当前位置： SCI文献检索 > EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY期刊下所有文献 > Novel 6β-acylaminomorphinans with analgesic activity.

Novel 6β-acylaminomorphinans with analgesic activity.

Abstract：

:Aminomorphinans are a relatively young class of opioid drugs among which substances of high in vitro efficacy and favorable in vivo action are found. We report the synthesis and pharmacological evaluation of novel 6β-acylaminomorphinans. 6β-Morphinamine and 6β-codeinamine were stereoselectively synthesized by Mitsunobu reaction. The aminomorphinans were subsequently acylated with diversely substituted cinnamic acids. In vitro binding studies on cinnamoyl morphinamines showed moderate affinity for all opiate receptors with some selectivity for mu opioid receptors, while cinnamoyl codeinamines only showed affinity for mu opioid receptors. In vivo analgesia studies showed significant analgesic activity of 6β-cinnamoylmorphinamine mediated by mu and delta receptors. The lead compound was found to be roughly equipotent to morphine (ED₅₀ 3.13 ± 1.09 mg/kg) but devoid of the dangerous side-effect respiratory depression, a major issue associated with traditional opioid therapy.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Váradi A,Hosztafi S,Le Rouzic V,Tóth G,Urai Á,Noszál B,Pasternak GW,Grinnell SG,Majumdar S

doi

10.1016/j.ejmech.2013.09.031

subject

Has Abstract

pub_date

2013-11-01 00:00:00

pages

786-9

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(13)00604-1

journal_volume

69

pub_type

杂志文章

相关文献

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY文献大全
  • The evaluation of 1,4-benzoquinones as inhibitors of human monoamine oxidase.

    abstract：:The monoamine oxidase (MAO) enzymes are of considerable pharmacological interest and inhibitors are used in the clinic for the treatment of major depressive disorder and Parkinson's disease. A limited number of studies have shown that the quinone class of compounds possesses MAO inhibition properties. Most notable amo...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2017.04.055

    authors： Mostert S,Petzer A,Petzer JP

    更新日期：2017-07-28 00:00:00

  • Development of resveratrol-curcumin hybrids as potential therapeutic agents for inflammatory lung diseases.

    abstract：:Acute lung injury (ALI) is a major cause of acute respiratory failure in critically-ill patients. Resveratrol and curcumin are proven to have potent anti-inflammatory efficacy, but their clinical application is limited by their metabolic instability. Here, a series of resveratrol and the Mono-carbonyl analogs of curcu...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2016.09.033

    authors： Pan J,Xu T,Xu F,Zhang Y,Liu Z,Chen W,Fu W,Dai Y,Zhao Y,Feng J,Liang G

    更新日期：2017-01-05 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

  • Synthesis and evaluation of mutual prodrugs of ibuprofen with menthol, thymol and eugenol.

    abstract：:The present works deals with simple and efficient method of improving therapeutic efficacy of racemic ibuprofen by retarding gastrointestinal side effects through masking of carboxylic group chemically. This is achieved by synthesis and evaluation of ester derivatives of ibuprofen as mutual prodrugs with naturally occ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2012.08.030

    authors： Redasani VK,Bari SB

    更新日期：2012-10-01 00:00:00

  • Design, synthesis, biological evaluation, and modeling studies of novel conformationally-restricted analogues of sorafenib as selective kinase-inhibitory antiproliferative agents against hepatocellular carcinoma cells.

    abstract：:Sorafenib is one of the clinically used anticancer agents that inhibits several kinases. In this study, novel indole-based rigid analogues of sorafenib were designed and synthesized in order to enhance kinase selectivity and hence minimize the side effects associated with its use. The target compounds possess differen...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2020.113081

    authors： Sbenati RM,Zaraei SO,El-Gamal MI,Anbar HS,Tarazi H,Zoghbor MM,Mohamood NA,Khakpour MM,Zaher DM,Omar HA,Alach NN,Shehata MK,El-Gamal R

    更新日期：2021-01-15 00:00:00

  • Evaluation of the local anaesthetic activity of 3-aminobenzo[d]isothiazole derivatives using the rat sciatic nerve model.

