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 efficacy. Especially the 4-nitro 20 and cyano 50 compounds excellently improved the cardiac function and reduced infarct size against ischemia/reperfusion injury.

journal_name

Bioorg Med Chem Lett

authors

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

doi

10.1016/j.bmcl.2005.04.046

subject

Has Abstract

pub_date

2005-06-15 00:00:00

pages

2998-3001

issue

12

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(05)00528-7

journal_volume

15

pub_type

杂志文章
  • Selective alpha1a adrenergic receptor antagonists based on 4-aryl-3,4-dihydropyridine-2-ones.

    abstract::A series of alpha1a receptor antagonists derived from a 4-aryl-3,4-dihydropyridine-2-one heterocycle is disclosed. Potency in the low nanomolar to picomolar range along with high selectivity was obtained. In vivo efficacy in a prostate contraction model in rats was observed with a few derivatives. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00696-4

    authors: Nantermet PG,Barrow JC,Selnick HG,Homnick CF,Freidinger RM,Chang RS,O'Malley SS,Reiss DR,Broten TP,Ransom RW,Pettibone DJ,Olah T,Forray C

    更新日期:2000-08-07 00:00:00

  • Activation of mitogen activated protein kinase (MAPK) during D-galactosamine intoxication in the rat liver.

    abstract::A significant increase in plasma glutamate-oxaloacetate transaminase and glutamate-pyruvate transaminase was observed 6 h after intraperitoneal administration of D-galactosamine (D-Galn). Three hours after administration of D-Galn, the vitamin C concentration in the liver decreased significantly compared to that in a ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.02.057

    authors: Nishioka H,Kishioka T,Iida C,Fujii K,Ichi I,Kojo S

    更新日期:2006-06-01 00:00:00

  • Enhanced pneumocystis carinii activity of new primaquine analogues.

    abstract::New analogues of the venerable antimalarial drug primaquine have been synthesized and bioassayed in vivo against Pneumocystis carinii, a life-threatening infection common among immunosuppressed patients. Two of these new compounds are significantly more active than primaquine itself, and provide new information for fu...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(00)00436-4

    authors: Goodwin TE,Boylan CJ,Current WL,Byrd JC,Edwards CB,Fuller DA,Green JL,Larocca CD,Raney KD,Ross AS,Tucker WA

    更新日期:2000-10-02 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

  • A simple method for predicting serum protein binding of compounds from IC(50) shift analysis for in vitro assays.

    abstract::The shift in apparent IC(50) that attends addition of serum proteins to in vitro cellular, enzymatic, and receptor binding assays can be used to determine the dissociation constant for compound-serum protein complexes. We show here that a simple linear relationship exists between the apparent IC(50) in the presence of...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.01.103

    authors: Rusnak DW,Lai Z,Lansing TJ,Rhodes N,Gilmer TM,Copeland RA

    更新日期:2004-05-03 00:00:00

  • Biotinylated-spiperone ligands for quantum dot labeling of the dopamine D2 receptor in live cell cultures.

    abstract::We have synthesized 3 analogs of the dopamine D2 receptor (D2 DR) antagonist spiperone that can be conjugated to streptavidin-coated quantum dots via a pegylated biotin derivative. Using fluorescent imaging we demonstrate that substitution on the spiro position is tolerated, whilst the length and rigidity of a spacer ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2019.02.024

    authors: Tomlinson ID,Kovtun O,Crescentini TM,Rosenthal SJ

    更新日期:2019-04-15 00:00:00

  • New coumarin-benzotriazole based hybrid molecules as inhibitors of acetylcholinesterase and amyloid aggregation.

    abstract::A novel series of triazole tethered coumarin-benzotriazole hybrids based on donepezil skeleton has been designed and synthesized as multifunctional agents for the treatment of Alzheimer's disease (AD). Among the synthesized compounds 13b showed most potent acetylcholinesterase (AChE) inhibition (IC50 = 0.059 μΜ) with ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2020.127477

    authors: Singh A,Sharma S,Arora S,Attri S,Kaur P,Kaur Gulati H,Bhagat K,Kumar N,Singh H,Vir Singh J,Mohinder Singh Bedi P

    更新日期:2020-10-15 00:00:00

  • Identification of urine metabolites of TFAP, a cyclooxygenase-1 inhibitor.

