Synthesis and antibacterial study of unsaturated Mannich ketones.

Abstract:

:Several Mannich ketones of 2-arylmethylenecycloalkanones were synthesised using the classical acid-catalysed Mannich reaction. Antibacterial activity of these new water-soluble compounds was reported against Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, Staphylococcus saprophyticus, Micrococcus luteus and Bacillus subtilis standard strains. Human cell line cytotoxicity of our new compounds was evaluated against HeLa cell lines. Some compounds showed low cytotoxicity (41.52 nM mL(-1) for 14 and 46.60 nM mL(-1) for 18) and proved to be efficient antibacterial agents against the Gram-positive strains. Minimum inhibitory concentrations varied from 1.56 to 100 microg mL(-1). The mechanism of action was examined, too.

journal_name

Eur J Med Chem

authors

Lóránd T,Kocsis B,Sohár P,Nagy G,Kispál G,Krane HG,Schmitt H,Weckert E

doi

10.1016/s0223-5234(01)01264-8

subject

Has Abstract

pub_date

2001-09-01 00:00:00

pages

705-17

issue

9

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(01)01264-8

journal_volume

36

pub_type

杂志文章
  • Biomimetic in vitro oxidation of lapachol: a model to predict and analyse the in vivo phase I metabolism of bioactive compounds.

    abstract::The bioactive naphtoquinone lapachol was studied in vitro by a biomimetic model with Jacobsen catalyst (manganese(III) salen) and iodosylbenzene as oxidizing agent. Eleven oxidation derivatives were thus identified and two competitive oxidation pathways postulated. Similar to Mn(III) porphyrins, Jacobsen catalyst main...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.06.042

    authors: Niehues M,Barros VP,Emery Fda S,Dias-Baruffi M,Assis Md,Lopes NP

    更新日期:2012-08-01 00:00:00

  • Discovery of a sulfamate-based steroid sulfatase inhibitor with intrinsic selective estrogen receptor modulator properties.

    abstract::Steroid sulfatase (STS), the enzyme which converts inactive sulfated steroid precursors into active hormones, is a promising therapeutic target for the treatment of estrogen-sensitive breast cancer. We report herein the synthesis and in vitro study of dual-action STS inhibitors with selective estrogen-receptor modulat...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.04.044

    authors: Ouellet C,Maltais R,Ouellet É,Barbeau X,Lagüe P,Poirier D

    更新日期:2016-08-25 00:00:00

  • Synthesis of new chiral 2,5-disubstituted 1,3,4-thiadiazoles possessing gamma-butenolide moiety and preliminary evaluation of in vitro anticancer activity.

    abstract::A new series of chiral 1,3,4-thiadiazoles derivatives possessing gamma-substituted butenolide moiety were synthesized and evaluated for in vitro anticancer properties. All the compounds showed good anticancer activities against Hela cell lines. Of all the studied compounds, compound 9e exhibited the best inhibitory ac...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2009.03.023

    authors: Wei MX,Feng L,Li XQ,Zhou XZ,Shao ZH

    更新日期:2009-08-01 00:00:00

  • Structure-activity relationships of new Organotin(IV) anticancer agents and their cytotoxicity profile on HL-60, MCF-7 and HeLa human cancer cell lines.

    abstract::There is a growing interest in the cancer cell growth inhibitory effects of organotin (IV) compounds and, accordingly, a new series of dimethyl-, di-(n-butyl)-, diphenyl- and chloro-phenyl tin(IV) complexes with a Schiff base core were prepared. Their binding to DNA was assessed by UV thermal denaturation showing no i...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.07.047

    authors: Ullah H,Previtali V,Mihigo HB,Twamley B,Rauf MK,Javed F,Waseem A,Baker RJ,Rozas I

    更新日期:2019-11-01 00:00:00

  • Novel benzopsoralen analogues: synthesis, biological activity and molecular docking studies.

    abstract::New benzopsoralen analogues were synthesized and their inhibitory effect on the growth of tumourtumour cell lines (MDA MB231 and TCC-SUP) was evaluated. The in vitro antitumour activity of the new benzopsoralen analogues was discussed in terms of structure-activity relationship. Molecular docking studies with human-CY...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.09.066

    authors: Francisco CS,Rodrigues LR,Cerqueira NM,Oliveira-Campos AM,Esteves AP

    更新日期:2014-11-24 00:00:00

  • Structure-based virtual screening of novel inhibitors of the uridyltransferase activity of Xanthomonas oryzae pv. oryzae GlmU.

