Synthesis, antiproliferative activity and inhibition of tubulin polymerization by anthracenone-based oxime derivatives.

Abstract:

:A series of anthracenone-based oxime ethers and -esters were synthesized in order to evaluate their antiproliferative activity. Several investigated compounds displayed strong antiproliferative activity against K562 leukemia cells and proved to be strong inhibitors of tubulin polymerization. In this context, anthracenone-based oxime ethers and -esters are considered to contribute to the development of novel antiproliferative drugs, based on tubulin interaction.

journal_name

Eur J Med Chem

authors

Surkau G,Böhm KJ,Müller K,Prinz H

doi

10.1016/j.ejmech.2010.04.019

subject

Has Abstract

pub_date

2010-08-01 00:00:00

pages

3354-64

issue

8

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(10)00301-6

journal_volume

45

pub_type

杂志文章
  • Activity profile relationships between structurally similar promiscuous compounds.

    abstract::Compound promiscuity results from specific interactions of a small molecule with multiple biological targets and is an emerging concept in medicinal chemistry and drug discovery as it provides the basis for polypharmacology. Recent studies have assessed the degree of promiscuity among drugs and bioactive compounds. On...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.08.044

    authors: Hu Y,Bajorath J

    更新日期:2013-11-01 00:00:00

  • The 4-N-acyl and 4-N-alkyl gemcitabine analogues with silicon-fluoride-acceptor: Application to 18F-Radiolabeling.

    abstract::The coupling of gemcitabine with functionalized carboxylic acids using peptide coupling conditions afforded 4-N-alkanoyl analogues with a terminal alkyne or azido moiety. Reaction of 4-N-tosylgemcitabine with azidoalkyl amine provided 4-N-alkyl gemcitabine with a terminal azido group. Click reaction with silane buildi...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.02.017

    authors: Gonzalez C,Sanchez A,Collins J,Lisova K,Lee JT,Michael van Dam R,Alejandro Barbieri M,Ramachandran C,Wnuk SF

    更新日期:2018-03-25 00:00:00

  • Structure activity relationships of quinoline-containing c-Met inhibitors.

    abstract::A series of quinoline-containing c-Met inhibitors were prepared and studied. Chemistry was developed to introduce a pyridyl moiety onto the 2-aryl ring present in a lead molecule which mitigated the potential for quinone formation relative to the original compound. The study also assessed the importance of an acylthio...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2007.08.011

    authors: Kung PP,Funk L,Meng J,Alton G,Padrique E,Mroczkowski B

    更新日期:2008-06-01 00:00:00

  • Structure-activity analysis of CJ-15,801 analogues that interact with Plasmodium falciparum pantothenate kinase and inhibit parasite proliferation.

    abstract::Survival of the human malaria parasite Plasmodium falciparum is dependent on pantothenate (vitamin B5), a precursor of the fundamental enzyme cofactor coenzyme A. CJ-15,801, an enamide analogue of pantothenate isolated from the fungus Seimatosporium sp. CL28611, was previously shown to inhibit P. falciparum proliferat...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.08.050

    authors: Spry C,Sewell AL,Hering Y,Villa MVJ,Weber J,Hobson SJ,Harnor SJ,Gul S,Marquez R,Saliba KJ

    更新日期:2018-01-01 00:00:00

  • Synthesis, biological characterization and molecular modeling insights of spirochromanes as potent HDAC inhibitors.

    abstract::In the last decades, inhibitors of histone deacetylases (HDAC) have become an important class of anti-cancer agents. In a previous study we described the synthesis of spiro[chromane-2,4'-piperidine]hydroxamic acid derivatives able to inhibit histone deacetylase enzymes. Herein, we present our exploration for new deriv...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.11.010

    authors: Thaler F,Moretti L,Amici R,Abate A,Colombo A,Carenzi G,Fulco MC,Boggio R,Dondio G,Gagliardi S,Minucci S,Sartori L,Varasi M,Mercurio C

