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 a single sharp EPR spectrum. In solution, the EPR linewidth of PTM-TE is highly sensitive to the dissolved oxygen content, thus enabling accurate measurement of oxygen concentration (oximetry). In addition, the radical also shows high reactivity towards superoxide. The ester radical has the potential for use as a high-sensitive probe for determination of oxygen concentration and superoxide in biological systems.

journal_name

Bioorg Med Chem Lett

authors

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

doi

10.1016/j.bmcl.2007.04.070

subject

Has Abstract

pub_date

2007-07-15 00:00:00

pages

4062-5

issue

14

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(07)00502-1

journal_volume

17

pub_type

杂志文章
  • Discovery of novel 7-membered cyclic amide derivatives that inhibit 11beta-hydroxysteroid dehydrogenase type 1.

    abstract::A series of novel 5-trans-hydroxyadamantan-2-yl-5,6,7,8-tetrahydropyrazolo[4,3-c]azepin-4(1H)-ones that inhibit 11beta-hydroxysteroid dehydrogenase type 1 are described. We discovered these 7-membered cyclic amide derivatives by introducing a distinctive linker through pharmacophore analysis of known ligands included ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.01.090

    authors: Udagawa S,Sakami S,Takemura T,Sato M,Arai T,Nitta A,Aoki T,Kawai K,Iwamura T,Okazaki S,Takahashi T,Kaino M

    更新日期:2013-03-15 00:00:00

  • Sensitivity of neuronal nicotinic acetylcholine receptors to the opiate antagonists naltrexone and naloxone: receptor blockade and up-regulation.

    abstract::In HEK293 cells stably expressing alpha4beta2 nAChRs, naltrexone, but not naloxone, blocked alpha4beta2 nAChRs via an open-channel blocking mechanism. In primary hippocampal cultures, naltrexone inhibited alpha7 nAChRs up-regulated by nicotine, and in organotypic hippocampal cultures naltrexone caused a time-dependent...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.01.004

    authors: Almeida LE,Pereira EF,Camara AL,Maelicke A,Albuquerque EX

    更新日期:2004-04-19 00:00:00

  • Conversion of A3 adenosine receptor agonists into selective antagonists by modification of the 5'-ribofuran-uronamide moiety.

    abstract::The highly selective agonists of the A(3) adenosine receptor (AR), Cl-IB-MECA (2-chloro-N(6)-(3-iodobenzyl)-5'-N-methylcarboxamidoadenosine), and its 4'-thio analogue, were successfully converted into selective antagonists simply by appending a second N-methyl group on the 5'-uronamide position. The 2-chloro-5'-(N,N-d...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.10.054

    authors: Gao ZG,Joshi BV,Klutz AM,Kim SK,Lee HW,Kim HO,Jeong LS,Jacobson KA

    更新日期:2006-02-01 00:00:00

  • Optimization of anti-proliferative activity using a screening approach with a series of bis-heterocyclic G-quadruplex ligands.

    abstract::Using a phenotypic screening and SAR optimization approach, a phenyl-bis-oxazole derivative has been identified with anti-proliferative activity, optimized with the use of a panel of cancer cell lines. The lead compound was synthesized by means of a short and effective two-step synthesis using Pd-catalyzed direct aryl...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.07.057

    authors: Ohnmacht SA,Ciancimino C,Vignaroli G,Gunaratnam M,Neidle S

    更新日期:2013-10-01 00:00:00

  • Novel, lipophilic derivatives of 2,5-dideoxy-2,5-imino-D-mannitol (DMDP) are powerful beta-glucosidase inhibitors.

    abstract::Novel derivatives of the D-glucosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol bearing lipophilic aliphatic or aromatic amides attached to C-1 have been found to inhibit beta-glucosidase from Agrobacterium sp. in the nanomolar range. One of them, a coumarin derivative, ranks amongst the most active compounds in the...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(01)00126-3

    authors: Wrodnigg TM,Withers SG,Stütz AE

    更新日期:2001-04-23 00:00:00

  • Design, synthesis and antithrombotic evaluation of novel dabigatran prodrugs containing methyl ferulate.

    abstract::A novel series of prodrugs containing dabigatran and methyl (E)-3-(4-hydroxy-2-methoxyphenyl)propenoate (methyl ferulate) were synthesized. All of them reveal the effect of thrombin-induced anti-platelet aggregation in vitro. In addition, in vivo experiment shows that one of the target compounds, X-2 (ED50=3.7 ± 1.0 μ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.01.126

    authors: Yang XZ,Diao XJ,Yang WH,Li F,He GW,Gong GQ,Xu YG

    更新日期:2013-04-01 00:00:00

  • Syntheses and studies of quinolone-cephalosporins as potential anti-tuberculosis agents.

