当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY期刊下所有文献 > Fluoroalkene modification of mercaptoacetamide-based histone deacetylase inhibitors.

Fluoroalkene modification of mercaptoacetamide-based histone deacetylase inhibitors.

Abstract：

:Inhibitors of histone deacetylases (HDAC) are emerging as a promising class of anti-cancer agents. The mercaptoacetoamide-based inhibitors are reported to be less toxic than hydroxamate and are worthy of further consideration. Therefore, we have designed a series of analogs as potential inhibitors of HDACs, in which the mercaptoacetamide group was replaced by (mercaptomethyl)fluoroalkene, and their HDAC inhibitory activity was evaluated. Subnanomolar inhibition was observed for all synthetic compounds.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Osada S,Sano S,Ueyama M,Chuman Y,Kodama H,Sakaguchi K

doi

10.1016/j.bmc.2009.12.005

subject

Has Abstract

pub_date

2010-01-15 00:00:00

pages

605-11

issue

2

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(09)01088-8

journal_volume

18

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY文献大全
  • Design and synthesis of novel pyrimido[4,5-b]azepine derivatives as HER2/EGFR dual inhibitors.

    abstract：:A novel 7,6 fused bicyclic scaffold, pyrimido[4,5-b]azepine was designed to fit into the ATP binding site of the HER2/EGFR proteins. The synthesis of this scaffold was accomplished by an intramolecular Claisen-type condensation. As the results of optimization lead us to 4-anilino and 6-functional groups, we discovered...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2013.02.014

    authors： Kawakita Y,Seto M,Ohashi T,Tamura T,Yusa T,Miki H,Iwata H,Kamiguchi H,Tanaka T,Sogabe S,Ohta Y,Ishikawa T

    更新日期：2013-04-15 00:00:00

  • The tetrahydroxanthone-dimer phomoxanthone A is a strong inducer of apoptosis in cisplatin-resistant solid cancer cells.

    abstract：:Platinum compounds are the first-line therapy for many types of cancer. However, drug resistance has frequently been reported for and is a major limitation of platinum-based chemotherapy in the clinic. In the current study, we examined the anti-tumor activity of phomoxanthone A (PXA), a tetrahydroxanthone dimer isolat...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2019.115044

    authors： Wang C,Engelke L,Bickel D,Hamacher A,Frank M,Proksch P,Gohlke H,Kassack MU

    更新日期：2019-10-01 00:00:00

  • Investigating the role of the geminal dimethyl groups of coenzyme A: synthesis and studies of a didemethyl analogue.

    abstract：:An analogue 2 of coenzyme A (CoA) has been prepared in which the geminal methyl groups are replaced with hydrogens. An NMR titration study was conducted and shifts in frequency of protons in the pantetheine portion of the molecule upon titration of the adenine base were observed as has been previously reported with Co...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(00)00189-9

    authors： Vogel KW,Stark LM,Mishra PK,Yang W,Drueckhammer DG

    更新日期：2000-10-01 00:00:00

  • Synthesis and study of the cancer cell growth inhibitory properties of alpha-, gamma-tocopheryl and gamma-tocotrienyl 2-phenylselenyl succinates.

    abstract：:Vitamin E succinate selenium-conjugated molecules were synthesized and their apoptogenic properties were evaluated. 4-Methyl-2-phenylselenyl succinate (4) was prepared by the reaction of sodium benzeneselenolate with 2-bromosuccinic anhydrite in methanol solution. The methyl ester was converted to the acid (5) by hydr...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2005.11.045

    authors： Vraka PS,Drouza C,Rikkou MP,Odysseos AD,Keramidas AD

    更新日期：2006-04-15 00:00:00

  • Effect of prime-site sequence of retro-inverso-modified HTLV-1 protease inhibitor.

