当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY LETTERS期刊下所有文献 > Design and synthesis of conformationally constrained 3-(N-alkylamino)propylphosphonic acids as potent agonists of sphingosine-1-phosphate (S1P) receptors.

Design and synthesis of conformationally constrained 3-(N-alkylamino)propylphosphonic acids as potent agonists of sphingosine-1-phosphate (S1P) receptors.

Abstract：

:A series of conformationally constrained 3-(N-alkylamino)propylphosphonic acids were systematically synthesized and their activities as S1P receptor agonists were evaluated. Several pyrrolidine and cyclohexane analogs had S1P receptor profiles comparable to the acyclic lead compound, 3-(N-tetradecylamino)propylphosphonic acid (3), lowered circulating lymphocytes in mice after iv administration and were thus identified as being suitable for further investigations.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Yan L,Hale JJ,Lynch CL,Budhu R,Gentry A,Mills SG,Hajdu R,Keohane CA,Rosenbach MJ,Milligan JA,Shei GJ,Chrebet G,Bergstrom J,Card D,Rosen H,Mandala SM

doi

10.1016/j.bmcl.2004.07.049

subject

Has Abstract

pub_date

2004-10-04 00:00:00

pages

4861-6

issue

19

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(04)00950-3

journal_volume

14

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS文献大全
  • Photo-controlled release of fipronil from a coumarin triggered precursor.

    abstract：:Developing efficient controlled release system of insecticide can facilitate the better use of insecticide. We described here a first example of photo-controlled release of an insecticide by linking fipronil with photoresponsive coumarin covalently. The generated coumarin-fipronil (CF) precursor could undergo cleavage...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2017.03.091

    authors： Gao Z,Yuan P,Wang D,Xu Z,Li Z,Shao X

    更新日期：2017-06-01 00:00:00

  • Synthesis, in vitro, and in vivo antibacterial activity of nocathiacin I thiol-Michael adducts.

    abstract：:The synthesis and antibacterial activity of a series of nocathiacin I derivatives (4-20) containing polar water solubilizing groups is described. Thiol-Michael adducts containing acidic polar groups have reduced antibacterial activity whereas those with basic polar groups have retained very good antibacterial activity...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2005.02.046

    authors： Naidu BN,Sorenson ME,Bronson JJ,Pucci MJ,Clark JM,Ueda Y

    更新日期：2005-04-15 00:00:00

  • Nonbenzamidine acylsulfonamide tissue factor-factor VIIa inhibitors.

    abstract：:Aminoisoquinoline and isoquinoline groups have successfully replaced the more basic P1 benzamidine group of an acylsulfonamide factor VIIa inhibitor. Inhibitory activity was optimized by the identification of additional hydrophobic and hydrophilic P' binding interactions. The molecular details of these interactions we...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2013.06.027

    authors： Glunz PW,Zhang X,Zou Y,Delucca I,Nirschl AH,Cheng X,Weigelt CA,Cheney DL,Wei A,Anumula R,Luettgen JM,Rendina AR,Harpel M,Luo G,Knabb R,Wong PC,Wexler RR,Priestley ES

    更新日期：2013-09-15 00:00:00

  • In vitro COX-1 and COX-2 enzyme inhibitory activities of iridoids from Penstemon barbatus, Castilleja tenuiflora, Cresentia alata and Vitex mollis.

    abstract：:A group of sixteen iridoids isolated from plants used as anti-inflammatory remedies in Mexican folk medicine were evaluated for their potential to inhibit cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) enzymes. From these assays, loganic acid (10) was identified as the most promising compound with both COX-1 (3...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2015.08.075

    authors： Ramírez-Cisneros MÁ,Rios MY,Aguilar-Guadarrama AB,Rao PP,Aburto-Amar R,Rodríguez-López V

    更新日期：2015-10-15 00:00:00

  • Synthesis and biological activity of retinoic acid receptor-alpha specific amides.

