Synthesis, characterization, antiamoebic activity and cytotoxicity of novel 2-(quinolin-8-yloxy) acetohydrazones and their cyclized products (1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives).

Abstract:

:A series of 1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives were synthesized by the cyclization of novel 2-(quinolin-8-yloxy) acetohydrazones. In vitro antiamoebic activity was performed against HM1: IMSS strain of Entamoeba histolytica. The results showed that all the 2-(quinolin-8-yloxy) acetohydrazones were more active than their cyclized products (1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives). SAR showed that the compounds having quinoline ring and hydrazone linkage with free N-H group are responsible for higher antiamoebic activity. The cytotoxic studies of these compounds on human breast cancer MCF-7 cell line showed that all the compounds were nontoxic at the concentration range of 1.56-50 μM.

journal_name

Eur J Med Chem

authors

Hayat F,Salahuddin A,Zargan J,Azam A

doi

10.1016/j.ejmech.2010.09.066

subject

Has Abstract

pub_date

2010-12-01 00:00:00

pages

6127-34

issue

12

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(10)00735-X

journal_volume

45

pub_type

杂志文章
  • Discovery of MGS0274, an ester prodrug of a metabotropic glutamate receptor 2/3 agonist with improved oral bioavailability.

    abstract::We previously reported that MGS0008 is a selective group II metabotropic glutamate receptor (mGlu2/3 receptor) agonist that is effective in animal models of schizophrenia. MGS0008 is a highly hydrophilic glutamate analog and is therefore expected to show low oral bioavailability in humans. To improve the oral bioavail...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112521

    authors: Urabe H,Miyakoshi N,Ohtake N,Nozoe A,Ochi M,Fukasawa M,Kinoshita K,Yamaguchi JI,Marumo T,Hikichi H,Chaki S,Hashihayata T

    更新日期:2020-10-01 00:00:00

  • Design, synthesis, and structure-activity relationships of novel benzothiazole derivatives bearing the ortho-hydroxy N-carbamoylhydrazone moiety as potent antitumor agents.

    abstract::A series of novel benzothiazole derivatives bearing the ortho-hydroxy N-carbamoylhydrazone moiety were designed and synthesized and their cytotoxic activities against five cancer cell lines (NCI-H226, SK-N-SH, HT29, MKN45, and MDA-MB-231) were screened in vitro. Most of them showed moderate to excellent activity again...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.08.058

    authors: Ma J,Chen D,Lu K,Wang L,Han X,Zhao Y,Gong P

    更新日期:2014-10-30 00:00:00

  • QSAR study of 4-phenylpiperidine derivatives as mu opioid agonists by neural network method.

    abstract::A nonlinear QSAR study was conducted on a series of 4-phenylpiperidine derivatives (4PPs) acting as mu opioid agonists by three-layer back-propagation neural network (NN) method. At first a variety of molecular descriptors were calculated and then selected with two-stage least squares combining partial least squares (...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2005.10.017

    authors: Wang XH,Tang Y,Xie Q,Qiu ZB

    更新日期:2006-02-01 00:00:00

  • 3D-QSAR analysis of human immunodeficiency virus entry-1 inhibitors by CoMFA and CoMSIA.

    abstract::3D-QSAR studies namely CoMFA, CoMFA region focusing and CoMSIA have been carried out on a series (36 compounds) of HIV-1 entry inhibitors. An alignment rule for the compounds was defined using Distill in SYBYL 7.3. Models were validated using a data set obtained by dividing the data set into a training set and test se...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.07.062

    authors: Pirhadi S,Ghasemi JB

    更新日期:2010-11-01 00:00:00

  • Biological potential of carbazole derivatives.

    abstract::Carbazole skeleton is the key structural motif of many biologically active compounds including synthetic and natural products. Over the past several years, a large number of research highlighting the significance of carbazole derivatives has been reported in the literature. The present review focuses on the recent pro...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2015.02.059

    authors: Głuszyńska A

    更新日期:2015-04-13 00:00:00

  • Design, synthesis and identification of silicon-containing HCV NS5A inhibitors with pan-genotype activity.

