Bioactive fused heterocycles: Nucleoside analogs with an additional ring.

Abstract:

:The following mini-review summarizes the basic literature data regarding synthesis, biological activity, structure-activity relationship, and discussion of the mechanisms of action of two major classes of nucleoside analogs with fused heterocyclic rings: (i) the ethenonucleosides and their related derivatives of the 5,9-dihydro-3-glycosyl-6-alkyl-9-oxo-5H-imidazo[1,2-a]purine type; (ii) the bicyclic nucleosides of 6-alkyl-2,3-dihydrofurano[2,3-d]-pyrimidin-2(3H)-one and 6-alkyl-2,3-dihydropyrrolo[2,3-d]-pyrimidin-2(3H,7H)-one.

journal_name

Eur J Med Chem

authors

Jahnz-Wechmann Z,Framski G,Januszczyk P,Boryski J

doi

10.1016/j.ejmech.2014.12.026

subject

Has Abstract

pub_date

2015-06-05 00:00:00

pages

388-96

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(14)01135-0

journal_volume

97

pub_type

杂志文章,评审
  • Anticonvulsant activity, crystal structures, and preliminary safety evaluation of N-trans-cinnamoyl derivatives of selected (un)modified aminoalkanols.

    abstract::Adequate control of seizures remains an unmet need in epilepsy. In order to identify new anticonvulsant agents, a series of N-trans-cinnamoyl derivatives of selected aminoalkanols was synthetized. The compounds were obtained in the reaction of N-acylation carried out in a two-phase system. The substances were tested i...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.10.051

    authors: Gunia-Krzyżak A,Żesławska E,Słoczyńska K,Koczurkiewicz P,Nitek W,Żelaszczyk D,Szkaradek N,Waszkielewicz AM,Pękala E,Marona H

    更新日期:2016-01-01 00:00:00

  • Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs.

    abstract::A series of novel analogs of pyrrole alkaloid were designed and synthesized by a facile method and their structures were characterized by 1H NMR, 13C NMR and high-resolution mass spectrometry (HRMS). The structure of compound 2a was identified by 2D NMR including heteronuclear multiple-quantum coherence (HMQC), hetero...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.01.031

    authors: Wang MZ,Xu H,Liu TW,Feng Q,Yu SJ,Wang SH,Li ZM

    更新日期:2011-05-01 00:00:00

  • Design, synthesis and bioevaluation of novel 6-(4-Hydroxypiperidino)naphthalen-2-ol-based potential Selective Estrogen Receptor Modulators for breast cancer.

    abstract::In a study directed towards development of novel Selective Estrogen Receptor Modulators (SERMs), 1-(4-(2-(dialkylamino)ethoxy)benzyl)-6-(4-hydroxypiperidin-1-yl)-2-naphthol and corresponding aryl methyl ethers were synthesized and bioevaluated against the estrogen-responsive human MCF-7 breast cancer cell line. The ph...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.12.037

    authors: Jha A,Yadav Y,Naidu AB,Rao VK,Kumar A,Parmar VS,MacDonald WJ,Too CK,Balzarini J,Barden CJ,Cameron TS

    更新日期:2015-03-06 00:00:00

  • N1-Alkylated 3,4-dihydropyrimidine-2(1H)-ones: Convenient one-pot selective synthesis and evaluation of their calcium channel blocking activity.

    abstract::It has been found that selective N1-alkylation of 3,4-dihydropyrimidine-2(1H)-ones can be achieved under solvent-less, mild phase transfer catalytic (PTC) conditions with tetrabutylammonium hydrogen sulfate and 50% aqueous NaOH as the catalyst and base, respectively. The procedure is tolerant to substitutional variati...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.10.002

    authors: Singh K,Arora D,Poremsky E,Lowery J,Moreland RS

    更新日期:2009-05-01 00:00:00

  • Antimalarial naphthoquinones. Synthesis via click chemistry, in vitro activity, docking to PfDHODH and SAR of lapachol-based compounds.