    更新日期:2016-01-27 00:00:00

  • Antifungal peptides at membrane interaction.

    abstract::Many drugs are available for the treatment of systemic or superficial mycoses, but only a limited number of them are effective antifungal drugs, devoid of toxic and undesirable side effects. Furthermore, resistance development and fungistatic rather than fungicidal activities represent limitations of current antifunga...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.02.037

    authors: Di Marino S,Scrima M,Grimaldi M,D'Errico G,Vitiello G,Sanguinetti M,De Rosa M,Soriente A,Novellino E,D'Ursi AM

    更新日期:2012-05-01 00:00:00

  • Structural and biological studies of mononuclear palladium(II) complexes containing N-substituted thiosemicarbazones.

    abstract::New complexes of Pd(II) with N-substituted thiosemicarbazone (1)-(3) have been synthesised and characterised by elemental analyses, IR, electronic, (1)H NMR spectroscopies. The electrochemical behaviour of the complexes has been tested by using cyclic voltammetry. The crystal structures of the complexes have been dete...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2007.03.006

    authors: Prabhakaran R,Renukadevi SV,Karvembu R,Huang R,Mautz J,Huttner G,Subashkumar R,Natarajan K

    更新日期:2008-02-01 00:00:00

  • Development and biological evaluation of ⁹⁹mTc-sulfonamide derivatives for in vivo visualization of CA IX as surrogate tumor hypoxia markers.

    abstract::In vivo visualization of tumor hypoxia related markers, such as the endogenous transmembrane protein CA IX may lead to novel therapeutic and diagnostic applications in the management of solid tumors. In this study 4-(2-aminoethyl)benzene sulfonamide (AEBS, K(i) = 33 nM for CA IX) has been conjugated with bis(aminoetha...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.10.027

    authors: Akurathi V,Dubois L,Celen S,Lieuwes NG,Chitneni SK,Cleynhens BJ,Innocenti A,Supuran CT,Verbruggen AM,Lambin P,Bormans GM

    更新日期:2014-01-01 00:00:00

  • Synthesis and antimicrobial activities of hexahydroimidazo[1,5-a]pyridinium bromides with varying benzyl substituents.

    abstract::Variously substituted benzyl bromides were employed to quaternize hexahydrobenzylimidazo[1,5-a]pyridine (A) and the resulting bromides (1-11) were evaluated for their in vitro antimicrobial activity against 10 pathogenic microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Bacillus cereus, Micrococcus lu...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.04.012

    authors: Türkmen H,Ceyhan N,Ulkü Karabay Yavaşoğlu N,Ozdemir G,Cetinkaya B

    更新日期:2011-07-01 00:00:00

  • Inhibitory effect of phenothiazine- and phenoxazine-derived chloroacetamides on Leishmania major growth and Trypanosoma brucei trypanothione reductase.

    abstract::A number of phenothiazine-, phenoxazine- and related tricyclics-derived chloroacetamides were synthesized and evaluated in vitro for antiprotozoal activities against Leishmania major (L. major) promastigotes. Several analogs were remarkably potent inhibitors, with antileishmanial activities being comparable or superio...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.11.023

    authors: Marcu A,Schurigt U,Müller K,Moll H,Krauth-Siegel RL,Prinz H

    更新日期:2016-01-27 00:00:00

  • Pharmacophore guided discovery of small-molecule interleukin 15 inhibitors.

    abstract::Upregulation of interleukin 15 (IL-15) contributes directly i.a. to the development of inflammatory and autoimmune diseases. Selective blockade of IL-15 aimed to treat rheumatoid arthritis, psoriasis and other IL-15-related disorders has been recognized as an efficient therapeutic method. The aim of the study was to i...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.05.034

    authors: Żyżyńska-Granica B,Trzaskowski B,Niewieczerzał S,Filipek S,Zegrocka-Stendel O,Dutkiewicz M,Krzeczyński P,Kowalewska M,Koziak K

