Synthesis, characterization and biological evaluation of some thiourea derivatives bearing benzothiazole moiety as potential antimicrobial and anticancer agents.

Abstract:

:Five series of thiourea derivatives bearing benzothiazole moiety (20 compounds) were efficiently synthesized and evaluated for antimicrobial and anticancer activities. The results indicated that the compounds possessed a broad spectrum of activity against the tested microorganisms and showed higher activity against fungi than bacteria. Compounds 1b, 2b, 3b, 4b and 5b exhibited the greatest antimicrobial activity. Preliminary study of the structure-activity relationship revealed that electronic factors in benzothiazole rings had a great effect on the antimicrobial activity of these compounds. In preliminary MTT cytotoxicity studies, the thiourea derivatives (2d, 5c and 5d) were found most potent. In MCF-7 and HeLa cells, the IC(50) values were observed in the range of 18-26 microM and 38-46 microM, respectively.

journal_name

Eur J Med Chem

authors

Saeed S,Rashid N,Jones PG,Ali M,Hussain R

doi

10.1016/j.ejmech.2009.12.016

subject

Has Abstract

pub_date

2010-04-01 00:00:00

pages

1323-31

issue

4

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(09)00642-4

journal_volume

45

pub_type

杂志文章
  • 5,10b-Ethanophenanthridine amaryllidaceae alkaloids inspire the discovery of novel bicyclic ring systems with activity against drug resistant cancer cells.

    abstract::Plants of the Amaryllidaceae family produce a large variety of alkaloids and non-basic secondary metabolites, many of which are investigated for their promising anticancer activities. Of these, crinine-type alkaloids based on the 5,10b-ethanophenanthridine ring system were recently shown to be effective at inhibiting ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.05.004

    authors: Henry S,Kidner R,Reisenauer MR,Magedov IV,Kiss R,Mathieu V,Lefranc F,Dasari R,Evidente A,Yu X,Ma X,Pertsemlidis A,Cencic R,Pelletier J,Cavazos DA,Brenner AJ,Aksenov AV,Rogelj S,Kornienko A,Frolova LV

    更新日期:2016-09-14 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

  • In vitro and in vivo biological evaluation of new 4,5-disubstituted 1,2,3-triazoles as cis-constrained analogs of combretastatin A4.

    abstract::To find new and better antivascular agents for cancer therapy, a series of combretastatin A4 (CA4) analogs were prepared from 1,3-diaryl-2-nitroprop-1-enes (6-12) obtained in a two-step synthesis from appropriate arylaldehydes and 2-aryl-1-nitroethanes (4 or 5). Treatment of these 1,3-diaryl-2-nitroprop-1-enes 6-12 by...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.04.017

    authors: Mur Blanch N,Chabot GG,Quentin L,Scherman D,Bourg S,Dauzonne D

    更新日期:2012-08-01 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

  • New 5-substituted thiazolo[3,2-b][1,2,4]triazol-6-ones: synthesis and anticancer evaluation.

    abstract::Following [2+3]-cyclocondensation reaction of 1,2,4-triazole-3(5)-thiol with N-arylmaleimides or with monochloroacetic acid and oxocompounds, N-(R-phenyl)-(6-oxo-5,6-dihydro[1,3]thiazol[3,2-b][1,2,4]triazol-5-yl)acetamides (1-5) and 5-ylidene-[1,3]thiazolo[3,2-b][1,2,4]triazol-6-ones (6-11) were synthesized as possibl...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2006.12.006

    authors: Lesyk R,Vladzimirska O,Holota S,Zaprutko L,Gzella A

    更新日期:2007-05-01 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

  • Development of certain new 2-substituted-quinazolin-4-yl-aminobenzenesulfonamide as potential antitumor agents.

    abstract::Carbonic anhydrases (CA I, II, IX and XII) are known to be highly expressed in various human malignancies. CA IX is overexpressed in colorectal cancer specifically in hereditary nonpolyposis colorectal cancer. Inhibition of CA activity by small molecular CA inhibitor like sulphonamides, sulphonamide derivative (SU.D2)...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.01.001

    authors: Alafeefy AM,Ahmad R,Abdulla M,Eldehna WM,Al-Tamimi AM,Abdel-Aziz HA,Al-Obaid O,Carta F,Al-Kahtani AA,Supuran CT

