当前位置： SCI文献检索 > EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY期刊下所有文献 > 6-Amino-2,4,5-trimethylpyridin-3-ols: a new general synthetic route and antiangiogenic activity.

6-Amino-2,4,5-trimethylpyridin-3-ols: a new general synthetic route and antiangiogenic activity.

Abstract：

:A new synthetic strategy for preparation of a wide range of 6-amino-2,4,5-trimethylpyridin-3-ols from pyridoxine·HCl via a six-step sequence has been developed. This approach features an introduction of various amino groups to C(6)-position of 3-benzyloxy-6-bromo-2,4,5-trimethylpyridine (13), a key intermediate, by a Buchwald-Hartwig amination reaction using palladium(0) transition metal, which certainly renders an expanded scope of amino substituents. Some analogs prepared using the methods described here showed high level of antiangiogenic and antitumor activities in chick chorioallantoic membrane (CAM) assay, demonstrating the potential of these new aminopyridinols as antiangiogenic agents.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Kim DG,Kang Y,Lee H,Lee EK,Nam TG,Kim JA,Jeong BS

doi

10.1016/j.ejmech.2014.03.045

subject

Has Abstract

pub_date

2014-05-06 00:00:00

pages

126-39

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(14)00258-X

journal_volume

78

pub_type

杂志文章

相关文献

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY文献大全
  • Novel ruthenium complexes ligated with 4-anilinoquinazoline derivatives: synthesis, characterisation and preliminary evaluation of biological activity.

    abstract：:The ruthenium DMSO complexes cis-Ru(II)C12(DMSO)4 and [(DMSO)2H][trans-Ru(III)Cl4(DMSO)2] reacted with 4-(3'-chloro-4'-fluoroanilino)-6-(2-(2-aminoethyl)aminoethoxy)-7-methoxyquinazoline (L1), 4-(3'-chloro-4'-fluoroanilino)-6-(2-(1H-imidazol-1-yl)ethoxy)-7-methoxy quinazoline (L2), N-(benzo[d]imidazol-4-yl)-6,7-dimeth...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2014.02.062

    authors： Ji L,Zheng W,Lin Y,Wang X,Lü S,Hao X,Luo Q,Li X,Yang L,Wang F

    更新日期：2014-04-22 00:00:00

  • Specific stabilization of promoter G-Quadruplex DNA by 2,6-disubstituted amidoanthracene-9,10-dione based dimeric distamycin analogues and their selective cancer cell cytotoxicity.

    abstract：:We have designed and synthesized anthraquinone containing compounds which have oligopyrrole side chains of varying lengths. These compounds stabilized the G-quadruplex DNA formed in the promoter regions of c-MYC oncogenes selectively over the duplex DNA. These observations were recorded using UV-vis spectroscopic titr...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2020.112202

    authors： Roy S,Ali A,Kamra M,Muniyappa K,Bhattacharya S

    更新日期：2020-06-01 00:00:00

  • A comprehensive review of salinomycin derivatives as potent anticancer and anti-CSCs agents.

    abstract：:Polyether ionophore antibiotics (ionophores) represent a large group of more than 120 lipid-soluble compounds that are widely used in veterinary medicine because of their significant antimicrobial activity. In addition to the industrial use of ionophores, some of them effectively and selectively inhibit properties of ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.ejmech.2019.01.034

    authors： Antoszczak M

    更新日期：2019-03-15 00:00:00

  • Synthesis and in vitro cytotoxic activity of pyrrolo[2,3-e]indole derivatives and a dihydro benzoindole analogue.

    abstract：:The synthesis of pyrrolo[2,3-e]indole derivatives with the structural characteristics of DNA bis- and mono-intercalators are described. A dihydro benzoindol analogue was also synthesised to elucidate the major structural requirements for cytotoxic activity. A biological evaluation of the test compounds was carried out...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0223-5234(01)01328-9

    authors： Chacón-García L,Martínez R

    更新日期：2002-03-01 00:00:00

  • Model for high-throughput screening of drug immunotoxicity--study of the anti-microbial G1 over peritoneal macrophages using flow cytometry.

    abstract：:Quantitative Structure-Activity (mt-QSAR) techniques may become an important tool for prediction of cytotoxicity and High-throughput Screening (HTS) of drugs to rationalize drug discovery process. In this work, we train and validate by the first time mt-QSAR model using TOPS-MODE approach to calculate drug molecular d...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2013.08.035

    authors： Tenorio-Borroto E,Peñuelas-Rivas CG,Vásquez-Chagoyán JC,Castañedo N,Prado-Prado FJ,García-Mera X,González-Díaz H

