Novel 1-(2-pyrimidin-2-yl)piperazine derivatives as selective monoamine oxidase (MAO)-A inhibitors.

Abstract:

:In the present study, a new series of 2-[4-(pyrimidin-2-yl)piperazin-1-yl]-2-oxoethyl 4-substituted piperazine-1-carbodithioate derivatives (2a-n) were synthesized and screened for their monoamine oxidase A and B inhibitory activity. The structures of compounds were elucidated using spectroscopic methods and some physicochemical properties of new compounds were predicted using Molinspiration and MolSoft programs. Compounds 2-[4-(pyrimidin-2-yl)piperazin-1-yl]-2-oxoethyl 4-(4-nitrophenyl)piperazine-1-carbodithioate (2j) and 2-[4-(pyrimidin-2-yl)piperazin-1-yl]-2-oxoethyl 4-benzhydrylpiperazine-1-carbodithioate (2m) exhibited selective MAO-A inhibitory activity with IC50 = 23.10, 24.14 µM, respectively. Some of the biological results were found in accordance with the obtained in silico data based on Lipinski's fule of five.

authors

Kaya B,Yurttaş L,Sağlik BN,Levent S,Özkay Y,Kaplancikli ZA

doi

10.1080/14756366.2016.1247054

subject

Has Abstract

pub_date

2017-12-01 00:00:00

pages

193-202

issue

1

eissn

1475-6366

issn

1475-6374

journal_volume

32

pub_type

杂志文章
  • Synthesis and evaluation of sulfonamide-bearing thiazole as carbonic anhydrase isoforms hCA I and hCA II.

    abstract::Sulfonamide-bearing thiazole compounds were synthesized and their inhibitory effects on the activity of purified human carbonic anhydrase I and II were evaluated. Human carbonic anhydrase isoenzymes (hCA-I and hCA-II) were purified from erythrocyte cells by affinity chromatography. The inhibitory effects of the 12 syn...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2015.1128426

    authors: Kılıcaslan S,Arslan M,Ruya Z,Bilen Ç,Ergün A,Gençer N,Arslan O

    更新日期:2016-12-01 00:00:00

  • Structural model of haptoglobin and its complex with the anticoagulant ecotin variants: structure-activity relationship study and analysis of interactions.

    abstract::Recently the literature described the binding of Haptoglobin (HP) with ecotin, a fold-specific serine-proteases inhibitor with an anticoagulant profile and produced by Escherichia coli. In this work, we used some in silico and in vitro techniques to evaluate HP 3D-fold and its interaction with wild-type ecotin and two...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2013.774389

    authors: Sathler PC,Lourenço AL,Miceli LA,Rodrigues CR,Albuquerque MG,Cabral LM,Castro HC

    更新日期:2014-04-01 00:00:00

  • Synthesis and anticonvulsant activity of new N-mannich bases derived from benzhydryl- and isopropyl-pyrrolidine-2,5-dione.

    abstract::Synthesis and anticonvulsant properties of 26 new N-Mannich bases of 3-benzhydryl-(5-17) and 3-isopropyl-pyrrolidine-2,5-diones (18-30) have been described. Initial anticonvulsant screening for these compounds was evaluated in mice after intraperitoneal administration in the maximal electroshock (MES) and subcutaneous...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2015.1088842

    authors: Rybka S,Obniska J,Rapacz A,Filipek B,Żmudzki P

    更新日期:2016-12-01 00:00:00

  • The inhibition mechanism of guanidine hydrochloride on the catalytic activity of recombinant human protein disulfide isomerase.

    abstract::Initial velocity enzyme kinetics was used to study the inhibition mechanism of guanidine hydrochloride (Gdm.Cl) on catalytic activity of recombinant human protein disulfide isomerase (rhPDI) in protein folding. Reduced C125A recombinant human interleukin 2 (C125A rhIL-2), the substrate, was dissolved in 8 M Gdm.Cl bef...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/1475636021000049212

    authors: Du C,Wolfe JL

    更新日期:2003-02-01 00:00:00

  • Synthesis, physico-chemical studies of manganese(II), cobalt(II), nickel(II), copper(II) and zinc(II) complexes with some p-substituted acetophenone benzoylhydrazones and their antimicrobial activity.