    更新日期:2016-02-15 00:00:00

  • Repurposed drug candidates for antituberculosis therapy.

    abstract::Antibiotics have been a key part of clinical treatments for more than 70 years. Long-term use of antimicrobial treatments has led to the development of severe bacterial resistance, which has become increasingly serious due to antibiotic abuse, resulting in the treatment of bacterial infections becoming challenging. Th...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2020.112175

    authors: An Q,Li C,Chen Y,Deng Y,Yang T,Luo Y

    更新日期:2020-04-15 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

  • N6-cycloalkyl-2-phenyl-3-deaza-8-azaadenines: a new class of A1 adenosine receptor ligands. A comparison with the corresponding adenines and 8-azaadenines.

    abstract::Several 9-benzyl-N6-cycloalkyl-2-phenyladenines, 9-benzyl-N6-cycloalkyl-2-phenyl-8-azaadenines and 4-cycloalkylamino-1-benzyl-6-phenyl-1H-1,2,3-triazolo[4,5-c]pyridines were prepared and assayed as A1 adenosine receptor ligands. The 1H-1,2,3-triazolo[4,5-c]pyridines were obtained starting from N,N-diethyl-1-benzyl-4-c...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2003.09.003

    authors: Biagi G,Giorgi I,Livi O,Nardi A,Pacchini F,Scartoni V,Lucacchini A

    更新日期:2003-11-01 00:00:00

  • Recent methodologies toward the synthesis of valdecoxib: a potential 3,4-diarylisoxazolyl COX-II inhibitor.

    abstract::Non-steroidal anti-inflammatory drugs are widely used therapeutic agents in the treatment of inflammation, pain and fever. Cyclooxygenase catalyzes the initial step of biotransformation of arachidonic acid to prostanoids, and exist as three distinct isozymes; COX-I, COX-II and COX-III. Selective COX-II inhibitors are ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2010.07.045

    authors: Dadiboyena S,Nefzi A

    更新日期:2010-11-01 00:00:00

  • Ni(II) curcumin complexes for cellular imaging and photo-triggered in vitro anticancer activity.

    abstract::Nickel(II) complexes [Ni(cur)(L)2](OAc) (1-3) where L is N,N-donor heterocyclic bases namely 1,10-phenanthroline (phen in 1), dipyrido[3,2-d:2',3'-f]quinoxaline (dpq in 2), dipyrido[3,2-a:2',3'-c]phenazine (dppz in 3) and Hcur is curcumin were prepared, fully characterized and light-induced in vitro anticancer activit...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112632

    authors: Banaspati A,Raza MK,Goswami TK

    更新日期:2020-10-15 00:00:00

  • Alpha (α-) and beta (β-carboranyl-C-deoxyribosides: syntheses, structures and biological evaluation.

    abstract::The syntheses of the unprotected neutral closo-carboranyl-C-deoxyriboses, starting from anomeric mixture of 1-ethynyldeoxyriboses, and their corresponding open-cage nido-derivatives have been described. The structures of both the α- and β-anomers were confirmed by single-crystal X-ray diffraction. While limited water ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.06.005

    authors: Šnajdr I,Janoušek Z,Takagaki M,Císařová I,Hosmane NS,Kotora M

    更新日期:2014-08-18 00:00:00

  • Rational approach to highly potent and selective apoptosis signal-regulating kinase 1 (ASK1) inhibitors.

    abstract::Many diseases are believed to be driven by pathological levels of reactive oxygen species (ROS) and oxidative stress has long been recognized as a driver for inflammatory disorders. Apoptosis signal-regulating kinase 1 (ASK1) has been reported to be activated by intracellular ROS and its inhibition leads to a down reg...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.12.041

    authors: Lovering F,Morgan P,Allais C,Aulabaugh A,Brodfuehrer J,Chang J,Coe J,Ding W,Dowty H,Fleming M,Frisbie R,Guzova J,Hepworth D,Jasti J,Kortum S,Kurumbail R,Mohan S,Papaioannou N,Strohbach JW,Vincent F,Lee K,Zapf CW