    abstract::The syntheses and anti-tuberculosis activity of quinolone-cephalosporin conjugates (1 and 2) are described. Both showed broad-spectrum antibacterial activity and significant anti-TB activity. The carbamate-linked quinolone-cephem 2 showed better antimycobacterial activity, including anti-TB activity, than the direct a...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.08.045

    authors: Zhao G,Miller MJ,Franzblau S,Wan B,Möllmann U

    更新日期:2006-11-01 00:00:00

  • Redox-responsive and calcium-dependent switching of glycosyldisulfide interactions with Concanavalin A.

    abstract::Glycosyldisulfides can interact efficiently with carbohydrate-binding entities. This has been shown for a range of thiosaccharide dimers when tested for their effects against the lectin Concanavalin A using a modified quartz crystal microbalance-technique. Contrary to the thiosaccharide monomers, showing no significan...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.04.024

    authors: Pei Z,Aastrup T,Anderson H,Ramström O

    更新日期:2005-06-02 00:00:00

  • Synthesis of C-1 homologues of pancratistatin and their preliminary biological evaluation.

    abstract::The synthesis of two C-1 analogues of pancratistatin has been accomplished in 17 steps from bromobenzene. The key steps involved the enzymatic dihydroxylation, regioselective opening of epoxyaziridine 9 with the alane derived from 8, a solid-state silica-gel-catalyzed intramolecular opening of aziridine to produce phe...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.06.068

    authors: Vshyvenko S,Scattolon J,Hudlicky T,Romero AE,Kornienko A

    更新日期:2011-08-15 00:00:00

  • Chemical space screening around Phe3 in opioid peptides: Modulating µ versus δ agonism by Suzuki-Miyaura cross-couplings.

    abstract::In this study, affinities and activities of derivatized analogues of Dmt-dermorphin[1-4] (i.e. Dmt-d-Ala-Phe-GlyNH2, Dmt = 2',6'-dimethyl-(S)-tyrosine) for the µ opioid receptor (MOP) and δ opioid receptor (DOP) were evaluated using radioligand binding studies, functional cell-based assays and isolated organ bath expe...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2018.05.015

    authors: Willemse T,Eiselt E,Hollanders K,Schepens W,van Vlijmen HWT,Chung NN,Blais V,Holleran B,Longpré JM,Schiller PW,Maes BUW,Sarret P,Gendron L,Ballet S

    更新日期:2018-07-15 00:00:00

  • Potent and selective inhibitors of the proteasome: dipeptidyl boronic acids.

    abstract::Potent and selective dipeptidyl boronic acid proteasome inhibitors are described. As compared to peptidyl aldehyde compounds, boronic acids in this series display dramatically enhanced potency. Compounds such as 15 are promising new therapeutics for treatment of cancer and inflammatory diseases. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(98)00029-8

    authors: Adams J,Behnke M,Chen S,Cruickshank AA,Dick LR,Grenier L,Klunder JM,Ma YT,Plamondon L,Stein RL

    更新日期:1998-02-17 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

  • Pyrrolo[2,3-h]quinolinones: synthesis and photochemotherapic activity.

    abstract::A series of derivatives of the new ring system pyrrolo[2,3-h]quinoline-2-one was synthesized and evaluated as photoreagents toward cultured human tumor cells. Remarkable phototoxycity resulted for some derivatives, especially those bearing the phenyl group at the 7-position. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(03)00529-8

    authors: Barraja P,Diana P,Lauria A,Montalbano A,Almerico AM,Dattolo G,Cirrincione G,Viola G,Dall'Acqua F

    更新日期:2003-08-18 00:00:00

  • A novel 99mTc-labeled testosterone derivative as a potential agent for targeting androgen receptors.

    abstract::With an insight that ligands possessing a N2S2 tetradentate array of donor atoms serve as ideal bifunctional chelating agents (BFCA) in the radiolabeling of target-specific agents, 5-hydroxy-3,7-diazanonan-1,9-dithiol (DAHPES) with a derivatizable substituent in the form of a hydroxyl group in the backbone was synthes...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.08.081

    authors: Das T,Banerjee S,Samuel G,Bapat K,Subramanian S,Pillai MR,Venkatesh M

    更新日期:2006-11-15 00:00:00

  • Structure-based design of ketone-containing, tripeptidyl human rhinovirus 3C protease inhibitors.

    abstract::Tripeptide-derived molecules incorporating C-terminal ketone electrophiles were evaluated as reversible inhibitors of the cysteine-containing human rhinovirus 3C protease (3CP). An optimized example of such compounds displayed potent 3CP inhibition activity (K = 0.0045 microM) and in vitro antiviral properties (EC50=0...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00587-9

    authors: Dragovich PS,Zhou R,Webber SE,Prins TJ,Kwok AK,Okano K,Fuhrman SA,Zalman LS,Maldonado FC,Brown EL,Meador JW 3rd,Patick AK,Ford CE,Brothers MA,Binford SL,Matthews DA,Ferre RA,Worland ST