    abstract::Modification of a HCV NS5A inhibitor, ombitasvir, led to the identification of 10d with improved pan-genotype NS5A inhibition and better pharmacokinetic properties. The key structural changes to ombitasvir include bioisosteric replacement of carbon with silicon atom. Compared with ombitasvir, the activity of anti-HCV ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.02.025

    authors: Liu B,Gai K,Qin H,Liu X,Cao Y,Lu Q,Lu D,Chen D,Shen H,Song W,Zhang Y,Wang X,Xu H,Zhang Y

    更新日期:2018-03-25 00:00:00

  • Targeting Aryl hydrocarbon receptor for next-generation immunotherapies: Selective modulators (SAhRMs) versus rapidly metabolized ligands (RMAhRLs).

    abstract::Aryl Hydrocarbon Receptor (AhR) constitutes a major network hub of genomic and non-genomic signaling pathways, connecting host's immune cells to environmental factors. It shapes innate and adaptive immune processes to environmental stimuli with species-, cell- and tissue-type dependent specificity. Although an ever in...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2019.111842

    authors: Dolciami D,Ballarotto M,Gargaro M,López-Cara LC,Fallarino F,Macchiarulo A

    更新日期:2020-01-01 00:00:00

  • Design, synthesis and biological evaluation of C(4) substituted monobactams as antibacterial agents against multidrug-resistant Gram-negative bacteria.

    abstract::A series of novel pyridone conjugated monobactams with various substituents at the (4) position were synthesized and evaluated for their antibacterial activities against a panel of multidrug-resistant (MDR) Gram-negative bacteria in vitro. Compounds 46d, 54 and 75e displayed good to moderate activities against P. aeru...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.03.058

    authors: Kou Q,Wang T,Zou F,Zhang S,Chen Q,Yang Y

    更新日期:2018-05-10 00:00:00

  • Design of antineoplastic agents based on the '2-phenylnaphthalene-type' structural pattern--synthesis and biological activity studies of 11H-indolo[3.2-c]quinoline derivatives.

    abstract::Designed as a new group of planar molecule containing the proposed 2-phenylnaphthalene-type structure, a number of 11H-indolo[3.2-c]quinoline derivatives were synthesized and evaluated biologically. Several compounds were found to possess cytotoxic activity against the growth of human promyelocytic leukemia cells (HL-...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(02)01420-4

    authors: He L,Chang HX,Chou TC,Savaraj N,Cheng CC

    更新日期:2003-01-01 00:00:00

  • Clubbed triazoles: a novel approach to antitubercular drugs.

    abstract::In last few decades, though significant progress has been made in the treatment and control strategies of tubercular infections by introducing new diagnostic and monitoring tools and combination therapy, it still continues to be a severe problem. Thus with the aim of developing novel molecules with improved potency fo...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2006.12.001

    authors: Shiradkar M,Suresh Kumar GV,Dasari V,Tatikonda S,Akula KC,Shah R

    更新日期:2007-06-01 00:00:00

  • Tetracyclic indolines as a novel class of β-lactam-selective resistance-modifying agent for MRSA.

    abstract::Antibiotic-resistant bacterial infections have seen a marked increase in recent years, while antibiotic discovery has waned. Resistance-modifying agents (RMA) offer an intriguing alternative strategy to fight against resistant bacteria. Here we report the discovery, antibiotic profiling, and structure-activity relatio...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.09.034

    authors: Zhu Y,Cleaver L,Wang W,Podoll JD,Walls S,Jolly A,Wang X

    更新日期:2017-01-05 00:00:00

  • Synthesis and cytostatic activity of purine nucleosides derivatives of allofuranose.