    abstract：:Retinoids are analogues of all-trans-retinoic acid, a powerful hormone that mediates many fundamental biological processes. Cancer and other serious hyperproliferative diseases are attractive therapeutic targets for retinoids, but the therapeutic use of retinoids is limited due to severe toxicity. We report here the d...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(02)00647-9

    authors： Beard RL,Duong TT,Teng M,Klein ES,Standevan AM,Chandraratna RA

    更新日期：2002-11-04 00:00:00

  • Enhancing the activity of membrane remodeling epsin-peptide by trimerization.

    abstract：:Modulating the structural dynamics of biomembranes by inducing bilayer curvature and lipid packing defects has been highlighted as a practical tool to modify membrane-dependent cellular processes. Previously, we have reported on an amphipathic helical peptide derived from the N-terminal segment (residues 1-18, EpN18) ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2020.127190

    authors： Hsu WY,Masuda T,Afonin S,Sakai T,Arafiles JVV,Kawano K,Hirose H,Imanishi M,Ulrich AS,Futaki S

    更新日期：2020-06-15 00:00:00

  • Sequence selective naked-eye detection of DNA harnessing extension of oligonucleotide-modified nucleotides.

    abstract：:DNA polymerases can efficiently and sequence selectively incorporate oligonucleotide (ODN)-modified nucleotides and the incorporated oligonucleotide strand can be employed as primer in rolling circle amplification (RCA). The effective amplification of the DNA primer by Φ29 DNA polymerase allows the sequence-selective ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2015.12.082

    authors： Verga D,Welter M,Marx A

    更新日期：2016-02-01 00:00:00

  • Microwave-assisted synthesis and in vitro antibacterial activity of novel steroidal thiosemicarbazone derivatives.

    abstract：:Herein, we reported the synthesis of 16 novel steroidal thiosemicarbazone derivatives via the condensation of steroidal ketones and substituted thiosemicarbazides under solvent-free conditions using microwave irradiation. The yields obtained are in the range of 84-96% using microwave method and 46-62% using convention...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2012.09.083

    authors： Zhao Z,Shi Z,Liu M,Liu X

    更新日期：2012-12-15 00:00:00

  • Increasing metabolic stability via the deuterium kinetic isotope effect: An example from a proline-amide-urea aminothiazole series of phosphatidylinositol-3 kinase alpha inhibitors.

    abstract：:In vitro metabolic identification studies with a PI3K-α inhibitor lead molecule 1 identified a single predominant site of oxidative metabolism to be occurring within a tert.butyl moiety. Modification of the tert.butyl group within the lead molecule 1, to the corresponding d9-tert.butyl analogue 2, led to an increase i...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2016.08.041

    authors： Fairhurst RA,Caravatti G,Guagnano V,Aichholz R,Blanz J,Blasco F,Wipfli P,Fritsch C,Maira SM,Schnell C,Seiler FH

    更新日期：2016-10-01 00:00:00

  • Pyrazole NNRTIs 1: design and initial optimisation of a novel template.

    abstract：:The design and synthesis of a novel series of non-nucleoside HIV reverse transcriptase inhibitors (NNRTIs) based on a pyrazole template is described. These compounds are active against wild type reverse transcriptase (RT) and retain activity against clinically important mutants. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2009.08.039

    authors： Mowbray CE,Burt C,Corbau R,Perros M,Tran I,Stupple PA,Webster R,Wood A

    更新日期：2009-10-01 00:00:00

  • Preliminary structure-antiangiogenic activity relationships of 4-senecioyloxymethyl-6,7-dimethoxycoumarin.

    abstract：:Through a systematic modification of the novel angiogenesis inhibitor 4-senecioyloxymethyl-6,7-dimethoxycoumarin (1) we found that a 6,7-dimethoxy moiety is important for bioactivity of 1. Replacement of the lactone functionality in coumarin 1 by an amide decreased its activity. By substitution of the senecioyl chain ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(02)00392-x

    authors： Nam NH,Kim Y,You YJ,Hong DH,Kim HM,Ahn BZ

    更新日期：2002-09-02 00:00:00

  • Setting expectations in molecular optimizations: Strengths and limitations of commonly used composite parameters.

