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 resulted in a precipitous increase in the antiamoebic activity of the compounds. Antiamoebic activity of the investigated compounds was found to be position and substituent dependent. In vitro cytotoxicity results revealed noncytotoxic nature of all the tested compounds up to a concentration of 25 μM. Compound 5c and 5d were obtained as least cytotoxic (IC(50) > 100 μM) and excellent Entamoeba histolytica inhibitors with IC(50) values of 1.05 μM and 1.02 μM respectively.

journal_name

Eur J Med Chem

authors

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

doi

10.1016/j.ejmech.2011.12.033

subject

Has Abstract

pub_date

2012-02-01 00:00:00

pages

313-20

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(11)00914-7

journal_volume

48

pub_type

杂志文章
  • 1,3,4-Thiadiazoles: a potent multi targeted pharmacological scaffold.

    abstract::Despite a significant work on thiadiazoles, continuous efforts are still being made to identify novel heterocyclic compounds with potent biological activities. This review may help the medicinal chemists to develop new leads possessing 1,3,4-thiadiazole nucleus with higher efficacy and reduced side effects. This revie...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2014.12.035

    authors: Haider S,Alam MS,Hamid H

    更新日期:2015-03-06 00:00:00

  • Conjugation of substituted ferrocenyl to thiadiazine as apoptosis-inducing agents targeting the Bax/Bcl-2 pathway.

    abstract::Ferrocene compounds are a class of biologically active compounds that has antitumour and antifungal properties. This study investigated the induction of apoptosis in human fibrosarcoma cells (HT1080) after treatment with a series of 6-ferrocenyl-3-subsituted7H-1,2,4-triazolo[3,4-b]- 1,3,4-thiadiazine (FTFs). We found ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.08.007

    authors: Miao R,Wei J,Lv M,Cai Y,Du Y,Hui X,Wang Q

    更新日期:2011-10-01 00:00:00

  • Synthesis, properties, and perspectives of gem-diphosphono substituted-thiazoles.

    abstract::A series of substituted arylidene thiazoles were allowed to react with Wittig-Horner (WH) reagent, tetraethyl methyl-1,1-bisphosphonate, to produce via Michael addition reaction the corresponding heteroarylmethylenebisphosphonates (BPs) in different yields according to the experimental conditions. Acid hydrolysis of t...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2007.07.005

    authors: Abdou WM,Ganoub NA,Geronikaki A,Sabry E

    更新日期:2008-05-01 00:00:00

  • Unraveling the structure-activity relationship of tomatidine, a steroid alkaloid with unique antibiotic properties against persistent forms of Staphylococcus aureus.

    abstract::Staphylococcus aureus (S. aureus) is responsible for difficult-to-treat and relapsing infections and constitutes one of the most problematic pathogens due to its multiple resistances to clinically available antibiotics. Additionally, the ability of S. aureus to develop small-colony variants is associated with a reduce...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.11.019

    authors: Chagnon F,Guay I,Bonin MA,Mitchell G,Bouarab K,Malouin F,Marsault É

    更新日期:2014-06-10 00:00:00

  • 2-Propargylamino-naphthoquinone derivatives as multipotent agents for the treatment of Alzheimer's disease.

    abstract::Alzheimer's disease is a progressive brain disorder with characteristic symptoms and several pathological hallmarks. The concept of "one drug, one target" has not generated any new drugs since 2004. The new era of drug development in the field of AD builds upon rationally designed multi-target directed ligands that ca...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.113112

    authors: Mezeiova E,Janockova J,Andrys R,Soukup O,Kobrlova T,Muckova L,Pejchal J,Simunkova M,Handl J,Micankova P,Capek J,Rousar T,Hrabinova M,Nepovimova E,Marco-Contelles JL,Valko M,Korabecny J

    更新日期:2021-02-05 00:00:00

  • 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

  • Design and synthesis of new imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrazine derivatives with antiproliferative activity against melanoma cells.

