeptide oxytocin antagonists: analogs of L-371,257 with improved potency.

    abstract：:Structure-activity studies on the oxytocin antagonist 1 (L-371,257; Ki = 9.3 nM) have led to the identification of a related series of compounds containing an ortho-trifluoroethoxyphenylacetyl core which are orally bioavailable and have significantly improved potency in vitro and in vivo, e.g., compound 8 (L-374,943; ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(99)00181-x

    authors： Williams PD,Bock MG,Evans BE,Freidinger RM,Gallicchio SN,Guidotti MT,Jacobson MA,Kuo MS,Levy MR,Lis EV,Michelson SR,Pawluczyk JM,Perlow DS,Pettibone DJ,Quigley AG,Reiss DR,Salvatore C,Stauffer KJ,Woyden CJ

    更新日期：1999-05-03 00:00:00

  • SAR and in vivo evaluation of 4-aryl-2-aminoalkylpyrimidines as potent and selective Janus kinase 2 (JAK2) inhibitors.

    abstract：:We report the discovery of a series of 4-aryl-2-aminoalkylpyrimidine derivatives as potent and selective JAK2 inhibitors. High throughput screening of our in-house compound library led to the identification of hit 1, from which optimization resulted in the discovery of highly potent and selective JAK2 inhibitors. Adva...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2012.10.007

    authors： Forsyth T,Kearney PC,Kim BG,Johnson HW,Aay N,Arcalas A,Brown DS,Chan V,Chen J,Du H,Epshteyn S,Galan AA,Huynh TP,Ibrahim MA,Kane B,Koltun ES,Mann G,Meyr LE,Lee MS,Lewis GL,Noguchi RT,Pack M,Ridgway BH,Shi X,

    更新日期：2012-12-15 00:00:00

  • Synthesis and evaluation of 9-O-substituted berberine derivatives containing aza-aromatic terminal group as highly selective telomeric G-quadruplex stabilizing ligands.

    abstract：:A series of new 9-O-substituted berberine derivatives (4a-j) as telomeric quadruplex ligands was synthesized and evaluated. The results from biophysical and biochemical assay indicated that introducing of positive charged aza-aromatic terminal group into the side chain of 9-position of berberine significantly improved...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2009.05.030

    authors： Ma Y,Ou TM,Tan JH,Hou JQ,Huang SL,Gu LQ,Huang ZS

    更新日期：2009-07-01 00:00:00

  • Asymmetric synthesis of novel alpha-amino acids with beta-branched side chains.

    abstract：:An asymmetric synthesis of alpha-amino acids with novel beta-branched side chains has been implemented. The syntheses feature a p-toluenesulfinylimine induced chiral Strecker approach and were found to be applicable to the introduction of both aliphatic and aromatic beta-branched sidechains for preparation of previous...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2007.02.041

    authors： Zhang M,Porte A,Diamantidis G,Sogi K,Kubrak D,Resnick L,Mayer SC,Wang Z,Kreft AF,Harrison BL

    更新日期：2007-05-01 00:00:00

  • New potential inhibitors of DNA topoisomerase. Part II: Design and synthesis of alpha-lapachone derivatives under microwave irradiation.

    abstract：:A new series of potential inhibitors of DNA topoisomerase II were synthesized from facile materials (aromatic aldehydes, Meldrum's acid and 2-hydroxynaphthalene-1,4-dione) under microwave irradiation. The method provides a valuable tool in designing new and more potent cytotoxic analogues. This procedure is advantageo...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2008.12.006

    authors： Wei P,Zhang X,Tu S,Yan S,Ying H,Ouyang P

    更新日期：2009-02-01 00:00:00

  • Aromatic glycosyl disulfide derivatives: evaluation of their inhibitory activities against Trypanosoma cruzi.

    abstract：:Aromatic oligovalent glycosyl disulfides and some diglycosyl disulfides were tested against three different Trypanosoma cruzi strains. Di-(β-D-galactopyranosyl-dithiomethylene) benzenes 2b and 4b proved to be the most active derivatives against all three strains of cell culture-derived trypomastigotes with IC50 values...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 信件

    doi：10.1016/j.bmcl.2013.04.030

    authors： Gutiérrez B,Muñoz C,Osorio L,Fehér K,Illyés TZ,Papp Z,Kumar AA,Kövér KE,Sagua H,Araya JE,Morales P,Szilágyi L,González J

    更新日期：2013-06-15 00:00:00

  • 4-Aminophenoxyacetic acids as a novel class of reversible cathepsin K inhibitors.

    abstract：:We have designed and synthesized a novel series of 3-biphenylamino acid amides as cathepsin K inhibitors based on compound I. In these inhibitors, we have discovered 4-aminophenoxyacetic acids 43 and 47 with good IC(50) values, although lipophilic groups are favorable for the hydrophobic S1' pocket. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2005.12.053

    authors： Shinozuka T,Shimada K,Matsui S,Yamane T,Ama M,Fukuda T,Taki M,Naito S

    更新日期：2006-03-15 00:00:00

  • Discovery of 5-hydroxyalkyl-4-phenylpyridines as a new class of glucagon receptor antagonists.

    abstract：:5-Hydroxyalkyl-4-phenylpyridines have been identified as a novel class of glucagon antagonists with potential utility for the treatment of diabetes. A lead structure with moderate activity was discovered through a high throughput screening assay. Structure-activity relationships led to the discovery of a potent antago...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(01)00766-1

    authors： Ladouceur GH,Cook JH,Doherty EM,Schoen WR,MacDougall ML,Livingston JN

    更新日期：2002-02-11 00:00:00

  • Discovery of highly potent and selective benzyloxybenzyl-based peroxisome proliferator-activator receptor (PPAR) delta agonists.

