Synthesis and preliminary biological evaluation of (2S,1'R,2'S)- and (2S,1'S,2'R)-2-(2'-phosphonocyclopropyl)glycines, two novel conformationally constrained l-AP4 analogues.

Abstract:

:Two novel constrained l-AP4 analogues, (2S,1'R,2'S)- and (2S,1'S,2'R)-2-(2'-phosphonocyclopropyl)glycines (7) and (8), were synthesized and evaluated as mGluR ligands. Compound 7 showed to be a group III mGluRs agonist with micromolar activity.

journal_name

Bioorg Med Chem Lett

authors

Amori L,Serpi M,Marinozzi M,Costantino G,Diaz MG,Hermit MB,Thomsen C,Pellicciari R

doi

10.1016/j.bmcl.2005.09.014

subject

Has Abstract

pub_date

2006-01-01 00:00:00

pages

196-9

issue

1

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(05)01163-7

journal_volume

16

pub_type

杂志文章
  • Optimization of benzimidazole series as opioid receptor-like 1 (ORL1) antagonists: SAR study directed toward improvement of selectivity over hERG activity.

    abstract::A structure-activity relationship (SAR) study on the benzimidazole series of opioid receptor-like 1 (ORL1) antagonists related to 1 is described. Optimization of 1 by introduction of a hydrophilic substituent into the thioether part resulted in identification of potent ORL1 antagonists with high selectivity over bindi...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.04.022

    authors: Kobayashi K,Kato T,Yamamoto I,Shimizu A,Mizutani S,Asai M,Kawamoto H,Ito S,Yoshizumi T,Hirayama M,Ozaki S,Ohta H,Okamoto O

    更新日期:2009-06-01 00:00:00

  • Understanding the structural requirements of 4-anilidopiperidine analogues for biological activities at mu and delta opioid receptors.

    abstract::New 4-anilidopiperidine analogues in which the phenethyl group of fentanyl was replaced by several aromatic ring-contained amino acids (or acids) were synthesized to study the biological effect of the substituents on mu and delta opioid receptor interactions. These analogues showed broad (47 nM-76 microM) but selectiv...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.01.114

    authors: Lee YS,Nyberg J,Moye S,Agnes RS,Davis P,Ma SW,Lai J,Porreca F,Vardanyan R,Hruby VJ

    更新日期:2007-04-15 00:00:00

  • Synthesis of aryl-1,2,4-triazine-3,5-diones as antagonists of the gonadotropin-releasing hormone receptor.

    abstract::Several efficient synthetic routes for 2-, 4-, and 6-aryl-1,2,4-triazine-3,5-diones were developed. Derivatives were synthesized and studied as gonadotropin-releasing hormone antagonists in an effort to understand structure-activity relationships of the monocyclic compounds. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.06.057

    authors: Pontillo J,Guo Z,Wu D,Struthers RS,Chen C

    更新日期:2005-10-01 00:00:00

  • Protective effect of Opuntia ficus-indica L. cladodes against UVA-induced oxidative stress in normal human keratinocytes.

    abstract::Opuntia ficus-indica L. is known for its beneficial effects on human health, but still little is known on cladodes as a potent source of antioxidants. Here, a direct, economic and safe method was set up to obtain water extracts from Opuntia ficus-indica cladodes rich in antioxidant compounds. When human keratinocytes ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.10.043

    authors: Petruk G,Di Lorenzo F,Imbimbo P,Silipo A,Bonina A,Rizza L,Piccoli R,Monti DM,Lanzetta R

    更新日期:2017-12-15 00:00:00

  • Novel pyridone EP4 agonists featuring allylic alcohol ω-chains.

    abstract::Novel prostaglandin E2 receptor 4 (EP4) agonists featuring a pyridone core and an allylic alcohol ω-chain were discovered. These agonists were shown to be selective over EP1, EP2 and EP3. Analogs harboring a 4-carboxylic acid phenethyl α-chain displayed improved potency over those containing an n-heptanoic acid chain....

