Salicylanilide diethyl phosphates: synthesis, antimicrobial activity and cytotoxicity.

Abstract:

:A series of 27 salicylanilide diethyl phosphates was prepared as a part of our on-going search for new antimicrobial active drugs. All compounds exhibited in vitro activity against Mycobacterium tuberculosis, Mycobacterium kansasii and Mycobacterium avium strains, with minimum inhibitory concentration (MIC) values of 0.5-62.5μmol/L. Selected salicylanilide diethyl phosphates also inhibit multidrug-resistant tuberculous strains at the concentration of 1μmol/L. Salicylanilide diethyl phosphates also exhibited mostly the activity against Gram-positive bacteria (MICs ≥1.95μmol/L), whereas their antifungal activity is significantly lower. The IC50 values for Hep G2 cells were within the range of 1.56-33.82μmol/L, but there is no direct correlation with MICs for mycobacteria.

journal_name

Bioorg Med Chem

authors

Vinšová J,Kozic J,Krátký M,Stolaříková J,Mandíková J,Trejtnar F,Buchta V

doi

10.1016/j.bmc.2013.12.016

subject

Has Abstract

pub_date

2014-01-15 00:00:00

pages

728-37

issue

2

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(13)01010-9

journal_volume

22

pub_type

杂志文章
  • Antibacterial activity of indolyl-quinolinium derivatives and study their mode of action.

    abstract::Filamenting temperature-sensitive mutant Z (FtsZ) is recognized as a promising target for new antibiotics development because of its high conservatism and pivotal role in the bacteria cell division. The aromatic heterocyclic scaffold of indole is known showing merit medical functions in antiviral and antimicrobial. In...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2019.02.024

    authors: Cai S,Yuan W,Li Y,Huang X,Guo Q,Tang Z,Fang Z,Lin H,Wong WL,Wong KY,Lu YJ,Sun N

    更新日期:2019-04-01 00:00:00

  • Bisquaternary caracurine V and iso-caracurine V salts as ligands for the muscle type of nicotinic acetylcholine receptors: SAR and QSAR studies.

    abstract::The binding constants (K(i) values) of 24 caracurine V and 6 iso-caracurine V analogues for the muscle type of nicotinic ACh receptors (nAChR) from Torpedo californica were determined in a binding assay using (+/-)-[(3)H]epibatidine as a radioligand. The allyl alcohol group present in the iso-caracurine V ring system ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.08.053

    authors: Zlotos DP,Gündisch D,Ferraro S,Tilotta MC,Stiefl N,Baumann K

    更新日期:2004-12-01 00:00:00

  • Yohimbine as a Starting Point to Access Diverse Natural Product-Like Agents with Re-programmed Activities against Cancer-Relevant GPCR Targets.

    abstract::G protein-coupled receptors (GPCRs) constitute the largest protein superfamily in the human genome. GPCRs play key roles in mediating a wide variety of physiological events including proliferation and cancer metastasis. Given the major roles that GPCRs play in mediating cancer growth, they present promising targets fo...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2020.115546

    authors: Paciaroni NG,Norwood VM 4th,Ratnayake R,Luesch H,Huigens RW 3rd

    更新日期:2020-07-15 00:00:00

  • Novel and potent calcium-sensing receptor antagonists: discovery of (5R)-N-[1-ethyl-1-(4-ethylphenyl)propyl]-2,7,7-trimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide monotosylate (TAK-075) as an orally active bone anabolic agent.

    abstract::The calcium-sensing receptor antagonist (CaSR) has been recognized as a promising target of anabolic agents for treating osteoporosis. In the course of developing a new drug candidate for osteoporosis, we found tetrahydropyrazolopyrimidine derivative 1 to be an orally active CaSR antagonist that stimulated transient P...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.02.001

    authors: Yoshida M,Mori A,Morimoto S,Kotani E,Oka M,Notoya K,Makino H,Ono M,Shirasaki M,Tada N,Fujita H,Ban J,Ikeda Y,Kawamoto T,Goto M,Kimura H,Baba A,Yasuma T

    更新日期:2011-03-15 00:00:00

  • Molecular docking, discovery, synthesis, and pharmacological properties of new 6-substituted-2-(3-phenoxyphenyl)-4-phenyl quinoline derivatives; an approach to developing potent DNA gyrase inhibitors/antibacterial agents.