    更新日期:2017-08-18 00:00:00

  • Synthesis and anti-oxidant activity evaluation of (±)-Anastatins A, B and their analogs.

    abstract::Two novel flavonoids (±)-Anastatins A and B as well as 14 analogs, which containing a benzofuran moiety, were synthesized by using halogenation, Suzuki coupling reaction and an oxidation/Oxa-Michael reaction cascade as the key steps. The structures of the new flavonoids were confirmed by 1H NMR, 13C NMR and HRMS. The ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.06.054

    authors: Pan G,Li X,Zhao L,Wu M,Su C,Li X,Zhang Y,Yu P,Teng Y,Lu K

    更新日期:2017-09-29 00:00:00

  • Condensed bridgehead nitrogen heterocyclic system: synthesis and pharmacological activities of 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole derivatives of ibuprofen and biphenyl-4-yloxy acetic acid.

    abstract::Several 3,6-disubstituted-1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazoles were prepared by condensation of 4-amino-5-substituted-3-mercapto-(4H)-1,2,4-triazoles (3a,b) with various substituted aromatic acids and aryl/alkyl isothiocyanates through a one-pot reaction. These compounds were investigated for their anti-inflammat...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2007.09.025

    authors: Amir M,Kumar H,Javed SA

    更新日期:2008-10-01 00:00:00

  • Heparin-polynitroxides: synthesis and preliminary evaluation as cardiovascular EPR/MR imaging probes and extracellular space-targeted antioxidants.

    abstract::We report here the synthesis of heparin-polynitroxide derivatives (HPNs) in which nitroxide moieties are linked either to uronic acid or glycosamine residues of the heparin macromolecule. HPNs have low anticoagulant activity, possess superoxide scavenging properties, bind to the vascular endothelium/extra-cellular mat...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.09.028

    authors: Kleschyov AL,Sen' V,Golubev V,Münnemann K,Hinderberger D,Lackner KJ,Weber S,Terekhov M,Schreiber LM,Münzel T

    更新日期:2012-12-01 00:00:00

  • Second-generation sulfonamide inhibitors of D-glutamic acid-adding enzyme: activity optimisation with conformationally rigid analogues of D-glutamic acid.

    abstract::D-Glutamic acid-adding enzyme (MurD) catalyses the essential addition of d-glutamic acid to the cytoplasmic peptidoglycan precursor UDP-N-acetylmuramoyl-l-alanine, and as such it represents an important antibacterial drug-discovery target enzyme. Based on a series of naphthalene-N-sulfonyl-d-Glu derivatives synthesise...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.04.011

    authors: Sosič I,Barreteau H,Simčič M,Sink R,Cesar J,Zega A,Grdadolnik SG,Contreras-Martel C,Dessen A,Amoroso A,Joris B,Blanot D,Gobec S

    更新日期:2011-07-01 00:00:00

  • The synthesis and biological evaluation of new DNA-directed alkylating agents, phenyl N-mustard-4-anilinoquinoline conjugates containing a urea linker.

    abstract::We synthesized a series of phenyl N-mustard-4-anilinoquinoline conjugates to study their antitumorigenic effects. These agents were prepared by the condensation of 4-[N,N-bis(2-chloroethyl)amino]phenyl isocyanate with 6-amino-4-methylamino or 4-anilinoquinolines. The structure-activity relationship (SAR) studies revea...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.06.066

    authors: Marvania B,Kakadiya R,Christian W,Chen TL,Wu MH,Suman S,Tala K,Lee TC,Shah A,Su TL

    更新日期:2014-08-18 00:00:00

  • Antagonizing STAT3 activation with benzo[b]thiophene 1, 1-dioxide based small molecules.

