Synthesis and antitumour activity of a new series of nitrosoureido sugars.

Abstract:

:New nitrosoureido derivatives of di- or tri-deoxy-sugars have been synthesized. Very potent antitumour activity against L1210 leukaemia was exhibited by the compounds derived from methyl 3-amino-3, 4-dideoxy-beta- and alpha- and 4-amino-2,4-dideoxy-beta- and alpha-D-arabino-hexopyranosides, 24, 26, 28 and 29, respectively. In further evaluation against B16 melanocarcinoma bearing mice, only compounds 24 and 26 displayed significant activity. Owing to its lower acute toxicity, methyl 3-[3-(2-chloroethyl)-3-nitrosoureido]-3, 4-dideoxy-beta-D-arabino-hexopyranoside 24 appeared as the best candidate for preclinical studies.

journal_name

Eur J Med Chem

authors

Monneret C,Rissé S,Ardouin P,Gouyette A

doi

10.1016/s0223-5234(00)00114-8

subject

Has Abstract

pub_date

2000-01-01 00:00:00

pages

137-46

issue

1

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(00)00114-8

journal_volume

35

pub_type

杂志文章
  • Peptidyl 3-substituted 1-hydroxyureas as isosteric analogues of succinylhydroxamate MMP inhibitors.

    abstract::To evaluate N-hydroxyurea as zinc binding group in the design of MMP inhibitors, two peptidyl 1-hydroxyureas were prepared by N-hydroxycarbamoylation of the diastereomeric dipeptides H-Leu-Phe-NHMe and H-D-Leu-Phe-NHMe. Peptidyl 1-hydroxyureas were more potent than the parent peptides, but dramatically weaker (4-5 ord...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2007.07.002

    authors: Campestre C,Tortorella P,Agamennone M,Preziuso S,Biasone A,Nuti E,Rossello A,Gallina C

    更新日期:2008-05-01 00:00:00

  • Synthesis, structure, toxicological and pharmacological investigations of 4-hydroxycoumarin derivatives.

    abstract::Twenty 4-hydroxycoumarin derivatives were synthesized. Five of them are described for the first time. The X-ray crystal structure analysis of 3,3'-(2,3,4-trimethoxyphenylmethylene)bis-(4-hydroxy-2H-1-benzopyran-2-one) (7) and 3,3'-(3,5-dimethoxy-4-hydroxyphenylmethylene)bis-(4-hydroxy-2H-1-benzopyran-2-one) (9) confir...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2006.03.007

    authors: Manolov I,Maichle-Moessmer C,Danchev N

    更新日期:2006-07-01 00:00:00

  • Integrating docking scores, interaction profiles and molecular descriptors to improve the accuracy of molecular docking: toward the discovery of novel Akt1 inhibitors.

    abstract::A set of forty-seven Akt1 inhibitors was used for the development of molecular docking based QSAR model by using nonlinear regression. The integration of docking scores, key interaction profiles and molecular descriptors remarkably improved the accuracy of the QSAR models, providing reasonable statistical parameters (...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.01.019

    authors: Zhan W,Li D,Che J,Zhang L,Yang B,Hu Y,Liu T,Dong X

    更新日期:2014-03-21 00:00:00

  • 4-Fluoro-3',4',5'-trimethoxychalcone as a new anti-invasive agent. From discovery to initial validation in an in vivo metastasis model.

    abstract::Invasion and metastasis are responsible for 90% of cancer-related mortality. Herein, we report on our quest for novel, clinically relevant inhibitors of local invasion, based on a broad screen of natural products in a phenotypic assay. Starting from micromolar chalcone hits, a predictive QSAR model for diaryl propenon...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.06.029

    authors: Roman BI,De Ryck T,Patronov A,Slavov SH,Vanhoecke BW,Katritzky AR,Bracke ME,Stevens CV

    更新日期:2015-08-28 00:00:00

  • Aminopropylindenes derived from Grundmann's ketone as a novel chemotype of oxidosqualene cyclase inhibitors.