    abstract::Complexes of the type [M(pabh)(H2O)Cl], [M(pcbh)(H2O)Cl] and [M(Hpabh)(H2O)2 (SO4)] where, M = Mn(II), Co(II), Ni(II), Cu(II) and Zn(II); Hpabh = p-amino acetophenone benzoyl hydrazone and Hpcbh = p-chloro acetophenone benzoyl hydrazone have been synthesized and characterized with the help of elemental analyses, elect...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756360802318662

    authors: Singh VP,Singh S,Katiyar A

    更新日期:2009-04-01 00:00:00

  • Docking study: PPARs interaction with the selected alternative plasticizers to di(2-ethylhexyl) phthalate.

    abstract::Phthalates, used in medical devices (MDs), have been identified as reproductive and developmental toxicants. Their toxicity varies somewhat depending on the specific phthalate and is in part linked to the activation of Peroxisome Proliferating-Activated Receptors (PPARs). So, the use of MDs containing targeted phthala...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2015.1037748

    authors: Kambia N,Farce A,Belarbi K,Gressier B,Luyckx M,Chavatte P,Dine T

    更新日期:2016-01-01 00:00:00

  • QSAR of aromatic substances: EGFR inhibitory activity of quinazoline analogues.

    abstract::The flip regression procedure that we used earlier for handling the xanthones system has been applied to phenylaminoquinazoline analogues. It is known that the substituents at the 6- and 7- positions of the polycyclic system have been identified as the most important structural features. The steric as well as the elec...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756360701608726

    authors: Deeb O,Clare BW

    更新日期:2008-12-01 00:00:00

  • Ranitidine induces inhibition and structural changes in sucrase.

    abstract::Ranitidine is an antagonist of histamine-2 (H(2)) receptor. It is employed to treat peptic ulcer and other conditions in which gastric acidity must be reduced. Sucrase is a hydrolytic enzyme that catalyzes the breakdown of sucrose to its monomer content. A liquid of yeast sucrase was developed for treatment of congeni...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2011.601414

    authors: Minai-Tehrani D,Ghaffari M,Sobhani-Damavandifar Z,Minoui S,Alavi S,Osmani R,Ahmadi S

    更新日期:2012-08-01 00:00:00

  • Synthesis of new 4-[2-(alkylamino) ethylthio]pyrrolo[1,2-a]quinoxaline and 5-[2-(alkylamino) ethylthio]pyrrolo[1,2-a]thieno[3,2-e]pyrazine derivatives, as potential bacterial multidrug resistance pump inhibitors.

    abstract::The synthesis of new 4-[2-(alkylamino)ethylthio]pyrrolo[1,2-a]quinoxaline derivatives la-1 is described in five or six steps starting from various substituted nitroanilines 2a-e. The bioisostere 5-[2-(alkylamino)ethylthio]pyrrolo[1,2- a]thieno[3,2-e]pyrazine 1m was also prepared. The new derivatives were evaluated as ...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756360701485406

    authors: Vidaillac C,Guillon J,Moreau S,Arpin C,Lagardère A,Larrouture S,Dallemagne P,Caignard DH,Quentin C,Jarry C

    更新日期:2007-10-01 00:00:00

  • Design, synthesis, and anticonvulsant effects evaluation of nonimidazole histamine H3 receptor antagonists/inverse agonists containing triazole moiety.

    abstract::Histamine H3 receptors (H3R) antagonists/inverse agonists are becoming a promising therapeutic approach for epilepsy. In this article, novel nonimidazole H3R antagonists/inverse agonists have been designed and synthesised via hybriding the H3R pharmacophore (aliphatic amine with propyloxy chain) with the 1,2,4-triazol...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756366.2020.1774573

    authors: Song M,Yan R,Zhang Y,Guo D,Zhou N,Deng X

    更新日期:2020-12-01 00:00:00

  • Synthesis and evaluation of antibacterial and antioxidant activity of novel 2-phenyl-quinoline analogs derivatized at position 4 with aromatically substituted 4H-1,2,4-triazoles.