    更新日期：2014-01-24 00:00:00

  • The conversion of oridonin to spirolactone-type or enmein-type diterpenoid: synthesis and biological evaluation of ent-6,7-seco-oridonin derivatives as novel potential anticancer agents.

    abstract：:Starting from commercial available natural product oridonin (1), a practical synthesis of ent-6,7-seco-oridonin derivatives (2, 3, 5, and 9) was accomplished and their biological activities were evaluated. The conversion of spirolactone-type diterpenoid to enmein-type was first completed. The results demonstrated that...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2012.03.024

    authors： Wang L,Li D,Xu S,Cai H,Yao H,Zhang Y,Jiang J,Xu J

    更新日期：2012-06-01 00:00:00

  • Pharmacological activity and hydrolysis behavior of novel ibuprofen glucopyranoside conjugates.

    abstract：:Novel ester prodrugs (II, III and IV) of ibuprofen (I) were synthesized using alpha-methyl, ethyl and propyl glucopyranoside as promoieties and tested for their anti-inflammatory, analgesic and ulcerogenic activities. Study of their chemical hydrolysis in aqueous buffer (pH 3.0-10.0) showed that these compounds acted ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2006.05.014

    authors： Zhao X,Tao X,Wei D,Song Q

    更新日期：2006-11-01 00:00:00

  • The carbonate analogues of 5'-halogenated resiniferatoxin as TRPV1 ligands.

    abstract：:A series of carbonate analogues of 5'-halogenated RTX have been investigated in order to examine the effect of the carbonate group as a linker and the role of halogens in the reversal of activity from agonism to antagonism for rat and human TRPV1 heterologously expressed in Chinese hamster ovary cells. The carbonate a...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2013.07.042

    authors： Lim KS,Lee H,Kim SE,Ha TH,Ann J,Son K,Choi S,Sun W,Pearce LV,DeAndrea-Lazarus IA,Blumberg PM,Lee J

    更新日期：2013-10-01 00:00:00

  • Dependence of fungistatic activity of 2, 4-dihydroxythiobenzanilideson the structure and lipophilic nature of the compounds.

    abstract：:The quantitative dependencies of in vitro fungistatic action on the physico-chemical parameters connected with the structure of 2, 4-dihydroxythiobenzanilides were investigated. It was stated that the action of these compounds depends on lipophilicity determined by substitution of the N-aryl moiety and on electron pro...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0223-5234(00)00136-7

    authors： Matysiak J,Niewiadomy A,Macik-Niewiadomy G,Kornillowicz T

    更新日期：2000-04-01 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

  • Systematic assessment of coordinated activity cliffs formed by kinase inhibitors and detailed characterization of activity cliff clusters and associated SAR information.

    abstract：:From currently available kinase inhibitors and their activity data, clusters of coordinated activity cliffs were systematically derived and subjected to cluster index and index map analysis. Type I-like inhibitors with well-defined IC50 measurements were found to provide a large knowledge base of activity cliff cluste...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2014.11.058

    authors： Dimova D,Stumpfe D,Bajorath J

    更新日期：2015-01-27 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

  • Novel inhibitors of nitric oxide synthase with antioxidant properties.

    abstract：:We previously described a series of imidazole-based inhibitors substituted at N-1 with an arylethanone chain as interesting inhibitors of neuronal nitric oxide synthase (nNOS), endowed with good selectivity vs endothelial nitric oxide synthase (eNOS). As a follow up of these studies, several analogs characterized by t...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2012.01.002

    authors： Salerno L,Modica MN,Romeo G,Pittalà V,Siracusa MA,Amato ME,Acquaviva R,Di Giacomo C,Sorrenti V

    更新日期：2012-03-01 00:00:00

  • Anthranilic acid based CCK1 receptor antagonists: preliminary investigation on their second "touch point".

    abstract：:In this phase of structure-affinity relationship study of VL-0395, a new anthranilic acid based CCK1 selective antagonist, we propose a series of unnatural aminoacidic derivatives. The result of this work is the identification of a new CCK ligand, which possesses an affinity (IC50 = 35 nm) one order of magnitude great...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2005.01.002

    authors： Varnavas A,Lassiani L,Valenta V,Mennuni L,Makovec F,Hadjipavlou-Litina D

    更新日期：2005-06-01 00:00:00

  • Synthesis and biological evaluation of rhein amides as inhibitors of osteoclast differentiation and bone resorption.

    abstract：:Approaches of targeting excessive activation and differentiation of osteoclasts were considered as an effective treatment option for osteoporosis or osteopenia. In the present work, a series of rhein derivatives were synthesized and employed for their cytotoxicity screening against bone marrow-derived macrophages cell...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2016.08.004

    authors： Xu X,Qi X,Yan Y,Qi J,Qian N,Guo L,Li C,Wang F,Huang P,Zhou H,Jiang M,Yang C,Deng L

