Synthesis and antimicrobial evaluation of farnesyl diphosphate mimetics.

Abstract:

:The synthesis and first antimicrobial evaluation of farnesyl diphosphate mimetics are described. Several analogues (10, 12, 13, and 20) are inhibitors of Candida albicans, Shizosaccharomyces pombe, and Saccharomyces cerevisiae. The activities of analogues 10, 12, and 13, which contain a omega-phenyl moiety and a diphosphate isostere, are not attributable to inhibition of sterol biosynthesis via squalene synthase. Two geranyl phenylsulphones (14 and 15) are potent inhibitors of Escherichia coli. Analogue 15 exhibits potent activity towards Salmonella typhimurium and Pseudomonas aeruginosa (MIC-2 microg/mL) and represents the first type of semi-synthetic terpenoid allylic sulphone active against these bacteria.

journal_name

Bioorg Chem

journal_title

Bioorganic chemistry

authors

Fairlamb IJ,Dickinson JM,O'Connor R,Cohen LH,van Thiel CF

doi

10.1016/s0045-2068(03)00025-7

subject

Has Abstract

pub_date

2003-02-01 00:00:00

pages

80-97

issue

1

eissn

0045-2068

issn

1090-2120

pii

S0045206803000257

journal_volume

31

pub_type

杂志文章
  • Drechmerin H, a novel 1(2), 2(18)-diseco indole diterpenoid from the fungus Drechmeria sp. as a natural agonist of human pregnane X receptor.

    abstract::A novel 1(2), 2(18)-diseco indole diterpenoid, drechmerin H (1), was isolated from the fermentation broth of Drechmeria sp. together with a new indole diterpenoid, 2'-epi terpendole A (3), and a known analogue, terpendole A (2). Their structures were determined by HRESIMS, 1D and 2D NMR, ECD, and X-ray single crystal ...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2018.05.001

    authors: Zhao JC,Luan ZL,Liang JH,Cheng ZB,Sun CP,Wang YL,Zhang MY,Zhang TY,Wang Y,Yang TM,Wu YY,Zhang YX,Zhao XY,Ma XC

    更新日期:2018-09-01 00:00:00

  • Design, synthesis and biological evaluation of novel pyrrole derivatives as potential ClpP1P2 inhibitor against Mycobacterium tuberculosis.

    abstract::In an effort to discover novel inhibitors of M. tuberculosis Caseinolytic proteases (ClpP1P2), a combination strategy of virtual high-throughput screening and in vitro assay was employed and a new pyrrole compound, 1-(2-chloro-6-fluorobenzyl)-2, 5-dimethyl-4-((phenethylamino)methyl)-1H-pyrrole-3-carboxylate was found ...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2018.06.004

    authors: Liu P,Yang Y,Ju Y,Tang Y,Sang Z,Chen L,Yang T,An Q,Zhang T,Luo Y

    更新日期:2018-10-01 00:00:00

  • Synthesis and biological evaluation of 4-imidazolylflavans as nonsteroidal aromatase inhibitors.

    abstract::A series of 4-imidazolylflavans having a variety of substituents on the 2-phenyl ring was synthesized and investigated for their inhibitory effect against aromatase. Structure-activity relationships of these compounds were determined. An additional chlorine atom or a cyano group at the 4' position did not enhance arom...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2004.06.008

    authors: Pouget C,Yahiaoui S,Fagnere C,Habrioux G,Chulia AJ

    更新日期:2004-12-01 00:00:00

  • A structure-activity relationship study of Forkhead Domain Inhibitors (FDI): The importance of halogen binding interactions.

    abstract::The Forkhead boX M1 (FOXM1) protein is an essential transcription factor required for the normal activation of human cell cycle. However, increasing evidence supports a correlation between FOXM1 overexpression and the onset of several types of cancer. Based on a previously reported molecular modeling and molecular dyn...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.103269

    authors: Tabatabaei Dakhili SA,Pérez DJ,Gopal K,Tabatabaei Dakhili SY,Ussher JR,Velázquez-Martínez CA

    更新日期:2019-12-01 00:00:00

  • Quinoxalines as potent selective CRFRs ligands for monitoring and brain diagnostic.

