Eta4-pyrone iron(0)carbonyl complexes as effective CO-releasing molecules (CO-RMs).

Abstract:

:The CO-releasing properties of iron(0)tricarbonyl complexes bearing a 2-pyrone ligand have been evaluated. In this report, we demonstrate that the intrinsic stability of the (eta4-2-pyrone)Fe(CO)3 complex influences the extent and rate of CO release, which is affected by the presence of a halogen substituent on the 2-pyrone ring. The cell viability index has been highlighted for the active carbon monoxide-releasing molecules (CO-RMs), demonstrating that these complexes and related derivatives are a promising new class of compounds with potential therapeutic applications.

journal_name

Bioorg Med Chem Lett

authors

Fairlamb IJ,Duhme-Klair AK,Lynam JM,Moulton BE,O'Brien CT,Sawle P,Hammad J,Motterlini R

doi

10.1016/j.bmcl.2005.10.085

subject

Has Abstract

pub_date

2006-02-15 00:00:00

pages

995-8

issue

4

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(05)01382-X

journal_volume

16

pub_type

杂志文章
  • Melanocortin subtype-4 receptor agonists containing a piperazine core with substituted aryl sulfonamides.

    abstract::The biological activity for a set of melanocortin-4 receptor (MC4R) agonists containing a piperazine core with an ortho-substituted aryl sulfonamide is described. Compounds from this set had binding and functional activities at MC4R less than 30 nM. The most selective compound in this series was >25,000-fold more pote...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.01.060

    authors: Fotsch C,Han N,Arasasingham P,Bo Y,Carmouche M,Chen N,Davis J,Goldberg MH,Hale C,Hsieh FY,Kelly MG,Liu Q,Norman MH,Smith DM,Stec M,Tamayo N,Xi N,Xu S,Bannon AW,Baumgartner JW

    更新日期:2005-03-15 00:00:00

  • One-pot synthesis of new triazole--Imidazo[2,1-b][1,3,4]thiadiazole hybrids via click chemistry and evaluation of their antitubercular activity.

    abstract::A new series of triazole-imidazo[2,1-b][1,3,4]thiadiazole hybrids (6a-s, 7a) were designed by a molecular hybridisation approach and the target molecules were synthesized via one pot click chemistry protocol. All the intermediates and final molecules were characterised using spectral methods and one of the target comp...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.08.009

    authors: Ramprasad J,Nayak N,Dalimba U,Yogeeswari P,Sriram D

    更新日期:2015-10-01 00:00:00

  • Novel oxazolidinone calcitonin gene-related peptide (CGRP) receptor antagonists for the acute treatment of migraine.

    abstract::In our efforts to develop CGRP receptor antagonists as backups to MK-3207, 2, we employed a scaffold hopping approach to identify a series of novel oxazolidinone-based compounds. The development of a structurally diverse, potent (20, cAMP+HS IC50=0.67 nM), and selective compound (hERG IC50=19 μM) with favorable rodent...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.07.021

    authors: Crowley BM,Stump CA,Nguyen DN,Potteiger CM,McWherter MA,Paone DV,Quigley AG,Bruno JG,Cui D,Culberson JC,Danziger A,Fandozzi C,Gauvreau D,Kemmerer AL,Menzel K,Moore EL,Mosser SD,Reddy V,White RB,Salvatore CA,Kane S

    更新日期:2015-11-01 00:00:00

  • Aminothiazoles as γ-secretase modulators.

    abstract::We herein report the discovery of a new γ-secretase modulator class with an aminothiazole core starting from a HTS hit (3). Synthesis and SAR of this series are discussed. These novel compounds demonstrate moderate to good in vitro potency in inhibiting amyloid beta (Aβ) peptide production. Overall γ-secretase is not ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.08.060

    authors: Lübbers T,Flohr A,Jolidon S,David-Pierson P,Jacobsen H,Ozmen L,Baumann K

    更新日期:2011-11-01 00:00:00

  • Second generation of BACE-1 inhibitors part 3: Towards non hydroxyethylamine transition state mimetics.