    abstract::A set of novel quinolone-triazole conjugates (12-31) were synthesized in three steps in good yields starting from 2-phenylquinoline-4-carboxylic acid. All the intermediates, as well as the final 1,2,4-triazolyl quinolines were fully characterized by their detailed spectral analysis utilizing different techniques such ...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756366.2016.1190714

    authors: Verbanac D,Malik R,Chand M,Kushwaha K,Vashist M,Matijašić M,Stepanić V,Perić M,Paljetak HČ,Saso L,Jain SC

    更新日期:2016-01-01 00:00:00

  • Studies on synthetic and structural characterization of new fluorine substituted phthalides of pharmaceutical interest.

    abstract::An efficient and economical synthesis of some new fluorine substituted phthalides was accomplished from two γ-keto acids, 2-(4-fluorobenzoyl)benzoic acid and 2-(3,5-dinitro-4-flurobenzoyl)benzoic acid. Each acid was reacted with various phenolic compounds in presence of catalytic quantity of concentrated sulphuric aci...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2011.606622

    authors: Chamoli T,Rawat MS,Jacob M

    更新日期:2012-10-01 00:00:00

  • Using C60 fullerenes for photodynamic inactivation of mosquito iridescent viruses.

    abstract::This article describes the photodynamic inactivation of mosquito iridescent virus (MIV) Aedes flavescens in the presence of water-soluble C(60) fullerenes. It has been observed that the photodynamic inactivation of MIV for about 1 h reduces the infectious titre of the virus in large wax-moth larvae Galleria mellonella...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2011.601303

    authors: Rud Y,Buchatskyy L,Prylutskyy Y,Marchenko O,Senenko A,Schütze Ch,Ritter U

    更新日期:2012-08-01 00:00:00

  • Synthesis of some novel heterocylic compounds derived from 2-[3-(4-chlorophenyl)-5-(4-methoxybenzyl)-4H-1,2,4-triazol-4-yl]acetohydrazide and investigation of their lipase and α-glucosidase inhibition.

    abstract::In the present study, 2-[3-(4-chlorophenyl)-5-(4-methoxybenzyl)-4H-1,2,4-triazol-4-yl]acetohydrazide (1) was used as starting compound for the synthesis of 2-{[3-(4-chlorophenyl)-5-(4-methoxybenzyl)-4H-1,2,4-triazol-4-yl]acetyl}-4-thiosemicarbazides (2a-c) and 5-{[3-(4-chlorophenyl)-5-(4-methoxybenzyl)-4H-1,2,4-triazo...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2014.1003213

    authors: Bekircan O,Ülker S,Menteşe E

    更新日期:2015-12-01 00:00:00

  • New flavonoid - N,N-dibenzyl(N-methyl)amine hybrids: Multi-target-directed agents for Alzheimer´s disease endowed with neurogenic properties.

    abstract::The design of multi-target directed ligands (MTDLs) is a valid approach for obtaining effective drugs for complex pathologies. MTDLs that combine neuro-repair properties and block the first steps of neurotoxic cascades could be the so long wanted remedies to treat neurodegenerative diseases (NDs). By linking two privi...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756366.2019.1581184

    authors: Estrada-Valencia M,Herrera-Arozamena C,Pérez C,Viña D,Morales-García JA,Pérez-Castillo A,Ramos E,Romero A,Laurini E,Pricl S,Rodríguez-Franco MI

    更新日期:2019-12-01 00:00:00

  • The human carbonic anhydrase isoenzymes I and II (hCA I and II) inhibition effects of trimethoxyindane derivatives.

    abstract::Carbonic anhydrases (CAs, EC 4.2.1.1) had six genetically distinct families described to date in various organisms. There are 16 known CA isoforms in humans. Human CA isoenzymes I and II (hCA I and hCA II) are ubiquitous cytosolic isoforms. Acetylcholine esterase (AChE. EC 3.1.1.7) is a hydrolase that hydrolyzes the n...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2015.1014476

    authors: Taslimi P,Gulcin I,Ozgeris B,Goksu S,Tumer F,Alwasel SH,Supuran CT

    更新日期:2016-01-01 00:00:00

  • Isoflurane prevents learning deficiencies caused by brief hypoxia and hypotension in adult Sprague Dawley rats.