    abstract::The paper highlighted quinoxalines as potent ligands to corticotropin-releasing factor receptor types 1 and 2. The content includes design and structure-activity relationship of 50 model substances to CRFR1, CRFR2α and CRF2β, respectively. It is important to bear in mind, that our concept has based on challenging rese...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2014.10.008

    authors: Ivanova B,Spiteller M

    更新日期:2015-02-01 00:00:00

  • Promising anti-inflammatory effects of chalcones via inhibition of cyclooxygenase, prostaglandin E2, inducible NO synthase and nuclear factor κb activities.

    abstract::Chalcones (1, 3-Diphenyl-2-propen-1-one) consist of a three carbon α, β-unsaturated carbonyl system and act as precursors for the biosynthesis of flavonoids in plants. However, laboratory synthesis of various chalcones has also been reported. Both natural and synthetic chalcones are known to exhibit a variety of pharm...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.bioorg.2019.03.033

    authors: Ur Rashid H,Xu Y,Ahmad N,Muhammad Y,Wang L

    更新日期:2019-06-01 00:00:00

  • Synthesis and biological evaluation of new bis-indolone-N-oxides.

    abstract::A series of bis-indolone-N-oxides, 1a-f, was prepared from bis(ethynyl)benzenes and o-halonitroaryls and studied for their in vitro antiplasmodial activities against Plasmodium falciparum and representative strains of bacteria and candida as well as for their cytotoxicity against a human tumor cell line (MCF7). They d...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2013.03.001

    authors: Najahi E,Valentin A,Téné N,Treilhou M,Nepveu F

    更新日期:2013-06-01 00:00:00

  • Probing the high potency of pyrazolyl pyrimidinetriones and thioxopyrimidinediones as selective and efficient non-nucleotide inhibitors of recombinant human ectonucleotidases.

    abstract::With the aim to discover novel, efficient and selective inhibitors of human alkaline phosphatase and nucleotide pyrophosphatase enzymes, two new series of pyrazolyl pyrimidinetriones (PPTs) (6a-g) and thioxopyrimidinediones (PTPs) (6h-n) were synthesized in good chemical yields using Knoevenagel condensation reaction ...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.03.067

    authors: Andleeb H,Hameed S,Ejaz SA,Khan I,Zaib S,Lecka J,Sévigny J,Iqbal J

    更新日期:2019-07-01 00:00:00

  • Imidazole-pyrazole hybrids: Synthesis, characterization and in-vitro bioevaluation against α-glucosidase enzyme with molecular docking studies.

    abstract::Herein, substituted imidazole-pyrazole hybrids (2a-2n) were prepared via a multi component reaction employing pyrazole-4-carbaldehydes (1a-1d), ammonium acetate, benzil and arylamines as reactants. All the new compounds were characterized through their spectral and elemental analyses. Further these compounds were test...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2018.10.047

    authors: Chaudhry F,Naureen S,Ashraf M,Al-Rashida M,Jahan B,Munawar MA,Khan MA

    更新日期:2019-02-01 00:00:00

  • Design, synthesis, and biological evaluation of novel imidazole derivatives possessing terminal sulphonamides as potential BRAFV600Einhibitors.

    abstract::BRAFV600E mutation has been detected in various malignant tumours. Developing of potent BRAFV600E inhibitors is considered a leading step in the way to cure different cancer types. In the current work, a series of 38 4-(1H-imidazol-5-yl)pyridin-2-amine derivatives was designed and synthesized using Dabrafenib as a lea...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.104508

    authors: Ali EMH,Abdel-Maksoud MS,Ammar UM,Mersal KI,Ho Yoo K,Jooryeong P,Oh CH

    更新日期:2021-01-01 00:00:00

  • Synthesis and in vitro antileishmanial activity of 5-substituted-2'-deoxyuridine derivatives.

    abstract::We report herein the synthesis and the in vitro antileishmanial evaluation of 5-substituted-2'-deoxyuridine nucleosides. The most active compound against Leishmania donovani promastigotes was Thia-dU (3a) with an IC50 =3 microM. This compound exhibited the same activity as zidovudine (3'-azido-2'-deoxythymidine) used ...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2005.07.001

    authors: Peyron C,Benhida R,Bories C,Loiseau PM

    更新日期:2005-12-01 00:00:00

  • Tacrine-hydroxamate derivatives as multitarget-directed ligands for the treatment of Alzheimer's disease: Design, synthesis, and biological evaluation.