    abstract::Our first generation of hydroxyethylamine BACE-1 inhibitors proved unlikely to provide molecules that would lower amyloid in an animal model at low oral doses. This observation led us to the discovery of a second generation of inhibitors having nanomolar activity in a cell-based assay and with the potential for improv...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.03.149

    authors: Charrier N,Clarke B,Cutler L,Demont E,Dingwall C,Dunsdon R,Hawkins J,Howes C,Hubbard J,Hussain I,Maile G,Matico R,Mosley J,Naylor A,O'Brien A,Redshaw S,Rowland P,Soleil V,Smith KJ,Sweitzer S,Theobald P,Vesey D,

    更新日期:2009-07-01 00:00:00

  • Estrogen receptor ligands. Part 10: Chromanes: old scaffolds for new SERAMs.

    abstract::The discovery, synthesis, and SAR of chromanes as ER alpha subtype selective ligands are described. X-ray studies revealed that the origin of the ER alpha-selectivity resulted from a C-4 trans methyl substitution to the cis-2,3-diphenyl-chromane platform. Selected compounds from this class demonstrated very potent in ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.01.046

    authors: Tan Q,Blizzard TA,Morgan JD 2nd,Birzin ET,Chan W,Yang YT,Pai LY,Hayes EC,DaSilva CA,Warrier S,Yudkovitz J,Wilkinson HA,Sharma N,Fitzgerald PM,Li S,Colwell L,Fisher JE,Adamski S,Reszka AA,Kimmel D,DiNinno F,Rohre

    更新日期:2005-03-15 00:00:00

  • Regioselective synthesis of 3-benzyl substituted pyrimidino chromen-2-ones and evaluation of anti-microbial and anti-biofilm activities.

    abstract::Regioselective synthesis of a number of highly functionalized 3-benzylpyrimidino chromen-2-ones (4) were accomplished in a one pot three component reaction in acetic acid and determined their anti-microbial and anti-biofilm activities. Compounds 4o and 4p showed an excellent anti-microbial activity against Micrococcus...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.12.038

    authors: Emmadi NR,Atmakur K,Bingi C,Godumagadda NR,Chityal GK,Nanubolu JB

    更新日期:2014-01-15 00:00:00

  • Inhibitory potential of flavonoids on PtdIns(3,4,5)P3 binding with the phosphoinositide-dependent kinase 1 pleckstrin homology domain.

    abstract::Many membrane-associated proteins are involved in various signaling pathways, including the phosphoinositide 3-kinase (PI3K) pathway, which has key roles in diverse cellular processes. Disruption of the activities of these proteins is involved in the development of disease in humans, making these proteins promising ta...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.12.051

    authors: Kang Y,Kim BG,Kim S,Lee Y,Yoon Y

    更新日期:2017-02-01 00:00:00

  • Cage amines as the stopper inhibitors of cholinesterases.

    abstract::Cage amines 1-4 are potent peripheral anionic site-bound reversible inhibitors of both acetylcholinesterase and butyrylcholinesterase. Cage amines 1-3 are selective butyrylcholinesterase inhibitor versus acetylcholinesterase. For both enzymes, the -log K(i) values linearly correlate with the difference of substituted ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(03)00599-7

    authors: Lin G,Tsai HJ,Tsai YH

    更新日期:2003-09-01 00:00:00

  • Diaryl-dialkyl-substituted pyrazoles: regioselective synthesis and binding affinity for the estrogen receptor.

    abstract::We have developed two novel series of tetrasubstituted pyrazoles, embodying 1,3-diaryl-4,5-dialkyl or 3,5-diaryl-1,4-dialkyl substitution patterns. The scope of a regioselective method, developed by us earlier, was expanded to allow the synthesis of the first series of these tetrasubstituted pyrazoles directly from al...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)00057-4

    authors: Nishiguchi GA,Rodriguez AL,Katzenellenbogen JA

    更新日期:2002-03-25 00:00:00

  • 4,4,14 alpha-trimethyl 9 beta,19-cyclo-5 alpha-26-homocholesta-24,26-dien-3 beta-ol: a potent mechanism-based inactivator of delta 24(25)- to delta 25(27)-sterol methyl transferase.