    abstract::Melanoma is an aggressive form of skin cancer and it is generally associated with poor prognosis in patients with late-stage disease. Due to the increasing occurrence of melanoma, there is a need for the development of novel therapies. A new series of diarylamide and diarylurea derivatives containing imidazo[1,2-a]pyr...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.12.001

    authors: Garamvölgyi R,Dobos J,Sipos A,Boros S,Illyés E,Baska F,Kékesi L,Szabadkai I,Szántai-Kis C,Kéri G,Őrfi L

    更新日期:2016-01-27 00:00:00

  • Glycosylation enhances the anti-migratory activities of isomalyngamide A analogs.

    abstract::Three, new, fully synthetic glycosylated isomalyngamide A analogs 4-6 were prepared and evaluated for their anti-migratory activities in human breast cancer cells. The results of the study show that two glycosylated derivatives 4 and 5, containing mannose and galactose appendages, suppress metastatic events (e.g., mig...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.03.044

    authors: More SV,Chang TT,Chiao YP,Jao SC,Lu CK,Li WS

    更新日期:2013-06-01 00:00:00

  • Design and synthesis of novel quinacrine-[1,3]-thiazinan-4-one hybrids for their anti-breast cancer activity.

    abstract::In an attempt to develop effective and safe anticancer agents, we designed, synthesized and examined 23 novel quinacrine (QC) derivatives by combining the 9-aminoacridine scaffold and the [1,3]thiazinan-4-ones group. Most of these hybrids showed strong anticancer activities, among which 3-(3-(6-chloro-2-methoxyacridin...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.11.097

    authors: Solomon VR,Pundir S,Le HT,Lee H

    更新日期:2018-01-01 00:00:00

  • Design and synthesis of Lapatinib derivatives containing a branched side chain as HER1/HER2 targeting antitumor drug candidates.

    abstract::A series of Lapatinib derivatives were designed and prepared by changing the straight alkyl side chain of Lapatinib into a branched one. ELISA assay and western blot analysis showed that these derivatives can significantly inhibit HER1/HER2 as well as their downstream signal transduction proteins. In vitro cytotoxicit...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.10.006

    authors: Lyu A,Fang L,Gou S

    更新日期:2014-11-24 00:00:00

  • New quinoxalinecarbonitrile 1,4-di-N-oxide derivatives as hypoxic-cytotoxic agents.

    abstract::We report the synthesis and biological in vitro activities of 16 new 2-quinoxalinecarbonitrile 1,4-di-N-oxides. These compounds present new basic lateral chains (piperazines and anilines) in the 3 position as well as different substituents in the 6 and/or 7 positions of the quinoxaline ring. Among piperazine derivativ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(00)00112-4

    authors: Ortega MA,Morancho MJ,Martínez-Crespo FJ,Sainz Y,Montoya ME,López de Ceráin A,Monge A

    更新日期:2000-01-01 00:00:00

  • Design and synthesis of potent and selective P2X₃ receptor antagonists derived from PPADS as potential pain modulators.

    abstract::Pyridoxalphosphate-6-azophenyl-2',4'-disulfonate (7a, PPADS), a nonselective P2X receptor antagonist, was extensively modified to develop more stable, potent, and selective P2X₃ receptor antagonists as potential antinociceptive agents. Based on the results of our previous report, all strong anionic groups in PPADS inc...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.10.026

    authors: Cho JH,Jung KY,Jung Y,Kim MH,Ko H,Park CS,Kim YC

    更新日期:2013-01-01 00:00:00

  • Structural variations of piritrexim, a lipophilic inhibitor of human dihydrofolate reductase: synthesis, antitumor activity and molecular modeling investigations.

