当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY LETTERS期刊下所有文献 > Discovery of new diphenyloxazole derivatives containing a pyrrolidine ring: orally active prostacyclin mimetics. Part 2.

Discovery of new diphenyloxazole derivatives containing a pyrrolidine ring: orally active prostacyclin mimetics. Part 2.

Abstract：

:Synthetic and biological evaluation of novel diphenyloxazole derivatives containing a pyrrolidine ring, as a prostacyclin mimetic without the PG skeleton, are described. Asymmetric reduction of a ketone using a chiral Ru complex and reductive amination by NaBH(4) produces four isomers of the tetrahydronaphthalene ring and the pyrrolidine ring with high stereoselectivity. FR193262 (4), (R,R)-diphenyloxazolyl pyrrolidine derivative, displays high potency and agonist efficacy at the IP receptor and has good bioavailability in rats and dogs.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Hattori K,Okitsu O,Tabuchi S,Taniguchi K,Nishio M,Koyama S,Seki J,Sakane K

doi

10.1016/j.bmcl.2005.04.042

subject

Has Abstract

pub_date

2005-07-01 00:00:00

pages

3279-83

issue

13

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(05)00524-X

journal_volume

15

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS文献大全
  • 1,2,3-Triazoles as inhibitors of indoleamine 2,3-dioxygenase 2 (IDO2).

    abstract：:Indoleamine 2,3-dioxygenase 2 (IDO2) is a potential therapeutic target for the treatment of diseases that involve immune escape such as cancer. In contrast to IDO1, only a very limited number of inhibitors have been described for IDO2 due to inherent difficulties in expressing and purifying a functionally active, solu...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2016.07.031

    authors： Röhrig UF,Majjigapu SR,Caldelari D,Dilek N,Reichenbach P,Ascencao K,Irving M,Coukos G,Vogel P,Zoete V,Michielin O

    更新日期：2016-09-01 00:00:00

  • Synthesis and characterization of a perchlorotriphenylmethyl (trityl) triester radical: a potential sensor for superoxide and oxygen in biological systems.

    abstract：:Synthesis and characterization of an inert perchlorotriphenylmethyl triester radical, PTM-TE, are reported. PTM-TE was prepared by a facile 3-step synthesis using Friedel-Crafts reaction of tetrachlorobenzene with chloroform followed by ethoxycarbonylation and subsequent oxidation. PTM-TE is paramagnetic and exhibits ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2007.04.070

    authors： Dang V,Wang J,Feng S,Buron C,Villamena FA,Wang PG,Kuppusamy P

    更新日期：2007-07-15 00:00:00

  • Absolute configurations of tubulin inhibitors taltobulin (HTI-286) and HTI-042 characterized by X-ray diffraction analysis and NMR studies.

    abstract：:The stereochemistry of the tubulin inhibitors taltobulin HTI-286 (2) and HTI-042 (3) was determined by utilizing the DPFGSE 1D NOE experiment. Single crystal X-ray diffraction analysis further confirmed the absolute configuration of these two compounds, which carry the (S,S,S)-configuration necessary for biological ac...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2010.01.047

    authors： Niu C,Ho DM,Williamson RT,Zask A,Ayral-Kaloustian S

    更新日期：2010-03-01 00:00:00

  • Identification of novel PPARalpha ligands by the structural modification of a PPARgamma ligand.

    abstract：:To develop novel PPARalpha ligands, we designed and synthesized several 3-{3-[2-(nonylpyridin-2-ylamino)ethoxy]phenyl}propanoic acid derivatives. Compound 10, the meta isomer of a PPARgamma agonist 1, has been identified as a PPARalpha ligand. The introduction of methyl and ethyl groups at the C-2 position of the prop...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2006.03.031

    authors： Usui S,Fujieda H,Suzuki T,Yoshida N,Nakagawa H,Miyata N

    更新日期：2006-06-15 00:00:00

  • Suzuki coupling based synthesis and in vitro cytotoxic evaluation of 7-heteroaryl-substituted camptothecin analogs.

