Structure-activity relationships in platelet-activating factor. Part 14: synthesis and biological evaluation of piperazine derivatives with dual anti-PAF and anti-HIV-1 activity.

Abstract:

:As HIV-associated dementia prevalence has risen with the lifespan of HIV-infected individuals, there is an important need for antiretroviral and anti-inflammatory drugs targeting the central nervous system. Platelet-activating factor, a mediator of inflammation, is an HIV-induced neurotoxin secreted in the infected brain. In this work, we developed piperazine derivatives bearing a heterocyclic moiety as PAF-antagonists and HIV-1 replication inhibitors with micromolar potency.

journal_name

Bioorg Med Chem

authors

Sallem W,Serradji N,Dereuddre-Bosquet N,Dive G,Clayette P,Heymans F

doi

10.1016/j.bmc.2006.07.043

subject

Has Abstract

pub_date

2006-12-01 00:00:00

pages

7999-8013

issue

23

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(06)00597-9

journal_volume

14

pub_type

杂志文章
  • Inhibition studies of the β-carbonic anhydrases from the bacterial pathogen Salmonella enterica serovar Typhimurium with sulfonamides and sulfamates.

    abstract::The two β-carbonic anhydrases (CAs, EC 4.2.1.1) from the bacterial pathogen Salmonella enterica serovar Typhimurium, stCA 1 and stCA 2, were investigated for their inhibition with a large panel of sulfonamides and sulfamates. Unlike inorganic anions, which are weak, millimolar inhibitors of the two enzymes [Vullo et a...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.06.038

    authors: Nishimori I,Minakuchi T,Vullo D,Scozzafava A,Supuran CT

    更新日期:2011-08-15 00:00:00

  • A para-nitrophenol phosphonate probe labels distinct serine hydrolases of Arabidopsis.

    abstract::Activity-based protein profiling represents a powerful methodology to probe the activity state of enzymes under various physiological conditions. Here we present the development of a para-nitrophenol phosphonate activity-based probe with structural similarities to the potent agrochemical paraoxon. We demonstrate that ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.06.041

    authors: Nickel S,Kaschani F,Colby T,van der Hoorn RA,Kaiser M

    更新日期:2012-01-15 00:00:00

  • N-substituted homopiperazine barbiturates as gelatinase inhibitors.

    abstract::Matrix metalloproteinases are implicated in a wide range of pathophysiological processes and potent selective inhibitors for these enzymes continue to be eagerly sought. 5,5-Disubstituted barbiturates hold promise as inhibitor types being stable in vivo and relatively selective for the gelatinases (MMP-2 and MMP-9). I...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.06.055

    authors: Wang J,Medina C,Radomski MW,Gilmer JF

    更新日期:2011-08-15 00:00:00

  • Investigating the activity of 2-substituted alkyl-6-(2,5-dioxopyrrolidin-1-yl)hexanoates as skin penetration enhancers.

    abstract::Skin penetration enhancers are used in the formulation of transdermal delivery systems for drugs that are otherwise not sufficiently skin-permeable. We generated two series of esters by multi-step synthesis with substituted 6-aminohexanoic acid as potential transdermal penetration enhancers by multi-step synthesis. Th...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.10.025

    authors: Brychtova K,Opatrilova R,Raich I,Kalinowski DS,Dvorakova L,Placek L,Csollei J,Richardson DR,Jampilek J

    更新日期:2010-12-15 00:00:00

  • Effects of detergents on the West Nile virus protease activity.

    abstract::Detergents such as Triton X-100 are often used in drug discovery research to weed out small molecule promiscuous and non-specific inhibitors which act by aggregation in solution and undesirable precipitation in aqueous assay buffers. We evaluated the effects of commonly used detergents, Triton X-100, Tween-20, Nonidet...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.03.050

    authors: Ezgimen MD,Mueller NH,Teramoto T,Padmanabhan R

    更新日期:2009-05-01 00:00:00

  • Chiral switch of enzymatic ketone reduction by addition of gamma-cyclodextrin.