    更新日期:2018-02-10 00:00:00

  • Design, synthesis and biological evaluation of novel thioquinazolinone-based 2-aminobenzamide derivatives as potent histone deacetylase (HDAC) inhibitors.

    abstract::A series of novel 2-aminobenzamide derivatives decorated with thioquinazolinone were designed and synthesized as histone deacetylase (HDAC) inhibitors. These derivatives were evaluated for their antiproliferative activities against several human cancer cell lines including A375, Hela, A549, HCT116 and SMMC7721. It's s...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.04.017

    authors: Cheng C,Yun F,He J,Ullah S,Yuan Q

    更新日期:2019-07-01 00:00:00

  • Substitution at the indole 3 position yields highly potent indolecombretastatins against human tumor cells.

    abstract::Resistance to combretastatin A-4 is mediated by metabolic modification of the phenolic hydroxyl and ether groups of the 3-hydroxy-4-methoxyphenyl (B ring). Replacement of the B ring of combretastatin A-4 by a N-methyl-5-indolyl reduces tubulin polymerization inhibition (TPI) and cytotoxicity against human cancer cell ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.08.078

    authors: Álvarez R,Gajate C,Puebla P,Mollinedo F,Medarde M,Peláez R

    更新日期:2018-10-05 00:00:00

  • Synthesis and preliminary in vitro biological evaluation of 7α-testosterone-chlorambucil hybrid designed for the treatment of prostate cancer.

    abstract::The synthesis of 7α-testosterone-chlorambucil hybrid is reported. This compound is made from testosterone in a 6 step reaction sequence and with 23% overall yield. An alternative convergent reaction sequence yielded the same hybrid through a Grubbs metathesis reaction between chlorambucil allyl ester and 7α-allyltesto...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.04.027

    authors: Bastien D,Hanna R,Leblanc V,Asselin É,Bérubé G

    更新日期:2013-06-01 00:00:00

  • Synthesis of some new pyrimido[2',1':2,3]thiazolo[4,5-b]quinoxaline derivatives as anti-inflammatory and analgesic agents.

    abstract::Treatment of 6-aminothiouracil (1) with 2,3-dichloroquinoxaline (2) in ethanol/TEA afforded 6-amino-2-(3-chloroquinoxalin-2-ylthio)pyrimidin-4(3H)-one (3), which was refluxed in DMF to give 2-aminopyrimido[2',1':2,3]thiazolo[4,5-b]quinoxaline-4-one (4). Compound 4 was utilized as a key intermediate for the synthesis o...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.01.042

    authors: Abu-Hashem AA,Gouda MA,Badria FA

    更新日期:2010-05-01 00:00:00

  • Synthesis and antitumor activity of emodin quaternary ammonium salt derivatives.

    abstract::A series of new emodin derivatives modified at the C-3 and the C-6 positions were synthesized, and evaluated for their anticancer activities in vitro and in vivo. Among them, Compounds 5g and 5h had more significant antiproliferative ability against HepG2, BGC-823, AGS cancer cell lines and low cytotoxicity to HELF no...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.07.047

    authors: Shao J,Zhang F,Bai Z,Wang C,Yuan Y,Wang W

    更新日期:2012-10-01 00:00:00

  • An improved synthesis of 5,6-dimethylxanthenone-4-acetic acid (DMXAA).

    abstract::5,6-Dimethylxanthenone-4-acetic acid (DMXAA) is a novel anticancer agent with a number of unique activities, and is in clinical trial. The current synthesis of DMXAA involves six steps, beginning with a heterogeneous reaction to form an isonitrosoacetanilide, and gives an overall yield of 11% from 2,3-dimethylaniline....