    abstract::N-Acetylglucosamine-1-phosphate uridyltransferase (GlmU) catalyzes the formation of UDP-GlcNAc, a fundamental precursor in cell wall biosynthesis. GlmU represents an attractive target for new antibacterial agents. In this study, a theoretical three-dimensional (3D) structure of GlmU from Xanthomonas oryzae pv. oryzae ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.03.051

    authors: Min J,Lin D,Zhang Q,Zhang J,Yu Z

    更新日期:2012-07-01 00:00:00

  • Colchicine prodrugs and codrugs: Chemistry and bioactivities.

    abstract::Antimitotic colchicine possesses low therapeutic index due to high toxicity effects in non-target cell. However, diverse colchicine analogs have been derivatized as intentions for toxicity reduction and structure-activity relationship (SAR) studying. Hybrid system of colchicine structure with nontoxic biofunctional co...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2017.12.029

    authors: Ghawanmeh AA,Chong KF,Sarkar SM,Bakar MA,Othaman R,Khalid RM

    更新日期:2018-01-20 00:00:00

  • Inhibitors of phosphopantetheine adenylyltransferase.

    abstract::Phosphopantetheine adenylyltransferase (PPAT) is an essential enzyme in Coenzyme A biosynthesis. Because bacterial PPAT and mammalian PPAT are dissimilar, this enzyme is an attractive antibacterial target. Based on the structure of the substrate, 4-phosphopantetheine, a dipeptide library was designed, synthesised and ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(03)00047-3

    authors: Zhao L,Allanson NM,Thomson SP,Maclean JK,Barker JJ,Primrose WU,Tyler PD,Lewendon A

    更新日期:2003-04-01 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

  • Structure-activity relationships study of 6-chloro-4-(2-chlorophenyl)-3-(2-hydroxyethyl) quinolin-2(1H)-one derivatives as novel non-nucleoside anti-hepatitis B virus agents.

    abstract::A series of novel 6-chloro-4-(2-chlorophenyl)-3-(2-hydroxyethyl) quinolin-2(1H)-one derivatives were synthesized and evaluated for anti-hepatitis B virus (anti-HBV) activities in vitro to explore their structure-activity relationships (SARs). Most of the synthesized compounds possessed potent anti-HBV activity, of whi...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.11.019

    authors: Guo RH,Zhang Q,Ma YB,Luo J,Geng CA,Wang LJ,Zhang XM,Zhou J,Jiang ZY,Chen JJ

    更新日期:2011-01-01 00:00:00

  • Synthesis and preliminary mechanistic evaluation of 5-(p-tolyl)-1-(quinolin-2-yl)pyrazole-3-carboxylic acid amides with potent antiproliferative activity on human cancer cell lines.

    abstract::We synthesized a series of novel amide derivatives of 5-(p-tolyl)-1-(quinolin-2-yl)pyrazole-3-carboxylic acid and assessed their antiproliferative activities against three human cancer cell lines (Huh7, human liver; MCF7, breast and HCT116, colon carcinoma cell lines) with the sulforhodamine B assay. Compound 4j with ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.09.056

    authors: Cankara Pirol Ş,Çalışkan B,Durmaz I,Atalay R,Banoglu E

    更新日期:2014-11-24 00:00:00

  • Addition of thiols to o-quinone methide: new 2-hydroxy-3-phenylsulfanylmethyl[1,4]naphthoquinones and their activity against the human malaria parasite Plasmodium falciparum (3D7).

    abstract::A series of 36 new phenylsulfanylmethyl[1,4]naphthoquinones (7-42) were synthesized by a three-component reaction that involves lawsone, the appropriate aldehyde and thiols with variable substitution patterns. These reactions involve the in situ generation of o-quinone methides (o-QM) via Knoevenagel condensation and ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.10.052

    authors: Sharma A,Santos IO,Gaur P,Ferreira VF,Garcia CR,da Rocha DR

    更新日期:2013-01-01 00:00:00

  • Synthesis, biological evaluation and 3D QSAR study of 2,4-disubstituted quinolines as anti-tuberculosis agents.

    abstract::The synthesis and anti-tuberculosis activity for three series of 2,4-disubstituted quinolines is reported. The synthesized compounds were evaluated for activity against M. tuberculosis H37Rv strain; most promising compounds from the series exhibited MIC99 values ranged between 3.125 and 6.25 μg/mL. None of the compoun...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.02.034

    authors: Patel SR,Gangwal R,Sangamwar AT,Jain R

    更新日期:2015-03-26 00:00:00

  • Structure-activity relationship studies of acridones as potential antipsoriatic agents. 2. Synthesis and antiproliferative activity of 10-substituted hydroxy-10H-acridin-9-ones against human keratinocyte growth.

    abstract::A series of 10-substituted hydroxy-10H-acridin-9-ones were synthesized and studied as potential antipsoriatic agents. The antiproliferative activity of the novel derivatives, which can be considered as aza-analogues of the antipsoriatic drug anthralin, was determined using the human keratinocyte cell line HaCaT. Struc...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.08.059

    authors: Putic A,Stecher L,Prinz H,Müller K

    更新日期:2010-11-01 00:00:00

  • Ni(II) curcumin complexes for cellular imaging and photo-triggered in vitro anticancer activity.