    abstract：:On the basis of computer prediction of biological activity by PASS and toxicity by DEREK, the most promising 32-alkylaminoacyl derivatives of 3-aminobenzo[d]isothiazole were selected for possible local anaesthetic action. This action was evaluated using an in vitro preparation of the isolated sciatic nerve of the rat ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2008.04.006

    authors： Geronikaki A,Vicini P,Dabarakis N,Lagunin A,Poroikov V,Dearden J,Modarresi H,Hewitt M,Theophilidis G

    更新日期：2009-02-01 00:00:00

  • 1,3-Dihydro-2H-indol-2-ones derivatives: design, synthesis, in vitro antibacterial, antifungal and antitubercular study.

    abstract：:1,3-dihydro-2H-indol-2-ones derivatives are reported to exhibit a wide variety of biodynamic activities such as antituberculer, anti HIV, fungicidal, antibacterial, anticonvulsant. These valid observations led us to synthesize some new indole-2-one derivative. Thus, herein we report synthesis of various 5-substituted-...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2011.09.023

    authors： Akhaja TN,Raval JP

    更新日期：2011-11-01 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

  • Lipid lowering agents of natural origin: An account of some promising chemotypes.

    abstract：:The role of natural products in the drug development and discovery has been phenomenal. There has been an enormous interest in exploring all possible natural sources to identify structures exhibiting pronounced hypolipidemic activity albeit with no toxicity. The present review describes the profile of some interesting...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.ejmech.2017.09.020

    authors： Singh SP,Sashidhara KV

    更新日期：2017-11-10 00:00:00

  • Anticancer boron-containing prodrugs responsive to oxidative stress from the tumor microenvironment.

    abstract：:Boronic acid (and ester) prodrugs targeting the overexpressed level of reactive oxygen species within tumor microenvironment represent a promising area for the discovery of new selective anticancer chemotherapy. This strategy that emerged only ten years ago is exponentially growing and could demonstrate its clinical u...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.ejmech.2020.112670

    authors： Maslah H,Skarbek C,Pethe S,Labruère R

    更新日期：2020-12-01 00:00:00

  • Synthesis and anticancer activity of γ-(triazolyl ethylidene)butenolides and polyfunctional pyrrolinones.

    abstract：:A series of novel γ-(triazolyl ethylidene)butenolides (4-23) were prepared from commercially available l-ascorbic acid in good yields. These butenolides on reaction with ethanolic ammonia/amines led to formation of respective 5-hydroxy pyrrolinones (24-33). The two of these pyrrolinones on dehydration with p-toluenesu...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2014.05.042

    authors： Devender N,Ramakrishna KK,Hamidullah,Shukla SK,Konwar R,Tripathi RP

    更新日期：2014-07-23 00:00:00

  • Synthesis and antiviral evaluation of α-L-2'-deoxythreofuranosyl nucleosides.

    abstract：:The synthesis of a series of α-L-2'-deoxythreofuranosyl nucleosides featuring the nucleobases A, T, C and U is described in seven steps from 1,2-O-isopropyledene-α-L-threose, involving a Vorbrüggen coupling and a Barton-McCombie deoxygenation protocol as the key steps. All analogues, including a phosphoramidate nucleo...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2011.05.036

    authors： Toti KS,Derudas M,McGuigan C,Balzarini J,Van Calenbergh S

    更新日期：2011-09-01 00:00:00

  • Synthesis and cytotoxicity assay of four ganglioside GM3 analogues.

    abstract：:A concise and efficient synthetic route for preparation of four ganglioside GM3 analogues was described. The key step is a highly regioselective and stereoselective α-sialylation from a suitably protected glycoside acceptor with a sialyl xanthate to provide the sialo-oligosaccharide in good yield. The cytotoxic proper...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2014.01.054

    authors： Qu H,Liu JM,Wdzieczak-Bakala J,Lu D,He X,Sun W,Sollogoub M,Zhang Y

    更新日期：2014-03-21 00:00:00

  • Free radicals and polyphenols: The redox chemistry of neurodegenerative diseases.

    abstract：:The oxidation of bioorganic materials by air and, particularly, the oxidative stress involved in the cell loss and other pathologies associated with neurodegenerative diseases (NDs) are of enormous social and economic importance. NDs generally involve free radical reactions, beginning with the formation of an initiati...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.ejmech.2017.03.061

    authors： Losada-Barreiro S,Bravo-Díaz C

    更新日期：2017-06-16 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

  • 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

  • Fructose-1,6-bisphosphatase inhibitors: A new valid approach for management of type 2 diabetes mellitus.