    abstract::In order to develop multitarget-directed ligands as potential treatments for Alzheimer's disease, twenty-eight new tacrine-hydroxamate derivatives were designed, synthesized, and biologically evaluated. As expected, most of the compounds exhibited inhibitory activities against cholinesterases (ChEs) and histone deacet...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.103721

    authors: Xu A,He F,Zhang X,Li X,Ran Y,Wei C,James Chou C,Zhang R,Wu J

    更新日期:2020-05-01 00:00:00

  • Synthesis and DNase I inhibitory properties of some 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidines.

    abstract::A series of six novel and six known thieno[2,3-d]pyrimidin-4-amines 2-13 were synthesized, and further were used as a starting material for preparation of a small series of eight novel thieno[2,3-d]pyrimidin-4-phthalimides 14-21. Eight compounds, five amine and three phthalimide derivatives, inhibited bovine pancreati...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2018.07.009

    authors: Ts Mavrova A,Dimov S,Yancheva D,Kolarević A,Ilić BS,Kocić G,Šmelcerović A

    更新日期:2018-10-01 00:00:00

  • Aminobenzosuberone derivatives as PfA-M1 inhibitors: Molecular recognition and antiplasmodial evaluation.

    abstract::Aminobenzosuberone-based PfA-M1 inhibitors were explored as novel antimalarial agents against two different Plasmodium falciparum strains. The 4-phenyl derivative 7c exhibited the most encouraging growth inhibitory activity with IC50 values of 6.5-11.2 µM. X-ray crystal structures and early assessment of DMPK/ADME-Tox...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.103750

    authors: Salomon E,Schmitt M,Mouray E,McEwen AG,Bounaadja L,Torchy M,Poussin-Courmontagne P,Alavi S,Tarnus C,Cavarelli J,Florent I,Albrecht S

    更新日期:2020-05-01 00:00:00

  • Functional studies of rat hydroxymethylbilane synthase.

    abstract::The structurally related tetrapyrrolic pigments are a group of natural products that participate in many of the fundamental biosynthetic and catabolic processes of living organisms. Hydroxymethylbilane synthase catalyzes a rate-limiting step for the biosyntheses of tetrapyrrolic natural products. We carried out extens...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2008.07.001

    authors: Li N,Chu X,Wu L,Liu X,Li D

    更新日期:2008-10-01 00:00:00

  • Bioactivity and molecular docking studies of some nickel complexes: New analogues for the treatment of Alzheimer, glaucoma and epileptic diseases.

    abstract::The interaction of the coordination compounds with biological molecules resulted in the investigation of the drug potential of these molecules. In this study, enzyme inhibition of DSA (1-3) coordination compounds that were previously investigated for their anticancer and antibacterial properties was investigated. Also...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.104066

    authors: Kısa D,Korkmaz N,Taslimi P,Tuzun B,Tekin Ş,Karadag A,Şen F

    更新日期:2020-08-01 00:00:00

  • Design, synthesis and molecular modeling studies of new series of s-triazine derivatives as antimicrobial agents against multi-drug resistant clinical isolates.

    abstract::Three novel series of s-triazine derivatives, including thirty-five new compounds 2a-d, 3a-3p, 4b-d, 5b-d, 6d-6d, and 7a-7f were synthesized comprising a diversity of substituents based on the structure of Astrazeneca arylaminotriazine DNA gyrase B inhibitor. The antimicrobial activity was determined for all compounds...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.103013

    authors: Haiba NS,Khalil HH,Moniem MA,El-Wakil MH,Bekhit AA,Khattab SN

    更新日期:2019-08-01 00:00:00

  • Novel Linezolid analogues with antiparasitic activity against Hymenolepis nana.

    abstract::The stereoselective synthesis and anti- Hymenolepis nana activity of six Linezolid-type compounds, obtained by chemical modification of l-Alanine, are reported in this work. The synthetic strategy was to prepare diasteromeric N,N-dibenzylamino oxazolidinones 1 and 2, and coupling with 4-(4-bromophenyl)morpholine (3) t...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.104359

    authors: Alcántar-Zavala E,Hernández-Guevara E,Ochoa-Terán A,Montes-Ávila J,Estrada-Zavala EA,Salazar-Medina AJ,Alday E,Cabrera A,Aguirre G,Miranda-Soto V,Velazquez C,Díaz-Camacho SP,Medina-Franco JL