    abstract：:The effects of additional substituents covering the prime-site of retro-inverso (RI)-modified HTLV-1 protease inhibitors containing a hydroxyethylamine isoster were clarified. Stereo-selective construction of the most potent isoster backbone was achieved by the Evans-aldol reaction. Addition of N-acetylated d-amino ac...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2014.02.050

    authors： Awahara C,Tatsumi T,Furuta S,Shinjoh G,Konno H,Nosaka K,Kobayashi K,Hattori Y,Akaji K

    更新日期：2014-04-15 00:00:00

  • A para-nitrophenol phosphonate probe labels distinct serine hydrolases of Arabidopsis.

    abstract：:Activity-based protein profiling represents a powerful methodology to probe the activity state of enzymes under various physiological conditions. Here we present the development of a para-nitrophenol phosphonate activity-based probe with structural similarities to the potent agrochemical paraoxon. We demonstrate that ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2011.06.041

    authors： Nickel S,Kaschani F,Colby T,van der Hoorn RA,Kaiser M

    更新日期：2012-01-15 00:00:00

  • Downsizing of an HIV-cell fusion inhibitor, T22 ([Tyr5,12, Lys7]-polyphemusin II), with the maintenance of anti-HIV activity and solution structure.

    abstract：:T22 ([Tyr5,12,Lys7]-polyphemusin II) has been shown to have strong anti-human immunodeficiency virus (HIV) activity comparable to that of 3'-azido-2',3'-dideoxythymidine (AZT). T22, an 18-residue peptide amide, takes an antiparallel beta-sheet structure that is maintained by two disulfide bridges. Herein we synthesize...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(97)10055-4

    authors： Tamamura H,Waki M,Imai M,Otaka A,Ibuka T,Waki K,Miyamoto K,Matsumoto A,Murakami T,Nakashima H,Yamamoto N,Fujii N

    更新日期：1998-04-01 00:00:00

  • Design, synthesis and biological activity evaluation of desloratadine analogues as H1 receptor antagonists.

    abstract：:A series of N-substituted desloratadine analogues were designed and synthesized. They were tested for H1 antihistamine activity by inhibiting histamine-induced contraction of isolated ileum muscles of guinea-pigs in vitro and inhibiting histamine-induced asthmatic reaction in guinea-pigs in vivo. All the evaluated com...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2013.05.004

    authors： Lin Y,Wang Y,Sima LF,Wang DH,Cao XH,Chen LG,Chen B

    更新日期：2013-07-15 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

  • Benzoic acid derivatives with improved antifungal activity: Design, synthesis, structure-activity relationship (SAR) and CYP53 docking studies.

    abstract：:Previously, we identified CYP53 as a fungal-specific target of natural phenolic antifungal compounds and discovered several inhibitors with antifungal properties. In this study, we performed similarity-based virtual screening and synthesis to obtain benzoic acid-derived compounds and assessed their antifungal activity...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.06.042

    authors： Berne S,Kovačič L,Sova M,Kraševec N,Gobec S,Križaj I,Komel R

    更新日期：2015-08-01 00:00:00

  • Dolichylpyrophosphate oligosaccharides: large-scale isolation and evaluation as oligosaccharyltransferase substrates.

    abstract：:Oligosaccharyltransferase (OST) catalyzes the transfer of a branched oligosaccharide from a dolichylpyrophosphate oligosaccharide (Dol-PP-OS) to the asparagine of a nascent polypeptide chain in vivo and peptide substrates in vitro. Here we report the isolation and purification of Dol-PP-OS from bovine pancreas and thy...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(98)00268-5

    authors： Gibbs BS,Coward JK

    更新日期：1999-03-01 00:00:00

  • Synthesis, biological assays and QSAR studies of N-(9-benzyl-2-phenyl-8-azapurin-6-yl)-amides as ligands for A1 adenosine receptors.

    abstract：:2-Phenyl-9-benzyl-8-azapurines, bearing at the 6 position an amido group interposed between the 8-azapurine moiety and an alkyl or a substituted phenyl group, have been synthesised and assayed as ligands for adenosine receptors. All the compounds show high affinity for the A(1) adenosine receptor, and many of them als...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.01.060

    authors： Giorgi I,Leonardi M,Pietra D,Biagi G,Borghini A,Massarelli I,Ciampi O,Bianucci AM