    abstract::A series of aminopropylindenes, designed as mimics of a cationic high energy intermediate in the oxidosqualene cyclase(1) (OSC)-mediated cyclization of 2,3-oxidosqualen to lanosterol was prepared from Grundmann's ketone. Screening on OSCs from five different organisms revealed interesting activities and selectivities ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.03.002

    authors: Lange S,Keller M,Müller C,Oliaro-Bosso S,Balliano G,Bracher F

    更新日期:2013-05-01 00:00:00

  • Design, synthesis and receptor affinity of novel conformationally restricted σ ligands based on the [4.3.3]propellane scaffold.

    abstract::A series of novel diastereoisomeric σ ligands 3 was designed, synthesized and pharmacologically evaluated. The highly rigid [4.3.3]propellane scaffold was used to fix the three dimensional orientation of the pharmacophoric moieties required for σ affinity. The syn,syn-configured aminocarbamate syn,syn-3a reveals the m...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.09.021

    authors: Torres-Gómez H,Lehmkuhl K,Schepmann D,Wünsch B

    更新日期:2013-01-01 00:00:00

  • Facile synthesis of active antitubercular, cytotoxic and antibacterial agents: a Michael addition approach.

    abstract::Spiro derivatives of oxindole and isoxazole-5-one were synthesized by using Michael addition reaction, highlighting the regioselective approach towards the synthesis of Michael diadduct followed by condensation of Michael diadduct. The spiro compound 4 showed antitubercular activity against Mycobacterium tuberculosis ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2005.06.004

    authors: Chande MS,Verma RS,Barve PA,Khanwelkar RR,Vaidya RB,Ajaikumar KB

    更新日期:2005-11-01 00:00:00

  • Designing dendrimers for ocular drug delivery.

    abstract::New series of phosphorus-containing dendrimers, having one quaternary ammonium salt as core and carboxylic acid terminal groups have been synthesized from generation 0 (3 carboxylic acid terminal groups) to generation 2 (12 carboxylic acid terminal groups). These dendrimers react with the neutral form of carteolol (an...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2009.10.017

    authors: Spataro G,Malecaze F,Turrin CO,Soler V,Duhayon C,Elena PP,Majoral JP,Caminade AM

    更新日期:2010-01-01 00:00:00

  • Structure-based drug design: Synthesis and biological evaluation of quinazolin-4-amine derivatives as selective Aurora A kinase inhibitors.

    abstract::Aurora kinases play critical roles in the regulation of the cell cycle and mitotic spindle assembly. Aurora A kinase, a member of the Aurora protein family, is frequently highly expressed in tumors, and selective Aurora A inhibition serves as a significant component of anticancer therapy. However, designing highly sel...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.08.053

    authors: Long L,Wang YH,Zhuo JX,Tu ZC,Wu R,Yan M,Liu Q,Lu G

    更新日期:2018-09-05 00:00:00

  • Synthesis of two platinum(II) complexes with 2-methyl-8-quinolinol derivatives as ligands and study of their antitumor activities.

    abstract::Two platinum(II) complexes, [Pt(ClQ)(DMSO)Cl] (ClQ-Pt) and [Pt(BrQ)(DMSO)Cl] (BrQ-Pt), with 5,7-dichloro-2-methyl-8-quinolinol (H-ClQ) and 5,7-dibromo-2-methyl-8-quinolinol (H-BrQ) as ligands, respectively, have been synthesized and characterized. The single-crystal X-ray diffraction characterization as well as other ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.10.051

    authors: Qin QP,Wang SL,Tan MX,Liu YC,Meng T,Zou BQ,Liang H

    更新日期:2019-01-01 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

  • A molecular model for cocaine binding by the immunotherapeutic human/mouse chimeric monoclonal antibody 2E2.