    abstract::Several new purine nucleosides derivatives of allofuranose were prepared according to Vorbrüggen method, starting from 1,2,5,6-di-O-isopropylidene-α-D-allofuranose and using 1,2,3,5,6-pentaacetoxy-β-D-allofuranose as key intermediate. The synthesized allofuranosyl nucleosides, as well as some acetyl derivatives, were ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.09.046

    authors: Besada P,Costas T,Teijeira M,Terán C

    更新日期:2010-12-01 00:00:00

  • A novel series of 6-substituted 3-(pyrrolidin-1-ylmethyl)chromen-2-ones as selective monoamine oxidase (MAO) A inhibitors.

    abstract::A series of 6-substituted 3-(pyrrolidin-1-ylmethyl)chromen-2-ones (coumarins) have been synthesized and their inhibitory activity to human monoamine oxidase A (MAO A) and B (MAO B) determined. Incorporation of a basic amino function in the C3 position together with substitution at the C6 position produced novel coumar...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.11.035

    authors: Mattsson C,Svensson P,Sonesson C

    更新日期:2014-02-12 00:00:00

  • Medicinal plants used as anthelmintics: Ethnomedical, pharmacological, and phytochemical studies.

    abstract::Intestinal parasites delay mental and physical development in children. Infection with these parasites can result in complications during pregnancy and alter the health of newborns, which has long-term effects on educational attainment and economic productivity. The appearance of resistance against classical drug trea...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2017.02.005

    authors: Romero-Benavides JC,Ruano AL,Silva-Rivas R,Castillo-Veintimilla P,Vivanco-Jaramillo S,Bailon-Moscoso N

    更新日期:2017-03-31 00:00:00

  • Synthesis of new 2-(5-substituted-3-phenyl-2-pyrazolinyl)-1,3-thiazolino[5,4-b]quinoxaline derivatives and evaluation of their antiamoebic activity.

    abstract::In an effort to develop potent antiamoebic agents, we have synthesized chalcones (1-8), amino-5-substituted-(3-phenyl(2-pyrazolinyl))methane-1-thione derivatives (1a-8a) and 2-(5-substituted-3-phenyl-2-pyrazolinyl)-1,3-thiazolino[5,4-b]quinoxaline derivatives (1b-8b) and evaluated for their in vitro antiamoebic activi...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.02.002

    authors: Budakoti A,Bhat AR,Azam A

    更新日期:2009-03-01 00:00:00

  • Synthesis and in vitro antitumour activity evaluation of 1-aryl-1H,3H-thiazolo[4,3-b]quinazolines.

    abstract::A series of 1H,3H-thiazolo[4,3-b]quinazolines (2a-i) were synthesized and evaluated for their in vitro antitumour activity against ca. 60 human tumour cell lines. They exhibited moderate (2c, 2d, 2f and 2g) to strong (2a, 2b, 2e, 2h and 2i) cell-growth inhibition at a concentration of 10(-4) M, but weak activity at lo...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(00)01195-8

    authors: Grasso S,Micale N,Monforte AM,Monforte P,Polimeni S,Zappalà M

    更新日期:2000-12-01 00:00:00

  • Synthesis and evaluation of thymidine kinase 1-targeting carboranyl pyrimidine nucleoside analogs for boron neutron capture therapy of cancer.

    abstract::A library of sixteen 2nd generation amino- and amido-substituted carboranyl pyrimidine nucleoside analogs, designed as substrates and inhibitors of thymidine kinase 1 (TK1) for potential use in boron neutron capture therapy (BNCT) of cancer, was synthesized and evaluated in enzyme kinetic-, enzyme inhibition-, metabol...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.05.042

    authors: Agarwal HK,Khalil A,Ishita K,Yang W,Nakkula RJ,Wu LC,Ali T,Tiwari R,Byun Y,Barth RF,Tjarks W

    更新日期:2015-07-15 00:00:00

  • Docking and 3D-QSAR studies of BMS-806 analogs as HIV-1 gp120 entry inhibitors.

    abstract::BMS-378806 (BMS-806) is a small molecule that blocks the binding of host-cell CD4 with viral gp120 protein and therefore inhibits the first steps of HIV-1 infection. Recently, 36 analogs compounds of BMS-806 were synthesized and their biological activity evaluated. Based on these compounds, a molecular docking was fir...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2009.03.028

    authors: Teixeira C,Serradji N,Maurel F,Barbault F

    更新日期:2009-09-01 00:00:00

  • Synthesis and cytotoxicity of novel ursolic acid derivatives containing an acyl piperazine moiety.

