当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY LETTERS期刊下所有文献 > The mechanism of the irreversible inhibition of estrone sulfatase (ES) through the consideration of a range of methane- and amino-sulfonate-based compounds.

The mechanism of the irreversible inhibition of estrone sulfatase (ES) through the consideration of a range of methane- and amino-sulfonate-based compounds.

Abstract：

:We report the results of our study into a series of simple phenyl and alkyl sulfamates and alkyl methanesulfonates as potential inhibitors of the enzyme estrone sulfatase (ES). The results of the study show that the substituted phenyl sulfamates are good irreversible inhibitors; the alkyl sulfamate compounds were found to lack inhibitory activity; whilst the large alkyl chain containing methanesulfonate-based compounds were found to possess weak reversible inhibitory activity. Using the results of the inhibition study, we postulate the probable mechanism for ES and suggest that an attack by the gem-diol is a major requirement prior to the hydrolysis of the sulfamate group, following which, attack on the active site C=O occurs and which therefore leads to the production of an imine type functionality, resulting in irreversible inhibition.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Ahmed S,James K,Owen CP,Patel CK,Sampson L

doi

10.1016/s0960-894x(02)00137-3

subject

Has Abstract

pub_date

2002-05-06 00:00:00

pages

1279-82

issue

9

eissn

0960-894X

issn

1464-3405

pii

S0960894X02001373

journal_volume

12

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS文献大全
  • Pyrazole NNRTIs 1: design and initial optimisation of a novel template.

    abstract：:The design and synthesis of a novel series of non-nucleoside HIV reverse transcriptase inhibitors (NNRTIs) based on a pyrazole template is described. These compounds are active against wild type reverse transcriptase (RT) and retain activity against clinically important mutants. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2009.08.039

    authors： Mowbray CE,Burt C,Corbau R,Perros M,Tran I,Stupple PA,Webster R,Wood A

    更新日期：2009-10-01 00:00:00

  • Bicyclo[3.2.1]octanes: synthesis and inhibition of binding at the dopamine and serotonin transporters.

    abstract：:Herein we report the synthesis of a series of bicyclo[3.2.1]octanes and their binding characteristics at the dopamine and serotonin transporters. The data confirm that a heteroatom at position 8 of the tropane nucleus is not a prerequisite for binding since the bicyclo[3.2.1]octanes prove potent inhibitors of both tra...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(99)00098-0

    authors： Meltzer PC,Blundell P,Chen Z,Yong YF,Madras BK

    更新日期：1999-03-22 00:00:00

  • Design, synthesis and antimalarial activity of benzene and isoquinoline sulfonamide derivatives.

    abstract：:A new series of benzene and isoquinoline sulfonamide derivatives were synthesized by nucleophilic displacement reaction on benzene and isoquinoline sulfonyl chlorides by substituted amines (primary and secondary). The title compounds were evaluated for antimalarial activity against Plasmodium falciparum in vitro and s...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2007.11.038

    authors： Kumar Parai M,Panda G,Srivastava K,Kumar Puri S

    更新日期：2008-01-15 00:00:00

  • Synthesis, characterization, and cellular localization of a fluorescent probe of the antimalarial 8-aminoquinoline primaquine.

    abstract：:Primaquine (PQ) is the only commercially available drug that clears dormant liver stages of malaria and blocks transmission to mosquito vectors. Although an old drug, much remains to be known about the mechanism(s) of action. Herein we develop a fluorescent tagged PQ to discover cellular localization in the human mala...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2017.09.030

    authors： McQueen A,Blake LD,Azhari A,Kemp MT,McGaha TW Jr,Namelikonda N,Larsen RW,Manetsch R,Kyle DE

    更新日期：2017-10-15 00:00:00

  • Synthesis and pharmacological evaluation of N-substituted 2-(2-oxo-2H-chromen-4-yloxy)propanamide as cyclooxygenase inhibitors.

