Novel NHC Precursors: Synthesis, Characterization, and Carbonic Anhydrase and Acetylcholinesterase Inhibitory Properties.


:Three series of imidazolidinium ligands (NHC precursors) substituted with 4-vinylbenzyl, 2-methyl-1,4-benzodioxane, and N-propylphthalimide were synthesized. N-Heterocyclic carbene (NHC) precursors were prepared from N-alkylimidazoline and alkyl halides. The novel NHC precursors were characterized by 1 H NMR, 13 C NMR, FTIR spectroscopy, and elemental analysis techniques. The enzymes inhibition activities of the NHC precursors were investigated against the cytosolic human carbonic anhydrase I and II isoenzymes (hCA I and II) and the acetylcholinesterase (AChE) enzyme. The inhibition parameters (IC50 and Ki values) were calculated by spectrophotometric method. The inhibition constants (Ki ) were found to be in the range of 166.65-635.38 nM for hCA I, 78.79-246.17 nM for hCA II, and 23.42-62.04 nM for AChE. Also, the inhibitory effects of the novel synthesized NHCs were compared to acetazolamide as a clinical CA isoenzymes inhibitor and tacrine as a clinical cholinergic enzymes inhibitor.


Arch Pharm (Weinheim)


Archiv der Pharmazie


Aktaş A,Taslimi P,Gülçin İ,Gök Y




Has Abstract


2017-06-01 00:00:00










  • Novel ametantrone-amsacrine related hybrids as topoisomerase IIβ poisons and cytotoxic agents.

    abstract::The precise definition of the structural requirements for effective topoisomerase II poisoning by drug molecules is still an elusive issue. In the attempt to better define a pharmacophoric pattern, we prepared several conjugates combining the chemical features of two well-known topoisomerase II poisons, amsacrine and ...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Zagotto G,Gianoncelli A,Sissi C,Marzano C,Gandin V,Pasquale R,Capranico G,Ribaudo G,Palumbo M

    更新日期:2014-10-01 00:00:00

  • Design and synthesis of novel benzopyran-2-one derivatives of expected antimicrobial activity through DNA gyrase-B inhibition.

    abstract::In an attempt to find a new class of antibacterial agents, we have synthesized thirty new coumarin (2H-benzopyran-2-one) analogues. These derivatives include substituted azetidin-2-ones (beta-lactam) 3a-f, pyrrolidin-2-ones 4a-f, 2H-1,3,4-oxadiazoles 5a-f, and thiazolidin-4-ones 6a-f attached to 4-phenyl-2H-benzopyran...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Hassan GS,Farag NA,Hegazy GH,Arafa RK

    更新日期:2008-11-01 00:00:00

  • [CNS-active substances: synthesis of epoxybenzoxocines].

    abstract::The 2-(2-Bromophenyl)-acetaldehyde acetals 8 are treated with n-BuLi and the aldehydes 7 and 11 to form the hydroxyacetales 9 and 12, respectively. 9 is cyclized under acidic conditions to the epoxybenzoxocine 2; analogously 12 yields the epoxydibenzoxocine 14. ...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Wünsch B

    更新日期:1990-11-01 00:00:00

  • Synthesis and evaluation of a dimer of 2-(4-pyridylmethyl)-1-indanone as a novel nonsteroidal aromatase inhibitor.

    abstract::A novel dimer of 2-(4-pyridylmethyl)-1-indanone (2) was obtained while carrying out aldol condensation of 1-indanone with pyridine-4-carboxaldehyde in potassium hydroxide. The structure of dimer 3 has been established using various spectral techniques and was screened for its ability to inhibit the cytochrome P(450) e...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Gupta R,Jindal DP,Jit B,Narang G,Palusczak A,Hartmann RW

    更新日期:2004-07-01 00:00:00

  • Synthesis of paullones with aminoalkyl side chains.