    更新日期：2009-03-01 00:00:00

  • Synthesis, anticoagulant and PIVKA-II induced by new 4-hydroxycoumarin derivatives.

    abstract：:The action of the coumarin-type drugs and related compounds is reviewed to their VKOR antagonistic effects. In our study, twenty 3-pyridinyl, pyrimidinyl and pyrazolyl-4-hydroxycoumarin derivatives were synthesized. A comparative in vivo (CT, PT determination) and in vitro (measurement of PIVKA-II levels) anticoagulan...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.04.009

    authors： Abdelhafez OM,Amin KM,Batran RZ,Maher TJ,Nada SA,Sethumadhavan S

    更新日期：2010-05-15 00:00:00

  • Glycosyl bis-porphyrin conjugates: synthesis and potential application in PDT.

    abstract：:Syntheses of new glycosylated neutral and cationic porphyrin dimers linked at the meso-position via a flexible hydrocarbon chain are described. A detailed 1H and 13C NMR study allows their complete structural elucidation. The UV-visible, fluorescence and MALDI mass spectra are also presented. Photocytotoxicities of th...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2006.08.004

    authors： Sol V,Chaleix V,Champavier Y,Granet R,Huang YM,Krausz P

    更新日期：2006-12-01 00:00:00

  • Chiral switch of enzymatic ketone reduction by addition of gamma-cyclodextrin.

    abstract：:We report a chiral switch in the configuration of 1-(p-methoxyphenyl)-propan-2-ol, synthesized in aqueous media by ketoreductase in the presence of high concentration of gamma-CD. NMR, ECD and fluorescence spectrometry were used in the effort to explain this unexpected effect. A comparison has been made between the ca...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.07.070

    authors： Petkova GA,Král V

    更新日期：2010-09-15 00:00:00

  • Synthesis and preliminary biological evaluation of O6-[4-(2-[18F]fluoroethoxymethyl)benzyl]guanine as a novel potential PET probe for the DNA repair protein O6-alkylguanine-DNA alkyltransferase in cancer chemotherapy.

    abstract：:A novel fluorine-18-labeled O6-benzylguanine (O6-BG) derivative, O6-[4-(2-[18F]fluoroethoxymethyl)benzyl]guanine (O6-[18F]FEMBG, [18F]1), has been synthesized for evaluation as a potential positron emission tomography (PET) probe for the DNA repair protein O6-alkylguanine-DNA alkyltransferase (AGT) in cancer chemother...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2005.05.061

    authors： Wang JQ,Kreklau EL,Bailey BJ,Erickson LC,Zheng QH

    更新日期：2005-10-15 00:00:00

  • Equol, a natural estrogenic metabolite from soy isoflavones: convenient preparation and resolution of R- and S-equols and their differing binding and biological activity through estrogen receptors alpha and beta.

    abstract：:Equol is a metabolite produced in vivo from the soy phytoestrogen daidzein by the action of gut microflora. It is known to be estrogenic, so human exposure to equol could have significant biological effects. Equol is a chiral molecule that can exist as the enantiomers R-equol and S-equol. To study the biological activ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2003.11.035

    authors： Muthyala RS,Ju YH,Sheng S,Williams LD,Doerge DR,Katzenellenbogen BS,Helferich WG,Katzenellenbogen JA

    更新日期：2004-03-15 00:00:00

  • Relationship between the lipophilicity of gallic acid n-alquil esters' derivatives and both myeloperoxidase activity and HOCl scavenging.

    abstract：:The gallic acid and several n-alkyl gallates, with the same number of hydroxyl substituents, varying only in the side carbonic chain length, with respective lipophilicity defined through the C log P, were studied. It evidenced the structure-activity relationship of the myeloperoxidase activity inhibition and the hypoc...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2006.05.038

    authors： Rosso R,Vieira TO,Leal PC,Nunes RJ,Yunes RA,Creczynski-Pasa TB

    更新日期：2006-09-15 00:00:00

  • The synthesis and anti-proliferative effects of beta-elemene derivatives with mTOR inhibition activity.