    abstract::The title compound (4A) was synthesized and tested as a mechanism-based inactivator of the sterol methyl transferase (SMT) enzyme from Prototheca wickerhamii. Using cycloartenol as substrate, 4A was found to exhibit time-dependent inactivation kinetics, generating a Ki value of 30 microM and Kinact value of 0.30 min-1...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(98)00651-9

    authors: Nes WD,He L,Mangla AT

    更新日期:1998-12-15 00:00:00

  • Synthesis and evaluation of 9-aminoacridines derived from benzyne click chemistry.

    abstract::A small set of 9-aminoacridine-3- and 4-carboxamides were synthesized efficiently using the benzyne/azide click chemistry. The products bind to duplex DNA but have different antitumour activity in the HL60 cell line. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.08.070

    authors: Howell LA,Howman A,O'Connell MA,Mueller A,Searcey M

    更新日期:2009-10-15 00:00:00

  • Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.

    abstract::Covalent enzyme inhibitors constitute a highly important group of biologically active compounds, with numerous drugs available on the market. Although the discovery of inhibitors of urease, a urea hydrolyzing enzyme crucial for the survival of some human pathogens, is a field of medicinal chemistry that has grown in r...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.02.022

    authors: Macegoniuk K,Kowalczyk R,Rudzińska A,Psurski M,Wietrzyk J,Berlicki Ł

    更新日期:2017-03-15 00:00:00

  • Enantioselective synthesis of (R)-(+)- and (S)-(-)-higenamine and their analogues with effects on platelet aggregation and experimental animal model of disseminated intravascular coagulation.

    abstract::Optically active tetrahydroisoquinoline alkaloids, (R)-(+)-higenamine (1R) and (S)-(-)-higenamine (1 S), and their optically active 1-naphthylmethyl analogues (2 and 3), were synthesized by enantioselective hydrogenation of the corresponding dihydroisoquinoline intermediates 7 as a key step. The evaluation of the plat...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.05.094

    authors: Pyo MK,Lee DH,Kim DH,Lee JH,Moon JC,Chang KC,Yun-Choi HS

    更新日期:2008-07-15 00:00:00

  • Bioisosteric modification of PETT-HIV-1 RT-inhibitors: synthesis and biological evaluation.

    abstract::Bioisosteric substitution of the thiourea (3, 5, 7, 9) and urea (10) moiety of PETT compounds with sulfamide (1), cyanoguanidine (2, 4) and guanidine (6, 8) functionalities, and replacement of the phenethyl group with benzoylethyl group (compounds 11-20) have been studied. Synthesis and antiviral activities are descri...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00675-7

    authors: Högberg M,Engelhardt P,Vrang L,Zhang H

    更新日期:2000-02-07 00:00:00

  • Synthesis and Vasorelaxant Evaluation of Novel 7-Methoxyl-2,3-disubstituted-quinoxaline Derivatives.

    abstract::An array of novel 7-methoxyl-2,3-disubstituted quinoxaline derivatives was designed, synthesized and their potential antihypertensive activities were examined, in an attempt to discover potent small molecules with vasorelaxant effects. The vasoactivities of these compounds on vascular tone, as well as underlying mecha...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2021.127785

    authors: Zheng CB,Gao WC,Pang PP,Ma X,Peng LC,Yang L,Li X

    更新日期:2021-01-11 00:00:00

  • Thiazolidine-2,4-diones derivatives as PPAR-γ agonists: synthesis, molecular docking, in vitro and in vivo antidiabetic activity with hepatotoxicity risk evaluation and effect on PPAR-γ gene expression.

    abstract::A library of conjugates of chromones and 2,4-thiazolidinedione has been synthesized by Knoevenagel condensation followed by reduction using hydrogen gas and Pd/C as a catalyst. Compounds 5c and 5e were most effective in lowering the blood glucose level comparable to standard drug pioglitazone. Compound 5e exhibited po...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2014.05.034

    authors: Nazreen S,Alam MS,Hamid H,Yar MS,Dhulap A,Alam P,Pasha MA,Bano S,Alam MM,Haider S,Kharbanda C,Ali Y,Pillai KK