    abstract：:A series of novel N-substituted 2-(2-oxo-2H-chromen-4-yloxy)propanamide derivatives were synthesized via converting the readily available 4-hydroxy coumarin to the corresponding ethyl 2-(2-oxo-2H-chromen-4-yloxy)propanoate followed by hydrolysis and then reacting with different substituted amines. The molecular struct...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2012.08.082

    authors： Rambabu D,Mulakayala N,Ismail,Kumar KR,Kumar GP,Mulakayala C,Kumar CS,Kalle AM,Rao MV,Oruganti S,Pal M

    更新日期：2012-11-01 00:00:00

  • An amide-based sulfenamide prodrug of gamma secretase inhibitor BMS-708163 delivers parent drug from an oral conventional solid dosage form in male beagle dog.

    abstract：:The objective of this Letter is to report the first (to our knowledge) in vivo proof of concept for a sulfenamide prodrug to orally deliver a poorly soluble drug containing a weakly-acidic NH-acid from a conventional solid dosage formulation. This proof of concept was established using BMS-708163 (1), a gamma secretas...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2019.126856

    authors： Guarino VR,Olson RE,Everlof JG,Wang N,McDonald I,Haskell R,Clarke W,Lentz KA

    更新日期：2020-02-01 00:00:00

  • Polycyclic aromatic compounds as anticancer agents: synthesis and biological evaluation of some chrysene derivatives.

    abstract：:Synthesis and biological evaluation of new chrysene derivatives aimed at the development of anticancer agents were carried out. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(98)00520-4

    authors： Becker FF,Banik BK

    更新日期：1998-10-20 00:00:00

  • Isoxazole carboxylic acids as protein tyrosine phosphatase 1B (PTP1B) inhibitors.

    abstract：:Guided by X-ray crystallography, we have extended the structure-activity relationship (SAR) study on an isoxazole carboxylic acid-based PTP1B inhibitor (1) and more potent and equally selective (>20-fold selectivity over the highly homologous T-cell PTPase, TCPTP) PTP1B inhibitors were identified. Inhibitor 7 demonstr...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2004.08.063

    authors： Zhao H,Liu G,Xin Z,Serby MD,Pei Z,Szczepankiewicz BG,Hajduk PJ,Abad-Zapatero C,Hutchins CW,Lubben TH,Ballaron SJ,Haasch DL,Kaszubska W,Rondinone CM,Trevillyan JM,Jirousek MR

    更新日期：2004-11-15 00:00:00

  • Discovery of a novel class of non-ATP site DFG-out state p38 inhibitors utilizing computationally assisted virtual fragment-based drug design (vFBDD).

    abstract：:Discovery of a new class of DFG-out p38α kinase inhibitors with no hinge interaction is described. A computationally assisted, virtual fragment-based drug design (vFBDD) platform was utilized to identify novel non-aromatic fragments which make productive hydrogen bond interactions with Arg 70 on the αC-helix. Molecule...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2011.09.078

    authors： Moffett K,Konteatis Z,Nguyen D,Shetty R,Ludington J,Fujimoto T,Lee KJ,Chai X,Namboodiri H,Karpusas M,Dorsey B,Guarnieri F,Bukhtiyarova M,Springman E,Michelotti E

    更新日期：2011-12-01 00:00:00

  • Identification of blapsins A and B as potent small-molecule 14-3-3 inhibitors from the insect Blaps japanensis.

    abstract：:In this study, we report three novel naturally occurring compounds, blapsins A (1) and B (2), and blapsamide (3) from the ethanol extract of the stink beetle, Blaps japanensis. The structures of these compounds were determined using spectroscopic methods. Compound 3 is a phenolic compound bearing a formamido group in ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2012.04.027

    authors： Yan YM,Dai HQ,Du Y,Schneider B,Guo H,Li DP,Zhang LX,Fu H,Dong XP,Cheng YX

    更新日期：2012-06-15 00:00:00

  • Site-specific effect of polar functional group-modification in lipids of TLR2 ligands for modulating the ligand immunostimulatory activity.