    更新日期:2000-01-03 00:00:00

  • 1-[4-(1H-Benzoimidazol-2-yl)-phenyl]-3-[4-(1H-benzoimidazol-2-yl)-phenyl]-urea derivatives as small molecule heparanase inhibitors.

    abstract::A novel class of 1-[4-(1H-benzoimidazol-2-yl)-phenyl]-3-[4-(1H-benzoimidazol-2-yl)-phenyl]-ureas are described as potent inhibitors of heparanase. Among them are 1,3-bis-[4-(1H-benzoimidazol-2-yl)-phenyl]-urea (7a) and 1,3-bis-[4-(5,6-dimethyl-1H-benzoimidazol-2-yl)-phenyl]-urea (7d), which displayed good heparanase i...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.09.069

    authors: Pan W,Miao HQ,Xu YJ,Navarro EC,Tonra JR,Corcoran E,Lahiji A,Kussie P,Kiselyov AS,Wong WC,Liu H

    更新日期:2006-01-15 00:00:00

  • Novel naftopidil derivatives containing methyl phenylacetate and their blocking effects on α1D/1A-adrenoreceptor subtypes.

    abstract::α1-Adrenoceptor (α1-AR) antagonists are considered to be the most effective monotherapy agents for lower urinary tract symptoms associated with benign prostatic hyperplasia (LUTS/BPH). In this study, we synthesized compounds 2-17, which are novel piperazine derivatives that contain methyl phenylacetate. We then evalua...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2018.01.068

    authors: Huang JJ,Zhang ZH,He F,Liu XW,Xu XJ,Dai LJ,Liu QM,Yuan M

    更新日期:2018-02-15 00:00:00

  • Discovery of novel nonsteroidal glucocorticoid receptor modulators.

    abstract::A new class of selective nonsteroidal glucocorticoid receptor modulators typified by N-[3-[benzyl-(4-chloro-2-fluoro-benzyl)-amino]-2-methyl-phenyl]-methanesulfonamide 19 has been discovered. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.02.013

    authors: Link JT,Sorensen BK,Patel J,Emery M,Grynfarb M,Goos-Nilsson A

    更新日期:2004-05-03 00:00:00

  • Duloxetine (Cymbalta), a dual inhibitor of serotonin and norepinephrine reuptake.

    abstract::A series of naphthalenyloxy-arylpropylamines have been prepared and are demonstrated to be inhibitors of both serotonin and norepinephrine reuptake. One member of this series, duloxetine (Cymbalta) has proven to be effective in clinical trials for the treatment of depression. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2003.08.079

    authors: Bymaster FP,Beedle EE,Findlay J,Gallagher PT,Krushinski JH,Mitchell S,Robertson DW,Thompson DC,Wallace L,Wong DT

    更新日期:2003-12-15 00:00:00

  • Discovery of 3-(trifluoromethyl)-1H-pyrazole-5-carboxamide activators of the M2 isoform of pyruvate kinase (PKM2).

    abstract::Activators of the pyruvate kinase M2 (PKM2) are currently attracting significant interest as potential anticancer therapies. They may achieve a novel antiproliferation response in cancer cells through modulation of the classic 'Warburg effect' characteristic of aberrant metabolism. In this Letter, we describe the opti...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.12.028

    authors: Xu Y,Liu XH,Saunders M,Pearce S,Foulks JM,Parnell KM,Clifford A,Nix RN,Bullough J,Hendrickson TF,Wright K,McCullar MV,Kanner SB,Ho KK

    更新日期:2014-01-15 00:00:00

  • Synthetic studies of cis-4-Amino-L-proline derivatives as novel lipid lowering agents.

    abstract::cis-4-Amino-L-proline derivatives 1 and 2 derived from quinazolinone and pyrazolo pyrimidone respectively were designed as novel lipid lowering agents. A preliminary in vivo screening indicates that 1b and 2a have moderate triglyceride lowering activity. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)00799-0

    authors: Das SK,Narasimha Rao Krovvidi VL,Jagadheshan H,Iqbal J

    更新日期:2002-12-16 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

  • Design, synthesis and optimization of 7-substituted-pyrazolo[4,3-b]pyridine ALK5 (activin receptor-like kinase 5) inhibitors.

    abstract::A series of potent ALK5 inhibitors were designed using a SBDD approach and subsequently optimized to improve drug likeness. Starting with a 4-substituted quinoline screening hit, SAR was conducted using a ALK5 binding model to understand the binding site and optimize activity. The resulting inhibitors displayed excell...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.03.026

    authors: Sabat M,Wang H,Scorah N,Lawson JD,Atienza J,Kamran R,Hixon MS,Dougan DR

    更新日期:2017-05-01 00:00:00

  • Identification of a 5-[3-phenyl-(2-cyclic-ether)-methylether]-4-aminopyrrolo[2,3-d]pyrimidine series of IGF-1R inhibitors.