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2020.127104

    authors: Dorich S,Cox JH,Burch JD,Chagnon F,Chen B,Léger S,St-Onge M,Fader LD

    更新日期:2020-05-15 00:00:00

  • Novel bis(indolyl)hydrazide-hydrazones as potent cytotoxic agents.

    abstract::A series of bis(indolyl) hydrazide-hydrazones 5a-n were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. The reaction of indole-3-carboxaldehyde 2 with indole-3-carbohydrazide 4 in presence of catalytic amount of acetic acid afforded 5a-n in good yields. Among the synthesized ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.11.031

    authors: Kumar D,Maruthi Kumar N,Ghosh S,Shah K

    更新日期:2012-01-01 00:00:00

  • Synthesis of novel amide functionalized 2H-chromene derivatives by Ritter amidation of primary alcohol using HBF4·OEt2 as a mild and versatile reagent and evaluation of their antimicrobial and anti-biofilm activities.

    abstract::A series of novel amide functionalized 2H-chromene derivatives 3 were prepared starting from ethyl-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate 1 via sodium borohydride reduction followed by Ritter amidation using HBF4·OEt2 as a mild and versatile reagent. All the products 3 were screened for antimicrobial ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.05.041

    authors: Ratnakar Reddy K,Poornachandra Y,Jitender Dev G,Mallareddy G,Nanubolu JB,Kumar CG,Narsaiah B

    更新日期:2015-08-01 00:00:00

  • Thiourea inhibitors of herpes viruses. Part 1: bis-(aryl)thiourea inhibitors of CMV.

    abstract::Bis-(aryl)thioureas were found to be potent and selective inhibitors of cytomegalovirus (CMV) in cultured HFF cells. Of these, the thiazole analogue 38 was investigated as a potential development candidate. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(03)00586-9

    authors: Bloom JD,DiGrandi MJ,Dushin RG,Curran KJ,Ross AA,Norton EB,Terefenko E,Jones TR,Feld B,Lang SA

    更新日期:2003-09-01 00:00:00

  • Structure-activity relationship of a series of cyclohexylpiperidines bearing an amide side chain as antagonists of the human melanocortin-4 receptor.

    abstract::A series of cyclohexylpiperazines was synthesized as potent and selective antagonists of the human MC4 receptor. Compound 14t displayed binding affinity (Ki) of 4.2 and 1100 nM at MC4R and MC3R, respectively. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.05.017

    authors: Tran JA,Pontillo J,Arellano M,Fleck BA,Tucci FC,Marinkovic D,Chen CW,Saunders J,Foster AC,Chen C

    更新日期:2005-07-15 00:00:00

  • Structural hybridization as a facile approach to new drug candidates.

    abstract::Structural hybridization of preclinically and clinically validated pharmacologically active molecules has emerged as a promising tool to develop new generations of safe and highly efficient drug candidates against various diseases including microbial infections, virus infections and cancer. Strategies of drug-drug com...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章,评审

    doi:10.1016/j.bmcl.2020.127514

    authors: Sampath Kumar HM,Herrmann L,Tsogoeva SB

    更新日期:2020-12-01 00:00:00

  • A fluorescent probe for GM1 gangliosidosis related β-galactosidase: N-(dansylamino)hexylaminocarbonylpentyl-1,5-dideoxy-1,5-imino-D-galactitol.

    abstract::N-(Dansylamino)hexylaminocarbonylpentyl-1,5-dideoxy-1,5-imino-D-galactitol, a strong competitive inhibitor of β-galactosidase, enhances residual β-galactosidase activities in fibroblasts and serves as lead en route to diagnostic compounds for tracking the fate of mutant β-gal as well as aberrant GM1 gangliosides by li...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.09.012

    authors: Fröhlich RF,Fantur K,Furneaux RH,Paschke E,Stütz AE,Wicki J,Withers SG,Wrodnigg TM