    abstract:CONTEXT:Hypotension causes histologic changes in the hippocampal CA1 area, while behavior remains unchanged. We believe that an even stronger insult may also cause behavioral changes. OBJECTIVE:We used a rat hemorrhagic shock model plus temporary hypoxia to assess functional outcome at different time points post-injur...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2013.866658

    authors: Chaparro E,Quiroga C,Erasso D,Bosco G,Rubini A,Mangar D,Camporesi E

    更新日期:2014-12-01 00:00:00

  • Antiproliferative activity of Humulus lupulus extracts on human hepatoma (Hep3B), colon (HT-29) cancer cells and proteases, tyrosinase, β-lactamase enzyme inhibition studies.

    abstract::The aims of this study were to examine the antiproliferation of Humulus lupulus extracts on human hepatoma carcinoma (Hep3B) and human colon carcinoma (HT-29) cell lines along with enzyme inhibitory effects of the crude extracts. Potential cell cytotoxicity of six different H. lupulus extracts were assayed on various ...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2015.1004060

    authors: Cömert Önder F,Ay M,Aydoğan Türkoğlu S,Tura Köçkar F,Çelik A

    更新日期:2016-01-01 00:00:00

  • Phosphoprotein levels, MAPK activities and NFkappaB expression are affected by fisetin.

    abstract::Flavonoids, polyphenolic phytochemicals, are ubiquitous in plants and are commonly present in the human diet. They may exert diverse beneficial effects, including antioxidant and anticarcinogenic activities. The present study was designed to evaluate three biomolecules that play important roles in the apoptotic proces...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756360601162063

    authors: de Sousa RR,Queiroz KC,Souza AC,Gurgueira SA,Augusto AC,Miranda MA,Peppelenbosch MP,Ferreira CV,Aoyama H

    更新日期:2007-08-01 00:00:00

  • Design, synthesis of 4-aminoquinoline-derived thiazolidines and their antimalarial activity and heme polymerization inhibition studies.

    abstract::The present study describes the synthesis of a series of new 4-aminoquinoline-derived thiazolidines and evaluation of their antimalarial activity against a NF-54 strain of Plasmodium falciparum in vitro and N-67 strain of Plasmodium yoelii in vivo. Among the series, two compounds, 2-(4-chloro-phenyl)-thiazolidine-4-ca...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2012.666537

    authors: Solomon VR,Haq W,Srivastava K,Puri SK,Katti SB

    更新日期:2013-06-01 00:00:00

  • A thermostable trypsin inhibitor with antiproliferative activity from small pinto beans.

    abstract::Small pinto bean is a cultivar of Phaseolus vulgaris. It produces a 16-kDa trypsin inhibitor that could be purified using anion exchange and size chromatography. Q-Sepharose, Mono Q and Superdex 75 columns were employed for the isolation process. Small pinto bean trypsin inhibitor demonstrated moderate pH stability (p...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2013.805756

    authors: Chan YS,Zhang Y,Sze SC,Ng TB

    更新日期:2014-08-01 00:00:00

  • Novel indole-based melatonin analogues substituted with triazole, thiadiazole and carbothioamides: studies on their antioxidant, chemopreventive and cytotoxic activities.

    abstract::Melatonin (MLT) is a well-known free-radical scavenger, involving in the prevention of cellular damage that can lead to cancer, ageing and a variety of neurodegenerative diseases. Research on MLT-related compounds has been required to optimise the maximum pharmaceutical activity with the lowest side effects. In our on...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2015.1132209

    authors: Shirinzadeh H,Ince E,Westwell AD,Gurer-Orhan H,Suzen S

    更新日期:2016-12-01 00:00:00

  • Synthesis of some 4-arylidenamino-4H-1,2,4-triazole-3-thiols and their antituberculosis activity.

    abstract::The increasing clinical importance of drug-resistant mycobacterial pathogens has lent additional urgency to microbiological research and new antimycobacterial compound development. For this purpose, new triazoles were synthesized and evaluated for antituberculosis activity. A series of 4-arylidenamino-4H-1,2,4-triazol...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756360601178424

    authors: Ozdemir A,Turan-Zitouni G,Kaplancikli ZA,Chevallet P

    更新日期:2007-08-01 00:00:00

  • Inhibitors of type 1 17beta-hydroxysteroid dehydrogenase with reduced estrogenic activity: modifications of the positions 3 and 6 of estradiol.