    abstract：:Over the past 15years there have been extensive efforts to understand and reduce the high attrition rates of drug candidates with an increased focus on physicochemical properties. The fruits of this labor have been the generation of numerous efficiency indices, metric-based rules and visualization tools to help guide ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2013.08.029

    authors： Shultz MD

    更新日期：2013-11-01 00:00:00

  • Discovery of tricyclic 5,6-dihydro-1H-pyridin-2-ones as novel, potent, and orally bioavailable inhibitors of HCV NS5B polymerase.

    abstract：:A novel series of non-nucleoside small molecules containing a tricyclic dihydropyridinone structural motif was identified as potent HCV NS5B polymerase inhibitors. Driven by structure-based design and building on our previous efforts in related series of molecules, we undertook extensive SAR studies, in which we ident...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2009.09.045

    authors： Ruebsam F,Murphy DE,Tran CV,Li LS,Zhao J,Dragovich PS,McGuire HM,Xiang AX,Sun Z,Ayida BK,Blazel JK,Kim SH,Zhou Y,Han Q,Kissinger CR,Webber SE,Showalter RE,Shah AM,Tsan M,Patel RA,Thompson PA,Lebrun LA,Hou HJ,

    更新日期：2009-11-15 00:00:00

  • 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

  • LAT-1 activity of meta-substituted phenylalanine and tyrosine analogs.

    abstract：:The transporter protein Large-neutral Amino Acid Transporter 1 (LAT-1, SLC7A5) is responsible for transporting amino acids such as tyrosine and phenylalanine as well as thyroid hormones, and it has been exploited as a drug delivery mechanism. Recently its role in cancer has become increasingly appreciated, as it has b...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2016.04.023

    authors： Augustyn E,Finke K,Zur AA,Hansen L,Heeren N,Chien HC,Lin L,Giacomini KM,Colas C,Schlessinger A,Thomas AA

    更新日期：2016-06-01 00:00:00

  • Quinuclidines as selective agonists for alpha-7 nicotinic acetylcholine receptors.

    abstract：:The alpha7 subtype of the neuronal nicotinic acetylcholine receptors (nAChRs) was targeted for the design of selective agonists deriving from the quinuclidine scaffold. Arylidene groups at the 3-position and N-methyl quinuclidine were found to be selective agonists with EC(50)s of 1.5 and 40 microM, respectively. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2007.01.003

    authors： Leonik FM,Papke RL,Horenstein NA

    更新日期：2007-03-15 00:00:00

  • "Cut and combine": an easy membrane-supported combinatorial synthesis technique.

    abstract：:A combinatorial synthesis process involving sequential cycles of cutting a membrane support into pieces and combining these into groups and subjecting the groups to simultaneous solid-phase chemical reactions is demonstrated by the rapid assembly of four hundred N-terminally biotinylated, soluble, octameric peptide po...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(98)00425-9

    authors： Dittrich F,Tegge W,Frank R

    更新日期：1998-09-08 00:00:00

  • The SAR of 4-substituted (6,6-bicyclic) piperidine cathepsin S inhibitors.

    abstract：:A series of competitive, reversible cathepsin S (CatS) inhibitors was investigated. An earlier disclosure detailed the discovery of the 4-(2-keto-1-benzimidazolinyl)-piperidin-1-yl moiety as an effective replacement for the 4-arylpiperazin-1-yl group found in our screening hit. Continued investigation into replacement...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2006.01.038

    authors： Grice CA,Tays K,Khatuya H,Gustin DJ,Butler CR,Wei J,Sehon CA,Sun S,Gu Y,Jiang W,Thurmond RL,Karlsson L,Edwards JP