    abstract::Only a few COX-1-selective inhibitors are currently available, and the research on COX-1 selective inhibitors is not fully developed. The authors have produced several COX-1 selective inhibitors including N-(5-amino-2-pyridinyl)-4-trifluoromethylbenzamide: TFAP (3). Although 3 shows potent analgesic effect without gas...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.01.161

    authors: Kakuta H,Fukai R,Xiaoxia Z,Ohsawa F,Bamba T,Hirata K,Tai A

    更新日期:2010-03-15 00:00:00

  • Structural measurements and cell line studies of the copper-PEG-Rifampicin complex against Mycobacterium tuberculosis.

    abstract::The bacterium responsible for tuberculosis is increasing its resistance to antibiotics resulting in new multidrug-resistant Mycobacterium tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB). In this study, several analytical techniques including NMR, FT-ICR, MALDI-MS, LC-MS and UV/Vis are used t...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2014.12.053

    authors: Manning T,Mikula R,Wylie G,Phillips D,Jarvis J,Zhang F

    更新日期:2015-02-01 00:00:00

  • Synthesis and molecular docking study of novel coumarin derivatives containing 4,5-dihydropyrazole moiety as potential antitumor agents.

    abstract::A series of novel coumarin derivatives containing 4,5-dihydropyrazole moiety as potential telomerase inhibitors were synthesized. The bioassay tests show that compound 3d exhibited potentially high activity against human gastric cancer cell SGC-7901 with IC(50) value of 2.69 ± 0.60 μg/mL. All title compounds were assa...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.08.017

    authors: Liu XH,Liu HF,Chen J,Yang Y,Song BA,Bai LS,Liu JX,Zhu HL,Qi XB

    更新日期:2010-10-01 00:00:00

  • Discovery and characterization of potent and selective 4-oxo-4-(5-(5-phenyl-1,2,4-oxadiazol-3-yl)indolin-1-yl)butanoic acids as S1P₁ agonists.

    abstract::S1P(1) receptor driven lymphopenia has proven utility in the treatment of an array of autoimmune disease states. As a part of our efforts to develop potent and selective S1P(1) receptor agonists, we have identified a novel chemical series of 4-oxo-4-(5-(5-phenyl-1,2,4-oxadiazol-3-yl)indolin-1-yl)butanoic acid S1P(1) r...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.05.110

    authors: Buzard D,Han S,Thoresen L,Moody J,Lopez L,Kawasaki A,Schrader T,Sage C,Gao Y,Edwards J,Barden J,Thatte J,Fu L,Solomon M,Liu L,Al-Shamma H,Gatlin J,Le M,Xing C,Espinola S,Jones RM

    更新日期:2011-10-01 00:00:00

  • Protein tyrosine phosphatase 1B inhibitory activity of triterpenes isolated from Astilbe koreana.

    abstract::Bioassay-guided fractionation of a MeOH extract of the rhizomes of Astilbe koreana (Saxifragaceae), using an in vitro protein tyrosine phosphatase 1B (PTP1B) inhibitory assay, resulted in the isolation of a new triterpene, 3alpha,24-dihydroxyolean-12-en-27-oic acid (4), along with four triterpenes, 3-oxoolean-12-en-27...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.03.036

    authors: Na M,Cui L,Min BS,Bae K,Yoo JK,Kim BY,Oh WK,Ahn JS

    更新日期:2006-06-15 00:00:00

  • Synthesis and evaluation of pretomanid (PA-824) oxazolidinone hybrids.

    abstract::Pretomanid (PA-824) is an important nitroimidazole antitubercular agent in late stage clinical trials. However, pretomanid is limited by poor solubility and high protein binding, which presents opportunities for improvement in its physiochemical properties. Conversely, the oxazolidinone linezolid has excellent physico...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.12.002

    authors: Rakesh,Bruhn DF,Scherman MS,Singh AP,Yang L,Liu J,Lenaerts AJ,Lee RE

    更新日期:2016-01-15 00:00:00

  • Synthesis and dopamine transporter affinity of chiral 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(2-hydroxypropyl)piperazines as potential cocaine abuse therapeutic agents.

    abstract::A series of optically pure phenyl-and non-phenyl-substituted 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(2-hydroxypropyl)piperazines was synthesized and their binding affinity for dopamine transporter (DAT) was investigated. The analogues with a hydroxyl group in the S configuration were more selective for the DAT over...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)00940-x

    authors: Hsin LW,Prisinzano T,Wilkerson CR,Dersch CM,Horel R,Jacobson AE,Rothman RB,Rice KC