    更新日期:2014-07-15 00:00:00

  • Cyclonatsudamine A, a new vasodilator cyclic peptide from Citrus natsudaidai.

    abstract::A new cyclic heptapeptide, cyclonatsudamine A (1), cyclo (-Gly-Tyr-Leu-Leu-Pro-Pro-Ser-), has been isolated from the peels of Citrus natsudaidai and the structure was elucidated by 2D NMR analysis and chemical degradation. Cyclonatsudamine A (1) relaxed norepinephrine-induced contractions of rat aorta, which may be me...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.07.036

    authors: Morita H,Enomoto M,Hirasawa Y,Iizuka T,Ogawa K,Kawahara N,Goda Y,Matsumoto T,Takeya K

    更新日期:2007-10-01 00:00:00

  • First fatty acylated dipeptides to affect muscarinic receptor ligand binding.

    abstract::Fatty acylated dipeptides homologous to Gi alpha N-termini affect ligand binding to muscarinic acetylcholine receptors. Myristylglycine-serine containing dipeptides decrease antagonist binding at both M1 and M2 muscarinic receptors. Palmitate on the serine analogous to native palmitoylated cysteine affords dipeptide w...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00604-6

    authors: Krishnan V,Pham WN,Messer WS Jr,Peseckis SM

    更新日期:1999-12-06 00:00:00

  • Discovery of benzylisothioureas as potent divalent metal transporter 1 (DMT1) inhibitors.

    abstract::Inhibition of intestinal brush border DMT1 offers a novel therapeutic approach to the prevention and treatment of disorders of iron overload. Several series of diaryl and tricyclic benzylisothiourea compounds as novel and potent DMT1 inhibitors were discovered from the original hit compound 1. These compounds demonstr...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.05.129

    authors: Zhang Z,Kodumuru V,Sviridov S,Liu S,Chafeev M,Chowdhury S,Chakka N,Sun J,Gauthier SJ,Mattice M,Ratkay LG,Kwan R,Thompson J,Cutts AB,Fu J,Kamboj R,Goldberg YP,Cadieux JA

    更新日期:2012-08-01 00:00:00

  • Preparation of 1-(4-methoxyphenyl)-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-ones as potent, selective and bioavailable inhibitors of coagulation factor Xa.

    abstract::Previously, potent factor Xa inhibitors were described based on a pyrazole core. Modifications of the pyrazole core have provided additional novel, highly potent factor Xa inhibitors. This manuscript will describe the synthesis and biological activity of factor Xa inhibitors containing the 1H-pyrazolo[4,3-d]pyrimidin-...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.04.044

    authors: Fevig JM,Cacciola J,Buriak J Jr,Rossi KA,Knabb RM,Luettgen JM,Wong PC,Bai SA,Wexler RR,Lam PY

    更新日期:2006-07-15 00:00:00

  • 5-(4-Hydroxyphenyl)-3H-1,2-dithiole-3-thione-based fibrates as potential hypolipidemic and hepatoprotective agents.

    abstract::Hypolipidemic effects of the newly synthesized 5-(4-hydroxyphenyl)-3H-1,2-dithiole-3-thione-based fibrates were evaluated in Triton WR-1339 and high-fat diet (HFD)-induced hyperlipidemic mice. Preliminary screening of all the synthesized compounds was done by using an acute model (Triton WR-1339 model), in which compo...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2018.10.003

    authors: Chen ZZ,Xie YD,Shao LH,Wang QT,Xu YH,Bian XL

    更新日期:2018-12-15 00:00:00

  • Design and synthesis of dual inhibitors for matrix metalloproteinase and cathepsin.

    abstract::The first example of dual inhibitors for matrix metalloproteinase (MMP) and cathepsin is described. An appropriate alignment of peptide-parts and two different specific functional groups in one molecule led to the discovery of a potent dual inhibitor (3a). ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(01)00755-7

    authors: Yamamoto M,Ikeda S,Kondo H,Inoue S

    更新日期:2002-02-11 00:00:00

  • DNA-templated click chemistry for creation of novel DNA binding molecules.