    abstract::We report a chiral switch in the configuration of 1-(p-methoxyphenyl)-propan-2-ol, synthesized in aqueous media by ketoreductase in the presence of high concentration of gamma-CD. NMR, ECD and fluorescence spectrometry were used in the effort to explain this unexpected effect. A comparison has been made between the ca...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.07.070

    authors: Petkova GA,Král V

    更新日期:2010-09-15 00:00:00

  • Structure-activity relationships of HIV-1 PR inhibitors containing AHPBA--II. Modification of pyrrolidine ring at P1' proline.

    abstract::Systematic replacement in the 3- or 4-position of the pyrrolidine ring at P1' proline was carried out. Compound 26, which has a Cl atom in the 4(S)-position was the most active among inhibitors substituted with other halogen atoms or other substituents. Furthermore, the replacement of the Z group in compound 26 with f...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/0968-0896(96)00130-7

    authors: Komai T,Higashida S,Sakurai M,Nitta T,Kasuya A,Miyamaoto S,Yagi R,Ozawa Y,Handa H,Mohri H,Yasuoka A,Oka S,Nishigaki T,Kimura S,Shimada K,Yabe Y

    更新日期:1996-08-01 00:00:00

  • Differential receptor binding characteristics of consecutive phenylalanines in micro-opioid specific peptide ligand endomorphin-2.

    abstract::Endogenous opioid peptides consist of a conserved amino acid residue of Phe(3) and Phe(4), although their binding modes for opioid receptors have not been elucidated in detail. Endomorphin-2, which is highly selective and specific for the mu opioid receptor, possesses two Phe residues at the consecutive positions 3 an...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.03.009

    authors: Honda T,Shirasu N,Isozaki K,Kawano M,Shigehiro D,Chuman Y,Fujita T,Nose T,Shimohigashi Y

    更新日期:2007-06-01 00:00:00

  • Synthesis and antiproliferative activity of novel 2-aryl-4-benzoyl-imidazole derivatives targeting tubulin polymerization.

    abstract::We previously reported the discovery of 2-aryl-4-benzoyl-imidazoles (ABI-I) as potent antiproliferative agents for melanoma. To further understand the structural requirements for the potency of ABI analogs, gain insight in the structure-activity relationships (SAR), and investigate metabolic stability for these compou...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.06.084

    authors: Chen J,Li CM,Wang J,Ahn S,Wang Z,Lu Y,Dalton JT,Miller DD,Li W

    更新日期:2011-08-15 00:00:00

  • Novel 3,6-bis(imidazolidine)acridines as effective photosensitizers for photodynamic therapy.

    abstract::The photoeffect of new proflavine derivatives with DNA-binding and antitumour activities, 3,6-bis((1-alkyl-5-oxo-imidazolidin-2-yliden)imino)acridine hydrochlorides (AcrDIMs), was studied to evaluate them as potential photosensitizers for photodynamic antitumor therapy. EPR measurements showed that superoxide radical ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.07.013

    authors: Cižeková L,Grolmusová A,Ipóthová Z,Barbieriková Z,Brezová V,Hunáková L,Imrich J,Janovec L,Dovinová I,Paulíková H

    更新日期:2014-09-01 00:00:00

  • Synthesis and structure-activity relationships of benzyloxyphenyl derivatives as a novel class of NCX inhibitors: effects on heart failure.

    abstract::In the context of heart failure and myocardial ischemia reperfusion, the activity of the sodium-calcium exchanger can lead to calcium overload, which in turn can lead to contractile dysfunction and arrhythmia. Therefore, NCX is an attractive target for treatment of heart failure and myocardial ischemia reperfusion. We...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.10.048

    authors: Kuramochi T,Kakefuda A,Yamada H,Ogiyama T,Taguchi T,Sakamoto S

    更新日期:2005-02-01 00:00:00

  • Structure-based design and discovery of novel inhibitors of protein tyrosine phosphatases.