    abstract::Synthesis and molecular validation of 6-substituted-2-(3-phenoxyphenyl)-4-phenylquinoline derivatives (4a-h) as antibacterial/DNA gyrase inhibitors reported. Primarily, 6-substituted-2-(3-phenoxyphenyl)-4-phenylquinoline derivatives were docked into the active sites of DNA gyrase A&B, to ensure the binding mode of the...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.01.007

    authors: Alagumuthu M,Arumugam S

    更新日期:2017-02-15 00:00:00

  • Synthesis of new arylalkoxy amido derivatives as melatoninergic ligands.

    abstract::Amido derivatives 10-18 of the corresponding oxyamines were synthesised as melatoninergic ligands by the reaction of hydroxyphtalimide with the halogeno derivatives or the corresponding alcohols using Mitsunobu reaction conditions. The affinity of the compounds for chicken brain melatonin receptors and recombinant hum...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(02)00328-0

    authors: Pégurier C,Morellato L,Chahed E,Andrieux J,Nicolas JP,Boutin JA,Bennejean C,Delagrange P,Langlois M,Mathé-Allainmat M

    更新日期:2003-03-06 00:00:00

  • Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.

    abstract::Members of the GATA family of transcription factors are zinc finger proteins that were shown to play evolutionary conserved roles in cell differentiation and proliferation in different organisms. We hypothesized that by finding new molecules that inhibit their function to be crucial in future therapeutical interventio...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.01.022

    authors: El-Hachem N,Nemer G

    更新日期:2011-03-01 00:00:00

  • Synthesis and biological evaluation of pyrido[2,3-d]pyrimidine-2,4-dione derivatives as eEF-2K inhibitors.

    abstract::A small molecule library of pyrido[2,3-d]pyrimidine-2,4-dione derivatives 6-16 was synthesized from 6-amino-1,3-disubstituted uracils 18, characterized, and screened for inhibitory activity against eukaryotic elongation factor-2 kinase (eEF-2K). To understand the binding pocket of eEF-2K, structural modifications of t...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.06.050

    authors: Edupuganti R,Wang Q,Tavares CD,Chitjian CA,Bachman JL,Ren P,Anslyn EV,Dalby KN

    更新日期:2014-09-01 00:00:00

  • Functionalized 6-(piperidin-1-yl)-8,9-diphenyl purines as inverse agonists of the CB1 receptor - SAR efforts towards selectivity and peripheralization.

    abstract::Antagonists of type 1 cannabinoid receptors (CB1) may be useful in treating diabetes, hepatic disorders, and fibrosis. Otenabant (1) is a potent and selective CB1 inverse agonist that was under investigation as an anti-obesity agent, but its development was halted once adverse effects associated with another marketed ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2019.07.002

    authors: Amato G,Wiethe R,Manke A,Vasukuttan V,Snyder R,Runyon S,Maitra R

    更新日期:2019-08-15 00:00:00

  • Synthesis of chondroitin sulfate CC and DD tetrasaccharides and interactions with 2H6 and LY111.

    abstract::We synthesized the biotinylated chondroitin sulfate tetrasaccharides CS-CC [-3)βGalNAc6S(1-4)βGlcA(1-]2 and CS-DD [-3)βGalNAc6S(1-4)βGlcA2S(1-]2 which possess sulfate groups at O-6 of GalNAc and an additional sulfate group at O-2 of GlcA, respectively. We also analyzed interactions among CS-CC and CS-DD and the antibo...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2018.01.011

    authors: Matsushita K,Nakata T,Takeda-Okuda N,Nadanaka S,Kitagawa H,Tamura JI

    更新日期:2018-03-01 00:00:00

  • Naphthoindole-based analogues of tryptophan and tryptamine: synthesis and cytotoxic properties.

    abstract::The efficacy of anthracycline based anticancer drugs is limited by pleiotropic drug resistance of tumor cells. Aiming at the design of anthracyclinone congeners capable of circumventing drug resistance, we synthesized naphthoindole containing derivatives of tryptophan and tryptamine. In doing so we adapted the traditi...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.01.034

    authors: Shchekotikhin AE,Dezhenkova LG,Susova OY,Glazunova VA,Luzikov YN,Sinkevich YB,Buyanov VN,Shtil AA,Preobrazhenskaya MN