    abstract::STAT3 is an attractive therapeutic target for cancer therapy. However, due to low potency or poor druggability, none of its inhibitors are clinically available. Herein, a series of aminobenzo[b]thiophene 1, 1-dioxides with good drug-likeness properties were designed, synthesized and evaluated as STAT3 inhibitors. Most...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.09.068

    authors: Zhang W,Ma T,Li S,Yang Y,Guo J,Yu W,Kong L

    更新日期:2017-01-05 00:00:00

  • Synthesis, antimicrobial, antimycobacterial and structure-activity relationship of substituted pyrazolo-, isoxazolo-, pyrimido- and mercaptopyrimidocyclohepta[b]indoles.

    abstract::A new class of heterocycles, specifically substituted pyrazolo-, isoxazolo- and pyrimidocyclohepta[b]indoles, has been prepared by condensation of substituted 7-(hydroxymethylene)-7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-ones with hydrazine hydrate, hydroxylamine hydrochloride, phenylhydrazine, urea and thiourea, r...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.10.046

    authors: Yamuna E,Kumar RA,Zeller M,Rajendra Prasad KJ

    更新日期:2012-01-01 00:00:00

  • Synthesis, in vitro β-glucuronidase inhibitory potential and molecular docking studies of quinolines.

    abstract::In this study synthesis and β-glucuronidase inhibitory potential of 3/5/8 sulfonamide and 8-sulfonate derivatives of quinoline (1-40) are discussed. Studies reveal that all the synthetic compounds were found to have good inhibitory activity against β-glucuronidase. Nonetheless, compounds 1, 2, 5, 13, and 22-24 having ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.08.052

    authors: Bano B,Arshia,Khan KM,Kanwal,Fatima B,Taha M,Ismail NH,Wadood A,Ghufran M,Perveen S

    更新日期:2017-10-20 00:00:00

  • Synthesis, anti-HIV-1 integrase, and cytotoxic activities of 4-chloro-N-(4-oxopyrimidin-2-yl)-2-mercaptobenzenesulfonamide derivatives.

    abstract::Several 4-chloro-N-(4-oxopyrimidin-2-yl)-2-mercaptobenzenesulfonamide derivatives 13-28 and 35-44 have been synthesized and tested as potential HIV-1 integrase (IN) inhibitors. Compounds 15-17, 19, 21-28, 36 and 41 inhibited IN with IC(50) values in the range of 3.3-63.0 microM. The compounds 13, 15, 16, 21-24 and 26-...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2007.08.013

    authors: Brzozowski Z,Sławiński J,Saczewski F,Sanchez T,Neamati N

    更新日期:2008-06-01 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

  • Discovery and optimization of benzenesulfonamides-based hepatitis B virus capsid modulators via contemporary medicinal chemistry strategies.

    abstract::Hepatitis B is a vaccine-preventable, but potentially life-threatening liver infection caused by the Hepatitis B virus (HBV). It represents an important health burden, with 257 million active cases globally. Current HBV treatments using nucleos(t)ide analogs and pegylated interferons cannot alleviate the situation com...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2020.112714

    authors: Ren Y,Ma Y,Cherukupalli S,Tavis JE,Menéndez-Arias L,Liu X,Zhan P

    更新日期:2020-11-15 00:00:00

  • Antifungal activities of novel non-azole molecules against S. cerevisiae and C. albicans.

    abstract::Because of the increasing number of immunocompromised patients and due to problems with antifungal treatment, especially with the most widely used antifungals, azoles, there is an urgent need for new, potent and safe antifungals with fewer cytochrome P450 (CYP)-mediated interactions with other drugs. In the present st...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.10.053

    authors: Tani N,Rahnasto-Rilla M,Wittekindt C,Salminen KA,Ritvanen A,Ollakka R,Koskiranta J,Raunio H,Juvonen RO

    更新日期:2012-01-01 00:00:00

  • Comparative study of microtubule inhibitors--estramustine and natural podophyllotoxin conjugated PAMAM dendrimer on glioma cell proliferation.