    abstract::Protein tyrosine phosphatases (PTPs) are important in the regulation of signal transduction processes. Certain enzymes of this class are considered as potential therapeutic targets in the treatment of a variety of diseases such as diabetes, inflammation, and cancer. However, many PTP inhibitors identified to date are ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(03)00039-7

    authors: Huang P,Ramphal J,Wei J,Liang C,Jallal B,McMahon G,Tang C

    更新日期:2003-04-17 00:00:00

  • Carbonic anhydrases as targets for medicinal chemistry.

    abstract::Carbonic anhydrases (CAs, EC 4.2.1.1) are zinc enzymes acting as efficient catalysts for the reversible hydration of carbon dioxide to bicarbonate. 16 different alpha-CA isoforms were isolated in mammals, where they play crucial physiological roles. Some of them are cytosolic (CA I, CA II, CA III, CA VII, CA XIII), ot...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.bmc.2007.04.020

    authors: Supuran CT,Scozzafava A

    更新日期:2007-07-01 00:00:00

  • The splicing modulator sulfonamide indisulam reduces AR-V7 in prostate cancer cells.

    abstract::Alternative splicing of the androgen receptor (AR) is frequently observed in castration resistant prostate cancer (CRPC). One AR isoform, the AR-V7 splice variant, is a constitutively active transcription factor which lacks a ligand binding domain and is therefore undruggable. AR-V7 expression correlates with resistan...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2020.115712

    authors: Melnyk JE,Steri V,Nguyen HG,Hann B,Feng FY,Shokat KM

    更新日期:2020-10-15 00:00:00

  • Synthesis and biological evaluation of novel quinazoline-derived human Pin1 inhibitors.

    abstract::A series of novel 2,4-disubstituted quinazoline derivatives were prepared and their inhibitory activities on hPin1 were evaluated. Of all the synthesized compounds, eight compounds displayed inhibitory activities with IC(50) value at the level of 10(-6)mol/L. Preliminary structure-activity relationships were analyzed ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.03.058

    authors: Zhu L,Jin J,Liu C,Zhang C,Sun Y,Guo Y,Fu D,Chen X,Xu B

    更新日期:2011-05-01 00:00:00

  • Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands.

    abstract::We have reported previously the novel δ opioid agonist KNT-127 which showed high affinity and selectivity for the δ receptor. Moreover, the analgesic effect of subcutaneously administered KNT-127 was more potent than that of a prototypical δ agonist (-)-TAN-67 in the acetic acid writhing test. This study of the struct...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.08.004

    authors: Ida Y,Matsubara A,Nemoto T,Saito M,Hirayama S,Fujii H,Nagase H

    更新日期:2012-10-01 00:00:00

  • Novel leucine ureido derivatives as aminopeptidase N inhibitors using click chemistry.

    abstract::The over-expression of aminopeptidase N on diverse malignant cells is associated with the tumor angiogenesis and metastasis. In this report, one new series of leucine ureido derivatives containing the triazole moiety was designed, synthesized and evaluated as APN inhibitors. Among them, compound 13v showed the best AP...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2018.04.041

    authors: Cao J,Ma C,Zang J,Gao S,Gao Q,Kong X,Yan Y,Liang X,Ding Q,Zhao C,Wang B,Xu W,Zhang Y

    更新日期:2018-07-23 00:00:00

  • Protease inhibitors. Part 8: synthesis of potent Clostridium histolyticum collagenase inhibitors incorporating sulfonylated L-alanine hydroxamate moieties.

    abstract::A series of hydroxamates was prepared by reaction of alkyl/arylsulfonyl halides with N-2-chlorobenzyl-L-alanine, followed by conversion of the COOH moiety to the CONHOH group, with hydroxylamine in the presence of carbodiimides. Other structurally related compounds were obtained by reaction of N-2-chlorobenzyl-L-alani...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(99)00316-8

    authors: Scozzafava A,Supuran CT

    更新日期:2000-03-01 00:00:00

  • The structural basis for kainoid selectivity at AMPA receptors revealed by low-mode docking calculations.