    更新日期:2007-04-01 00:00:00

  • Synthesis of a novel potent cyclic peptide MC4-ligand by ring-closing metathesis.

    abstract::The synthesis of a novel potent cyclic peptide MC4-ligand by ring-closing metathesis (RCM) is described. Based on the Ac-Nle-Gly-Lys-D-Phe-Arg-Trp-Gly-NH2-MC4 ligand, Ac-Nle-Alg-Lys-D-Phe-Arg-Trp-Alg-NH2 was designed and synthesized followed by cyclization using RCM. Both compounds are high affinity and selective MC4-...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.04.027

    authors: Wels B,Kruijtzer JA,Garner K,Nijenhuis WA,Gispen WH,Adan RA,Liskamp RM

    更新日期:2005-07-01 00:00:00

  • Effect of alkyl group on transnitrosation of N-nitrosothiazolidine thiocarboxamides.

    abstract::S-Nitrosoglutathione (GSNO) relaxes vascular smooth muscles, prevents platelet aggregation, and acts as a potential in vivo nitric oxide donor. 3-Nitroso-1,3-thiazolidine-4-thiocarboxamide (1), a N-nitrosothio-proline analogue, exhibited a high GSNO formation activity. In this study, two compounds (2 and 3) based on c...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.09.008

    authors: Inami K,Ono Y,Kondo S,Nakanishi I,Ohkubo K,Fukuzumi S,Mochizuki M

    更新日期:2015-10-15 00:00:00

  • Synthesis and binding mode of heterocyclic analogues of suramin inhibiting the human basic fibroblast growth factor.

    abstract::The design, synthesis, and biological evaluation of a series of pyrrole and pyrazole congeners 2 of suramin, directed toward the development and identification of new ligands that complex the human fibroblast growth factor (bFGF), thereby inhibiting tumor-promoted angiogenesis, is reported. Compounds 2 were evaluated ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(98)00052-2

    authors: Manetti F,Cappello V,Botta M,Corelli F,Mongelli N,Biasoli G,Borgia AL,Ciomei M

    更新日期:1998-07-01 00:00:00

  • Transdermal penetration behaviour of drugs: CART-clustering, QSPR and selection of model compounds.

    abstract::A set of 116 structurally very diverse compounds, mainly drugs, was characterized by 1630 molecular descriptors. The biological property modelled in this study was the transdermal permeability coefficient logK(p). The main objective was to find a limited set of suitable model compounds for skin penetration studies. Th...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.07.050

    authors: Baert B,Deconinck E,Van Gele M,Slodicka M,Stoppie P,Bodé S,Slegers G,Vander Heyden Y,Lambert J,Beetens J,De Spiegeleer B

    更新日期:2007-11-15 00:00:00

  • Probing the human estrogen receptor-α binding requirements for phenolic mono- and di-hydroxyl compounds: a combined synthesis, binding and docking study.

    abstract::Various estrogen analogs were synthesized and tested for binding to human ERα using a fluorescence polarization displacement assay. Binding affinity and orientation were also predicted using docking calculations. Docking was able to accurately predict relative binding affinity and orientation for estradiol, but only i...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.11.024

    authors: McCullough C,Neumann TS,Gone JR,He Z,Herrild C,Wondergem Nee Lukesh J,Pandey RK,Donaldson WA,Sem DS

    更新日期:2014-01-01 00:00:00

  • Synthesis and in vitro binding of N,N-dialkyl-2-phenylindol-3-yl-glyoxylamides for the peripheral benzodiazepine binding sites.

    abstract::A series of N,N-dialkyl-2-phenylindol-3-ylglyoxylamides bearing the halogens iodine and bromine were synthesised and their binding affinity for the peripheral benzodiazepine binding sites (PBBS) in rat kidney mitochondrial membranes was evaluated using [(3)H]PK11195. Central benzodiazepine receptor (CBR) affinities we...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.01.039

    authors: Homes TP,Mattner F,Keller PA,Katsifis A

    更新日期:2006-06-01 00:00:00

  • Preparation and biological properties of biotinylated PhTX derivatives.