    abstract：:In an effort to discover potent antitumor agents, a series of novel C-7-heteroaryl-substituted camptothecin derivatives were designed and synthesized via microwave-promoted Suzuki coupling reaction. These analogs were then assessed for cytotoxicity against three human tumor cell lines, A549, HCT116, HT-29, and inhibit...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2014.01.049

    authors： Wang L,Huang Y,Zhang J,Tong L,Chen Y,Lu W,Huang Q

    更新日期：2014-03-15 00:00:00

  • Synthesis, crystal structures, molecular docking, and in vitro biological activities of transition metals with 4-(2,3-dichlorophenyl)piperazine-1-carboxylic acid.

    abstract：:Four novel mononuclear complexes, [Cd(L)2·2H2O] (1), [Ni(L)2·2H2O] (2) [Cu(L)2·H2O] (3), and [Zn(L)2·2H2O] (4) (CCDC numbers: 1444630-1444633 for complexes 1-4) (HL=4-(2,3-dichlorophenyl)piperazine-1-carboxylic acid) were synthesized, and have been characterized by IR spectroscopy, elemental analysis, and X-ray crysta...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2016.05.051

    authors： Yang DD,Chen YN,Wu YS,Wang R,Chen ZJ,Qin J,Qian SS,Zhu HL

    更新日期：2016-07-15 00:00:00

  • Design and synthesis of a tetrahydropyran-based inhibitor of mammalian ribonucleotide reductase.

    abstract：:A tetrahydropyran-based inhibitor (2) of mammalian ribonucleotide reductase (mRR) has been designed and synthesized based on the heptapeptide, N-AcFTLDADF (1), corresponding to the C-terminus of the R2 subunit of mRR. Inhibition studies revealed that 2 is indeed a competent inhibitor, albeit less potent than 1. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(98)00575-7

    authors： Smith AB 3rd,Sasho S,Barwis BA,Sprengeler P,Barbosa J,Hirschmann R,Cooperman BS

    更新日期：1998-11-17 00:00:00

  • Polarization in the structures of uracil and thiouracils: Implication for binding with orotidine 5'-monophosphate decarboxylase.

    abstract：:The structures of the uracil and thiouracils were examined using NMR spectroscopy and crystal structure data when available. The relationships between the extent of polarization and the C5-C6 bond length as well as the H5-H6 coupling constants were probed. It was found that the bond length and coupling constants corre...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2011.08.109

    authors： Huang S,Gronert S,Wu W

    更新日期：2011-11-01 00:00:00

  • 1-Amido-1-phenyl-3-piperidinylbutanes--CCR5 antagonists for the treatment of HIV: part 2.

    abstract：:Optimisation of a series of 4-piperidinyltriazoles led to the identification of compound 28a which showed good whole cell antiviral activity, excellent selectivity over the hERG ion channel and complete oral absorption. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2009.01.008

    authors： Barber CG,Blakemore DC,Chiva JY,Eastwood RL,Middleton DS,Paradowski KA

    更新日期：2009-03-01 00:00:00

  • Synthesis of novel lignan-like compounds and their antimicrobial activity.

    abstract：:Herein we report the preparation of 3,4-dibenzylfurans and some oxidized derivatives with lignan backbone. The compounds were prepared using the Friedel-Crafts reaction with BF3 etherate as catalyst, demethylation with iodocyclohexane, acetylation and oxidation reactions. The antimicrobial activity was evaluated throu...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2020.127413

    authors： Tufano I,Buommino E,Iesce MR,De Filippis A,Grieco P,Lembo F,DellaGreca M

    更新日期：2020-09-01 00:00:00

  • Synthesis of some new 1,3,5-trisubstituted pyrazolines bearing benzene sulfonamide as anticancer and anti-inflammatory agents.

    abstract：:Thirteen new 2-pyrazoline derivatives bearing benzenesulfonamide moiety (2a-m) were synthesized by condensing appropriate chalcones with 4-hydrazinonbenzenesulfonamide hydrochloride and tested for anticancer and anti-inflammatory actions. According to the protocol of the National Cancer Institute (NCI) in vitro diseas...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2011.05.061

    authors： Bashir R,Ovais S,Yaseen S,Hamid H,Alam MS,Samim M,Singh S,Javed K

    更新日期：2011-07-15 00:00:00

  • New nemadectin congeners with acaricidal and nematocidal activity from Streptomyces microflavus neau3 Y-3.