    abstract::Nickel(II) complexes [Ni(cur)(L)2](OAc) (1-3) where L is N,N-donor heterocyclic bases namely 1,10-phenanthroline (phen in 1), dipyrido[3,2-d:2',3'-f]quinoxaline (dpq in 2), dipyrido[3,2-a:2',3'-c]phenazine (dppz in 3) and Hcur is curcumin were prepared, fully characterized and light-induced in vitro anticancer activit...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112632

    authors: Banaspati A,Raza MK,Goswami TK

    更新日期:2020-10-15 00:00:00

  • Design, synthesis, biological evaluation, and comparative docking study of 1,2,4-triazolones as CB1 receptor selective antagonists.

    abstract::Cannabinoids are potentially useful for the treatment of several diseases. In the present work, we report the syntheses and biological evaluations of 1,2,4-triazolone derivatives designed using a combined approach of scaffold hopping and pharmacophore-oriented method. These compounds exhibited interesting antagonistic...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.12.018

    authors: Han S,Zhang FF,Xie X,Chen JZ

    更新日期:2014-03-03 00:00:00

  • Antitumor activity and carrier properties of novel hemocyanins coupled to a mimotope of GD2 ganglioside.

    abstract::Conjugation to carrier proteins is a way to improve the immunogenicity of peptides. Such is the case for peptides mimicking carbohydrate tumor-associated antigens in cancer vaccine development. The most used protein for this purpose is the keyhole limpet hemocyanin (KLH) from Megathura crenulata. Its limited bioavaila...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.02.082

    authors: Palacios M,Tampe R,Del Campo M,Zhong TY,López MN,Salazar-Onfray F,Becker MI

    更新日期:2018-04-25 00:00:00

  • Synthesis and biological evaluation of novel C-indolylxylosides as sodium-dependent glucose co-transporter 2 inhibitors.

    abstract::Sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors are the current focus on the indication for the management of hyperglycemia in diabetes. Here, a novel series of C-linked indolylxyloside-based inhibitors of SGLT2 has been discovered. Structure-activity relationship studies revealed that substituents at the...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.06.053

    authors: Yao CH,Song JS,Chen CT,Yeh TK,Hsieh TC,Wu SH,Huang CY,Huang YL,Wang MH,Liu YW,Tsai CH,Kumar CR,Lee JC

    更新日期:2012-09-01 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

  • Structure--activity relationship studies of novel arylsulfonylimidazolidinones for their anticancer activity.

    abstract::To define the SAR, a series of novel N-arylsulfonylimidazolidinone derivatives were evaluated for their in vitro anticancer activity against five human tumor cell lines, including A549, COLO205, KATO III, K562, SK-OV-3 and murine leukemia (P288D1) cell line. Among them, N-(2-chloroacetyl)-6-(2-oxo-4-phenylimidazolidin...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.04.042

    authors: Subramanian S,Kim NS,Thanigaimalai P,Sharma VK,Lee KC,Kang JS,Kim HM,Jung SH

    更新日期:2011-08-01 00:00:00

  • Development of potent dipeptide-type SARS-CoV 3CL protease inhibitors with novel P3 scaffolds: design, synthesis, biological evaluation, and docking studies.

    abstract::We report the design and synthesis of a series of dipeptide-type inhibitors with novel P3 scaffolds that display potent inhibitory activity against SARS-CoV 3CLpro. A docking study involving binding between the dipeptidic lead compound 4 and 3CLpro suggested the modification of a structurally flexible P3 N-(3-methoxyp...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.07.037

    authors: Thanigaimalai P,Konno S,Yamamoto T,Koiwai Y,Taguchi A,Takayama K,Yakushiji F,Akaji K,Chen SE,Naser-Tavakolian A,Schön A,Freire E,Hayashi Y

    更新日期:2013-10-01 00:00:00

  • 2-[N-Alkyl(R-phenyl)-aminomethyl]-3-phenyl-7-trifluoromethylquinoxalines as anticancer agents inhibitors of folate enzymes.

    abstract::Based on our previous results on the ascertained potent growth inhibition effect against a panel of 60 human tumors cell lines at National Cancer Institute of Bethesda (NCI), we have synthesized a novel series of thirty-one 2-[N-methyl(R-phenyl)-aminomethyl]-3-phenyl-7-trifluoromethylquinoxalines (1-31). The lead comp...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.01.048

    authors: Piras S,Carta A,Briguglio I,Corona P,Paglietti G,Luciani R,Costi MP,Ferrari S