    更新日期：2006-04-15 00:00:00

  • Carbonic anhydrase inhibitors: inhibition of the β-class enzyme from the pathogenic yeast Candida glabrata with sulfonamides, sulfamates and sulfamides.

    abstract：:The fungal pathogen Candida glabrata encodes for a β-carbonic anhydrase (CA, EC 4.2.1.1), CgNce103, recently discovered. Only anions have been investigated as CgNce103 inhibitors up until now. Here we report the first sulfonamides inhibition study of this enzyme. Simple sulfonamides showed weak or moderate CgNce103 in...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2013.02.092

    authors： Vullo D,Leewattanapasuk W,Mühlschlegel FA,Mastrolorenzo A,Capasso C,Supuran CT

    更新日期：2013-05-01 00:00:00

  • Synthesis and evaluation of N-alkyl-9-aminoacridines with antibacterial activity.

    abstract：:A series of 9-alkylaminoacridines were synthesized and evaluated for activity against two strains of methicillin-resistant and one strain of methicillin-sensitive Staphylococcus aureus. Results are presented that show a clear structure activity relationship between the N-alkyl chain length and antibacterial activity w...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2014.05.037

    authors： Benoit AR,Schiaffo C,Salomon CE,Goodell JR,Hiasa H,Ferguson DM

    更新日期：2014-07-15 00:00:00

  • Native chemical ligation derived method for recombinant peptide/protein C-terminal amidation.

    abstract：:C-terminal amidation is often a requisite structural feature for peptide hormone bio-activity. We report a chemical amidation method that converts peptide/protein thioesters into their corresponding C-terminal amides. The peptide/protein thioester is treated with 1-(2,4-dimethoxyphenyl)-2-mercaptoethyl auxiliary (1b) ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2013.06.095

    authors： Sun C,Luo G,Neravetla S,Ghosh SS,Forood B

    更新日期：2013-09-15 00:00:00

  • Synthesis, characterization and preliminary analysis of in vivo biological activity of chitosan/celecoxib microcapsules.

    abstract：:The use of chitosan as the wall of microcapsule designed for delivery of encapsulated celecoxib is reported. Microcapsules were characterised with respect to size and encapsulation efficiency of celecoxib. In vivo animals demonstrated that both free celecoxib administration and chitosan/celecoxib microcapsules adminis...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2010.05.054

    authors： Cheng SY,Yuen MC,Lam PL,Gambari R,Wong RS,Cheng GY,Lai PB,Tong SW,Chan KW,Lau FY,Kok SH,Lam KH,Chui CH

    更新日期：2010-07-15 00:00:00

  • A novel approach to the synthesis of cytotoxic C2-C3 unsaturated pyrrolo[2,1-c]benzodiazepines (PBDs) with conjugated acrylyl C2-substituents.

    abstract：:A concise synthesis of three novel C2-C3 unsaturated pyrrolo[2,1-c][1,4]benzodiazepine analogues (18-20) containing conjugated acrylyl C2-substituents is reported that utilises Heck coupling to install the C2-acrylyl side chains. These analogues possess significant cytotoxicity according to the NCI 60-cell line screen...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2003.12.094

    authors： Chen Z,Gregson SJ,Howard PW,Thurston DE

    更新日期：2004-03-22 00:00:00

  • Discovery of mu-opioid selective ligands derived from 1-aminotetralin scaffolds made via metal-catalyzed ring-opening reactions.

    abstract：:A series of 1-aminotetralin scaffolds was synthesized via metal-catalyzed ring-opening reactions of heterobicyclic alkenes. Small libraries of amides and amines were made using the amino group of each scaffold as a handle. Screening of these libraries against human opioid receptors led to the identification of (S)-(S)...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2008.12.095

    authors： Dockendorff C,Jin S,Olsen M,Lautens M,Coupal M,Hodzic L,Spear N,Payza K,Walpole C,Tomaszewski MJ

    更新日期：2009-02-15 00:00:00

  • Cyclohexanedione herbicides are inhibitors of rat heart acetyl-CoA carboxylase.