    abstract::Immunotherapy by cocaine-binding monoclonal antibodies (mAbs) has emerged as a promising strategy for the treatment of cocaine addiction. The human (gamma1 heavy chain)/murine (lambda light chain) chimeric mAb 2E2 has excellent affinity and specificity for cocaine and recent animal studies have demonstrated 2E2's abil...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.02.004

    authors: Lape M,Paula S,Ball WJ Jr

    更新日期:2010-06-01 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

  • Structural studies and cytotoxic activity of N(4)-phenyl-2-benzoylpyridine thiosemicarbazone Sn(IV) complexes.

    abstract::Structural studies and an investigation of the cytotoxic activity of Sn(IV) complexes with N(4)-phenyl-2-benzoylpyridine thiosemicarbazone (H2Bz4Ph) were carried out. The crystal and molecular structures of [Sn(2Bz4Ph)Cl3].CH3CH2OH (1) and [Sn(2Bz4Ph)BuCl2].H2O (Bu = butyl group) (2) were determined. Both compounds pr...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2005.01.006

    authors: Perez-Rebolledo A,Ayala JD,de Lima GM,Marchini N,Bombieri G,Zani CL,Souza-Fagundes EM,Beraldo H

    更新日期:2005-05-01 00:00:00

  • Design, synthesis and antitumor evaluation of new 1,8-naphthalimide derivatives targeting nuclear DNA.

    abstract::Four series of new 3-nitro naphthalimides derivatives, 4(4a‒4f), 5(5a‒5i), 6(6a‒6e) and 7 (7a‒7j), were designed and synthesized as antitumor agents. Methyl thiazolyl tetrazolium (MTT) screening assay results revealed that some compounds displayed effective in vitro antiproliferative activity on SMMC-7721, T24, SKOV-3...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112951

    authors: Liang GB,Wei JH,Jiang H,Huang RZ,Qin JT,Wang HL,Wang HS,Zhang Y

    更新日期:2021-01-15 00:00:00

  • 2-Amino-thiophene derivatives present antileishmanial activity mediated by apoptosis and immunomodulation in vitro.

    abstract::This study evaluated the effects of 2-amino-thiophene derivatives on the promastigote and amastigote forms of Leishmania (Leishmania) amazonensis and their possible mechanisms of action. Initially, we evaluated the antileishmanial activity of ten 2-amino-thiophene derivatives on promastigote and axenic amastigote form...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.10.011

    authors: Rodrigues KA,Dias CN,Néris PL,Rocha Jda C,Scotti MT,Scotti L,Mascarenhas SR,Veras RC,de Medeiros IA,Keesen Tde S,de Oliveira TB,de Lima Mdo C,Balliano TL,de Aquino TM,de Moura RO,Mendonça Junior FJ,de Oliveira MR

    更新日期:2015-12-01 00:00:00

  • 7-Chloroquinolinotriazoles: synthesis by the azide-alkyne cycloaddition click chemistry, antimalarial activity, cytotoxicity and SAR studies.

    abstract::Twenty-seven 7-chloroquinolinotriazole derivatives with different substituents in the triazole moiety were synthesized via copper-catalyzed cycloaddition (CuAAC) click chemistry between 4-azido-7-chloroquinoline and several alkynes. All the synthetic compounds were evaluated for their in vitro activity against Plasmod...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.11.022

    authors: Pereira GR,Brandão GC,Arantes LM,de Oliveira HA Jr,de Paula RC,do Nascimento MF,dos Santos FM,da Rocha RK,Lopes JC,de Oliveira AB

    更新日期:2014-02-12 00:00:00

  • Discovery and optimization of adamantane carboxylic acid derivatives as potent diacylglycerol acyltransferase 1 inhibitors for the potential treatment of obesity and diabetes.

    abstract::We have developed a series of adamantane carboxylic acid derivatives exhibiting potent diacylglycerol acyltransferase 1 (DGAT1) inhibitory activities. Optimization of the series led to the discovery of E-adamantane carboxylic acid compound 43c, which showed excellent in vitro activity with an IC50 value of 5 nM agains...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.06.043

    authors: Pagire SH,Pagire HS,Lee GB,Han SJ,Kwak HJ,Kim JY,Kim KY,Rhee SD,Ryu JI,Song JS,Bae MA,Park MJ,Kim D,Lee DH,Ahn JH