    abstract::Paullones 3 and 4 with aminoalkyl side chains in 2- or 3-position were synthesized as derivatives of kenpaullone 1. Both 3 and 4 showed the characteristic CDK1-inhibitory activity of the paullones and a modest antiproliferative activity on cultured human tumor cell lines. Hence, 3 and 4 appear to be suitable tools for...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Wieking K,Knockaert M,Leost M,Zaharevitz DW,Meijer L,Kunick C

    更新日期:2002-07-01 00:00:00

  • Synthesis and 5-HT2A radioligand receptor binding assays of DOMCl and DOMOM, two novel 5-HT2A receptor ligands.

    abstract::A synthesis of two new active substances, DOMCl (1-(4-chloromethyl-2, 5-dimethoxyphenyl)-2-propanamine; 2) and DOMOM (1-(2, 5-dimethoxy-4-methoxymethylphenyl)-2-propanamine; 3), was developed. Unexpectedly, the Blanc reaction permitted successful synthesis of 2, 5-dimethoxyphenylpropylamine derivatives having a substi...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Harms A,Ulmer E,Kovar KA

    更新日期:2003-06-01 00:00:00

  • Synthesis and antitumor activity of some substituted indazole derivatives.

    abstract::Some new N-[6-indazolyl]arylsulfonamides and N-[alkoxy-6-indazolyl]arylsulfonamides were prepared by the reduction of 2-alkyl-6-nitroindazoles with SnCl2 in different alcohols, followed by coupling the corresponding amine with arylsulfonyl chlorides in pyridine. The newly synthesized compounds were evaluated for their...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Abbassi N,Rakib el M,Chicha H,Bouissane L,Hannioui A,Aiello C,Gangemi R,Castagnola P,Rosano C,Viale M

    更新日期:2014-06-01 00:00:00

  • Semi-synthesis and biological evaluation of 1,2,3-triazole-based podophyllotoxin congeners as potent antitumor agents inducing apoptosis in HepG2 cells.

    abstract::A series of 4β-[(4-substituted)-1,2,3-triazol-1-yl]podophyllotoxin congeners were synthesized by employing click chemistry and further evaluated for their antitumor activity by MTT assay. Among them, six congeners (10, 11, 12, 13, 22, and 24) exhibited approximately 100-fold more potent inhibitory activity against fou...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Chen J,Ma L,Zhang R,Tang J,Lai H,Wang J,Wang G,Xu Q,Chen T,Peng F,Qiu J,Liang X,Cao D,Ran Y,Peng A,Wei Y,Chen L

    更新日期:2012-12-01 00:00:00

  • Synthesis, tautomeric structures, and antitumor activity of new perimidines.

    abstract::New series of perimidine derivatives and fused perimidines were derived from the reaction of ketene aminals 1 and 2 with diazotized anilines or hydrazonoyl chlorides. In addition, 8,10-disubstituted-[1,2,4]triazolo[4,3-a]perimidines (20a-m) were prepared through the reaction of perimidine-2-thione (15) with hydrazonoy...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Farghaly TA,Mahmoud HK

    更新日期:2013-05-01 00:00:00

  • Investigations into neuroprotectivity, stability, and water solubility of 7-O-cinnamoylsilibinin, its hemisuccinate and dehydro derivatives.

    abstract::Derivatives of the recently described potent neuroprotective 7-O-cinnamoylsilibinin ester were prepared: its hemisuccinate to improve water solubility and the dehydrosilibinin ester that was shown to form in assay media to investigate its role in overall neuroprotective effects. 7-O-Cinnamoyl-2,3-dehydrosilibinin is l...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Schramm S,Gunesch S,Lang F,Saedtler M,Meinel L,Högger P,Decker M

    更新日期:2018-11-01 00:00:00

  • Novel pyridine-2,4,6-tricarbohydrazide thiourea compounds as small key organic molecules for the potential treatment of type-2 diabetes mellitus: In vitro studies against yeast α- and β-glucosidase and in silico molecular modeling.