    更新日期：2016-11-10 00:00:00

  • Synthesis and biological screening of some novel amidocarbamate derivatives of ketoprofen.

    abstract：:A series of novel ketoprofen derivatives 4a-j bearing both amide and carbamate functionalities were prepared using benzotriazole. Selective reduction of ketoprofen produced hydroxy derivative 2, which reacts with one or 2 mol of 1-benzotriazole carboxylic acid chloride (1) gave benzotriazole derivatives 3a and 3b resp...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章,收录出版

    doi：10.1016/j.ejmech.2010.04.008

    authors： Sahoo PK,Behera P

    更新日期：2010-07-01 00:00:00

  • The new facile and straightforward method for the synthesis of 4H-1,2,3-thiadiazolo[5,4-b]indoles and determination of their antiproliferative activity.

    abstract：:A series of 4H-1,2,3-thiadiazolo[5,4-b]indoles were synthesized by novel tandem of oxidative cyclization of 3-alkoxycarbonylhydrazonoindoline-2-thiones, 1,5-H-shift and elimination of tert-butoxy(ethoxy)carbonyl group. The simple method for their modifications by the reactions with electrophilic agents were elaborated...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2015.11.011

    authors： Belskaya NP,Lugovik KI,Bakulev VA,Bauer J,Kitanovic I,Holenya P,Zakhartsev M,Wölfl S

    更新日期：2016-01-27 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

  • 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

  • New pseudodimeric aurones as palm pocket inhibitors of Hepatitis C virus RNA-dependent RNA polymerase.

    abstract：:The NS5B RNA-dependent RNA polymerase (RdRp) is a key enzyme for Hepatitis C Virus (HCV) replication. In addition to the catalytic site, this enzyme is characterized by the presence of at least four allosteric pockets making it an interesting target for development of inhibitors as potential anti-HCV drugs. Based on a...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2016.03.005

    authors： Meguellati A,Ahmed-Belkacem A,Nurisso A,Yi W,Brillet R,Berqouch N,Chavoutier L,Fortuné A,Pawlotsky JM,Boumendjel A,Peuchmaur M

    更新日期：2016-06-10 00:00:00

  • Synthesis and neuromuscular blocking activity of 16beta-piperidinosteroidal derivatives.

    abstract：:The synthesis and pharmacological profiles of some new steroidal mono- and bisquaternary ammonium derivatives have been described. The compounds featured have been conceptually derived structurally from two lead structures: pancuronium bromide 1 and chandonium iodide 2. In vitro and in vivo neuromuscular blocking stud...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0223-5234(00)01205-8

    authors： Jindal DP,Piplani P,Fajrak H,Prior C,Marshall IG

    更新日期：2001-02-01 00:00:00

  • Synthesis, in vitro anticancer and antibacterial activities and in silico studies of new 4-substituted 1,2,3-triazole-coumarin hybrids.

    abstract：:The 4-substituted 1,2,3-triazole core in designed coumarin hybrids (4-35) with diverse physicochemical properties was introduced by eco-friendly copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition under microwave irradiation. Coumarin-1,2,3-triazole-benzofused heterocycle hybrids emerged as the class of compounds ex...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2016.08.062

    authors： Kraljević TG,Harej A,Sedić M,Pavelić SK,Stepanić V,Drenjančević D,Talapko J,Raić-Malić S

    更新日期：2016-11-29 00:00:00

  • Diminutive effect on T and B-cell proliferation of non-cytotoxic α-santonin derived 1,2,3-triazoles: a report.

    abstract：:α-Santonin derived new series of 1,2,3-triazoles synthesized through Azide-Alkyne Huisgen 1,3-dipolar cycloaddition reaction between substituted aryl azide and a propargylated α-desmotrosantonin were bio-evaluated for their diminutive effect on ConA induced T-cell and LPS induced B-cell proliferation. Interestingly, m...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2012.12.018

    authors： Chinthakindi PK,Sangwan PL,Farooq S,Aleti RR,Kaul A,Saxena AK,Murthy YL,Vishwakarma RA,Koul S

    更新日期：2013-02-01 00:00:00

  • Design, synthesis and antitumor activity of novel thiophene-pyrimidine derivatives as EGFR inhibitors overcoming T790M and L858R/T790M mutations.