    更新日期:2020-12-01 00:00:00

  • Fusicoccane-derived diterpenoids with bridgehead double-bond-containing tricyclo[9.2.1.03,7]tetradecane ring systems from Alternaria brassicicola.

    abstract::Fusicoccane-derived diterpenoids bearing a unique bridgehead double-bond-containing tricyclo[9.2.1.03,7]tetradecane (5-9-5 ring system) core skeleton represent a rarely reported class of rearranged terpenoids, which traced back to fusicoccanes with a classical dicyclopenta[a,d]cyclooctane (5-8-5 ring system) core skel...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.103887

    authors: Li F,Pan L,Lin S,Zhang S,Li H,Yang B,Liu J,Wang J,Hu Z,Zhang Y

    更新日期:2020-07-01 00:00:00

  • Spectroscopic investigation of the interaction of water-soluble azocalix[4]arenes with bovine serum albumin.

    abstract::In this work, three hydrosoluble azocalix[4]arene derivatives, 5-(o-methylphenylazo)-25,26,27-tris(carboxymethoxy)-28-hydroxycalix[4]arene (o-MAC-Calix), 5-(m-methylphenylazo)-25,26,27-tris(carboxymethoxy)-28-hydroxycalix[4]arene (m-MAC-Calix) and 5-(p-methylphenylazo)-25,26,27-tris(carboxymethoxy)-28-hydroxycalix[4]a...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2014.12.002

    authors: Fan P,Wan L,Shang Y,Wang J,Liu Y,Sun X,Chen C

    更新日期:2015-02-01 00:00:00

  • Design, synthesis and anticancer evaluation of thieno[2,3-d]pyrimidine derivatives as dual EGFR/HER2 inhibitors and apoptosis inducers.

    abstract::Deregulation of many kinases is directly linked to cancer development and the tyrosine kinase family is one of the most important targets in current cancer therapy regimens. In this study, we have designed and synthesized a series of thieno[2,3-d]pyrimidine derivatives as an EGFR and HER2 tyrosine kinase inhibitors. A...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.102944

    authors: Elmetwally SA,Saied KF,Eissa IH,Elkaeed EB

    更新日期:2019-07-01 00:00:00

  • Design, synthesis, biological evaluation and molecular docking of new 1,3,4-oxadiazole homonucleosides and their double-headed analogs as antitumor agents.

    abstract::A novel series of homonucleosides and their double-headed analogs containing theophylline, 1,3,4-oxadiazole, and variant nucleobases was designed and synthesized. The new derivatives were fully characterized by HRMS, FT-IR, 1H NMR, and 13C NMR. The cytotoxic activities of all prepared compounds were screened in vitro ...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.104558

    authors: El Mansouri AE,Oubella A,Mehdi A,AitItto MY,Zahouily M,Morjani H,Lazrek HB

    更新日期:2020-12-15 00:00:00

  • Discovery of monoamine oxidase A inhibitory peptides from hairtail (Trichiurus japonicus) using in vitro simulated gastrointestinal digestion and in silico studies.

    abstract::The aim of this study was to effectively obtain monoamine oxidase A (MAO-A) inhibitory peptides from in vitro simulated gastrointestinal digestion and to assess the correspondences between in silico prediction and in vitro confirmation. Fractions (<3 kDa) from ultrafiltration of pepsin and simulated gastrointestinal e...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.104032

    authors: Yang X,Wang K,Liu Q,Zhang X

    更新日期:2020-08-01 00:00:00

  • Activity and mechanism of action of insect oostatic peptides in flesh fly.

    abstract::The relationship between structure and activity of insect oostatic decapeptide (Aed-TMOF) analogues in flesh fly was analyzed. The highest oostatic activity was exhibited by the pentapetide and tetrapeptide analogues, H-Tyr-Asp-Pro-Ala-Pro-OH and H-Tyr-Asp-Pro-Ala-OH, respectively. The tetrapeptide, either native or t...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2004.05.003

    authors: Slaninová J,Bennettová B,Nazarov ES,Simek P,Holík J,Vlasáková V,Hlavácek J,Cerný B,Tykva R