    abstract::A range of novel pyridine-2,4,6-tricarbohydrazide thiourea compounds (4a-i) were synthesized in good to excellent yields (63-92%). The enzyme inhibitory potentials of these compounds were investigated against α- and β-glucosidases because these enzymes play a crucial role in treating type-2 diabetes mellitus (T2DM). A...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Rehman TU,Riaz S,Khan IU,Ashraf M,Bajda M,Gawalska A,Yar M

    更新日期:2018-01-01 00:00:00

  • Synthesis and smooth muscle calcium channel antagonist effects of dialkyl 1,4-dihydro-2,6-dimethyl-4-aryl-3,5-pyridinedicarboxylates containing a nitrooxy or nitrophenyl moiety in the 3-alkyl ester substituent.

    abstract::A group of racemic 3-[2-nitrooxyethyl (1,3-dinitrooxy-2-propyl or 4-nitrophenylethyl)] 5-isopropyl 1,4-dihydro-2,6-dimethyl-4-[2- trifluoromethylphenyl (2-nitrophenyl or 3-nitrophenyl)]-3,5-pyridinedicarboxylates 13-15 were prepared using the Hantzsch reaction that involved the condensation of 2-nitrooxyethyl 9a, 1,3-...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Iqbal N,Knaus EE

    更新日期:1996-01-01 00:00:00

  • Synthesis and molluscicidal activity of 5-oxo-5,6,7,8-tetrahydro-4H-chromene derivatives.

    abstract::Furfurylidenemalononitriles and thienylidenemalononitriles were treated with 1,3-cyclohexanediones to afford 2-amino-4-hetaryl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile derivatives. The molluscicidal activity of these compounds was investigated. ...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Abdelrazek FM,Metz P,Farrag EK

    更新日期:2004-09-01 00:00:00

  • Discovery of novel aldose reductase inhibitors characterized by an alkoxy-substituted phenylacetic acid core.

    abstract::In continuation of our effort aimed towards the development of novel aldose reductase inhibitors, several phenylacetic acids bearing an alkoxy substituent in position 3 or 4, respectively, were prepared and screened. The latter represent formal ring opening products of the cyclohexylmethyloxyphenylacetic acids IIa and...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Rakowitz D,Gmeiner A,Matuszczak B

    更新日期:2006-10-01 00:00:00

  • Synthesis and antitumor activity of enantiomerically pure [1,2-diamino-1-(4-fluorophenyl)propane]dichloroplatinum(II) complexes.

    abstract::Enantiomerically pure 1, 2-diamino-1-(4-fluorophenyl)propanes were synthesized by stereospecific and stereoselective procedures by use of the (1R, 2S)- and (1S, 2R)-2-amino-1-(4-fluorophenyl)propanols (12a) as intermediates. The enantiomeric purity was determined by (1)H NMR spectroscopy after conversion of the propan...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Dufrasne F,Gelbcke M,Schnurr B,Gust R

    更新日期:2002-05-01 00:00:00

  • Synthesis and antibacterial activity of new 7-piperazinyl-quinolones containing a functionalized 2-(furan-3-yl)ethyl moiety.

    abstract::A number of 7-piperazinylquinolones carrying a functionalized 2-(furan-3-yl)ethyl moiety attached to the piperazine ring have been synthesized and evaluated as antibacterial agents against a panel of Gram-positive and Gram-negative bacteria. Most of the synthesized compounds exhibited significant antibacterial activit...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Foroumadi A,Mohammadhosseini N,Emami S,Letafat B,Faramarzi MA,Samadi N,Shafiee A

    更新日期:2007-01-01 00:00:00

  • Synthesis, antibacterial evaluation, and DNA gyrase inhibition profile of some new quinoline hybrids.

    abstract::Antibiotic-resistant bacteria continue to play an important role in human health and disease. Inventive strategies are necessary to develop new therapeutic leads to challenge drug-resistance problems. From this perception, new quinoline hybrids bearing bioactive pharmacophores were synthesized. The newly synthesized c...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Rizk OH,Bekhit MG,Hazzaa AAB,El-Khawass EM,Abdelwahab IA