    abstract::Piritrexim (PTX) (1), a lipophilic inhibitor of the human dihydrofolate reductase, has been evaluated as an anticancer agent. The synthesis of four structural variations (2-5) of PTX is reported. The PTX analogues 2-5 were obtained by reaction of suitable C3-building blocks with pyrimidine-2,4,6-triamine (14) or with ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2004.09.001

    authors: Zink M,Lanig H,Troschütz R

    更新日期:2004-12-01 00:00:00

  • α-D-mannose derivatives as models designed for selective inhibition of Golgi α-mannosidase II.

    abstract::Human Golgi α-mannosidase II (hGM) is a pharmaceutical target for the design of inhibitors with anti-tumor activity. Nanomolar inhibitors of hGM exhibit unwanted co-inhibition of the human lysosomal α-mannosidase (hLM). Hence, improving specificity of the inhibitors directed toward hGM is desired in order to use them ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.01.012

    authors: Poláková M,Šesták S,Lattová E,Petruš L,Mucha J,Tvaroška I,Kóňa J

    更新日期:2011-03-01 00:00:00

  • New glycosidic derivatives of histidine-containing dipeptides with antioxidant properties and resistant to carnosinase activity.

    abstract::Synthesis, antioxidant properties and resistance to carnosinase hydrolysis of histidine-containing dipeptides are reported in this study. Carnosine (beta-alanyl-l-histidine), homocarnosine (gamma-aminobutyryl-l-histidine) and anserine (beta-alanyl-3-methyl-l-histidine) were covalently derivatized with beta-cyclodextri...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2007.03.038

    authors: Bellia F,Amorini AM,La Mendola D,Vecchio G,Tavazzi B,Giardina B,Di Pietro V,Lazzarino G,Rizzarelli E

    更新日期:2008-02-01 00:00:00

  • Studies on quinones. Part 46. Synthesis and in vitro antitumor evaluation of aminopyrimidoisoquinolinequinones.

    abstract::In the search of structure-activity relationship studies and to explore the antitumor effect associated with the pyrimidoisoquinolinequinone scaffold, several diversily substituted 8-aminopyrimido[4,5-c]isoquinolinequinones were regioselectively synthesized. Variation in the structure of the nitrogen substituent bonde...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.08.040

    authors: Vásquez D,Rodríguez JA,Theoduloz C,Calderon PB,Valderrama JA

    更新日期:2010-11-01 00:00:00

  • Dimetallic Ru(II) arene complexes appended on bis-salicylaldimine induce cancer cell death and suppress invasion via p53-dependent signaling.

    abstract::A series of bis-salicylaldimine ligands bearing two ON-donor functions were reacted with dichloro(p-cymene)ruthenium(II) dimer in the presence of base (NaOAc) and a series of four dimetallic Ru(II) arene complexes (Ru(p-cymene))2(bis-salicylaldimine)Cl2 (C1C4) were prepared. These complexes were obtained in excellent ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.08.054

    authors: Rahman FU,Bhatti MZ,Ali A,Duong HQ,Zhang Y,Ji X,Lin Y,Wang H,Li ZT,Zhang DW

    更新日期:2018-09-05 00:00:00

  • Recent advances in the discovery of potent and selective HDAC6 inhibitors.

    abstract::Histone deacetylase HDAC6, a member of the class IIb HDAC family, is unique among HDAC enzymes in having two active catalytic domains, and has unique physiological function. In addition to the modification of histone, HDAC6 targets specific substrates including α-tubulin and HSP90, and are involved in protein traffick...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2017.10.040

    authors: Wang XX,Wan RZ,Liu ZP

    更新日期:2018-01-01 00:00:00

  • Design, synthesis and screening of 1, 2, 4-triazinone derivatives as potential antitumor agents with apoptosis inducing activity on MCF-7 breast cancer cell line.