    abstract::Lapachol is an abundant prenyl naphthoquinone occurring in Brazilian Bignoniaceae that was clinically used, in former times, as an antimalarial drug, despite its moderate effect. Aiming to search for potentially better antimalarials, a series of 1,2,3-triazole derivatives was synthesized by chemical modification of la...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.12.051

    authors: Brandão GC,Rocha Missias FC,Arantes LM,Soares LF,Roy KK,Doerksen RJ,Braga de Oliveira A,Pereira GR

    更新日期:2018-02-10 00:00:00

  • Discovery of novel HSP90 inhibitors that induced apoptosis and impaired autophagic flux in A549 lung cancer cells.

    abstract::Heat shock protein 90 (HSP90) inhibition has aroused increasing enthusiasm in antitumor strategies in recent years. According to our previous studies, we synthesized a series of coumarin pyrazoline compounds HCP1-HCP6 that might be HSP90 inhibitors. Interactions between HCP1-HCP6 and HSP90 were examined and antitumor ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.01.024

    authors: Wei Q,Ning JY,Dai X,Gao YD,Su L,Zhao BX,Miao JY

    更新日期:2018-02-10 00:00:00

  • N-Aryl-N'-(chroman-4-yl)ureas and thioureas display in vitro anticancer activity and selectivity on apoptosis-resistant glioblastoma cells: screening, synthesis of simplified derivatives, and structure-activity relationship analysis.

    abstract::A series of chroman derivatives previously reported as potassium channel openers, as well as some newly synthesized simplified structures, were examined for their in vitro effects on the growth of three human high-grade glioma cell lines: U373, T98G, and Hs683. Significant in vitro growth inhibitory activity was obser...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.06.050

    authors: Goffin E,Lamoral-Theys D,Tajeddine N,de Tullio P,Mondin L,Lefranc F,Gailly P,Rogister B,Kiss R,Pirotte B

    更新日期:2012-08-01 00:00:00

  • Para-sulfonatocalix[n]arene-based biomaterials: Recent progress in pharmaceutical and biological applications.

    abstract::The history, properties, and characteristics of para-sulfonato-calixarenes are described. On the one hand, the inherent antibacterial and antifungal properties against microorganisms, and on the other hand non-toxicity of these supramolecules toward human organs are analyzed. The resulting biocompatibility of para-sul...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2020.112121

    authors: Bahojb Noruzi E,Molaparast M,Zarei M,Shaabani B,Kariminezhad Z,Ebadi B,Shafiei-Irannejad V,Rahimi M,Pietrasik J

    更新日期:2020-03-15 00:00:00

  • Symmetry-based inhibitors of HIV-1 protease. Design, synthesis and preliminary structure-activity studies of acylated 2,3-diamino-1-hydroxypropanes and 2,4 diamino-1-hydroxybutanes.

    abstract::Two series of peptidomimetics containing a novel C(2) pseudosymmetrical hydroxyalkyldiamino core structure were prepared from amino acid starting materials and tested for inhibitory activity against the HIV-1 protease (HIV-1 Pr) and the virus in cell culture. In the 2,3-diamino-1-hydroxypropane series, compound 6a, co...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(00)80034-3

    authors: Marastoni M,Bazzaro M,Bortolotti F,Salvadori S,Tomatis R

    更新日期:1999-07-01 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

  • Comparative chemometric modeling of cytochrome 3A4 inhibitory activity of structurally diverse compounds using stepwise MLR, FA-MLR, PLS, GFA, G/PLS and ANN techniques.

    abstract::Twenty-eight structurally diverse cytochrome 3A4 (CYP3A4) inhibitors have been subjected to quantitative structure-activity relationship (QSAR) studies. The analyses were performed with electronic, spatial, topological, and thermodynamic descriptors calculated using Cerius 2 version 10 software. The statistical tools ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.12.004

    authors: Roy K,Pratim Roy P

    更新日期:2009-07-01 00:00:00

  • Carboline- and phenothiazine-derivated heterocycles as potent SIGMA-1 protein ligands.