    abstract::The synthetic estramustine (EM) and natural podophyllotoxin (PODO) anti-mitotic agents that inhibit tubulin polymerization are known anticancer agents. As low bioavailability limits their anticancer properties, we investigated whether conjugation with PAMAM dendrimer (D) could enhance the activity of D-EM and D-PODO b...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.07.007

    authors: Sk UH,Dixit D,Sen E

    更新日期:2013-10-01 00:00:00

  • Synthesis and biological activities of dithiocarbamates containing 2(5H)-furanone-piperazine.

    abstract::A series of new dithiocarbamates containing a 2(5H)-furanone-piperazine group was synthesized. These compounds show good in vitro cytoxic activity. Among them, compound 6c exhibits the best inhibitory activity against HeLa cell lines with an IC50 of 0.06 ± 0.01 μM for 72 h, and it has good inhibitory activity against ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.05.056

    authors: Wei MX,Zhang J,Ma FL,Li M,Yu JY,Luo W,Li XQ

    更新日期:2018-07-15 00:00:00

  • Inhibition of vertebrate aldehyde oxidase as a therapeutic treatment for cancer, obesity, aging and amyotrophic lateral sclerosis.

    abstract::The aldehyde oxidases (AOXs) are a small sub-family of cytosolic molybdo-flavoenzymes, which are structurally conserved proteins and broadly distributed from plants to animals. AOXs play multiple roles in both physiological and pathological processes and AOX inhibition is of increasing significance in the development ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2019.111948

    authors: Qiao Y,Maiti K,Sultana Z,Fu L,Smith R

    更新日期:2020-02-01 00:00:00

  • Rigid aromatic linking moiety in cationic lipids for enhanced gene transfection efficiency.

    abstract::Although numerous cationic lipids have been developed as non-viral gene vectors, the structure-activity relationship (SAR) of these materials remains unclear and needs further investigation. In this work, a series of lysine-derived cationic lipids containing linkages with different rigidity were designed and synthesiz...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.05.038

    authors: Wang B,Zhao RM,Zhang J,Liu YH,Huang Z,Yu QY,Yu XQ

    更新日期:2017-08-18 00:00:00

  • Novel pentacyclic triterpenes exhibiting strong neuroprotective activity in SH-SY5Y cells in salsolinol- and glutamate-induced neurodegeneration models.

    abstract::Novel triterpene derivatives were prepared and evaluated in salsolinol (SAL)- and glutamate (Glu)-induced models of neurodegeneration in neuron-like SH-SY5Y cells. Among the tested compounds, betulin triazole 4 bearing a tetraacetyl-β-d-glucose substituent showed a highly potent neuroprotective effect. Further studies...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2021.113168

    authors: Gonzalez G,Hodoň J,Kazakova A,D'Acunto CW,Kaňovský P,Urban M,Strnad M

    更新日期:2021-01-16 00:00:00

  • Guanidine-modified cyclometalated iridium(III) complexes for mitochondria-targeted imaging and photodynamic therapy.

    abstract::PDT is a well-established therapeutic modality for many types of cancer. Photoluminescent cyclometalated iridium(III) complexes are one of the most commonly used classes of organometallic compounds with potential beneficial applications in bioimaging and as promising anticancer agents. In the present study, three new ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.06.045

    authors: Song XD,Chen BB,He SF,Pan NL,Liao JX,Chen JX,Wang GH,Sun J

    更新日期:2019-10-01 00:00:00

  • CODES, a novel procedure for ligand-based virtual screening: PDE7 inhibitors as an application example.

    abstract::Phosphodiesterase (PDE) 7 is a high affinity cAMP-specific PDE whose functional role in T-cells has been the subject of some controversy. Recent findings on tissue distribution, however, support the hypothesis that PDE7 could be a good target for the treatment of airway diseases, T-cell related diseases or central ner...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2007.10.027

    authors: Castro A,Jerez MJ,Gil C,Calderón F,Doménech T,Nueda A,Martínez A

    更新日期:2008-07-01 00:00:00