    abstract::We have developed a new methodology for producing new molecules that bind to dsDNA using DNA-templated click chemistry. The click reactions between the minor groove binding peptide and acridine intercalators were accelerated by the addition of dsDNA. Furthermore, the resulting peptide-acridine conjugate showed a sligh...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.08.074

    authors: Imoto S,Hirohama T,Nagatsugi F

    更新日期:2008-10-15 00:00:00

  • N-(4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl, butenyl and butynyl)arylcarboxamides as novel dopamine D(3) receptor antagonists.

    abstract::The dopamine D(3) receptor subtype has been targeted as a potential neurochemical modulator of the behavioral actions of psychomotor stimulants, such as cocaine. Previous synthetic studies provided structural requirements for high affinity binding to D(3) receptors which included a 2,3-dichloro-phenylpiperazine linked...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(03)00389-5

    authors: Newman AH,Cao J,Bennett CJ,Robarge MJ,Freeman RA,Luedtke RR

    更新日期:2003-07-07 00:00:00

  • Carbonic anhydrase inhibitors. Inhibition of the newly isolated murine isozyme XIII with anions.

    abstract::The inhibition of the newly discovered cytosolic carbonic anhydrase (CA, EC 4.2.1.1) isozyme XIII of murine origin (mCA XIII) has been investigated with a series of anions, such as the physiological ones (bicarbonate, chloride), or the metal complexing anions (cyanate, cyanide, azide, hydrogen sulfide, etc), nitrate, ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.07.086

    authors: Innocenti A,Lehtonen JM,Parkkila S,Scozzafava A,Supuran CT

    更新日期:2004-11-01 00:00:00

  • 'Naked-eye' quinoline-based 'reactive' sensor for recognition of Hg²⁺ ion in aqueous solution.

    abstract::A new 'naked-eye' quinoline-based 'reactive' ratiometric fluorescent probe was prepared. The reactive stoichiometry of the probe with Hg²⁺ ion was 2:1. The probe exhibited high selectivity towards Hg²⁺ ion to other metal ions with a 410-fold increase in absorbance intensity ratio (A₄₀₂/A₃₄₀) in aqueous solution over a...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2014.10.052

    authors: Zhang Y,Yan Y,Chen S,Gao Z,Xu H

    更新日期:2014-12-01 00:00:00

  • Synthesis and anti-Candida activity of novel 2-hydrazino-1,3-thiazole derivatives.

    abstract::Eighteen new hydrazino-1,3-thiazole derivatives were evaluated against 8 strains of multi-resistant Candida spp. Introduction of an indolyl moiety linked to the hydrazone function enhanced the in vitro anti-Candida activity, with an activity spectrum towards Candida albicans strains. Introduction of a (S)-2-aminoethyl...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.01.039

    authors: Maillard LT,Bertout S,Quinonéro O,Akalin G,Turan-Zitouni G,Fulcrand P,Demirci F,Martinez J,Masurier N

    更新日期:2013-03-15 00:00:00

  • Saponarin activates AMPK in a calcium-dependent manner and suppresses gluconeogenesis and increases glucose uptake via phosphorylation of CRTC2 and HDAC5.

    abstract::This study investigated the molecular mechanism of saponarin, a flavone glucoside, in the regulation of insulin sensitivity. Saponarin suppressed the rate of gluconeogenesis and increased cellular glucose uptake in HepG2 and TE671 cells by regulating AMPK. Using an in vitro kinase assay, we showed that saponarin did n...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.09.057

    authors: Seo WD,Lee JH,Jia Y,Wu C,Lee SJ

    更新日期:2015-11-15 00:00:00

  • A comparison of the alpha-helix forming propensities and hydrogen bonding properties of serine phosphate and alpha-amino-gamma-phosphonobutyric acid.

    abstract::The ability of serine phosphate (SerP) or alpha-amino-gamma-phosphonobutyric acid (AbuP) and arginine to form a salt bridge between their side chains appears to be much greater when they are spaced i/i+4 than when they are spaced i/i+3. The side chain-side chain interaction between SerP/Arg and AbuP/Arg, positioned i/...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00469-2

    authors: Liehr S,Chenault HK

    更新日期:1999-09-20 00:00:00