    abstract::Sigma 1 receptors are associated with neurodegenerative and psychiatric disorders. These receptors, via their chaperoning functions that counteract endoplasmic reticulum stress and block neurodegeneration, may serve as a target for a new generation of antidepressants or neuroprotective agents. The involvement of these...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.10.053

    authors: Donnier-Maréchal M,Larchanché PE,Le Broc D,Furman C,Carato P,Melnyk P

    更新日期:2015-01-07 00:00:00

  • Synthesis and antimycobacterial activity of new quinoxaline-2-carboxamide 1,4-di-N-oxide derivatives.

    abstract::As a continuation of our research and with the aim of obtaining new anti-tuberculosis agents which can improve the current chemotherapeutic anti-tuberculosis treatments, forty-three new quinoxaline-2-carboxamide 1,4-di-N-oxide derivatives were synthesized and evaluated for in vitro anti-tuberculosis activity against M...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.06.036

    authors: Moreno E,Ancizu S,Pérez-Silanes S,Torres E,Aldana I,Monge A

    更新日期:2010-10-01 00:00:00

  • Novel 2,4- thiazolidinediones: Synthesis, in vitro cytotoxic activity, and mechanistic investigation.

    abstract::Two thiazolidinedione scaffolds different in the position of the thiazolidinedione ring in the molecule were tested for in vitro cytotoxic activity in a panel of human cancer cell lines namely, prostate cancer cells PC-3, breast carcinoma cells MDA-MB-231, and fibrosarcoma cells HT-1080. Some of the target compounds o...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.03.052

    authors: Metwally K,Pratsinis H,Kletsas D

    更新日期:2017-06-16 00:00:00

  • β-Glucuronidase-responsive prodrugs for selective cancer chemotherapy: an update.

    abstract::The design of novel antitumor agents allowing the destruction of malignant cells while sparing healthy tissues is one of the major challenges in medicinal chemistry. In this context, the use of non-toxic prodrugs programmed to be selectively activated by beta-glucuronidase present at high concentration in the microenv...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.12.045

    authors: Tranoy-Opalinski I,Legigan T,Barat R,Clarhaut J,Thomas M,Renoux B,Papot S

    更新日期:2014-03-03 00:00:00

  • 4-Aminoquinoline derived antimalarials: synthesis, antiplasmodial activity and heme polymerization inhibition studies.

    abstract::A new series of 4-aminoquinoline derivatives have been synthesized and found to be active against both susceptible and resistant strains of Plasmodium falciparum in vitro. Compound 1-[3-(7-chloro-quinolin-4-ylamino)-propyl]-3-cyclopropyl-thiourea (7) exhibited superior in vitro activity against resistant strains of P....

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.07.068

    authors: Solomon VR,Haq W,Smilkstein M,Srivastava K,Puri SK,Katti SB

    更新日期:2010-11-01 00:00:00

  • New thiazole-2(3H)-thiones containing 4-(3,4,5-trimethoxyphenyl) moiety as anticancer agents.

    abstract::A new series of thiazole-2(3H)-thiones containing 4-(3,4,5-trimethoxyphenyl) moiety were synthesized as diaryl-heterocylic analogs of combretastatin A-4 with anticancer activity. The cytotoxicity evaluation of synthesized compounds against cancer cell lines (A549, MCF-7 and SKOV3) revealed that most of them had potent...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.111784

    authors: Ansari M,Shokrzadeh M,Karima S,Rajaei S,Fallah M,Ghassemi-Barghi N,Ghasemian M,Emami S

    更新日期:2020-01-01 00:00:00

  • Discovery of caffeic acid phenethyl ester derivatives as novel myeloid differentiation protein 2 inhibitors for treatment of acute lung injury.

    abstract::Myeloid differentiation protein 2 (MD2) is an essential molecule which recognizes lipopolysaccharide (LPS), leading to initiation of inflammation through the activation of Toll-like receptor 4 (TLR4) signaling. Caffeic acid phenethyl ester (CAPE) from propolis of honeybee hives could interfere interactions between LPS...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.11.066

    authors: Chen L,Jin Y,Chen H,Sun C,Fu W,Zheng L,Lu M,Chen P,Chen G,Zhang Y,Liu Z,Wang Y,Song Z,Liang G