    abstract：:Toll-like receptor 2 (TLR2), a member of the TLR innate immune receptor family, recognizes lipoproteins from bacteria and modulates the immune response by inducing the expression of various cytokines. TLR2 has a large hydrophobic pocket that recognizes long fatty acyl groups on TLR2 ligands. However, few studies have ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2018.03.042

    authors： Arai Y,Inuki S,Fujimoto Y

    更新日期：2018-05-15 00:00:00

  • Uridine phosphorylase inhibitors: chemical modification of benzyloxybenzyl-barbituric acid and its effects on urdpase inhibition.

    abstract：:5-(o-Benzyloxy)benzylbarbituric acid (6) and 5-(p-benzyloxy)benzylbarbituric acid (7) were prepared and their inhibitory activities compared to 5-(m-benzyloxy)-benzylbarbituric acid (BBB) a known, potent inhibitor of uridine phosphorylase (UrdPase). Compounds 6 and 7 were 18-fold and 51-fold less active, respectively,...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(99)00238-3

    authors： Guerin DJ,Mazeas D,Musale MS,Naguib FN,Al Safarjalani ON,el Kouni MH,Panzica RP

    更新日期：1999-06-07 00:00:00

  • 4,4,14 alpha-trimethyl 9 beta,19-cyclo-5 alpha-26-homocholesta-24,26-dien-3 beta-ol: a potent mechanism-based inactivator of delta 24(25)- to delta 25(27)-sterol methyl transferase.

    abstract：:The title compound (4A) was synthesized and tested as a mechanism-based inactivator of the sterol methyl transferase (SMT) enzyme from Prototheca wickerhamii. Using cycloartenol as substrate, 4A was found to exhibit time-dependent inactivation kinetics, generating a Ki value of 30 microM and Kinact value of 0.30 min-1...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(98)00651-9

    authors： Nes WD,He L,Mangla AT

    更新日期：1998-12-15 00:00:00

  • A novel approach toward bacteriochlorophylls-e and f.

    abstract：:Methyl bacteriopheophorbide-f was prepared from methyl bacteriopheophorbide-d with retention of the 3(1)-chirality. The transformation of the methyl to the formyl group at the 7-position of the chlorin moiety will provide an alternative route for the synthesis of bacteriochlorophylls-e and f. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(99)00258-9

    authors： Tamiaki H,Omoda M,Kubo M

    更新日期：1999-06-21 00:00:00

  • pH-Dependant fluorescence switching of an i-motif structure incorporating an isomeric azobenzene/pyrene fluorophore.

    abstract：:In this study, we synthesized an Azo-py phosphoramidite, featuring azobenzene and pyrene units, as a novel fluorescent and isomeric (trans- and cis-azobenzene units) material, which we incorporated in an i-motif DNA sequence. We then monitored the structural dynamics and changes in fluorescence as the modified DNA seq...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2017.04.015

    authors： Joo HN,Van Thi Nguyen T,Chae HK,Seo YJ

    更新日期：2017-06-01 00:00:00

  • Synthesis of VS-105: A novel and potent vitamin D receptor agonist with reduced hypercalcemic effects.

    abstract：:We have synthesized a novel vitamin D receptor agonist VS-105 ((1R,3R)-5-((E)-2-((3αS,7αS)-1-((R)-1-((S)-3-hydroxy-2,3-dimethylbutoxy)ethyl)-7α-methyldihydro-1H-inden-4(2H,5H,6H,7H,7αH)-ylidene)ethylidene)-2-methylenecyclohexane-1,3-diol). Preparation of a-ring phenylphosphine oxide 11, followed by Wittig-Horner coupl...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2013.08.076

    authors： Chen B,Kawai M,Wu-Wong JR

    更新日期：2013-11-01 00:00:00

  • A novel approach to the synthesis of cytotoxic C2-C3 unsaturated pyrrolo[2,1-c]benzodiazepines (PBDs) with conjugated acrylyl C2-substituents.

    abstract：:A concise synthesis of three novel C2-C3 unsaturated pyrrolo[2,1-c][1,4]benzodiazepine analogues (18-20) containing conjugated acrylyl C2-substituents is reported that utilises Heck coupling to install the C2-acrylyl side chains. These analogues possess significant cytotoxicity according to the NCI 60-cell line screen...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2003.12.094

    authors： Chen Z,Gregson SJ,Howard PW,Thurston DE

    更新日期：2004-03-22 00:00:00

  • Synthesis and neurotrophic activity of nonimmunosuppressant cyclosporin A derivatives.