    abstract::This study designed and synthesized a series of novel ursolic acid derivatives in an attempt to develop potent antitumor agents. Their structures were confirmed using MS, IR, (1)H NMR and (13)C NMR. The inhibitory activities of the title compounds against the MGC-803 (gastric cancer cell) and Bcap-37 (breast cancer ce...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.08.048

    authors: Liu MC,Yang SJ,Jin LH,Hu DY,Xue W,Song BA,Yang S

    更新日期:2012-12-01 00:00:00

  • Benzothienoquinazolinones as new multi-target scaffolds: Dual inhibition of human Topoisomerase I and tubulin polymerization.

    abstract::3-(Alkyl(dialkyl)amino)benzothieno[2,3-f]quinazolin-1(2H)-ones (4-9) have been designed using Ellipticine structure as a model, replacing the carbazole core and the pyridine ring with a dibenzothiophene and a pyrimidine moiety, respectively. New benzothienoquinazolinones (4-9) have been synthesized by a simple one-pot...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.111583

    authors: Ceramella J,Caruso A,Occhiuzzi MA,Iacopetta D,Barbarossa A,Rizzuti B,Dallemagne P,Rault S,El-Kashef H,Saturnino C,Grande F,Sinicropi MS

    更新日期:2019-11-01 00:00:00

  • Angiotensin II--AT1 receptor antagonists: design, synthesis and evaluation of substituted carboxamido benzimidazole derivatives.

    abstract::A series of 5-(alkyl and aryl)carboxamido benzimidazole derivatives had been designed, synthesized and evaluated for in vitro angiotensin II--AT1 receptor antagonism and in vivo antihypertensive activities. The pharmacological activities were inversely related to the size of alkyl and aryl substituents. It can be sugg...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2007.11.008

    authors: Shah DI,Sharma M,Bansal Y,Bansal G,Singh M

    更新日期:2008-09-01 00:00:00

  • Synthesis of tropolone derivatives and evaluation of their in vitro neuroprotective activity.

    abstract::beta-Thujaplicin (hinokitiol or 2-hydroxy-4-isopropyl-2,4,6-cycloheptatrien-1-one), a natural tropolone, shows numerous activities while its synthetic analogues were found to exhibit anticancer and anti-ischemic activity. However, the ability of tropolone derivatives to protect neuronal cells from oxidative stress-ind...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2009.12.006

    authors: Koufaki M,Theodorou E,Alexi X,Nikoloudaki F,Alexis MN

    更新日期:2010-03-01 00:00:00

  • Synthesis of novel galeterone derivatives and evaluation of their in vitro activity against prostate cancer cell lines.

    abstract::Prostate cancer is one of the main causes of male cancer-related deaths worldwide and the suppression of androgen receptor signalling is established as an effective strategy for the treatment. A series of galeterone analogues including several steroid-fused azacycles, as well as 17-(benzimidazol-1-ylimino), 16α-(benzi...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.06.040

    authors: Jorda R,Řezníčková E,Kiełczewska U,Maj J,Morzycki JW,Siergiejczyk L,Bazgier V,Berka K,Rárová L,Wojtkielewicz A

    更新日期:2019-10-01 00:00:00

  • Microwave assisted synthesis of fragrant jasmone heterocyclic analogues.

    abstract::cis-Jasmone, from jasmonoid group, is an important jasmine odor fragrance compound. The syntheses of new heterocyclic analogues of jasmone were described. Five analogues of this compound were prepared under microwave irradiation and the results of the microwave assisted syntheses were compared with classical, thermall...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2005.09.012

    authors: Pawełczyk A,Zaprutko L

    更新日期:2006-05-01 00:00:00

  • Enaminonitrile in heterocyclic synthesis: synthesis and antimicrobial evaluation of some new pyrazole, isoxazole and pyrimidine derivatives incorporating a benzothiazole moiety.