    abstract：:The rising incidence of diabetes and confines allied with clinical therapies emphasized the need to explore new molecular targets to develop novel, effective and safer antihyperglycemic agents. Excessive endogenous glucose production by gluconeogenesis is a primary determinant of hyperglycemia in patients with type 2 ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.ejmech.2017.09.029

    authors： Kaur R,Dahiya L,Kumar M

    更新日期：2017-12-01 00:00:00

  • Photo-inducible cytotoxic and clastogenic activities of 3,6-di-substituted acridines obtained by acylation of proflavine.

    abstract：:The cytotoxicity and photo-enhanced cytotoxicity of a series of 18 3,6-di-substituted acridines were evaluated on both tumour CHO cells and human normal keratinocytes, and compared to their corresponding clastogenicity as assessed by the micronucleus assay. Compounds 2f tert-butyl N-[(6-tert-butoxycarbonylamino)acridi...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2009.01.010

    authors： Benchabane Y,Di Giorgio C,Boyer G,Sabatier AS,Allegro D,Peyrot V,De Méo M

    更新日期：2009-06-01 00:00:00

  • Anti-nitric oxide production activity of isothiocyanates correlates with their polar surface area rather than their lipophilicity.

    abstract：:There is increasing demand for novel anti-inflammatory drugs with different mechanisms of action. We synthesized a series of isothiocyanates 2b-h based on 6-(methylsulfinyl)hexyl isothiocyanate (6-MITC) found in the pungent spice Wasabia japonica. Inhibitory activities against in-vitro growth of tumor cells and produc...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2009.08.005

    authors： Noshita T,Kidachi Y,Funayama H,Kiyota H,Yamaguchi H,Ryoyama K

    更新日期：2009-12-01 00:00:00

  • Pyrazolo[4,3-b]pyrimido[4,5-e][1,4]diazepine derivatives as new multi-targeted inhibitors of Aurora A/B and KDR.

    abstract：:Aurora A, Aurora B and Kinase Insert Domain-containing Receptor (KDR) play essential roles in sustained cancer growth. In the present study, eighteen pyrazolo[4,3-b]pyrimido[4,5-e][1,4]diazepine derivatives were designed and synthesized. Most of the prepared compounds exhibited obviously enzymatic (Aurora A/B and KDR)...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2018.09.032

    authors： Zhang Q,Shen Q,Gao L,Tong L,Li J,Chen Y,Lu W

    更新日期：2018-10-05 00:00:00

  • Classification of estrogen receptor-beta ligands on the basis of their binding affinities using support vector machine and linear discriminant analysis.

    abstract：:Classification models of estrogen receptor-beta ligands were proposed using linear and nonlinear models. The data set was divided into active and inactive classes on the basis of their binding affinities. The two-class problem (active, inactive) was firstly explored by linear classifier approach, linear discriminant a...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2007.03.002

    authors： Luan F,Liu HT,Ma WP,Fan BT

    更新日期：2008-01-01 00:00:00

  • Natural oxyprenylated coumarins are modulators of melanogenesis.

    abstract：:Naturally occurring coumarins 7-isopentenyloxycoumarin, auraptene, and umbelliprenin are able to modulate the biosynthesis of melanin in murine Melan-a cells probably through the interaction with selected biological targets like estrogen receptor β and aryl hydrocarbon receptor. Such a modulation strictly depends on t...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2018.04.051

    authors： Fiorito S,Epifano F,Preziuso F,Cacciatore I,di Stefano A,Taddeo VA,de Medina P,Genovese S

    更新日期：2018-05-25 00:00:00

  • Synthesis and antitumor activities of naturally occurring oleanolic acid triterpenoid saponins and their derivatives.

    abstract：:Twenty-six naturally occurring oleanolic acid saponins and their derivatives, 16 of which were synthesized in this study, were preliminarily evaluated against human cancer cells. From SAR studies, the presence of α-l-rhamnosyl residue at the terminal of both C-3 and C-28 position for oleanolic acid bidesmosides was im...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2013.04.016

    authors： Liu Q,Liu H,Zhang L,Guo T,Wang P,Geng M,Li Y

    更新日期：2013-06-01 00:00:00

  • Synthesis and biological evaluation in U87MG glioma cells of (ethynylthiophene)sulfonamido-based hydroxamates as matrix metalloproteinase inhibitors.