    更新日期:2003-02-10 00:00:00

  • Studies on the interactions between some flavonols and cyclodextrins.

    abstract::The interactions of some natural flavonols with alpha, beta- and gamma-Cds have been investigated. Guest molecules were galangin, kaempferol and quercetin. Inclusion complexes were prepared by kneading and freeze-drying. The complexes were characterized using different physico-chemical methods based on differential sc...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.08.067

    authors: Bergonzi MC,Bilia AR,Di Bari L,Mazzi G,Vincieri FF

    更新日期:2007-11-01 00:00:00

  • 4-Alkyl and 4,4'-dialkyl 1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione derivatives as new inhibitors of bacterial cell wall biosynthesis.

    abstract::Over 195 4-alkyl and 4,4-dialkyl 1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione derivatives were synthesized, utilizing microwave accelerated synthesis, for evaluation as new inhibitors of bacterial cell wall biosynthesis. Many of them demonstrated good activity against MurB in vitro and low MIC values against gram-pos...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.03.058

    authors: Kutterer KM,Davis JM,Singh G,Yang Y,Hu W,Severin A,Rasmussen BA,Krishnamurthy G,Failli A,Katz AH

    更新日期:2005-05-16 00:00:00

  • Synthesis and biological evaluation of clovamide analogues with catechol functionality as potent Parkinson's disease agents in vitro and in vivo.

    abstract:: ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2018.11.030

    authors: Feng JH,Hu XL,Lv XY,Wang BL,Lin J,Zhang XQ,Ye WC,Xiong F,Wang H

    更新日期:2019-01-15 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

  • Simple and an efficient method for the synthesis of 1-[2-dimethylamino-1-(4-methoxy-phenyl)-ethyl]-cyclohexanol hydrochloride: (+/-) venlafaxine racemic mixtures.

    abstract::A novel synthetic method was developed for the synthesis of venlafaxine using inexpensive reagents. An improvement in the method, in the yield was achieved for the conversion of the venlafaxine. This is an improved version, simple and efficient method for the large-scale synthesis of venlafaxine. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.03.098

    authors: Basappa,Kavitha CV,Rangappa KS

    更新日期:2004-06-21 00:00:00

  • Identification of potent and novel small-molecule inhibitors of caspase-3.

    abstract::The design and synthesis of a series of novel, reversible, small molecule inhibitors of caspase-3 are described. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2003.08.024

    authors: Allen DA,Pham P,Choong IC,Fahr B,Burdett MT,Lew W,DeLano WL,Gordon EM,Lam JW,O'Brien T,Lee D

    更新日期:2003-11-03 00:00:00

  • First synthesis of separable isomeric testosterone dimers showing differential activities on prostate cancer cells.

    abstract::The synthesis of two separable isomeric testosterone dimers is reported. The dimers are made from testosterone in a 5 step sequence and with 36% overall yield. The key dimerization step was performed using Hoveyda-Grubb's metathesis catalysts on 7alpha-allyltestosterone with 75% yield. The synthesis led to separable i...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.02.077

    authors: Bastien D,Leblanc V,Asselin E,Bérubé G

    更新日期:2010-04-01 00:00:00

  • A new class of sulfoxide surfactants derived from Tris. Synthesis and preliminary assessments of their properties.

    abstract::A new class of non-ionic amphiphilic molecules suitable for biological purposes, especially extraction of membrane proteins, is reported. Such surfactants were prepared in two steps: addition of alkyl or fluoroalkyl mercaptan on Tris(hydroxymethyl)acrylamidomethane (THAM) derivatives, followed by the oxydation of sulf...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(98)00263-7

    authors: Barthélémy P,Maurizis JC,Lacombe JM,Pucci B

    更新日期:1998-06-16 00:00:00

  • Lithospermic acid derivatives from Lithospermum erythrorhizon increased expression of serine palmitoyltransferase in human HaCaT cells.

    abstract::A MeOH extract of the dry root of Lithospermum erythrorhizon showed strong increasing effect on serine palmitoyltransferase (SPT) in normal human keratinocyte cells (HaCaT cells). Bioassay-guided separation on this extract using repeated chromatography resulted in the isolation of lithospermic acid (1) and two derivat...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.01.052

    authors: Thuong PT,Kang KW,Kim JK,Seo DB,Lee SJ,Kim SH,Oh WK

    更新日期:2009-03-15 00:00:00

  • Design and synthesis of a new, conformationally constrained, macrocyclic small-molecule inhibitor of STAT3 via 'click chemistry'.