    abstract::Breast cancer is the second most frequent cancer affecting women. Among all endocrine therapies for the treatment of breast cancer, inhibition of estrogen biosynthesis is becoming an interesting complementary approach to the use of antiestrogens. The enzyme type 1 17beta-hydroxysteroid dehydrogenase (17beta-HSD) plays...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756360500043307

    authors: Tremblay MR,Boivin RP,Luu-The V,Poirier D

    更新日期:2005-04-01 00:00:00

  • [60]Fullerene-peptides: bio-nano conjugates with structural and chemical diversity.

    abstract::[60]Fullerene-peptides represent a simple yet chemically diverse example of a bio-nano conjugate. The C60 moiety provides the following attributes to the conjugate: (a) precise three-dimensional architecture, (b) a large hydrophobic mass and (c) unique electronic properties. Conversely, the peptide component provides:...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1080/14756366.2016.1177524

    authors: Barron AR

    更新日期:2016-01-01 00:00:00

  • A review of the effects of some endocrinological factors on respiratory mechanics.

    abstract:CONTEXT:Endocrinological factors have been recently described to affect respiratory mechanics. OBJECTIVE:To review recent literature data, most of all obtained by the end-inflation occlusion method, describing the effects of molecules of endocrinological interest such as endothelin, erythropoietin and renin-angiotensi...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.3109/14756366.2016.1158174

    authors: Rubini A,Frigo A,Carniel EL

    更新日期:2016-12-01 00:00:00

  • Isoform-selective inhibitory profile of 2-imidazoline-substituted benzene sulfonamides against a panel of human carbonic anhydrases.

    abstract::A series of novel benzene sulfonamides (previously evaluated as selective cyclooxygenase-2 inhibitors) has been profiled against human carbonic anhydrases I, II, IV and VII in an attempt to observe the manifestation of the well established "tail" approach for designing potent, isoform-selective inhibitors of carbonic ...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756366.2016.1178248

    authors: Supuran CT,Kalinin S,Tanç M,Sarnpitak P,Mujumdar P,Poulsen SA,Krasavin M

    更新日期:2016-01-01 00:00:00

  • Measurement of antioxidant ability of melatonin and serotonin by the DMPD and CUPRAC methods as trolox equivalent.

    abstract::Melatonin (N-acetyl-5-methoxytryptamine) is the chief secretory product of the pineal gland and synthesized enzymatically from serotonin (5-hydroxytryptamine). These indoleamine derivatives play an important role in the prevention of oxidative damage. In the present study, DMPD radical scavenging and cupric ion (Cu(2+...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756360701626223

    authors: Gulçin I

    更新日期:2008-12-01 00:00:00

  • Donepezil + chromone + melatonin hybrids as promising agents for Alzheimer's disease therapy.

    abstract::We describe herein the design, multicomponent synthesis and biological studies of new donepezil + chromone + melatonin hybrids as potential agents for Alzheimer's disease (AD) therapy. We have identified compound 14n as promising multitarget small molecule showing strong BuChE inhibition (IC50 = 11.90 ± 0.05 nM), mode...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756366.2018.1545766

    authors: Pachón-Angona I,Refouvelet B,Andrýs R,Martin H,Luzet V,Iriepa I,Moraleda I,Diez-Iriepa D,Oset-Gasque MJ,Marco-Contelles J,Musilek K,Ismaili L

    更新日期:2019-12-01 00:00:00

  • Newer human inosine 5'-monophosphate dehydrogenase 2 (hIMPDH2) inhibitors as potential anticancer agents.

    abstract::Human inosine 5'-monophosphate dehydrogenase 2 (hIMPDH2), being an age-old target, has attracted attention recently for anticancer drug development. Mycophenolic acid (MPA), a well-known immunosuppressant drug, was used a lead structure to design and develop modestly potent and selective analogues. The steep structure...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756366.2018.1474211

    authors: Shah CP,Kharkar PS

    更新日期:2018-12-01 00:00:00