    abstract::The kainoids are a class of excitatory and excitotoxic pyrrolidine dicarboxylates that act at ionotropic glutamate receptors. The kainoids bind kainate receptors with high affinity and, while binding affinity is lower at AMPA (alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid) receptors, they are active in func...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(02)00448-0

    authors: Carcache LM,Rodriguez J,Rein KS

    更新日期:2003-02-20 00:00:00

  • Synthesis and biological evaluation of novel phthalazinone derivatives as topically active phosphodiesterase 4 inhibitors.

    abstract::Inhibitors of phosphodiesterase 4 (PDE4) are an important class of anti-inflammatory drug that act by inhibiting the production of proinflammatory cytokines, including tumor necrosis factor-alpha (TNF-alpha). We have synthesized and evaluated a series of 2-substituted phthalazinone derivatives as PDE4 inhibitors. Stru...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.08.014

    authors: Kagayama K,Morimoto T,Nagata S,Katoh F,Zhang X,Inoue N,Hashino A,Kageyama K,Shikaura J,Niwa T

    更新日期:2009-10-01 00:00:00

  • Coordination of iron ions in the form of histidinyl dinitrosyl complexes does not prevent their genotoxicity.

    abstract::Formation of dinitrosyl iron complexes (DNICs) was observed in a wide spectrum of pathophysiological conditions associated with overproduction of NO. To gain insight into the possible genotoxic effects of DNIC, we examined the interaction of histidinyl dinitrosyl iron complexes (HIS-DNIC) with DNA by means of circular...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.09.032

    authors: Lewandowska H,Stępkowski TM,Sadło J,Wójciuk GP,Wójciuk KE,Rodger A,Kruszewski M

    更新日期:2012-11-15 00:00:00

  • The novel GABA adamantane derivative (AdGABA): design, synthesis, and activity relationship with gabapentin.

    abstract::A facile preparation of 2-aminomethyl-2-tricyclo[3.3.1.1(1,7)]decaneacetic acid hydrochloride 5 (AdGABA) is described. The synthesis of AdGABA involves the hydrogenation of 2-cyano-2-tricyclo[3.3.1.1(1,7)]decaneacetic acid 11, which was synthesized by two different synthetic routes. AdGABA was found to antagonize the ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.02.030

    authors: Zoidis G,Papanastasiou I,Dotsikas I,Sandoval A,Dos Santos RG,Papadopoulou-Daifoti Z,Vamvakides A,Kolocouris N,Felix R

    更新日期:2005-04-15 00:00:00

  • 18F-Labeled indole-based analogs as highly selective radioligands for imaging sigma-2 receptors in the brain.

    abstract::We have designed and synthesized a series of indole-based σ2 receptor ligands containing 5,6-dimethoxyisoindoline or 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline as pharmacophore. In vitro competition binding assays showed that all ten ligands possessed low nanomolar affinity (Ki=1.79-5.23nM) for σ2 receptors and high...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.05.019

    authors: Wang L,Ye J,He Y,Deuther-Conrad W,Zhang J,Zhang X,Cui M,Steinbach J,Huang Y,Brust P,Jia H

    更新日期:2017-07-15 00:00:00

  • Synthesis, biological evaluation, and molecular modeling of cinnamic acyl sulfonamide derivatives as novel antitubulin agents.

    abstract::A series of novel cinnamic acyl sulfonamide derivatives (9a-16e) have been designed and synthesized and their biological activities were also evaluated as potential tubulin polymerization inhibitors. Among all the compounds, 10c showed the most potent growth inhibitory activity against B16-F10 cancer cell line in vitr...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.06.088

    authors: Luo Y,Qiu KM,Lu X,Liu K,Fu J,Zhu HL

    更新日期:2011-08-15 00:00:00

  • Further insights on the structural aspects of PLA(2) inhibition by gamma-hydroxybutenolide-containing natural products: a comparative study on petrosaspongiolides M-R.