    abstract：:Two nemadectin congeners 1 and 2 were isolated from the fermentation broth of a mutant strain (Y-3) of Streptomyces microflavus neau3. Their structures were determined on the basis of extensive spectroscopic analysis and comparison with data from the literature. Compound 2 possessed a 5-membered ring lactone that is u...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2013.08.002

    authors： Yang LY,Wang JD,Zhang J,Xue CY,Zhang H,Wang XJ,Xiang WS

    更新日期：2013-10-15 00:00:00

  • Novel bis-arylsulfonamides and aryl sulfonimides as inactivators of plasminogen activator inhibitor-1 (PAI-1).

    abstract：:Inactivators of plasminogen activator inhibitor-1 (PAI-1) have been identified as possible treatments for a range of conditions, including atherosclerosis, venous thrombosis, and obesity. We describe the synthesis and inhibitory activity of a novel series of compounds based on bis-arylsulfonamide and aryl sulfonimide ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2009.12.051

    authors： El-Ayache NC,Li SH,Warnock M,Lawrence DA,Emal CD

    更新日期：2010-02-01 00:00:00

  • A new backbone of artificial enzymes obtained by cross-linkage of poly(ethylenimine).

    abstract：:Cross-linkage of the branches of poly(ethylenimine) (PEI) suppresses flexibility of the polymer as revealed by decreased affinity of the amino groups on PEI backbone towards proton or Ni(II) ion. The cross-linkage improves ability of the PEI derivative equipped with beta-cyclodextrin to deacylate an ester containing t...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(98)00212-1

    authors： Suh J,Noh YS

    更新日期：1998-06-02 00:00:00

  • Discovery and optimization of potent broad-spectrum arenavirus inhibitors derived from benzimidazole and related heterocycles.

    abstract：:A series of potent arenavirus inhibitors sharing a benzimidazole core were previously reported by our group. SAR studies were expanded beyond the previous analysis, which involved the attached phenyl rings and methylamino linker portion, to include modifications focused on the benzimidazole core. These changes include...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2012.11.093

    authors： Burgeson JR,Moore AL,Gharaibeh DN,Larson RA,Cerruti NR,Amberg SM,Hruby DE,Dai D

    更新日期：2013-02-01 00:00:00

  • Solid-phase synthesis of quinol fatty alcohols, design of N/O-substituted quinol fatty alcohols and comparative activities on axonal growth.

    abstract：:Following the promising activity of Q2FA15 on axonal growth, two new series of N/O-substituted QFAs were synthesized, based on a SN2-type reaction. O-alkylated QFA bearing 14 carbon atoms on the side chain (n=14) shows a very potent activity on axonal growth though lowered when compared to Q2FA15. While O-alkylation a...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2006.05.027

    authors： Hanbali M,Bagnard D,Luu B

    更新日期：2006-08-01 00:00:00

  • Synthesis, thermal stability, antimalarial activity of symmetrically and asymmetrically substituted tetraoxanes.

    abstract：:Symmetrically and asymmetrically substituted 1,2,4,5-tetraoxanes were synthesized by the oxidative system H(2)O(2)/TFE in presence of MeReO(3) as a catalyst. All of the synthesized compounds were characterized spectroscopically, and evaluated for cytotoxicity, and antimalarial activity. Several of these tetraoxanes ex...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2007.12.069

    authors： Atheaya H,Khan SI,Mamgain R,Rawat DS

    更新日期：2008-02-15 00:00:00

  • Biological properties of synthetic glycoconjugate mimics of heparin comprising different molecular spacers.

    abstract：:The in vitro antithrombotic activity of synthetic glycoconjugates I and II, comprising a flexible polyethylene glycol type and a rigid polyglucose type spacer, respectively, are compared to heparin. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(98)00382-5

    authors： Dreef-Tromp CM,Basten JE,Broekhoven MA,van Dinther TG,Petitou M,van Boeckel CA