    abstract::Some triazinone derivatives are designed and synthesized as potential antitumor agents. Triazinone derivatives 4c, 5e and 7c show potent anticancer activity over MCF-7 breast cancer cells higher than podophyllotoxin (podo) by approximate 6-fold. DNA flow cytometry analysis for the compounds 3c, 4c, 5e, 6c and 7c show ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.07.003

    authors: Zaki I,Abdelhameid MK,El-Deen IM,Abdel Wahab AHA,Ashmawy AM,Mohamed KO

    更新日期:2018-08-05 00:00:00

  • New bis(hydroxymethyl) alkanoate curcuminoid derivatives exhibit activity against triple-negative breast cancer in vitro and in vivo.

    abstract::Novel bis(hydroxymethyl) alkanoate curcuminoid derivatives were designed, synthesized and screened for in vitro antiproliferative and in vivo antitumor activity. Selected new compound 9a and curcumin were further evaluated for inhibitory activity against ER+/PR+ breast cancer (MCF-7, T47D), HER 2+ breast cancer (SKBR3...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.03.006

    authors: Hsieh MT,Chang LC,Hung HY,Lin HY,Shih MH,Tsai CH,Kuo SC,Lee KH

    更新日期:2017-05-05 00:00:00

  • Estrogen signaling: An emanating therapeutic target for breast cancer treatment.

    abstract::Breast cancer, a most common malignancy in women, was known to be associated with steroid hormone estrogen. The discovery of estrogen receptor (ER) gave us not only a powerful predictive and prognostic marker, but also an efficient target for the treatment of hormone-dependent breast cancer with various estrogen ligan...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2019.05.023

    authors: Saha T,Makar S,Swetha R,Gutti G,Singh SK

    更新日期:2019-09-01 00:00:00

  • Synthesis, characterization and anticancer screening of some novel piperonyl-tetrazole derivatives.

    abstract::A series of new 1,2-substituted tetrazole derivatives were synthesized and evaluated on MCF-7 (ER positive), MDA-MB-231 and ZR-75 (ER negative) breast cancer cell lines. Out of the fourteen compounds, three compounds 10, 12 and 14 showed higher inhibitory effects on MCF-7 cells. Whereas, compound 8 exhibited higher in...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.11.008

    authors: Arshad M,Bhat AR,Pokharel S,Kim JE,Lee EJ,Athar F,Choi I

    更新日期:2014-01-01 00:00:00

  • Synthesis and primary cytotoxicity evaluation of new 5-nitroindole-2,3-dione derivatives.

    abstract::A new series of 5-nitro-1H-indole-2,3-dione-3-thiosemicarbazones (3a-k) obtained by condensation of 5-nitro-1H-indole-2,3-dione (1) with N-substituted-thiosemicarbazides (2a-k) were treated with morpholine or piperidine and formaldehyde to yield 1-morpholino/piperidinomethyl-5-nitroindole-2,3-dione-3-thiosemicarbazone...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(02)01416-2

    authors: Karali N

    更新日期:2002-11-01 00:00:00

  • Synthesis, anticancer activity and effects on cell cycle profile and apoptosis of novel thieno[2,3-d]pyrimidine and thieno[3,2-e] triazolo[4,3-c]pyrimidine derivatives.

    abstract::Motivated by the widely reported anticancer activity of thieno[2,3-d]pyrimidines a series of 24 new 2-substitutedhexahydrocycloocta[4,5] thieno[2,3-d]pyrimidines with different substituents at C-4 position and hexahydrocycloocta[4,5]thieno[3,2-e]-1,2,4-triazolo[4,3-c]pyrimidines were synthesized. The anticancer activi...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.12.009

    authors: Kandeel MM,Refaat HM,Kassab AE,Shahin IG,Abdelghany TM

    更新日期:2015-01-27 00:00:00

  • Synthesis and in vitro anticancer activity evaluation of novel bioreversible phosphate inositol derivatives.