    abstract：:Matrix metalloproteinases (MMPs) are important factors in gliomas since these enzymes facilitate invasion into the surrounding brain and participate in neovascularization. In particular, the gelatinases (MMP-2 and MMP-9), and more recently MMP-25, have been shown to be highly expressed in gliomas and have been associa...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2011.03.033

    authors： Nuti E,Casalini F,Santamaria S,Gabelloni P,Bendinelli S,Da Pozzo E,Costa B,Marinelli L,La Pietra V,Novellino E,Margarida Bernardo M,Fridman R,Da Settimo F,Martini C,Rossello A

    更新日期：2011-07-01 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

  • Synthesis of substituted 3-amino-N-phenyl-1H-indazole-1-carboxamides endowed with antiproliferative activity.

    abstract：:Several new N-phenyl-1H-indazole-1-carboxamides 1c-h and 4l,m were prepared by reacting phenyl isocyanate derivatives 3a,b with 3-amino-1H-indazole derivatives 2c,e,g or 1H-indazole 2l respectively. Chemical transformations of compounds 1a,b and 1g,h gave 3-acetamido-N-phenyl-1H-indazole-1-carboxamide derivatives 5a,b...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2010.10.032

    authors： Maggio B,Raimondi MV,Raffa D,Plescia F,Cascioferro S,Plescia S,Tolomeo M,Di Cristina A,Pipitone RM,Grimaudo S,Daidone G

    更新日期：2011-01-01 00:00:00

  • Structural basis and anticancer properties of ruthenium-based drug complexed with human serum albumin.

    abstract：:Ruthenium-based anticancer complexes have become increasingly popular for study over the last two decades. Although ruthenium complexes are currently being investigated in clinical trials, there are still some difficulties with their delivery and associated side effects. Human serum albumin (HSA)-based delivery system...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2014.08.071

    authors： Zhang Y,Ho A,Yue J,Kong L,Zhou Z,Wu X,Yang F,Liang H

    更新日期：2014-10-30 00:00:00

  • Synthesis and anticholinesterase activity of coumarin-3-carboxamides bearing tryptamine moiety.

    abstract：:A number of N-(2-(1H-indol-3-yl)ethyl)-2-oxo-2H-chromene-3-carboxamides were synthesized and tested against AChE and BuChE. The in vitro assessment of the synthesized compounds 4a-o revealed that most of them had significant activity toward AChE. The SAR study demonstrated that the introduction of benzyloxy moiety on ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2016.05.014

    authors： Ghanei-Nasab S,Khoobi M,Hadizadeh F,Marjani A,Moradi A,Nadri H,Emami S,Foroumadi A,Shafiee A

    更新日期：2016-10-04 00:00:00

  • An overview on crystal structures of InhA protein: Apo-form, in complex with its natural ligands and inhibitors.

    abstract：:The enoyl-ACP reductase InhA from the mycobacterial fatty acid biosynthesis pathway has become a target of interest for the development of new anti-tubercular drugs. This protein has been identified as essential for the survival of Mycobacterium tuberculosis, the causative agent of tuberculosis, and as the main target...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.ejmech.2018.01.047

    authors： Chollet A,Maveyraud L,Lherbet C,Bernardes-Génisson V

    更新日期：2018-02-25 00:00:00

  • Highly potent non-steroidal FXR agonists protostane-type triterpenoids: Structure-activity relationship and mechanism.

    abstract：:Farnesoid X receptor (FXR) is a key regulator in charge of bile acid synthesis, transport, and metabolism. Activation of FXR represses bile acid synthesis and increases its excretion and transport, consequently protecting the liver functions. Thus, FXR is considered as a critical therapeutic target of cholestasis and ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2019.111652

    authors： Luan ZL,Huo XK,Dong PP,Tian XG,Sun CP,Lv X,Feng L,Ning J,Wang C,Zhang BJ,Ma XC

    更新日期：2019-11-15 00:00:00