    更新日期：1998-08-18 00:00:00

  • Heteroarylureas with fused bicyclic diamine cores as inhibitors of fatty acid amide hydrolase.

    abstract：:A series of mechanism-based heteroaryl urea fatty acid amide hydrolase (FAAH) inhibitors with fused bicyclic diamine cores is described. In contrast to compounds built around a piperazine core, most of the fused bicyclic diamine bearing analogs prepared exhibited greater potency against rFAAH than the human enzyme. Se...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2020.127463

    authors： Keith JM,Jones W,Pierce JM,Seierstad M,Palmer JA,Webb M,Karbarz M,Scott BP,Wilson SJ,Luo L,Wennerholm M,Chang L,Rizzolio M,Rynberg R,Chaplan S,Guy Breitenbucher J

    更新日期：2020-10-15 00:00:00

  • Eicosapentaenoic-acid-derived isoprostanes: synthesis and discovery of two major isoprostanes.

    abstract：:The stereospecific synthesis of two all-syn-EPA-derived isoprostanes (iPs), 5-epi-8,12-iso-iPF(3alpha)-VI 17 and 8,12-iso-iPF(3alpha)-VI 18, has been accomplished. These two synthetic probes have been used to discover and identify their presence in human urine. The eventual quantitative measurement of these two iPs ma...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2008.09.008

    authors： Chang CT,Patel P,Kang N,Lawson JA,Song WL,Powell WS,FitzGerald GA,Rokach J

    更新日期：2008-10-15 00:00:00

  • 2-Substituted 4,5-dihydrothiazole-4-carboxylic acids are novel inhibitors of metallo-β-lactamases.

    abstract：:Bacterial resistance to β-lactam antibiotics caused by class B metallo-β-lactamases (MBL), especially for certain hospital-acquired, Gram-negative pathogens, poses a significant threat to public health. We report several 2-substituted 4,5-dihydrothiazole-4-carboxylic acids to be novel MBL inhibitors. Structure activit...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2012.08.012

    authors： Chen P,Horton LB,Mikulski RL,Deng L,Sundriyal S,Palzkill T,Song Y

    更新日期：2012-10-01 00:00:00

  • Discovery of novel phenethylpyridone derivatives as potent melanin-concentrating hormone 1 receptor antagonists.

    abstract：:Novel phenethylpyridone derivatives were identified as potent human melanin-concentrating hormone 1 receptor (MCH-1R) antagonists. A search for surrogates for the 4-(2-aminoethoxy)phenyl moiety of 1 resulted in discovery of 2-[4-(aminomethyl)phenyl]ethyl substructure as in 6a. Successive optimization of the right-hand...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2009.07.023

    authors： Ando M,Sekino E,Haga Y,Moriya M,Ito M,Ito J,Iwaasa H,Ishihara A,Kanatani A,Ohtake N

    更新日期：2009-09-01 00:00:00

  • Effective molarity in a nucleic acid-controlled reaction.

    abstract：:Positioning of reactive functional groups within a DNA duplex can enable chemical reactions that otherwise would not occur to an appreciable extent. However, few studies have quantitatively defined the extent to which the enforced proximity of reaction partners in duplex DNA can favor chemical processes. Here, we meas...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2016.04.022

    authors： Catalano MJ,Price NE,Gates KS

    更新日期：2016-06-01 00:00:00

  • Discovery of novel sphingosine kinase-1 inhibitors. Part 2.

    abstract：:Building on our initial work, we have identified additional novel inhibitors of sphingosine kinase-1 (SK1). These new analogs address the shortcomings found in our previously reported compounds. Inhibitors 51 and 54 demonstrated oral bioavailability in a rat PK study. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2010.06.019

    authors： Xiang Y,Hirth B,Kane JL Jr,Liao J,Noson KD,Yee C,Asmussen G,Fitzgerald M,Klaus C,Booker M

    更新日期：2010-08-01 00:00:00

  • Contribution of site-specific PEGylation to the dipeptidyl peptidase IV stability of glucose-dependent insulinotropic polypeptide.