    abstract：:In order to exploit cyclophilin as a potential target for neurological drug design, we demonstrate in this presentation that several nonimmunosuppressant analogues of cyclosporin A, modified at the various positions in the 'effector' domain, are equipotent nerve growth agents compared to cyclosporin A. Our results sug...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2004.06.028

    authors： Wei L,Steiner JP,Hamilton GS,Wu YQ

    更新日期：2004-09-06 00:00:00

  • Advances toward new antidepressants beyond SSRIs: 1-aryloxy-3-piperidinylpropan-2-ols with dual 5-HT1A receptor antagonism/SSRI activities. Part 5.

    abstract：:A series of 1-aryloxy-3-piperidinylpropan-2-ols possessing potent dual 5-HT1A receptor antagonism and serotonin reuptake inhibition was discovered. 1-(1H-Indol-4-yloxy)-3-(4-benzo[b]thiophen-2-ylpiperidinyl)propan-2-ols exhibited selective and high affinities at the 5-HT1A receptor and serotonin reuptake site in vitro...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2005.11.007

    authors： Takeuchi K,Kohn TJ,Honigschmidt NA,Rocco VP,Spinazze PG,Hemrick-Luecke SK,Thompson LK,Evans DC,Rasmussen K,Koger D,Lodge D,Martin LJ,Shaw J,Threlkeld PG,Wong DT

    更新日期：2006-05-01 00:00:00

  • Synthesis and evaluation of imidazo[1,5-a]pyrazines as corticotropin releasing hormone receptor ligands.

    abstract：:A novel series of imidazo[1,5-a]pyrazines was synthesized and evaluated as corticotropin releasing hormone (CRH) receptor ligands. SAR studies focused primarily on dialkylamino side chain optimization. SAR of the aryl and small alkyl substituents was also explored. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(01)00741-7

    authors： Hartz RA,Gilligan PJ,Nanda KK,Tebben AJ,Fitzgerald LW,Miller K

    更新日期：2002-02-11 00:00:00

  • In vivo incorporation of an alkyne into proteins in Escherichia coli.

    abstract：:Using a genetic selection we identified mutants of the M. janaschii tyrosyl-tRNA synthetase that selectively charge an amber suppressor tRNA with para-propargyloxyphenylalanine in Escherichia coli. These evolved tRNA-synthetase pairs were used to site-specifically incorporate an alkynyl group into a protein, which was...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2004.12.065

    authors： Deiters A,Schultz PG

    更新日期：2005-03-01 00:00:00

  • Synthesis and antimicrobial activity of novel 5-aminoimidazole-4-carboxamidrazones.

    abstract：:A mild and simple method was developed to prepare a series of fifteen 5-aminoimidazole 4-carboxamidrazones, starting from the easily accessible 5-amino-4-cyanoformimidoyl imidazoles. The antimicrobial activity of these novel amidrazones was screened against Gram positive (Staphylococcus aureus) and Gram negative (Esch...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2014.08.025

    authors： Ribeiro AI,Gabriel C,Cerqueira F,Maia M,Pinto E,Sousa JC,Medeiros R,Proença MF,Dias AM

    更新日期：2014-10-01 00:00:00

  • Total synthesis and cytotoxic activities of longamide B, longamide B methyl ester, hanishin, and their analogues.

    abstract：:The marine alkaloids, longamide B (1), longamide B methyl ester (2), hanishin (3), and a series of non-naturally occurring analogues were synthesized in an efficient manner from inexpensive commercially available dl-aspartic acid dimethyl ester. The cytotoxicities of these natural products (1-3) and their analogues (9...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2015.11.069

    authors： Zhao DG,Ma YY,Peng W,Zhou AY,Zhang Y,Ding L,Du Z,Zhang K

    更新日期：2016-01-01 00:00:00

  • Copper dipicolinates as peptidomimetic ligands for the Src SH2 domain.