    更新日期:2011-11-15 00:00:00

  • Synthesis of chlorophyll-f analogs possessing the 2-formyl group by modifying chlorophyll-a.

    abstract::A methyl group at the 2-position of methyl mesopyropheophorbide-a was transformed to the 2-formyl group to give methyl mesopyropheophorbide-f, one of the chlorophyll-f analogs. The 2-formylation moved the redmost electronic absorption band in a solution to a longer wavelength and the bathochromic shift was comparable ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2014.06.022

    authors: Xu M,Kinoshita Y,Tamiaki H

    更新日期:2014-08-15 00:00:00

  • Antibacterial activity of Mannich bases derived from 2-naphthols, aromatic aldehydes and secondary aliphatic amines.

    abstract::A small library of 1-aminoalkyl 2-naphthols has been synthesized through the direct Mannich reaction of 2-naphthols with (hetero)aromatic aldehydes and secondary amines. All of the Mannich bases having a thiophen-2-yl ring in their structure had good activity against Gram-positive bacteria, irrespective of the nature ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.03.098

    authors: Roman G,Năstasă V,Bostănaru AC,Mareş M

    更新日期:2016-05-15 00:00:00

  • 1,3,4-Trisubstituted pyrrolidine CCR5 receptor antagonists: modifications of the arylpropylpiperidine side chains.

    abstract::The 4-(3-phenylprop-1-yl)piperidine moiety of the 1,3,4-trisubstituted pyrrolidine CCR5 antagonist 1 was modified with electron deficient aromatics as well as replacement of the benzylic methylene with sulfones, gem-difluoromethylenes and alcohols in an effort to balance the antiviral potency with reasonable pharmacok...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)00829-6

    authors: Lynch CL,Willoughby CA,Hale JJ,Holson EJ,Budhu RJ,Gentry AL,Rosauer KG,Caldwell CG,Chen P,Mills SG,MacCoss M,Berk S,Chen L,Chapman KT,Malkowitz L,Springer MS,Gould SL,DeMartino JA,Siciliano SJ,Cascieri MA,Carella

    更新日期:2003-01-06 00:00:00

  • Neamphamide B, new cyclic depsipeptide, as an anti-dormant mycobacterial substance from a Japanese marine sponge of Neamphius sp.

    abstract::A new cyclic depsipeptide, designated neamphamide B (1), was isolated from a marine sponge of Neamphius sp. collected at Okinawa, Japan in 1993 as an anti-mycobacterial substance against active and dormant bacilli. The planar structure of neamphamide B (1) was determined on the basis of spectroscopic analysis, and ste...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.05.071

    authors: Yamano Y,Arai M,Kobayashi M

    更新日期:2012-07-15 00:00:00

  • Synthesis and protonation behavior of a water-soluble N-fused porphyrin: conjugation with an oligoarginine by click chemistry.

    abstract::A water-soluble derivative of N-fused porphyrin (NFP) possessing a nona-arginine (R9) peptide tail was synthesized for the first time by a Cu(I)-catalyzed azide-alkyne 'click' reaction. In aqueous solution, at pH 8, the conjugated molecule (NFP-R9) exists as free base and protonated below pH<6.5 to form monoprotonated...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.03.066

    authors: Ikawa Y,Harada H,Toganoh M,Furuta H

    更新日期:2009-05-01 00:00:00

  • Arylanthranilodinitriles: a new biaryl class of antileishmanial agents.

    abstract::A series of anthranilodinitrile-based biaryls were synthesized and evaluated in vitro against extracellular promastigotes and intracellular amastigotes of Leishmania donovani. Among various screened compounds, a biaryl with trifluoromethyl group 5f showed 83% inhibition against promastigotes and 70% inhibition against...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.02.012

    authors: Singh FV,Vatsyayan R,Roy U,Goel A

    更新日期:2006-05-15 00:00:00

  • 4-Substituted (benzo[b]thiophene-2-carbonyl)guanidines as novel Na+/H+ exchanger isoform-1 (NHE-1) inhibitors.