    abstract::We report the synthesis of several highly functionalized biotinylated philanthotoxin (PhTX) analogues (7, 8, 10, 13-16) designed on the basis of earlier structure-activity relationship studies. Despite the extensive modifications, the binding to nicotinic acetylcholine receptor (nAChR) is in the low micromolar range a...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(99)00054-1

    authors: Hashimoto M,Liu Y,Fang K,Li HY,Campiani G,Nakanishi K

    更新日期:1999-06-01 00:00:00

  • Controllable synthesis of polymerizable ester and amide prodrugs of acyclovir by enzyme in organic solvent.

    abstract::A facile control of the acylation position at the primary hydroxyl and amino of acyclovir, respectively, was achieved and five polymerizable acyclovir prodrugs were synthesized. Various reaction conditions were studied in detail. Thus, lipase acrylic resin from Candida antarctica (CAL-B) in pyridine or acetone showed ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.12.050

    authors: Li X,Wu Q,Lv DS,Lin XF

    更新日期:2006-05-15 00:00:00

  • Design, synthesis and primary activity evaluation of L-arginine derivatives as amino-peptidase N/CD13 inhibitors.

    abstract::A series of L-arginine derivatives were designed, synthesized and assayed for their activities against amino-peptidase N (APN)/CD13 and metalloproteinase-2 (MMP-2). The results showed that most compounds exhibited high inhibitory activities against APN and low activities against MMP-2. Within this series, two compound...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.04.056

    authors: Mou J,Fang H,Jing F,Wang Q,Liu Y,Zhu H,Shang L,Wang X,Xu W

    更新日期:2009-07-01 00:00:00

  • Evaluation of sequence variability in HIV-1 gp41 C-peptide helix-grafted proteins.

    abstract::Many therapeutically-relevant protein-protein interactions (PPIs) have been reported that feature a helix and helix-binding cleft at the interface. Given this, different approaches to disrupting such PPIs have been developed. While short peptides (<15 amino acids) typically do not fold into a stable helix, researchers...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.07.064

    authors: Tennyson RL,Walker SN,Ikeda T,Harris RS,McNaughton BR

    更新日期:2018-03-15 00:00:00

  • Design, synthesis and biological evaluation of novel indanone containing spiroisoxazoline derivatives with selective COX-2 inhibition as anticancer agents.

    abstract:OBJECTIVE:A new family of 3'-(Mono, di or tri-substituted phenyl)-4'-(4-(methylsulfonyl) phenyl) spiroisoxazoline derivatives containing indanone spirobridge was designed, synthesized, and evaluated for their selective COX-2 inhibitory potency and cytotoxicity on different cell lines. METHODS:A synthetic reaction base...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2020.115960

    authors: Abolhasani H,Zarghi A,Komeili Movahhed T,Abolhasani A,Daraei B,Dastmalchi S

    更新日期:2021-01-02 00:00:00

  • Activation of lysine-specific demethylase 1 inhibitor peptide by redox-controlled cleavage of a traceless linker.

    abstract::We have previously employed cyclization of a linear peptide as a strategy to modulate peptide function and properties, but cleavage to regenerate the linear peptide left parts of the linker structure on the peptide, interfering with its activity. Here, we focused on cyclization of a linear peptide via a "traceless" di...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.12.033

    authors: Amano Y,Umezawa N,Sato S,Watanabe H,Umehara T,Higuchi T

    更新日期:2017-02-01 00:00:00

  • 3-D-QSAR analysis of N-(3-acyloxy-2-benzylpropyl)-N'-dihydroxytetrahydrobenzazepine and tetrahydroisoquinoline and N-(3-acyloxy-2-benzylpropyl)-N'-(4-hydroxy-3-methoxybenzyl) thioureas analogues as potent vanilloid receptor ligands.

    abstract::3-D-Quantitative structure--activity relationships of N-(3-acyloxy-2-benzylpropyl)-N'-dihydroxytetrahydro-benzazepine and tetrahydroisoquinoline and N-(3-acyloxy-2-benzylpropyl)-N'-(4-hydroxy-3-methoxybenzyl) thiourea analogues as potent vanilloid receptor ligands were investigated using the CoMFA and the COMSIA metho...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(01)00404-7

    authors: Kim KH

    更新日期:2002-05-01 00:00:00

  • A new dihydroxanthenone from a plant-associated strain of the fungus Chaetomium globosum demonstrates anticancer activity.