    abstract：:The introduction of copper chelates into peptide mimetics creates the Src SH2 binding ligands and paramagnetic complexes suitable for EPR studies of peptide protein interactions. The dipicolinic acid was attached to SH2 domain targeting fragments by two different linkers. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2004.06.018

    authors： Schmidt B,Jiricek J,Titz A,Ye G,Parang K

    更新日期：2004-08-16 00:00:00

  • Secoiridoid glucosides and related compounds from Syringa reticulata and their antioxidant activities.

    abstract：:A 70% EtOH extract from the bark of Syringareticulata has shown significant antioxidant activity. Chemical study on the extract resulted in the isolation of seventeen compounds (1-17), including a novel oleoside-type secoiridoid glucoside, reticuloside (1), and the structures were elucidated on the basis of extensive ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2011.08.089

    authors： Bi X,Li W,Sasaki T,Li Q,Mitsuhata N,Asada Y,Zhang Q,Koike K

    更新日期：2011-11-01 00:00:00

  • Trifluoromethyl ketones as inhibitors of histone deacetylase.

    abstract：:Trifluoromethyl ketones were found to be inhibitors of histone deacetylases (HDACs). Optimization of this series led to the identification of submicromolar inhibitors such as 20 that demonstrated antiproliferative effects against the HT1080 and MDA 435 cell lines. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(02)00754-0

    authors： Frey RR,Wada CK,Garland RB,Curtin ML,Michaelides MR,Li J,Pease LJ,Glaser KB,Marcotte PA,Bouska JJ,Murphy SS,Davidsen SK

    更新日期：2002-12-02 00:00:00

  • Molecular determinants for improved activity at PPARα: structure-activity relationship of pirinixic acid derivatives, docking study and site-directed mutagenesis of PPARα.

    abstract：:Peroxisome proliferator-activated receptors (PPARs) are attractive targets for the treatment of the metabolic syndrome. Especially a combination of PPARα and PPARγ agonistic activity seems worthwhile to be pursued. Herein we present the design and synthesis of a series of pirinixic acid derivatives as potent PPARα par...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2014.05.058

    authors： Lamers C,Dittrich M,Steri R,Proschak E,Schubert-Zsilavecz M

    更新日期：2014-08-15 00:00:00

  • Praziquantel derivatives I: Modification of the aromatic ring.

    abstract：:Several analogues of the potent anthelmintic praziquantel were prepared with variation in the aromatic ring. The biological activity of these analogues was evaluated and compared against known analogues. Amination of the ring was tolerated while other variations were not. These results have important implications for ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2007.05.063

    authors： Ronketti F,Ramana AV,Chao-Ming X,Pica-Mattoccia L,Cioli D,Todd MH

    更新日期：2007-08-01 00:00:00

  • Identification of a new biaryl scaffold generating potent renin inhibitors.

    abstract：:The discovery and SAR of a series of potent renin inhibitors possessing a novel biaryl scaffold are described herein. Molecular modeling revealed that the cyclopropylamide spacer present in 1 can be replaced by a simple, substituted aromatic ring such as a toluene in 2. The resulting compounds exhibit subnanomolar ren...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2010.07.127

    authors： Lacombe P,Aspiotis R,Bayly C,Chen A,Dubé D,Fortin R,Gallant M,Juteau H,Liu S,McKay D,Roy P,Wu T

    更新日期：2010-10-01 00:00:00

  • Antiangiogenic properties of substituted (Z)-(±)-2-(N-benzylindol-3-ylmethylene)quinuclidin-3-ol/one analogs and their derivatives.

    abstract：:In the past half century research efforts have defined a critical role for angiogenesis in tumor growth and metastasis. We previously reported that inhibition of a novel target, ENOX1, by a (Z)-2-benzylindol-3-ylmethylene) quinuclidin-3-ol, suppressed tumor angiogenesis. The present study was undertaken in order to es...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2010.10.060

    authors： Venkateswaran A,Reddy YT,Sonar VN,Muthusamy V,Crooks PA,Freeman ML,Sekhar KR

    更新日期：2010-12-15 00:00:00