    abstract::A series of 4-substituted (benzo[b]thiophene-2-carbonyl)guanidines was synthesized and evaluated for the NHE-1 inhibitory activity and cardioprotective efficacy both in vitro and in vivo. Several analogs exhibited a strong inhibition on NHE-1, and which was generally well correlated with their cardioprotective efficac...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.04.046

    authors: Lee S,Lee H,Yi KY,Lee BH,Yoo SE,Lee K,Cho NS

    更新日期:2005-06-15 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

  • A conformationally constrained inhibitor with an enhanced potency for β-tryptase and stability against semicarbazide-sensitive amine oxidase (SSAO).

    abstract::A novel β-tryptase inhibitor with a basic benzylamine P1 group, a piperidine-amide linker, and a substituted indole P4 group was discovered. A substitution at 4-indole position was introduced to constrain the conformational flexibility of the inhibitor to the bioactive conformation exhibited by X-ray structures so tha...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.08.141

    authors: Liang G,Choi-Sledeski YM,Poli G,Chen X,Shum P,Minnich A,Wang Q,Tsay J,Sides K,Cairns J,Stoklosa G,Nieduzak T,Zhao Z,Wang J,Vaz RJ

    更新日期:2010-11-15 00:00:00

  • Synthesis, antibacterial and antifungal activities of some carbazole derivatives.

    abstract::A series of N-substituted carbazole derivatives were synthesized and evaluated for antibacterial and antifungal activities against Staphylococcus aureus, methicillin-resistant Staphylococcus aureus (MRSA), Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa, Bacillus proteus, Candida albicans and Aspergillus f...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.01.159

    authors: Zhang FF,Gan LL,Zhou CH

    更新日期:2010-03-15 00:00:00

  • Evaluation of HIV-1 inhibition by stereoisomers and analogues of the sesquiterpenoid hydroquinone peyssonol A.

    abstract::Peyssonol A, a brominated natural product with documented anti-HIV-1 activity, was synthesized racemically along with 6 isomers and 15 truncated analogues and synthetic precursors. These compounds were screened in a cell-based assay against a recombinant HIV-1 strain to investigate structure-activity relationships. Th...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.01.098

    authors: Treitler DS,Li Z,Krystal M,Meanwell NA,Snyder SA

    更新日期:2013-04-01 00:00:00

  • Investigating small molecules to inhibit germinal center kinase-like kinase (GLK/MAP4K3) upstream of PKCθ phosphorylation: Potential therapy to modulate T cell dependent immunity.

    abstract::Germinal center kinase-like kinase (GLK, also known as MAP4K3) has been hypothesized to have an effect on key cellular activities, including inflammatory responses. GLK is required for activation of protein kinase C-θ (PKCθ) in T cells. Controlling the activity of T helper cell responses could be valuable for the trea...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2018.03.032

    authors: May-Dracka TL,Arduini R,Bertolotti-Ciarlet A,Bhisetti G,Brickelmaier M,Cahir-McFarland E,Enyedy I,Fontenot JD,Hesson T,Little K,Lyssikatos J,Marcotte D,McKee T,Murugan P,Patterson T,Peng H,Rushe M,Silvian L,Spilker K

    更新日期:2018-06-01 00:00:00

  • pH-Dependant fluorescence switching of an i-motif structure incorporating an isomeric azobenzene/pyrene fluorophore.

    abstract::In this study, we synthesized an Azo-py phosphoramidite, featuring azobenzene and pyrene units, as a novel fluorescent and isomeric (trans- and cis-azobenzene units) material, which we incorporated in an i-motif DNA sequence. We then monitored the structural dynamics and changes in fluorescence as the modified DNA seq...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.04.015

    authors: Joo HN,Van Thi Nguyen T,Chae HK,Seo YJ

    更新日期:2017-06-01 00:00:00

  • Design and synthesis of pyridin-2-ylmethylaminopiperidin-1-ylbutyl amide CCR5 antagonists that are potent inhibitors of M-tropic (R5) HIV-1 replication.