    abstract::Petrosaspongiolides M-R (PM-PR, 1-5) are marine sesterterpenes structurally characterised by a gamma-hydroxybutenolide moiety. They have shown an in vitro and in vivo potent anti-inflammatory activity, mediated by specific inhibition of secretory phospholipase A(2) (sPLA(2) enzymes). The molecular mechanism underlying...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2003.12.038

    authors: Monti MC,Casapullo A,Riccio R,Gomez-Paloma L

    更新日期:2004-03-15 00:00:00

  • Design, synthesis, conformational analysis, and biological studies of urotensin-II lactam analogues.

    abstract::Human urotensin II (hU-II; H-Glu-Thr-Pro-Asp-cyclo[Cys-Phe-Trp-Lys-Tyr-Cys]-Val-OH) is a disulfide bridged undecapeptide recently identified as the ligand of an orphan G protein-coupled receptor. hU-II has been described as the most potent vasoconstrictor compound identified to date. With the aim of replacing the disu...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(02)00372-3

    authors: Grieco P,Carotenuto A,Patacchini R,Maggi CA,Novellino E,Rovero P

    更新日期:2002-12-01 00:00:00

  • Protein linear indices of the 'macromolecular pseudograph alpha-carbon atom adjacency matrix' in bioinformatics. Part 1: prediction of protein stability effects of a complete set of alanine substitutions in Arc repressor.

    abstract::A novel approach to bio-macromolecular design from a linear algebra point of view is introduced. A protein's total (whole protein) and local (one or more amino acid) linear indices are a new set of bio-macromolecular descriptors of relevance to protein QSAR/QSPR studies. These amino-acid level biochemical descriptors ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.01.062

    authors: Marrero-Ponce Y,Medina-Marrero R,Castillo-Garit JA,Romero-Zaldivar V,Torrens F,Castro EA

    更新日期:2005-04-15 00:00:00

  • Thieno[2,3-d]pyrimidine-2-carboxamides bearing a carboxybenzene group at 5-position: highly potent, selective, and orally available MMP-13 inhibitors interacting with the S1″ binding site.

    abstract::On the basis of X-ray co-crystal structures of matrix metalloproteinase-13 (MMP-13) in complex with its inhibitors, our structure-based drug design (SBDD) strategy was directed to achieving high affinity through optimal protein-ligand interaction with the unique S1″ hydrophobic specificity pocket. This report details ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.07.025

    authors: Nara H,Sato K,Naito T,Mototani H,Oki H,Yamamoto Y,Kuno H,Santou T,Kanzaki N,Terauchi J,Uchikawa O,Kori M

    更新日期:2014-10-01 00:00:00

  • A simple synthesis of four stereoisomers of roseoside and their inhibitory activity on leukotriene release from mice bone marrow-derived cultured mast cells.

    abstract::Four stereoisomers of roseoside (vomifoliol glucosides) were synthesized using glucose as a chiral resolving reagent. The four synthetic stereoisomers exhibited inhibitory activity on leukotriene release from mouse bone marrow-derived cultured mast cells (BMCMC). The (6S)-isomers of roseoside were about twice as activ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.11.002

    authors: Yajima A,Oono Y,Nakagawa R,Nukada T,Yabuta G

    更新日期:2009-01-01 00:00:00

  • Analogs of iso-azepinomycin as potential transition-state analog inhibitors of guanase: synthesis, biochemical screening, and structure-activity correlations of various selectively substituted imidazo[4,5-e][1,4]diazepines.

    abstract::Guanase is an important enzyme of the purine salvage pathway of nucleic acid metabolism and its inhibition has beneficial implications in viral, bacterial, and cancer therapy. The work described herein is based on a hypothesis that azepinomycin, a heterocyclic natural product and a purported transition state analog in...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.06.069

    authors: Tantravedi S,Chakraborty S,Shah NH,Fishbein JC,Hosmane RS

    更新日期:2013-09-01 00:00:00