    abstract：:Acetyl CoA carboxylase (ACC) catalyzes the carboxylation of acetyl CoA to form malonyl CoA. In skeletal muscle and heart, malonyl CoA functions to regulate lipid oxidation by inhibition of carnitine palmitoyltransferase-1, an enzyme which controls the entry of long chain fatty acids into mitochondria. We have found th...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(03)00664-4

    authors： Seng TW,Skillman TR,Yang N,Hammond C

    更新日期：2003-10-06 00:00:00

  • T-type Ca2+ channel blocker, KYS05047 induces G1 phase cell cycle arrest by decreasing intracellular Ca2+ levels in human lung adenocarcinoma A549 cells.

    abstract：:In a previous study, we found that the 3,4-dihydroquinazoline derivative, 4-(Benzylcarbamoylmethyl)-2-(biphenyl-4-ylamino)-3-(5-tert-butyloxycarbamoyl-1-pentyl)-3,4-dihydroquinazoline (KYS05047), was a selective T-type Ca(2+) channel blocker with anti-proliferative effects against various cancer cells. However, the me...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2012.09.076

    authors： Rim HK,Lee HW,Choi IS,Park JY,Choi HW,Choi JH,Cho YW,Lee JY,Lee KT

    更新日期：2012-12-01 00:00:00

  • Identification of a new biaryl scaffold generating potent renin inhibitors.

    abstract：:The discovery and SAR of a series of potent renin inhibitors possessing a novel biaryl scaffold are described herein. Molecular modeling revealed that the cyclopropylamide spacer present in 1 can be replaced by a simple, substituted aromatic ring such as a toluene in 2. The resulting compounds exhibit subnanomolar ren...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2010.07.127

    authors： Lacombe P,Aspiotis R,Bayly C,Chen A,Dubé D,Fortin R,Gallant M,Juteau H,Liu S,McKay D,Roy P,Wu T

    更新日期：2010-10-01 00:00:00

  • Synthesis and evaluation of novel prenylated chalcone derivatives as anti-leishmanial and anti-trypanosomal compounds.

    abstract：:Chalcones form a class of compounds that belong to the flavonoid family and are widely distributed in plants. Their simple structure and the ease of preparation make chalcones attractive scaffolds for the synthesis of a large number of derivatives enabling the evaluation of the effects of different functional groups o...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2015.05.072

    authors： Passalacqua TG,Dutra LA,de Almeida L,Velásquez AM,Torres FA,Yamasaki PR,dos Santos MB,Regasini LO,Michels PA,Bolzani Vda S,Graminha MA

    更新日期：2015-08-15 00:00:00

  • 3-Substituted-(5-arylfuran-2-ylcarbonyl)guanidines as NHE-1 inhibitors.

    abstract：:The C-3 substituents effect on NHE-1 inhibitory activity of (5-arylfuran-2-ylcarbonyl)guanidines, previously identified as potent NHE-1 inhibitors, was investigated. The introduction of amine or alkyl groups at the 3-position of the furan ring, next to the acylguanidine moiety, remarkably improves NHE-1 inhibitory pot...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2006.12.012

    authors： Lee S,Kim T,Lee BH,Yoo SE,Lee K,Yi KY

    更新日期：2007-03-01 00:00:00

  • Synthesis and structure-activity relationships of 1,5-diazaanthraquinones as antitumour compounds.

    abstract：:1,5-Diazaanthraquinone derivatives were synthesized employing single and double hetero Diels-Alder strategies. Their in vitro antitumour activity was assayed using three cell lines. Some of these compounds, specially those bearing methyl or ethyl groups at the C-3,7 positions or chloro at C-4 and methyl at C-7, showed...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2004.05.055

    authors： Avendaño C,Pérez JM,Blanco Mdel M,de la Fuente JA,Manzanaro S,Vicent MJ,Martín MJ,Salvador-Tormo N,Menéndez JC

    更新日期：2004-08-02 00:00:00