    abstract：:Fourteen beta-elemene derivatives containing a piperazine, a morpholine, a tetrahydropyrrole, a thiophenylethylamine, or a cyclohexamine group were synthesized. The structures of these beta-elemene derivatives were characterized with IR, 1H NMR, MS, and elemental analyses. All these derivatives had an increased anti-p...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2006.03.041

    authors： Xu L,Tao S,Wang X,Yu Z,Wang M,Chen D,Jing Y,Dong J

    更新日期：2006-08-01 00:00:00

  • Design and structure-activity relationship of thrombin inhibitors with an azaphenylalanine scaffold: potency and selectivity enhancements via P2 optimization.

    abstract：:Theoretical and structural studies followed by the directed synthesis and in vitro biological tests lead us to novel noncovalent thrombin pseudopeptide inhibitors. We have incorporated an azapeptide scaffold into the central part of the classical tripeptide D-Phe-Pro-Arg inhibitor structure thus eliminating one stereo...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(01)00202-4

    authors： Zega A,Mlinsek G,Sepic P,Golic Grdadolnik S,Solmajer T,Tschopp TB,Steiner B,Kikelj D,Urleb U

    更新日期：2001-10-01 00:00:00

  • A convenient synthesis and hepatoprotective activity of imidazo[1,2-c]pyrimido[5,4-e]pyrimidine, tetraazaacenaphthene and tetraazaphenalene from cyclic ketene aminals through tandem addition-cyclization reactions.

    abstract：:A novel one-pot synthesis of imidazo[1,2-c]pyrimido[5,4-e]pyrimidinones (2), tetraazaacenaphthene-3,6-diones (4), tetarazaphenalene-1,7-dione (4d) is delineated from the reaction of cyclic ketene aminal (1) and alkyl or aryl isothiocyanate through tandem addition-cyclization reactions. However, reaction of ketene amin...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(01)00423-0

    authors： Ram VJ,Goel A,Sarkhel S,Maulik PR

    更新日期：2002-05-01 00:00:00

  • Inactivation of the human papillomavirus-16 E6 oncoprotein by organic disulfides.

    abstract：:We are investigating compounds that could be useful in the treatment of neoplastic lesions of the cervix by acting on the oncoprotein E6 of human papillomavirus-16. The E6 protein contains two potential zinc-binding domains that are required for most of its functions. We have published tests that measure (i) the relea...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(00)00193-0

    authors： Beerheide W,Sim MM,Tan YJ,Bernard HU,Ting AE

    更新日期：2000-11-01 00:00:00

  • Criteria for the mode of binding of DNA binding agents.

    abstract：:A complete characterization of DNA binding agents requires that their mode of binding to DNA be established. In the absence of high resolution structural data, the mode of binding is, of necessity, usually inferred indirectly from various solution studies. The purpose of this study is to show that only certain methods...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/0968-0896(95)00053-j

    authors： Suh D,Chaires JB

    更新日期：1995-06-01 00:00:00

  • Design, synthesis, and biological evaluation of water-soluble amino acid prodrug conjugates derived from combretastatin, dihydronaphthalene, and benzosuberene-based parent vascular disrupting agents.

    abstract：:Targeting tumor vasculature represents an intriguing therapeutic strategy in the treatment of cancer. In an effort to discover new vascular disrupting agents with improved water solubility and potentially greater bioavailability, various amino acid prodrug conjugates (AAPCs) of potent amino combretastatin, amino dihyd...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2016.01.007

    authors： Devkota L,Lin CM,Strecker TE,Wang Y,Tidmore JK,Chen Z,Guddneppanavar R,Jelinek CJ,Lopez R,Liu L,Hamel E,Mason RP,Chaplin DJ,Trawick ML,Pinney KG