    abstract::Bioassay-guided fractionation of a cytotoxic EtOAc extract of the fungal strain, Chaetomium globosum, inhabiting the rhizosphere of the Christmas cactus, Opuntia leptocaulis, of the Sonoran desert afforded a new dihydroxanthenone, globosuxanthone A (1), a new tetrahydroxanthenone, globosuxanthone B (2), two new xantho...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.07.048

    authors: Wijeratne EM,Turbyville TJ,Fritz A,Whitesell L,Gunatilaka AA

    更新日期:2006-12-01 00:00:00

  • Synthesis and structure–activity relationships of small molecule inhibitors of the simian virus 40 T antigen oncoprotein, an anti-polyomaviral target.

    abstract::Polyomavirus infections are common and relatively benign in the general human population but can become pathogenic in immunosuppressed patients. Because most treatments for polyomavirusassociated diseases nonspecifically target DNA replication, existing treatments for polyomavirus infection possess undesirable side ef...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.09.019

    authors: Ireland AW,Gobillot TA,Gupta T,Seguin SP,Liang M,Resnick L,Goldberg MT,Manos-Turvey A,Pipas JM,Wipf P,Brodsky JL

    更新日期:2014-11-15 00:00:00

  • Comparison of the dark and light-induced toxicity of thio and seleno analogues of the thiopyrylium dye AA1.

    abstract::2,6-Bis(4-anilino)-4-(4-N,N-dimethylanilino)thiopyrylium chloride (AA1) and -selenopyrylium chloride (AA1-Se) and 2,6-bis(4-anilino)-4-(4-N-morpholinophenyl)thiopyrylium chloride (1) and -selenopyrylium chloride (2) were prepared via the addition of 4-N,N-dimethylanilino magnesium bromide and 4-N-morpholinophenyl magn...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.03.025

    authors: Detty MR,Gibson SL,Hilf R

    更新日期:2004-05-15 00:00:00

  • Identification of an achiral analogue of J-113397 as potent nociceptin/orphanin FQ receptor antagonist.

    abstract::To date, J-113397 represents the most potent and selective non peptide NOP receptor antagonist widely used in pharmacological studies. However, the synthesis, purification, and enantiomer separation of this molecule, which contains two chiral centers, is rather difficult and low-yielding. Here, we synthesized and test...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.08.049

    authors: Trapella C,Guerrini R,Piccagli L,Calo' G,Carra' G,Spagnolo B,Rubini S,Fanton G,Hebbes C,McDonald J,Lambert DG,Regoli D,Salvadori S

    更新日期:2006-02-01 00:00:00

  • Synthesis and phosphodiesterase 5 inhibitory activity of novel phenyl ring modified sildenafil analogues.

    abstract::New sildenafil analogues containing an ether ring fused into the phenyl moiety, 6a--d and 7a--d, were efficiently synthesized from the readily available starting materials, 1a--d and 2, in five steps. Ab initio calculations indicated that introduction of a cyclic ether to the phenyl group might enhance the co-planarit...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(01)00055-4

    authors: Kim DK,Lee N,Lee JY,Ryu DH,Kim JS,Lee SH,Choi JY,Chang K,Kim YW,Im GJ,Choi WS,Kim TK,Ryu JH,Kim NH,Lee K

    更新日期:2001-06-01 00:00:00

  • RNA interference with 2',4'-bridged nucleic acid analogues.

    abstract::In this study, a number of 2',4'-BNA- and 2',4'-BNA(NC)-modified siRNAs were designed and synthesized. Their thermal stability, nuclease resistance and gene silencing properties against cultured mammalian cells were evaluated and compared with those of natural siRNAs. The 2',4'-BNA- and 2',4'-BNA(NC)-modified siRNAs (...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.03.076

    authors: Abdur Rahman SM,Sato H,Tsuda N,Haitani S,Narukawa K,Imanishi T,Obika S

    更新日期:2010-05-15 00:00:00