    更新日期:2014-03-21 00:00:00

  • Discovery of 2,4-diarylaminopyrimidines bearing a resorcinol motif as novel ALK inhibitors to overcome the G1202R resistant mutation.

    abstract::To address drug resistance caused by ALK kinase mutations, especially the most refractory and predominant mutation G1202R for the second-generation ALK inhibitor, a series of new diarylaminopyrimidine analogues were designed by incorporating a resorcinol moiety (A-ring) to interact the ALK kinase domain where the G120...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.12.060

    authors: Geng K,Xia Z,Ji Y,Zhang RR,Sun D,Ai J,Song Z,Geng M,Zhang A

    更新日期:2018-01-20 00:00:00

  • Structure-based approach to nanomolar, water soluble matrix metalloproteinases inhibitors (MMPIs).

    abstract::N-arylsulfonyl-based MMPs inhibitors (MMPIs) are among the most prominent inhibitors possessing nanomolar affinity. However, their poor bioavailability remains critical for the drug development of this family of molecules. The structural analysis of the complex of NNGH (the most representative member of the family) wi...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.09.057

    authors: Attolino E,Calderone V,Dragoni E,Fragai M,Richichi B,Luchinat C,Nativi C

    更新日期:2010-12-01 00:00:00

  • Convenient synthesis of novel geiparvarin analogs with potential anti-cancer activity via click chemistry.

    abstract::Based on the advantages of natural products in new anti-cancer drug development, we synthesized a series of novel benzopyran-4-one derivatives and evaluated their in vitro anti-cancer activities. The bioassays showed that the majority of the resultant compounds exerted anti-tumor effect against six human cancer cell l...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.04.026

    authors: Zhang Y,Lv Z,Zhong H,Geng D,Zhang M,Zhang T,Li Y,Li K

    更新日期:2012-07-01 00:00:00

  • New azole antifungals with a fused triazinone scaffold.

    abstract::We identified a new series of azole antifungal agents bearing a pyrrolotriazinone scaffold. These compounds exhibited a broad in vitro antifungal activity against pathogenic Candida spp. (fluconazole-susceptible and fluconazole-resistant) and were 10- to 100-fold more active than voriconazole against two Candida albic...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112082

    authors: Montoir D,Guillon R,Gazzola S,Ourliac-Garnier I,Soklou KE,Tonnerre A,Picot C,Planchat A,Pagniez F,Le Pape P,Logé C

    更新日期:2020-03-01 00:00:00

  • PASS-assisted design, synthesis and antioxidant evaluation of new butylated hydroxytoluene derivatives.

    abstract::New multipotent antioxidants (MPAOs), namely 1,3,4-thiadiazoles and 1,2,4-triazoles bearing the well-known free radical scavenger butylated hydroxytoluene (BHT), were designed and synthesized using an acid-(base-) catalyzed intramolecular dehydrative cyclization reaction of the corresponding 1-acylthiosemicarbazides. ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.10.001

    authors: Ariffin A,Rahman NA,Yehye WA,Alhadi AA,Kadir FA

    更新日期:2014-11-24 00:00:00

  • Dibenzo[1,4,5]thiadiazepine: a hardly-known heterocyclic system with neuroprotective properties of potential usefulness in the treatment of neurodegenerative diseases.

    abstract::In this work we describe a new family of dibenzo[1,4,5]thiadiazepines (2-12) that showed an interesting in vitro biological profile, namely neuroprotective and antioxidant properties, as well as blockade of cytosolic calcium entry. They showed no cytotoxic effects and the majority were predicted as CNS-permeable compo...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.04.075

    authors: González-Muñoz GC,Arce MP,Pérez C,Romero A,Villarroya M,López MG,Conde S,Rodríguez-Franco MI

    更新日期:2014-06-23 00:00:00

  • Microwave assisted synthesis of unsaturated jasmone heterocyclic analogues as new fragrant substances.

    abstract::Taking the rising interest in jasmone structure based fragrant compounds into account it has been decided to take up an attempt to synthesize the new heterocyclic derivatives of this 2,3-disubstituted cyclopentenone, which could be characterized by the ability of interaction with the same receptors with which jasmone ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.07.028

    authors: Pawełczyk A,Zaprutko L

    更新日期:2009-07-01 00:00:00

  • 2-Azetidinone derivatives: design, synthesis and evaluation of cholesterol absorption inhibitors.

    abstract::Fourteen new derivatives of the 2-azetidinone cholesterol absorption inhibitors have been synthesized, and three of them were enantiomerically pure. All the new compounds were evaluated for their activity to inhibit cholesterol absorption in rats, and most of them showed comparable effects in lowering the levels of to...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.09.033

    authors: Wang Y,Zhang H,Huang W,Kong J,Zhou J,Zhang B

    更新日期:2009-04-01 00:00:00