    abstract：:A series of 1,4-benzyloxybenzylsulfanylaryl carboxylic acids were prepared and their activities for PPAR receptor subtypes (alpha, delta, and gamma) with potential indications for the treatment of dyslipidemia were investigated. Analog 13a displayed the greatest binding affinity (IC(50)=10nM) and selectivity (120-fold...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2007.04.046

    authors： Bratton LD,Filzen GF,Geyer A,Hoffman JK,Lu G,Pulaski J,Trivedi BK,Unangst PC,Xu X

    更新日期：2007-07-01 00:00:00

  • Analogues of dealanylalahopcin are inhibitors of human HIF prolyl hydroxylases.

    abstract：:Analogues of the naturally occurring cyclic hydroxamate dealanylalahopcin, which is an inhibitor of procollagen prolyl-4-hydroxylase, were synthesised and shown to be inhibitors of the human hypoxia-inducible factor prolyl hydroxylases. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(03)00149-5

    authors： Schlemminger I,Mole DR,McNeill LA,Dhanda A,Hewitson KS,Tian YM,Ratcliffe PJ,Pugh CW,Schofield CJ

    更新日期：2003-04-17 00:00:00

  • Structure-activity and in vivo evaluation of a novel lipoprotein lipase (LPL) activator.

    abstract：:Elevated triglycerides (TG) contribute towards increased risk for cardiovascular disease. Lipoprotein lipase (LPL) is an enzyme that is responsible for the metabolism of core triglycerides of very-low density lipoproteins (VLDL) and chylomicrons in the vasculature. In this study, we explored the structure-activity rel...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2016.11.053

    authors： Geldenhuys WJ,Caporoso J,Leeper TC,Lee YK,Lin L,Darvesh AS,Sadana P

    更新日期：2017-01-15 00:00:00

  • Wortmannilactones I-L, new NADH-fumarate reductase inhibitors, induced by adding suberoylanilide hydroxamic acid to the culture medium of Talaromyces wortmannii.

    abstract：:With the aim of finding more potential inhibitors against NADH-fumarate reductase (specific target for treating helminthiasis and cancer) from natural resources, Talaromyces wortmannii was treated with the epigenome regulatory agent suberoylanilide hydroxamic acid, which resulted in the isolation of four new wortmanni...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2016.09.032

    authors： Liu WC,Wang YY,Liu JH,Ke AB,Zheng ZH,Lu XH,Luan YS,Xiu ZL,Dong YS

    更新日期：2016-11-01 00:00:00

  • Synthesis and anti-angiogenesis activity of coumarin derivatives.

    abstract：:A series of 7-diethylaminocoumarin compounds were synthesized and the cytotoxicities were tested against human umbilical vein endothelial cell (HUVEC) and some cancer cells. We found that the introduction of cyano groups at the 4-position will promote the bioactivity. In particular, compounds 9 and 10 strongly inhibit...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2006.06.007

    authors： Lee S,Sivakumar K,Shin WS,Xie F,Wang Q

    更新日期：2006-09-01 00:00:00

  • Inhibitory effect on NO production of triterpenes from the fruiting bodies of Ganoderma lucidum.

    abstract：:Four new lanostane triterpenes, butyl lucidenate P (1), butyl lucidenate D(2) (2), butyl lucidenate E(2) (3) and butyl lucidenate Q (4) along with 11 known compounds (5-15) were isolated from the fruiting bodies of Ganoderma lucidum. Their chemical structures were established mainly by 1D and 2D NMR techniques and mas...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2012.12.066

    authors： Tung NT,Cuong TD,Hung TM,Lee JH,Woo MH,Choi JS,Kim J,Ryu SH,Min BS

    更新日期：2013-03-01 00:00:00

  • Convergent solution-phase synthesis of a nucleopeptide using a protected oligonucleotide.

    abstract：:A nucleopeptide was prepared in a convergent manner via segmental coupling of the protected biopolymers in solution. The resulting nucleopeptide (4b, 72%) containing the binding site of lambda repressor and a peptide containing the consensus sequence of the DNA binding helix of the helix turn-helix-proteins was obtain...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(99)00051-7

    authors： McMinn DL,Greenberg MM

    更新日期：1999-02-22 00:00:00

  • Tags for labeling protein N-termini with subtiligase for proteomics.

    abstract：:The peptide ligase subtiligase, derived from subtilisin, has been employed in the identification of protein N-termini in complex mixtures. Here, the peptide ester substrates for the ligation reaction were optimized with respect to solubility, resulting in greater incorporation of the N-terminal tags. Additionally, the...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2008.08.044

    authors： Yoshihara HA,Mahrus S,Wells JA

    更新日期：2008-11-15 00:00:00

  • Highly potent, broadly active antifungal agents for the treatment of invasive fungal infections.

    abstract：:Invasive fungal infections have become an important healthcare issue due in large part to high mortality rates under standard of care (SOC) therapies creating an urgent need for new and effective anti-fungal agents. We have developed a series of non-peptide, structurally-constrained analogs of host defence proteins th...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2020.127727

    authors： Baugh SDP,Chaly A,Weaver DG,Pelletier JC,Thanna S,Freeman KB,Reitz AB,Scott RW

    更新日期：2020-12-13 00:00:00