    更新日期:2015-08-28 00:00:00

  • Probing the antiamoebic and cytotoxicity potency of novel tetrazole and triazine derivatives.

    abstract::A series of compounds bearing a Tetrazole and Triazine ring motif conjugated with a SO(2)NH function were synthesized and investigated for their antiamoebic potency. Cytotoxicity of the compounds was checked on human hepatocellular carcinoma cell line HepG2. Incorporation of Triazine ring in place of tetrazole resulte...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.12.033

    authors: Wani MY,Bhat AR,Azam A,Choi I,Athar F

    更新日期:2012-02-01 00:00:00

  • Design, synthesis and biological evaluation of novel benzoxaborole derivatives as potent PDE4 inhibitors for topical treatment of atopic dermatitis.

    abstract::In this work, a series of structurally novel benzoxaborole derivatives were designed, synthesized and biologically evaluated as PDE4 inhibitors for battling atopic dermatitis (AD). Among them, the majority exhibited superior PDE4B inhibitory activities to that of the lead compound Crisaborole, an approved PDE4 inhibit...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2021.113171

    authors: Chu Z,Xu Q,Zhu Q,Ma X,Mo J,Lin G,Zhao Y,Gu Y,Bian L,Shao L,Guo J,Ye W,Li J,He G,Xu Y

    更新日期:2021-01-12 00:00:00

  • Leishmanicidal and cytotoxic activity of hederagenin-bistriazolyl derivatives.

    abstract::Aiming to obtain new potent leishmanicidal and cytotoxic compounds from natural sources, the triterpene hederagenin was converted into several new 1,2,3-triazolyl derivatives tethered at C-23 and C-28. For this work hederagenin was isolated from fruits of Sapindus saponaria and reacted with propargyl bromide to afford...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.09.045

    authors: Rodríguez-Hernández D,Barbosa LCA,Demuner AJ,Nain-Perez A,Ferreira SR,Fujiwara RT,de Almeida RM,Heller L,Csuk R

    更新日期:2017-11-10 00:00:00

  • Synthetic phenylethanoid glycoside derivatives as potent neuroprotective agents.

    abstract::Several phenylethanoid glycoside derivatives were designed and synthesized. Most of the synthetic compounds showed significant neuroprotective effects, including antioxidative and anti-apoptotic properties. Specifically, target compounds displayed potent effects against various toxicities such as H2O2 and 6-hydroxydop...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.03.038

    authors: Liu YG,Li X,Xiong DC,Yu B,Pu X,Ye XS

    更新日期:2015-05-05 00:00:00

  • Amaryllidaceae alkaloids with new framework types from Zephyranthes candida as potent acetylcholinesterase inhibitors.

    abstract::Three new Amaryllidaceae alkaloids, named zephycandidines I-III (1-3), were isolated from Zephyranthes candida. The structures of 1-3 were elucidated by spectroscopic analyses including HRESIMS, 1H NMR, 13C NMR, DEPT, HSQC, 1H-1H COSY, HMBC, ROESY, and electronic circular dichroism (ECD), as well as ECD calculation. T...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.10.057

    authors: Zhan G,Liu J,Zhou J,Sun B,Aisa HA,Yao G

    更新日期:2017-02-15 00:00:00

  • Synthesis and biological evaluation of a new series of 2-amino-3-aroyl thiophene derivatives as agonist allosteric modulators of the A1 adenosine receptor. A position-dependent effect study.

    abstract::The 2-amino-3-(p-chlorobenzoyl)thiophene scaffold has been widely employed as a pharmacophore for the identification of small molecules acting as allosteric modulators at the adenosine A1 receptor. A new series of 2-amino-3-(p-chlorobenzoyl)-4-benzyl-5-arylthiophene derivatives, characterized by the absence as well as...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.06.041

    authors: Romagnoli R,Baraldi PG,Lopez-Cara C,Cruz-Lopez O,Moorman AR,Massink A,IJzerman AP,Vincenzi F,Borea PA,Varani K