    abstract::A series of CCR5 antagonists were optimized for potent inhibition of R5 HIV-1 replication in peripheral blood mononuclear cells. Compounds that met acceptable ADME criteria, selectivity, human plasma protein binding, potency shift in the presence of α-glycoprotein were evaluated in rat and dog pharmacokinetics. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.09.133

    authors: Skerlj R,Bridger G,Zhou Y,Bourque E,McEachern E,Langille J,Harwig C,Veale D,Yang W,Li T,Zhu Y,Bey M,Baird I,Sartori M,Metz M,Mosi R,Nelson K,Bodart V,Wong R,Fricker S,Mac Farland R,Huskens D,Schols D

    更新日期:2011-12-01 00:00:00

  • An amide-based sulfenamide prodrug of gamma secretase inhibitor BMS-708163 delivers parent drug from an oral conventional solid dosage form in male beagle dog.

    abstract::The objective of this Letter is to report the first (to our knowledge) in vivo proof of concept for a sulfenamide prodrug to orally deliver a poorly soluble drug containing a weakly-acidic NH-acid from a conventional solid dosage formulation. This proof of concept was established using BMS-708163 (1), a gamma secretas...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2019.126856

    authors: Guarino VR,Olson RE,Everlof JG,Wang N,McDonald I,Haskell R,Clarke W,Lentz KA

    更新日期:2020-02-01 00:00:00

  • Discovery of peptidic miR-21 processing inhibitor by mirror image phage display: A novel method to generate RNA binding D-peptides.

    abstract::A novel method to generate RNA binding D-peptide has been developed. To achieve the screening method, phage display was applied to "Mirrored" RNA (L-enantiomer of RNA). We have selected pre-miR21 as an initial screening target to demonstrate the method. The mirrored pre-miR-21 binding peptide sequences were successful...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.01.023

    authors: Sakamoto K,Otake K,Umemoto T

    更新日期:2017-02-15 00:00:00

  • A three-step protocol for lead optimization: quick identification of key conformational features and functional groups in the SAR studies of non-ATP competitive MK2 (MAPKAPK2) inhibitors.

    abstract::A three-step protocol for SAR development was introduced and applied to the SAR studies of the MK2 inhibitor program. Following this protocol, key conformational features and functional groups for improving MK2 inhibitor activity were quickly identified. Through this effort, the initial gap observed between in vitro b...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.11.074

    authors: Huang X,Zhu X,Chen X,Zhou W,Xiao D,Degrado S,Aslanian R,Fossetta J,Lundell D,Tian F,Trivedi P,Palani A

    更新日期:2012-01-01 00:00:00

  • Discovery of a potent and selective series of pyrazole bacterial methionyl-tRNA synthetase inhibitors.

    abstract::Starting with a micromolar lead identified from high-throughput screening, a series of pyrazoles were discovered with significantly improved potency on bacterial methionyl-tRNA synthetase and selectivity over human methionyl-tRNA synthetase. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(03)00298-1

    authors: Finn J,Mattia K,Morytko M,Ram S,Yang Y,Wu X,Mak E,Gallant P,Keith D

    更新日期:2003-07-07 00:00:00

  • Synthesis, biological evaluation of prenylflavonoids as vasorelaxant and neuroprotective agents.

    abstract::A series of prenylflavonoids with multiple hydroxyl groups were synthesized and evaluated for their vasorelaxant activities against rat aorta rings pre-contracted by phenylephrine (PE), as well as their neuroprotective effects against OGD induced PC12 cell injury. The results indicated that the prenyl group at A-ring ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.04.120

    authors: Dong X,Qi L,Jiang C,Chen J,Wei E,Hu Y

    更新日期:2009-06-15 00:00:00