    abstract：:The effects of PEGylation of glucose-dependent insulinotropic polypeptide (GIP) on potency and dipeptidyl peptidase IV (DPPIV) stability are reported. N-terminal modification of GIP(1-30) with 40 kDa polyethylene glycol (PEG) abrogates functional activity. In contrast, C-terminal PEGylation of GIP(1-30) maintains full...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2005.06.002

    authors： Salhanick AI,Clairmont KB,Buckholz TM,Pellegrino CM,Ha S,Lumb KJ

    更新日期：2005-09-15 00:00:00

  • Substituted 2H-isoquinolin-1-one as potent Rho-Kinase inhibitors. Part 1: Hit-to-lead account.

    abstract：:Two closely related scaffolds were identified through an uHTS campaign as desirable starting points for the development of Rho-Kinase (ROCK) inhibitors. Here, we describe our hit-to-lead evaluation process which culminated in the rapid discovery of potent leads such as 22 which successfully demonstrated an early in vi...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2010.04.070

    authors： Wu F,Büttner FH,Chen R,Hickey E,Jakes S,Kaplita P,Kashem MA,Kerr S,Kugler S,Paw Z,Prokopowicz A,Shih CK,Snow R,Young E,Cywin CL

    更新日期：2010-06-01 00:00:00

  • The first synthesis of [(11)C]SB-216763, a new potential PET agent for imaging of glycogen synthase kinase-3 (GSK-3).

    abstract：:SB-216763 is a novel, potent and selective glycogen synthase kinase-3 (GSK-3) inhibitor with an IC(50) value of 34 nM. [(11)C]SB-216763 (3-(2,4-dichlorophenyl)-4-(1-[(11)C]methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione), a new potential PET agent for imaging of GSK-3, was first designed and synthesized in 20-30% decay cor...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2010.11.026

    authors： Wang M,Gao M,Miller KD,Sledge GW,Hutchins GD,Zheng QH

    更新日期：2011-01-01 00:00:00

  • Amides of xanthurenic acid as zinc-dependent inhibitors of Lp-PLA(2).

    abstract：:AX10185, the phenyl amide of xanthurenic acid, was found to be a sub-100nM inhibitor of Lp-PLA(2). However, in the presence of EDTA the inhibitory activity of AX10185 was extinguished while the enzymatic activity of Lp-PLA(2) did not change. Subsequent metal screening experiments determined the inhibition to be Zn(2+)...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2011.12.045

    authors： Lin EC,Hu Y,Amantea CM,Pham LM,Cajica J,Okerberg E,Brown HE,Fraser A,Du L,Kohno Y,Ishiyama J,Kozarich JW,Shreder KR

    更新日期：2012-01-15 00:00:00

  • In vitro selection of a 3' terminal short protector that stabilizes transcripts to improve the translation efficiency in a wheat germ extract.

    abstract：:Wheat cell-free expression systems based on wheat germ extract (WGE) enable us to briefly synthesize various types of proteins in vitro merely by exogenously adding their mRNA templates. Moreover, it is possible to produce larger amounts of protein by thoroughly removing the endosperm, which contains many translation ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 信件

    doi：10.1016/j.bmcl.2019.06.058

    authors： Ogawa A,Kutsuna A,Takamatsu M,Okuzono T

    更新日期：2019-08-15 00:00:00

  • Synthesis and biological evaluation of L- and D-configuration 1,3-dioxolane 5-azacytosine and 6-azathymine nucleosides.

    abstract：:Novel L- and D-configuration dioxolane 5-azacytosine and 6-azathymine nucleosides have been synthesized and evaluated for biological activity. (-)-(2S,4S)-1-[2-(Hydroxymethyl)-1,3-dioxolan-4-yl]-5-azacytosine (6) showed significant activity against HBV, whereas the D-configuration analogue (14) has been found to exhib...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(00)00418-2

    authors： Luo MZ,Liu MC,Mozdziesz DE,Lin TS,Dutschman GE,Gullen EA,Cheng YC,Sartorelli AC

    更新日期：2000-09-18 00:00:00