    更新日期:2015-08-28 00:00:00

  • Synthesis and antiinflammatory activity of heterocyclic indole derivatives.

    abstract::Chalcones of indole 1-5 and their corresponding products; pyrazolines 6-10 and azo compounds 11-15 were synthesised and evaluated for their antiinflammatory activity against carrageenan induced oedema in albino rats at a dose of 50 mg x kg(-1) oral. The structure of compounds was confirmed by IR, (1)H-NMR and mass spe...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2003.11.002

    authors: Rani P,Srivastava VK,Kumar A

    更新日期:2004-05-01 00:00:00

  • Synthesis of sulfamoylbenzamide derivatives as HBV capsid assembly effector.

    abstract::The synthesis of novel series of sulfamoylbenzamides as HBV capsid assembly effector is reported. The structure was divided into five parts which were independently modified as part of our lead optimization. All synthesized compounds were evaluated for their anti-HBV activity and toxicity in human hepatocytes, lymphoc...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.06.062

    authors: Sari O,Boucle S,Cox BD,Ozturk T,Russell OO,Bassit L,Amblard F,Schinazi RF

    更新日期:2017-09-29 00:00:00

  • Design, synthesis, antitumor activities and biological studies of novel diaryl substituted fused heterocycles as dual ligands targeting tubulin and katanin.

    abstract::Microtubule is one of the important targets for cancer treatment. A novel class of diaryl substituted imidazo[4,5-c]pyridin-2-ones and imidazo[4,5-c]pyridines were designed based on combination principles by merging the structures of β-lactams and purine-type compounds known as tubulin polymerization inhibitor and kat...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.05.072

    authors: Gao F,Liang Y,Zhou P,Cheng J,Ding K,Wang Y

    更新日期:2019-09-15 00:00:00

  • Antiparasitic hybrids of Cinchona alkaloids and bile acids.

    abstract::A series of 16 hybrids of Cinchona alkaloids and bile acids (4a-h, 5a-h) was prepared by means of a Barton-Zard decarboxylation reaction. Quinine, quinidine, cinchonine and cinchonidine were functionalized at position C-2 of the quinoline nucleus by radical attack of a norcholane substituent. The newly synthesized hyb...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.06.004

    authors: Leverrier A,Bero J,Frédérich M,Quetin-Leclercq J,Palermo J

    更新日期:2013-08-01 00:00:00

  • Further optimization of plakortin pharmacophore: structurally simple 4-oxymethyl-1,2-dioxanes with promising antimalarial activity.

    abstract::For the optimization of the plakortin pharmacophore, we recently proposed a straightforward synthesis of 4-carbomethoxy-3-methoxy-1,2-dioxanes as potential antimalarial drug candidates. Herein we report the chemoselective reduction of the 4-carbomethoxy group which has allowed us to prepare in good yields twenty-four ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.10.050

    authors: Persico M,Parapini S,Chianese G,Fattorusso C,Lombardo M,Petrizza L,Quintavalla A,Rondinelli F,Basilico N,Taramelli D,Trombini C,Fattorusso E,Taglialatela-Scafati O

    更新日期:2013-01-01 00:00:00

  • Triazole incorporated thiazoles as a new class of anticonvulsants: design, synthesis and in vivo screening.

    abstract::Various 3-[4-(substituted phenyl)-1,3-thiazol-2-ylamino]-4-(substituted phenyl)-4,5-dihydro-1H-1,2,4-triazole-5-thiones (7a-t) were designed keeping in view the structural requirements suggested in the pharmacophore model for anticonvulsant activity. Thiazole and triazole moieties being anticonvulsants were clubbed to...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2009.12.062

    authors: Siddiqui N,Ahsan W

    更新日期:2010-04-01 00:00:00