    更新日期:2019-10-01 00:00:00

  • Salicylamides containing amino acid or pyran moieties with molluscicidal activity.

    abstract::Salicylamide amino acid conjugates were prepared utilizing 5-formyl-, 5-dicyanoethenyl-, and 5-nitroethenylsalicylic acid. 5-Substituted salicylanilides were treated with glycine and formaldehyde in a Mannich type reaction affording the corresponding 3-(N-glycino)salicylanilides. The reactions of anilines with pyrans ...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Nawwar GA

    更新日期:1994-04-01 00:00:00

  • [Indoles. 10. Synthesis, structure and D2-affinity of beta-carboline analogs of flutroline].

    abstract::10 is a beta-carboline analogue of the neuroleptic flutroline2a,b) with significant lower affinity at the dopamine D2 binding site. Various synthetic routes to 10 and the solid state structure of 8 are described, structure activity relations, in particular the importance of the "S-shape" and the rigid dopamine conform...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Lehmann J,Knoch F,Jiang N

    更新日期:1993-12-01 00:00:00

  • 3D pharmacophore models for 1,2,3,4-tetrahydroisoquinoline derivatives acting as anticonvulsant agents.

    abstract::A 3D pharmacophore model predicting anticonvulsant activity was obtained for a series of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives recently disclosed as a new class of noncompetitive AMPA receptor antagonists. The training set included 17 compounds with varying potency against audiogenic seizures in DBA...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: De Luca L,Gitto R,Barreca ML,Caruso R,Quartarone S,Citraro R,De Sarro G,Chimirri A

    更新日期:2006-07-01 00:00:00

  • Synthesis and biological evaluation of novel 1,2,3-triazolonucleotides.

    abstract::A general procedure for the preparation of 1,2,3-triazole analogs of nucleosides from diethyl 2-azidoethoxymethyl- and 2-azidoethoxyethylphosphonates was elaborated. The application of microwave irradiation shortened the reaction time to 10 min in comparison to ca. 48 h when 1,3-dipolar cycloadditions were performed u...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Głowacka IE,Balzarini J,Wróblewski AE

    更新日期:2013-04-01 00:00:00

  • Synthesis, cleavage profile, and antitumor efficacy of an albumin-binding prodrug of methotrexate that is cleaved by plasmin and cathepsin B.

    abstract::Cathepsin B and plasmin are intra- or extracellular proteases that are overexpressed by several solid tumors. In order to exploit both proteases as molecular targets for tumor-specific cleavage of prodrugs, an albumin-binding formulation of methotrexate was developed that incorporated the peptide sequence D-Ala-Phe-Ly...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Warnecke A,Fichtner I,Sass G,Kratz F

    更新日期:2007-08-01 00:00:00

  • Synthesis, cytotoxicity testing, and structure-activity relationships of novel 6-chloro-7-(4-phenylimino-4H-3,1-benzoxazin-2-yl)-3-(substituted)-1,4,2-benzodithiazine 1,1-dioxides.

    abstract::A new series of 16 6-chloro-1,1-dioxo-7-{4-[(4-R(1)-phenyl)imino]-4H-3,1-benzoxazin-2-yl}-3-(substituted amino)-1,4,2-benzodithiazines 7-22 was prepared in order to evaluate the cytotoxic activity against six human cancer cell lines. The structures of the new compounds were confirmed by IR, (1)H-, and (13)C-NMR, eleme...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Pomarnacka E,Kornicka A,Kuchnio A,Heinrichs M,Grünert R,Gdaniec M,Bednarski PJ

    更新日期:2011-07-01 00:00:00

  • N-Substituted-4-phenylphthalazin-1-amine-derived VEGFR-2 inhibitors: Design, synthesis, molecular docking, and anticancer evaluation studies.

    abstract::In accordance with the significant impetus of the discovery of potent vascular endothelial growth factor receptor 2 (VEGFR-2) inhibitors, herein, we report the design, synthesis, and anticancer evaluation of 12 new N-substituted-4-phenylphthalazin-1-amine derivatives against HepG2, HCT-116, and MCF-7 cells as VEGFR-2 ...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: El-Adl K,Ibrahim MK,Khedr F,Abulkhair HS,Eissa IH