    更新日期:2018-01-01 00:00:00

  • Stereoselective synthesis and antimicrobial activity of steroidal C-20 tertiary alcohols with thiazole/pyridine side chain.

    abstract::Stereoselective synthesis of novel steroidal C-20 tertiary alcohols with thiazole and pyridine side chain using Grignard reaction of steroidal ketones and thiazole/pyridine magnesium bromide have been realized. These molecules were evaluated in vitro for their antifungal and antibacterial activities. Most of the compo...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.05.032

    authors: Shingate BB,Hazra BG,Salunke DB,Pore VS,Shirazi F,Deshpande MV

    更新日期:2011-09-01 00:00:00

  • High anticancer potency on tumor cells of dehydroabietylamine Schiff-base derivatives and a copper(II) complex.

    abstract::Five bioactive dehydroabietylamine Schiff-base derivatives (L1-L5) had been synthesized from Dehydroabietylamine (L0), and the complex Cu(L1)2 had been obtained from the compound L1 and copper(II) acetate. Their activities against Hela (cervix), MCF-7 (breast), A549 (lung), HepG2 (liver) and HUVEC (umbilical vein, nor...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.01.041

    authors: Zhao F,Wang W,Lu W,Xu L,Yang S,Cai XM,Zhou M,Lei M,Ma M,Xu HJ,Cao F

    更新日期:2018-02-25 00:00:00

  • Novel 9'-substituted-noscapines: synthesis with Suzuki cross-coupling, structure elucidation and biological evaluation.

    abstract::Tubulin is a major molecular target for anticancer drugs. The dynamic process of microtubule assembly and disassembly can be blocked by various agents that bind to distinct sites on tubulin, usually its β-subunit. Among the antimitotic agents that perturb microtubule dynamics, noscapinoids represent an emerging class ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.07.050

    authors: Porcù E,Sipos A,Basso G,Hamel E,Bai R,Stempfer V,Udvardy A,Bényei AC,Schmidhammer H,Antus S,Viola G

    更新日期:2014-09-12 00:00:00

  • Synthesis and antiproliferative activity of novel polynuclear heterocyclic compounds derived from 2,3-diaminophenazine.

    abstract::2,3-Diaminophenazine 1 was used as a precursor for the preparation of some novel phenazine derivatives such as imidazo[4,5-b]phenazine-2-thione 2, its methylthio 3, ethyl 1-aryl-3H-[1,2,4]triazolo[2,3-a]imidazo[4,5-b]phenazines 8a-c, ethyl (2Z)-[3-aminophenazin-2-yl)amino](phenylhydrazono)ethanoate 9, pyrazino[2,3-b]p...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.12.007

    authors: Mahran AM,Ragab SSh,Hashem AI,Ali MM,Nada AA

    更新日期:2015-01-27 00:00:00

  • Synthesis and evaluation against Leishmania amazonensis of novel pyrazolo[3,4-d]pyridazinone-N-acylhydrazone-(bi)thiophene hybrids.

    abstract::A new series of pyrazolo[3,4-d]pyridazin-7-one derivatives were synthesised and evaluated for their in vitro antileishmanial activity against Leishmania amazonensis promastigote and axenic amastigote forms. The results showed that the pyrazolo[3,4-d]-pyridazin-7-one-N-acylhydrazone-(bi)thiophene hybrids 5b, 6b and 6d ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.08.048

    authors: Jacomini AP,Silva MJV,Silva RGM,Gonçalves DS,Volpato H,Basso EA,Paula FR,Nakamura CV,Sarragiotto MH,Rosa FA

    更新日期:2016-11-29 00:00:00

  • Design, synthesis and biological evaluation of monobactams as antibacterial agents against gram-negative bacteria.