    abstract::The chemistry and biology of phosphorylated inositols have become intense areas of research during the last two decades due to their involvement in various cellular signaling processes. However, the metabolic instability by phosphatases or kinases and poor penetration make it difficult to become a drug used in the cli...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.01.064

    authors: Chen W,Deng Z,Chen K,Dou D,Song F,Li L,Xi Z

    更新日期:2015-03-26 00:00:00

  • Structural-activity relationship study on C-4 carbon atom of the CB1 antagonist SR141716: synthesis and pharmacological evaluation of 1,2,4-triazole-3-carboxamides.

    abstract::A series of 1,2,4-triazole-3-carboxamides has been prepared from alkyl-1,2,4-triazole-3-carboxylates under mild conditions. The ability of these triazoles to displace [3H]-CP55940 from CB1 cannabinoid receptor was measured. However, they showed only poor to moderate binding affinities, indicating that substitution of ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2005.06.012

    authors: Jagerovic N,Hernandez-Folgado L,Alkorta I,Goya P,Martín MI,Dannert MT,Alsasua A,Frigola J,Cuberes MR,Dordal A,Holenz J

    更新日期:2006-01-01 00:00:00

  • Efficient synthesis and activity of beneficial intestinal flora of two lactulose-derived oligosaccharides.

    abstract::Lactulose is considered as a prebiotic because it promotes the intestinal proliferation of Lactobacillus acidophilus which is added to various milk products. Moreover, lactulose is used in pharmaceuticals as a gentle laxative and to treat hyperammonemia. This study was aimed at the total synthesis of two Lactulose-der...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.03.007

    authors: Zhu ZY,Cui D,Gao H,Dong FY,Liu XC,Liu F,Chen L,Zhang YM

    更新日期:2016-05-23 00:00:00

  • Synthesis and evaluation of xanthine oxidase inhibitory and antioxidant activities of 2-arylbenzo[b]furan derivatives based on salvianolic acid C.

    abstract::Xanthine oxidase (XO) is the key enzyme in humans which is related to a variety of diseases such as gout, hyperuricemia and cardiovascular diseases. In this work, a series of 2-arylbenzo[b]furan derivatives were synthesized based on salvianolic acid C, and they were evaluated for xanthine oxidase inhibitory and antiox...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.08.019

    authors: Tang HJ,Zhang XW,Yang L,Li W,Li JH,Wang JX,Chen J

    更新日期:2016-11-29 00:00:00

  • Synthesis and structure-activity relationship of 3-O-acylated (-)-epigallocatechins as 5α-reductase inhibitors.

    abstract::A series of 3-O-acylated (-)-epigallocatechins were synthesized and their inhibition of steroid 5α-reductase was studied. They were prepared from the reaction of EGCG with tert-butyldimethylsilyl chloride followed by reductive cleavage of the ester bond. The resultant (-)-epigallocatechins penta-O-tert-butyldimethylsi...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.10.011

    authors: Lin SF,Lin YH,Lin M,Kao YF,Wang RW,Teng LW,Chuang SH,Chang JM,Yuan TT,Fu KC,Huang KP,Lee YS,Chiang CC,Yang SC,Lai CL,Liao CB,Chen P,Lin YS,Lai KT,Huang HJ,Yang JY,Liu CW,Wei WY,Chen CK,Hiipakka RA,Liao S

    更新日期:2010-12-01 00:00:00

  • Xanthine oxidase inhibitory activity of natural and hemisynthetic flavonoids from Gardenia oudiepe (Rubiaceae) in vitro and molecular docking studies.

    abstract::Xanthine oxidase (XO), an enzyme widely distributed among mammalian tissues, is associated with the oxidation of xanthine and hypoxanthine to form uric acid. Reactive oxygen species are also released during this process, leading to oxidative damages and to the pathology called gout. Available treatments mainly based o...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.11.071

    authors: Santi MD,Paulino Zunini M,Vera B,Bouzidi C,Dumontet V,Abin-Carriquiry A,Grougnet R,Ortega MG

    更新日期:2018-01-01 00:00:00