    更新日期:2020-11-16 00:00:00

  • Non-steroidal anti-inflammatory agents, Part 24. Pyrrolidino enaminones as models to mimic arachidonic acid.

    abstract::The pyrrolidino enaminones, with the carboxylic acid chain fixed at the nitrogen, inhibit cyclooxygenase more potently or selectively than 5-lipoxygenase. According to the structure-activity relationships discussed the potency depends significantly on the chain length of the carboxylic acid, the substitution pattern o...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Dannhardt G,Bauer A,Nowe U

    更新日期:1997-03-01 00:00:00

  • Syntheses and selective inhibitory activities of terphenyl-bisamidines for serine proteases.

    abstract::Biphenyl nitriles 5a-c, terphenyl dinitriles 11a-d, and naphthalene-bis(benzonitrile) 11c were prepared by palladium-catalyzed cross coupling reactions and subsequently converted to biphenyl amidines 8a-c and bis(benzamidines) 4a-e. Among the biphenyl amidines 8 only the meta-derivative 8b inhibits factor Xa and tryps...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: von der Saal W,Engh RA,Eichinger A,Gabriel B,Kucznierz R,Sauer J

    更新日期:1996-02-01 00:00:00

  • Availability of NSAIDH beta-cyclodextrin inclusion complexes.

    abstract::The diffusion of a series of non steroidal antiinflammatory drugs through a silicone rubber membrane has been studied from suspensions both of the free and beta-cyclodextrin complexes forms at different pH values of the medium. Higher diffusion rates of the complexed forms as compared with the free ones and a rate-lim...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Orienti I,Cavallari C,Zecchi V,Fini A

    更新日期:1989-04-01 00:00:00

  • Structure activity relationship of homochiral 7-substituted 1-aminoindans as 5-HT1A receptor ligands.

    abstract::A series of homochiral 7-substituted 1-aminoindans was prepared by means of asymmetric reductive amination from racemic 7-substituted 1-indanones via E-imines and E-imine/enamine mixtures, respectively, and subjected to 5-hydroxytryptamine (5-HT) receptor subtype binding studies. The ee's of the title compounds were d...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Landsiedel-Maier D,Frahm AW

    更新日期:1998-02-01 00:00:00

  • Synthesis, cytotoxicity, and molecular docking of substituted 3-(2-methylbenzofuran-3-yl)-5-(phenoxymethyl)-1,2,4-oxadiazoles.

    abstract::A series of new benzofuran/oxadiazole hybrids (8a-n) was synthesized from 2H-chromene-3-carbonitriles (3a-c) through the multistep synthetic methodology, and these hybrids are known to exhibit anticancer activities. All the compounds were evaluated for their in vitro cytotoxicity against the HCT116 and MIA PaCa2 cell ...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Mokenapelli S,Thalari G,Vadiyaala N,Yerrabelli JR,Irlapati VK,Gorityala N,Sagurthi SR,Chitneni PR

    更新日期:2020-06-01 00:00:00

  • Convenient synthesis and antimicrobial activity of new 3-substituted 5-(benzofuran-2-yl)-pyrazole derivatives.

    abstract::The reaction of ethyl 4-(benzofuran-2-yl)-2,4-dioxobutanoate 2 with two moles of hydrazine hydrate afforded 5-(benzofuran-2-yl)-1H-pyrazole-3-carbohydrazide 4a, while its reaction with equimolar amount of phenylhydrazine gave ester 3b which then converted to 5-(benzofuran-2-yl)-1-phenyl-1H-pyrazole-3-carbohydrazide 4b...

    journal_title:Archiv der Pharmazie

    pub_type: 杂志文章


    authors: Abdel-Wahab BF,Abdel-Aziz HA,Ahmed EM

    更新日期:2008-11-01 00:00:00