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(02)01406-x

    authors: Atwell GJ,Yang S,Denny WA

    更新日期:2002-10-01 00:00:00

  • Design, synthesis and docking studies of benzimidazole derivatives as potential EGFR inhibitors.

    abstract::In this study, a series of benzimidazoles bearing thiosemicarbazide chain or triazole and thiadiazole rings were designed and synthesized. Crystal and molecular structure of the compound 5c has been characterized by single crystal X-ray crystallographic analysis. EGFR kinase inhibitory potencies of synthesized compoun...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.04.012

    authors: Celik İ,Ayhan-Kılcıgil G,Guven B,Kara Z,Gurkan-Alp AS,Karayel A,Onay-Besikci A

    更新日期:2019-07-01 00:00:00

  • Recent insights into synthetic β-carbolines with anti-cancer activities.

    abstract::Cancer, an uncontrolled and rapid proliferation of abnormal cells, has become one of the leading cause of death worldwide. The development of resistance among the numerous drugs in clinical use has provided strong impetus for the identification and development of novel cancer therapeutics. β-carbolines constitute an i...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2017.05.059

    authors: Kumar S,Singh A,Kumar K,Kumar V

    更新日期:2017-12-15 00:00:00

  • Synthesis and in vitro Trichomonacidal activities of some new dialkylperoxides and 1,2,4-trioxanes.

    abstract::Two series of three trioxanes and 18 disubstituted peroxides were synthesised and evaluated for their in vitro trichomonacidal activity against Trichomonas vaginalis. The most active compound, 2-methylprop-2-yl 2-methoxyeth-1-yl peroxide exhibited an IC(50) value of 1.0+/-0.2 microM whereas other dialkyl peroxides had...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(01)01278-8

    authors: Camuzat-Dedenis B,Provot O,Cointeaux L,Peyrou V,Berrien JF,Bories C,Loiseau PM,Mayrargue J

    更新日期:2001-10-01 00:00:00

  • Synthesis and antimicrobial activities of hexahydroimidazo[1,5-a]pyridinium bromides with varying benzyl substituents.

    abstract::Variously substituted benzyl bromides were employed to quaternize hexahydrobenzylimidazo[1,5-a]pyridine (A) and the resulting bromides (1-11) were evaluated for their in vitro antimicrobial activity against 10 pathogenic microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Bacillus cereus, Micrococcus lu...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.04.012

    authors: Türkmen H,Ceyhan N,Ulkü Karabay Yavaşoğlu N,Ozdemir G,Cetinkaya B

    更新日期:2011-07-01 00:00:00

  • Synthesis of novel diarylpyrimidine analogues of TMC278 and their antiviral activity against HIV-1 wild-type and mutant strains.

    abstract::Novel diarylpyrimidines (DAPY), which represent next generation of non-nucleoside reverse transcriptase inhibitors (NNRTIs), were synthesized and their activities against human immunodeficiency virus type I (HIV-1) assessed. Modulations at positions 2 and 6 of the left phenyl ring generated interesting derivatives of ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2006.11.014

    authors: Mordant C,Schmitt B,Pasquier E,Demestre C,Queguiner L,Masungi C,Peeters A,Smeulders L,Bettens E,Hertogs K,Heeres J,Lewi P,Guillemont J

    更新日期:2007-05-01 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

  • Indoles as therapeutics of interest in medicinal chemistry: Bird's eye view.

    abstract::Indoles constitute extensively explored heterocyclic ring systems with wide range of applications in pathophysiological conditions that is, cancer, microbial and viral infections, inflammation, depression, migraine, emesis, hypertension, etc. Presence of indole nucleus in amino acid tryptophan makes it prominent in ph...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2017.04.003

    authors: Chadha N,Silakari O

    更新日期:2017-07-07 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

  • 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

  • Design, economical synthesis and antiplasmodial evaluation of vanillin derived allylated chalcones and their marked synergism with artemisinin against chloroquine resistant strains of Plasmodium falciparum.

    abstract::The in vitro blood stage antiplasmodial activity of a series of allylated chalcones based on the licochalcone A as lead molecule was investigated against chloroquine (CQ) sensitive Pf3D7 and CQ resistant PfINDO strains of Plasmodium falciparum using SYBR Green I assay. Of the forty two chalcones tested, eight showed I...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.03.079

    authors: Sharma N,Mohanakrishnan D,Sharma UK,Kumar R,Richa,Sinha AK,Sahal D

    更新日期:2014-05-22 00:00:00