    abstract::We report structure-guided modifications of the benzyloxy substituent of the Insulin-like Growth Factor-1 Receptor (IGF-1R) inhibitor NVP-AEW541. This chemical group has been shown to confer selectivity against other protein kinases but at the expense of a metabolism liability. X-ray crystallography has revealed that ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.02.074

    authors: Stauffer F,Cowan-Jacob SW,Scheufler C,Furet P

    更新日期:2016-04-15 00:00:00

  • Fragment-based discovery of 6-substituted isoquinolin-1-amine based ROCK-I inhibitors.

    abstract::Fragment-based NMR screening of a small literature focused library led to identification of a historical thrombin/FactorXa building block, 17A, that was found to be a ROCK-I inhibitor. In the absence of an X-ray structure, fragment growth afforded 6-substituted isoquinolin-1-amine derivatives which were profiled in th...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.11.060

    authors: Ray P,Wright J,Adam J,Bennett J,Boucharens S,Black D,Cook A,Brown AR,Epemolu O,Fletcher D,Haunso A,Huggett M,Jones P,Laats S,Lyons A,Mestres J,de Man J,Morphy R,Rankovic Z,Sherborne B,Sherry L,van Straten N,We

    更新日期:2011-01-01 00:00:00

  • Molecular basis for cis-urocanic acid as a 5-HT(2A) receptor agonist.

    abstract::The underlying mechanisms of urocanic acid (UA) to induce immune suppression remain elusive until the recent finding that cis-UA acts via the serotonin, 5-hydroxytryptamine (5-HT) receptor subtype 5-HT(2A). In the present study, the interactions of cis-UA to 5-HT(2A) receptor were explored and compared with those of 5...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.07.143

    authors: Shen L,Ji HF

    更新日期:2009-09-15 00:00:00

  • Evaluation of novel TGR5 agonist in combination with Sitagliptin for possible treatment of type 2 diabetes.

    abstract::TGR5 is a member of G protein-coupled receptor (GPCR) superfamily, a promising molecular target for metabolic diseases. Activation of TGR5 promotes secretion of glucagon-like peptide-1 (GLP-1), which activates insulin secretion. A series of 2-thio-imidazole derivatives have been identified as novel, potent and orally ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2018.04.011

    authors: Agarwal S,Sasane S,Kumar J,Deshmukh P,Bhayani H,Giri P,Giri S,Soman S,Kulkarni N,Jain M

    更新日期:2018-06-01 00:00:00

  • Synthesis and SAR study of pyrrolo[3,4-b]pyridin-7(6H)-one derivatives as melanin concentrating hormone receptor 1 (MCH-R1) antagonists.

    abstract::The discovery and optimization of novel pyrrolo[3,4-b]pyridin-7(6H)-one MCH-R1 antagonists are described. A systematic SAR study probing the effects of aryl-, benzyl- and arylthio-substituents at the 2-position of the pyrrolo[3,4-b]pyridin-7(6H)-ones led to identification of the 2-[(4-fluorophenyl)thio] derivative 7b ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.01.053

    authors: Lim CJ,Kim JY,Lee BH,Oh KS,Yi KY

    更新日期:2013-03-15 00:00:00

  • Antibacterial activity of quinolone-macrocycle conjugates.

    abstract::Novel quinolone-macrocycle conjugates displayed submicromolar antibacterial activity against Escherichia coli and Staphylococcus aureus bacterial strains. An analogous open-chain structure was not active at 100 microM against the same pathogenic strains. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(03)00285-3

    authors: Jefferson EA,Swayze EE,Osgood SA,Miyaji A,Risen LM,Blyn LB

    更新日期:2003-05-19 00:00:00

  • Discovery of MK-1439, an orally bioavailable non-nucleoside reverse transcriptase inhibitor potent against a wide range of resistant mutant HIV viruses.

    abstract::The optimization of a novel series of non-nucleoside reverse transcriptase inhibitors (NNRTI) led to the identification of pyridone 36. In cell cultures, this new NNRTI shows a superior potency profile against a range of wild type and clinically relevant, resistant mutant HIV viruses. The overall favorable preclinical...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.12.070

    authors: Côté B,Burch JD,Asante-Appiah E,Bayly C,Bédard L,Blouin M,Campeau LC,Cauchon E,Chan M,Chefson A,Coulombe N,Cromlish W,Debnath S,Deschênes D,Dupont-Gaudet K,Falgueyret JP,Forget R,Gagné S,Gauvreau D,Girardin M,Guir

    更新日期:2014-02-01 00:00:00