    abstract::Enaminonitrile 2 was used as key intermediate for the synthesis of polyfunctionally substituted heterocycles (e.g. pyrazoles, isoxazole, pyrimidines, thiazolo[3,2-a]pyrimidine, tetrazolo[1,5-a]pyrimidine, pyrido[1,2-a]pyrimidine, 1,5-benzodiazepine, and pyrazolo[1,5-a]pyrimidine) incorporating benzothiazole moiety via...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2009.07.024

    authors: Bondock S,Fadaly W,Metwally MA

    更新日期:2009-12-01 00:00:00

  • Xanthine oxidase inhibitory activity of natural and hemisynthetic flavonoids from Gardenia oudiepe (Rubiaceae) in vitro and molecular docking studies.

    abstract::Xanthine oxidase (XO), an enzyme widely distributed among mammalian tissues, is associated with the oxidation of xanthine and hypoxanthine to form uric acid. Reactive oxygen species are also released during this process, leading to oxidative damages and to the pathology called gout. Available treatments mainly based o...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.11.071

    authors: Santi MD,Paulino Zunini M,Vera B,Bouzidi C,Dumontet V,Abin-Carriquiry A,Grougnet R,Ortega MG

    更新日期:2018-01-01 00:00:00

  • The computer-aided discovery of novel family of the 5-HT6 serotonin receptor ligands among derivatives of 4-benzyl-1,3,5-triazine.

    abstract::The work describes a discovery of new chemical family of potent ligands for the 5-HT6 serotonin receptors. During the search for new histamine H4 receptor antagonists among 1,3,5-triazine derivatives, compound 2 (4-benzyl-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-amine) was found. Compound 2, weakly active for the H4...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.04.033

    authors: Łażewska D,Kurczab R,Więcek M,Kamińska K,Satała G,Jastrzębska-Więsek M,Partyka A,Bojarski AJ,Wesołowska A,Kieć-Kononowicz K,Handzlik J

    更新日期:2017-07-28 00:00:00

  • Recent advances in small organic molecules as DNA intercalating agents: synthesis, activity, and modeling.

    abstract::The interaction of small molecules with DNA plays an essential role in many biological processes. As DNA is often the target for majority of anticancer and antibiotic drugs, study about the interaction of drug and DNA has a key role in pharmacology. Moreover, understanding the interactions of small molecules with DNA ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2013.11.029

    authors: Rescifina A,Zagni C,Varrica MG,Pistarà V,Corsaro A

    更新日期:2014-03-03 00:00:00

  • Design, economical synthesis and antiplasmodial evaluation of vanillin derived allylated chalcones and their marked synergism with artemisinin against chloroquine resistant strains of Plasmodium falciparum.

    abstract::The in vitro blood stage antiplasmodial activity of a series of allylated chalcones based on the licochalcone A as lead molecule was investigated against chloroquine (CQ) sensitive Pf3D7 and CQ resistant PfINDO strains of Plasmodium falciparum using SYBR Green I assay. Of the forty two chalcones tested, eight showed I...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.03.079

    authors: Sharma N,Mohanakrishnan D,Sharma UK,Kumar R,Richa,Sinha AK,Sahal D

    更新日期:2014-05-22 00:00:00

  • Symmetry-based inhibitors of HIV-1 protease. Design, synthesis and preliminary structure-activity studies of acylated 2,3-diamino-1-hydroxypropanes and 2,4 diamino-1-hydroxybutanes.

    abstract::Two series of peptidomimetics containing a novel C(2) pseudosymmetrical hydroxyalkyldiamino core structure were prepared from amino acid starting materials and tested for inhibitory activity against the HIV-1 protease (HIV-1 Pr) and the virus in cell culture. In the 2,3-diamino-1-hydroxypropane series, compound 6a, co...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(00)80034-3

    authors: Marastoni M,Bazzaro M,Bortolotti F,Salvadori S,Tomatis R

    更新日期:1999-07-01 00:00:00