    abstract::STAT3 is a promising molecular target for the design of new anticancer drugs. In this paper, we report the design and synthesis of a conformationally constrained macrocyclic peptidomimetic 2 via click chemistry. Compound 2 was determined to bind to STAT3 with a K(i) value of 7.3 microM in a competitive fluorescence-po...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.04.096

    authors: Chen J,Nikolovska-Coleska Z,Yang CY,Gomez C,Gao W,Krajewski K,Jiang S,Roller P,Wang S

    更新日期:2007-07-15 00:00:00

  • The effect of pK(a) on pyrimidine/pyridine-derived histamine H4 ligands.

    abstract::During the course of our efforts toward the discovery of human histamine H4 antagonists from a series of 2-aminiopyrimidines, it was noted that a 6-trifluoromethyl group dramatically reduced affinity of the series toward the histamine H4 receptor. This observation was further investigated by synthesizing a series of l...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2014.10.013

    authors: Savall BM,Meduna SP,Venable J,Wei J,Smith RC,Hack MD,Thurmond RL,McGovern P,Edwards JP

    更新日期:2014-12-01 00:00:00

  • Synthesis of L-(+)-3-(3-hydroxy-4-pivaloyloxybenzyl)-2,5-diketomorpholine as potential prodrug of L-dopa.

    abstract::The synthesis and in vitro chemical and enzymatic stability of L-(+)-3-(3-hydroxy-4-pivaloyloxybenzyl)-2,5-diketomorpholine (9) as L-Dopa prodrug are described. Prodrug 9 possesses a good lipophilicity (log P = 2.153 +/- 0.017), is stable in aqueous buffer solutions (pH 1.3 and 7.4), and in 80% rat and human plasma it...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(00)00249-3

    authors: Cingolani GM,Di Stefano A,Mosciatti B,Napolitani F,Giorgioni G,Ricciutelli M,Claudi F

    更新日期:2000-06-19 00:00:00

  • DNA triplex structures are stabilized by the incorporation of 3'-endo blocked pyrimidine nucleosides in the Hoogsteen strand.

    abstract::A short route to pyrimidine locked nucleosides has been developed for their incorporation in triplex forming oligonucleotides (TFO). Compared to oligonucleotides built with standard nucleosides, the modified TFOs containing 3'-endo blocked residues formed, with their corresponding DNA duplexes, more stable triple heli...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(00)00434-0

    authors: Savy P,Benhida R,Fourrey JL,Maurisse R,Sun JS

    更新日期:2000-10-16 00:00:00

  • Tetradehydrohalicyclamine B, a new proteasome inhibitor from the marine sponge Acanthostrongylophora ingens.

    abstract::A new halicyclamine derivative, tetradehydrohalicyclamine B (1), was isolated from the marine sponge Acanthostrongylophora ingens, along with halicyclamine B (2) as proteasome inhibitors. Compound 1 is the second example found to have a pyridinium ring in the halicyclamine family. Although the relative configuration o...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2018.11.028

    authors: Kato H,El-Desoky AH,Takeishi Y,Nehira T,Angkouw ED,Mangindaan REP,de Voogd NJ,Tsukamoto S

    更新日期:2019-01-01 00:00:00

  • Differential modulation of the antifungal activity of amphotericin B by natural and ent-cholesterol.

    abstract::The addition of exogenous ent-cholesterol suppressed the antifungal activity of the amphotericin B when added to cultures of Candida albicans, but to a lesser extent than natural cholesterol. There were no detectable differences between added 2a or 2b on the antifungal activities of jaspamide or bengazole A, two unrel...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2003.10.018

    authors: Richter RK,Mickus DE,Rychnovsky SD,Molinski TF

    更新日期:2004-01-05 00:00:00

  • Synthesis of novel bivalent mimetic ligands for mannose-6-phosphate receptors.

    abstract::Mannose-6-phosphate (M6P)-containing N-linked glycans are essential signaling molecules for sorting hydrolases in eukaryotic cells. Their receptors, especially the cation-independent M6P receptors (CI-MPRs), have emerged as promising protein targets for targeted drug delivery for the treatment of lysosomal storage dis...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.02.068

    authors: Liu Y,Marshall J,Li Q,Edwards N,Chen G

    更新日期:2013-04-15 00:00:00