    更新日期:2004-08-01 00:00:00

  • Synthesis and biological evaluation of some N-(3-(1H-tetrazol-5-yl) phenyl)acetamide derivatives as novel non-carboxylic PTP1B inhibitors designed through bioisosteric modulation.

    abstract::Described herein is the synthesis and biological evaluation of a series of non-carboxylic inhibitors of Protein Tyrosine Phosphatase 1B designed using bioisosteric replacement strategy. Six N-(3-(1H-tetrazol-5-yl)phenyl)acetamide derivatives designed employing the aforementioned strategy were synthesized and screened ...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2018.06.016

    authors: Maheshwari N,Karthikeyan C,Bhadada SV,Sahi C,Verma AK,Hari Narayana Moorthy NS,Trivedi P

    更新日期:2018-10-01 00:00:00

  • Synthesis of novel 2-aminobenzothiazole derivatives as potential antimicrobial agents with dual DNA gyrase/topoisomerase IV inhibition.

    abstract::Novel benzothiazole-based compounds were designed and synthesized as potential antimicrobial agents with dual DNA gyrase/topoisomerase IV inhibitory activity. The structures of the newly synthesized compounds were established on the basis of spectral (IR, NMR, MS) and elemental analyses. Most of the studied compounds ...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.103437

    authors: Ismail MMF,Abdulwahab HG,Nossier ES,El Menofy NG,Abdelkhalek BA

    更新日期:2020-01-01 00:00:00

  • First evaluation of organotellurium derivatives as carbonic anhydrase I, II, IV, VII and IX inhibitors.

    abstract::A series of tellurides was evaluated as carbonic anhydrase (CA, EC 4.2.1.1) inhibitors against the human (h) carbonic anhydrase isoforms hCA I, II, IV, VII and IX, involved in a variety of diseases, including glaucoma, retinitis pigmentosa, epilepsy, arthritis and tumors. These compounds, which are the first tellurium...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2017.12.010

    authors: Angeli A,Tanini D,Capperucci A,Supuran CT

    更新日期:2018-02-01 00:00:00

  • Novel triazolophthalazine-hydrazone hybrids as potential PCAF inhibitors: Design, synthesis, in vitro anticancer evaluation, apoptosis, and molecular docking studies.

    abstract::Three novel series of triazolophthalazine derivatives bearing hydrazone moiety were designed, synthesized, and evaluated for their anticancer activity against four human cancer cell lines by MTT assay. Six derivatives demonstrated comparable activity with Doxorubicin reference drug against the selected cancer cells. E...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.103899

    authors: Abulkhair HS,Turky A,Ghiaty A,Ahmed HEA,Bayoumi AH

    更新日期:2020-07-01 00:00:00

  • An alkali tolerant α-l-rhamnosidase from Fusarium moniliforme MTCC-2088 used in de-rhamnosylation of natural glycosides.

    abstract::Analkali tolerant α-l-rhamnosidase has been purified to homogeneity from the culture filtrate of a new fungal strain, Fusarium moniliforme MTCC-2088, using concentration by ultrafiltration and cation exchange chromatography on CM cellulose column. The molecular mass of the purified enzyme has been found to be 36.0 kDa...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2018.11.027

    authors: Kumar D,Yadav S,Yadava S,Yadav KDS

    更新日期:2019-03-01 00:00:00

  • Synthesis, biological evaluation and in silico modelling studies of 1,3,5-trisubstituted pyrazoles carrying benzenesulfonamide as potential anticancer agents and selective cancer-associated hCA IX isoenzyme inhibitors.

    abstract::Inhibition of carbonic anhydrases (CAs, EC 4.2.1.1) has clinical importance for the treatment of several diseases. They participate in crucial regulatory mechanisms for balancing intracellular and extracellular pH of the cells. Among CA isoforms, selective inhibition of hCA IX has been linked to decreasing of cell gro...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.103222

    authors: Yamali C,Gul HI,Ece A,Bua S,Angeli A,Sakagami H,Sahin E,Supuran CT

    更新日期:2019-11-01 00:00:00