    abstract::A series of monobactam derivatives were prepared and evaluated for their antibacterial activities against susceptible and resistant Gram-negative strains, taking Aztreonam and BAL30072 as the leads. Six conjugates (12a-f) bearing PIH-like siderophore moieties were created to enhance the bactericidal activities against...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.01.024

    authors: Fu HG,Hu XX,Li CR,Li YH,Wang YX,Jiang JD,Bi CW,Tang S,You XF,Song DQ

    更新日期:2016-03-03 00:00:00

  • Novel 4-aryl-pyrido[1,2-c]pyrimidines with dual SSRI and 5-HT(1A) activity. Part 5.

    abstract::A series of novel 4-aryl-pyrido[1,2-c]pyrimidine derivatives containing a 1-(2-quinoline)piperazine moiety was synthesized. The chemical structure of new compounds was confirmed by FT-IR, (1)H NMR, (13)C NMR and HRMS spectra as well as elemental analysis. Affinity of the novel pyrido[1,2-c]pyrimidine derivatives for 5...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.05.003

    authors: Gomółka A,Ciesielska A,Wróbel MZ,Chodkowski A,Kleps J,Dawidowski M,Siwek A,Wolak M,Stachowicz K,Sławińska A,Nowak G,Satała G,Bojarski AJ,Belka M,Ulenberg S,Bączek T,Skowronek P,Turło J,Herold F

    更新日期:2015-06-15 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

  • Synthesis and biological evaluation of 1-(4'-Indolyl and 6'-Quinolinyl) indoles as a new class of potent anticancer agents.

    abstract::A novel series of the biheterocycles-based compounds with core structure distinguished from combretastatin A-4 (1) and colchicine (5) have been synthesized and evaluated as potent anti-mitotic agents. Compound 1-(4'-Indolyl and 6'-quinolinyl)-4,5,6-trimethoxyindoles 13 and 19 showed substantial anti-proliferative acti...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.04.065

    authors: Lai MJ,Chang JY,Lee HY,Kuo CC,Lin MH,Hsieh HP,Chang CY,Wu JS,Wu SY,Shey KS,Liou JP

    更新日期:2011-09-01 00:00:00

  • Chemical preparation, biological evaluation and 3D-QSAR of ethoxysulfuron derivatives as novel antifungal agents targeting acetohydroxyacid synthase.

    abstract::Accetohydroxyacid synthase (AHAS) is the first enzyme involved in the biosynthetic pathway of branched-chain amino acids. Earlier gene mutation of Candida albicans in a mouse model suggested that this enzyme is a promising target of antifungals. Recent studies have demonstrated that some commercial AHAS-inhibiting sul...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.11.005

    authors: Wu RJ,Ren T,Gao JY,Wang L,Yu Q,Yao Z,Song GQ,Ruan WB,Niu CW,Song FH,Zhang LX,Li M,Wang JG

    更新日期:2019-01-15 00:00:00

  • Dibenzo[1,4,5]thiadiazepine: a hardly-known heterocyclic system with neuroprotective properties of potential usefulness in the treatment of neurodegenerative diseases.

    abstract::In this work we describe a new family of dibenzo[1,4,5]thiadiazepines (2-12) that showed an interesting in vitro biological profile, namely neuroprotective and antioxidant properties, as well as blockade of cytosolic calcium entry. They showed no cytotoxic effects and the majority were predicted as CNS-permeable compo...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.04.075

    authors: González-Muñoz GC,Arce MP,Pérez C,Romero A,Villarroya M,López MG,Conde S,Rodríguez-Franco MI

    更新日期:2014-06-23 00:00:00

  • Discovery of hydrazone containing thiadiazoles as Mycobacterium tuberculosis growth and enoyl acyl carrier protein reductase (InhA) inhibitors.

    abstract::Tuberculosis, caused by Mycobacterium tuberculosis, is a serious infectious disease and remains a global health problem. There is an increasing need for the discovery of novel therapeutic agents for its treatment due to the emerging multi-drug resistance. Herein, we present the rational design and the synthesis of eig...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112035

    authors: Doğan H,Doğan ŞD,Gündüz MG,Krishna VS,Lherbet C,Sriram D,Şahin O,Sarıpınar E

    更新日期:2020-02-15 00:00:00