    更新日期：2016-03-01 00:00:00

  • Small-molecular, non-peptide, non-ATP-competitive polo-like kinase 1 (Plk1) inhibitors with a terphenyl skeleton.

    abstract：:Polo-like kinase (Plk) 1 is a serine-threonine protein kinase that plays a role in cell division, and its overexpression is highly correlated with aggressiveness and prognosis of many cancers. We have designed, synthesized and evaluated a series of terphenyl compounds as inhibitors of the kinase activity of Plk1. Some...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2012.11.054

    authors： Mita Y,Noguchi-Yachide T,Ishikawa M,Hashimoto Y

    更新日期：2013-02-01 00:00:00

  • Synthesis and alpha-adrenoreceptor blocking properties of phenoxybenzamine-related (2-chloroethyl)-(2,3-dihydrobenzo[1,4]dioxin- 2-ylmethyl)-(2-phenoxyethyl) amines.

    abstract：:A series of beta-chloroethylamines, structural hybrids of WB 4101, a competitive alpha 1-adrenoreceptor antagonist, and phenoxybenzamine, an irreversible alpha-adrenoreceptor antagonist, has been synthesized and tested in isolated rat vas deferens alpha-adrenoreceptors. Although, for all compounds, apparent blocking p...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/0968-0896(94)00150-2

    authors： Giardinà D,Crucianelli M,Marucci G,Paparelli F,Melchiorre C

    更新日期：1995-01-01 00:00:00

  • Aza-THIP and related analogues of THIP as GABA C antagonists.

    abstract：:The potency of a series of eight compounds structurally related with 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-ol (THIP), a potent GABA(A) partial agonist exhibiting GABA(C) rho(1) antagonist effect (K(i)=25 microM), was determined electrophysiologically using homomeric human GABA(C) rho(1) receptors expressed in Xe...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2003.09.016

    authors： Krehan D,Frølund B,Ebert B,Nielsen B,Krogsgaard-Larsen P,Johnston GA,Chebib M

    更新日期：2003-11-17 00:00:00

  • QSAR models for Daphnia toxicity of pesticides based on combinations of topological parameters of molecular structures.

    abstract：:A topological parameter is defined as an integer value of a given local or global invariant of a molecular graph. We examined three types of local graph invariants, the vertex degrees (0EC), the extended connectivity of first order (1EC), and the numbers of paths of length two (P2), as elementary invariants for constr...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2005.11.060

    authors： Toropov AA,Benfenati E

    更新日期：2006-04-15 00:00:00

  • A novel fluorescent probe based on naphthalimide for imaging nitroreductase (NTR) in bacteria and cells.

    abstract：:A nitroreductase (NTR) responsive fluorescent probe, Na-NO2, comprising p-nitrobenzyl as the unique recognition group and 1,8-naphthalimide as fluorophore, was synthesized. Na-NO2 showed remarkable fluorescence "turn-on" signal in the presence of NTR under DMSO/H2O (1:19, v/v) buffered with PBS (pH = 7) solution in th...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2019.115280

    authors： Zhang Z,Lv T,Tao B,Wen Z,Xu Y,Li H,Liu F,Sun S

    更新日期：2020-02-01 00:00:00

  • Novel iron complexes bearing N6-substituted adenosine derivatives: synthesis, magnetic, 57Fe Mössbauer, DFT, and in vitro cytotoxicity studies.

    abstract：:Iron complexes (1-7) involving N6-benzyladenosine derivatives of the predominant composition [Fe(L(n))Cl(3)].H(2)O {where L(1)=N6-(2-fluorobenzyl)adenosine (1), L(2)=N6-(4-fluorobenzyl)adenosine (2), L(3)=N6-(2-trifluoromethylbenzyl)adenosine (3), L(4)=N6-(3-trifluoromethylbenzyl)adenosine (4), L(5)=N6-(4-trifluoromet...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.07.082

    authors： Trávnícek Z,Mikulík J,Cajan M,Zboril R,Popa I

    更新日期：2008-09-15 00:00:00