    abstract：:Five series of novel thiophene-pyrimidine derivatives (9a-h, 10a-f, 11a-f, 12a-f, 13a-f) have been synthesized and tested for their anti-proliferative activity against several cancer cell lines in which EGF is highly expressed. Most of the target compounds showed excellent activity against one or more cancer cell line...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2020.112511

    authors： Xiao Z,Zhou Z,Chu C,Zhang Q,Zhou L,Yang Z,Li X,Yu L,Zheng P,Xu S,Zhu W

    更新日期：2020-10-01 00:00:00

  • Potential of aryl-urea-benzofuranylthiazoles hybrids as multitasking agents in Alzheimer's disease.

    abstract：:New benzofuranylthiazole derivatives containing the aryl-urea moiety were synthesized and evaluated in vitro as dual acetylcholinesterase (AChE)-butyrylcholinesterase (BuChE) inhibitors. In addition, the cupric reducing antioxidant capacities (CUPRAC) and ABTS cation radical scavenging abilities of the synthesized com...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2015.07.005

    authors： Kurt BZ,Gazioglu I,Basile L,Sonmez F,Ginex T,Kucukislamoglu M,Guccione S

    更新日期：2015-09-18 00:00:00

  • Concise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells.

    abstract：:We report a convenient synthesis of carbazole-1,4-quinone alkaloid koeniginequinones A and B using a tandem ring-closing metathesis with the dehydrogenation reaction sequence under an O2 atmosphere as an important step. Using this method, carbazole-1,4-quinones substituted at the 5-, 6-, 7-, and/or 8-positions have be...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2016.05.065

    authors： Nishiyama T,Hatae N,Yoshimura T,Takaki S,Abe T,Ishikura M,Hibino S,Choshi T

    更新日期：2016-10-04 00:00:00

  • Discovery and structure-activity relationship of novel diphenylthiazole derivatives as BTK inhibitor with potent activity against B cell lymphoma cell lines.

    abstract：:By the analysis of different binding modes with Bruton's tyrosine kinase (BTK), series of novel diphenylthiazole derivatives were rationally designed, synthesized and characterized. Biologically evaluation in biochemistry and cellular assay indicated that, compounds 5m, 5o, 6b, 6c, 6g, 6i, 7h, 7i, 7k, 7m, 7n, 7o and 7...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2019.06.035

    authors： Guo X,Yang D,Fan Z,Zhang N,Zhao B,Huang C,Wang F,Ma R,Meng M,Deng Y

    更新日期：2019-09-15 00:00:00

  • Synthesis and evaluation of the cytotoxic activity of novel ethyl 4-[4-(4-substitutedpiperidin-1-yl)]benzyl-phenylpyrrolo[1,2-a]quinoxaline-carboxylate derivatives in myeloid and lymphoid leukemia cell lines.

    abstract：:Leukemia is the most common blood cancer, and its development starts at diverse points, leading to distinct subtypes that respond differently to therapy. This heterogeneity is rarely taken into account in therapies, so it is still essential to look for new specific drugs for leukemia subtypes or even for therapy-resis...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2016.02.047

    authors： Desplat V,Vincenzi M,Lucas R,Moreau S,Savrimoutou S,Pinaud N,Lesbordes J,Peyrilles E,Marchivie M,Routier S,Sonnet P,Rossi F,Ronga L,Guillon J

    更新日期：2016-05-04 00:00:00

  • Novel inhibitors of the sodium-calcium exchanger: benzene ring analogues of N-guanidino substituted amiloride derivatives.

    abstract：:A series of N-guanidino substituted 2,4-diamino-5-carbonylguanidine molecules related to amiloride were synthesised and evaluated for their ability to inhibit the sodium-calcium exchanger in rat insulinoma cells (RINm5F) and human platelets. Specific chemical pathways were used to prepare the benzene derivatives desig...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0223-5234(01)01247-8

    authors： Rogister F,Laeckmann D,Plasman P,Van Eylen F,Ghyoot M,Maggetto C,Liégeois J,Géczy J,Herchuelz A,Delarge J,Masereel B

    更新日期：2001-07-01 00:00:00

  • Synthesis, evaluation against Leishmania amazonensis and cytotoxicity assays in macrophages of sixteen new congeners Morita-Baylis-Hillman adducts.

    abstract：:We report the design, synthesis, in vitro evaluation against Leishmania amazonensis (IC(50)), cytotoxicity assays in macrophages (CC(50)), and selectivity index (SICC(50)/IC(50)) of sixteen new congeners aromatic Morita-Baylis-Hillman adducts 1-16. The 1-16 were prepared in good to excellent yields (58%-97%) from the ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2011.06.036

    authors： Silva FP,de Assis PA,Junior CG,de Andrade NG,da Cunha SM,Oliveira MR,Vasconcellos ML

    更新日期：2011-09-01 00:00:00