当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY期刊下所有文献 > Synthesis, induced-fit docking investigations, and in vitro aldose reductase inhibitory activity of non-carboxylic acid containing 2,4-thiazolidinedione derivatives.

Synthesis, induced-fit docking investigations, and in vitro aldose reductase inhibitory activity of non-carboxylic acid containing 2,4-thiazolidinedione derivatives.

Abstract：

:In continuation of our studies, we here report a series of non-carboxylic acid containing 2,4-thiazolidinedione derivatives, analogues of previously synthesized carboxylic acids which we had found to be very active in vitro aldose reductase (ALR2) inhibitors. Although the replacement of the carboxylic group with the carboxamide or N-hydroxycarboxamide one decreased the in vitro ALR2 inhibitory effect, this led to the identification of mainly non-ionized derivatives with micromolar ALR2 affinity. The 5-arylidene moiety deeply influenced the activity of these 2,4-thiazolidinediones. Our induced-fit docking studies suggested that 5-(4-hydroxybenzylidene)-substituted derivatives may bind the polar recognition region of the ALR2 active site by means of the deprotonated phenol group, while their acetic chain and carbonyl group at position 2 of the thiazolidinedione ring form a tight net of hydrogen bonds with amino acid residues of the lipophilic specificity pocket of the enzyme.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Maccari R,Ottanà R,Ciurleo R,Rakowitz D,Matuszczak B,Laggner C,Langer T

doi

10.1016/j.bmc.2008.04.072

subject

Has Abstract

pub_date

2008-06-01 00:00:00

pages

5840-52

issue

11

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(08)00417-3

journal_volume

16

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY文献大全
  • Study on the multiple mechanisms underlying the reaction between hydroxyl radical and phenolic compounds by qualitative structure and activity relationship.

    abstract：:The activity-structure relationships (ASR) of phenolic compounds as hydroxyl-radical scavengers have mostly been studied and discussed with regard to their iron-chelating and hydrogen-donation properties in Fenton-type system, but extensive elucidation of multiple mechanisms underlying the hydroxyl radical scavenging ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(02)00267-5

    authors： Cheng Z,Ren J,Li Y,Chang W,Chen Z

    更新日期：2002-12-01 00:00:00

  • Medicinal attributes of pyrazolo[3,4-d]pyrimidines: a review.

    abstract：:Pyrazolopyrimidines are the fused heterocyclic ring systems which structurally resemble purines which prompted biological investigations to assess their potential therapeutic significance. They are known to play a crucial role in numerous disease conditions. The advent of their first bioactivity as adenosine antagonis...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.bmc.2013.07.027

    authors： Chauhan M,Kumar R

    更新日期：2013-09-15 00:00:00

  • DNA double helix destabilizing properties of cyclobisintercaland compounds and competition with a single strand binding protein.

    abstract：:The DNA helix destabilizing activity of a series of cyclobisintercaland compounds (CBIs) has been evaluated by measuring their ability to displace a 32P-labelled oligonucleotide primer (17-mer) hybridized to the single stranded DNA of M13. This destabilizing activity appears to be strongly dependent on the cyclic stru...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(99)00283-7

    authors： Teulade-Fichou MP,Fauquet M,Baudoin O,Vigneron JP,Lehn JM

    更新日期：2000-01-01 00:00:00

  • Studies on 6-chloro-5-(1-naphthyloxy)-2-(trifluoromethyl)-1H-benzimidazole/2-hydroxypropyl-β-cyclodextrin association: Characterization, molecular modeling studies, and in vivo anthelminthic activity.

    abstract：:The purpose of this work is to study the molecular association that occurs between 2-hydroxypropyl-β-cyclodextrin (HPβCD) and 6-chloro-5-(1-naphthyloxy)-2-(trifluoromethyl)-1H-benzimidazole (RCB20), an antiparasitic compound recently found by our research group, with poor aqueous solubility. The complex stability cons...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.12.015

    authors： Rojas-Aguirre Y,Yépez-Mulia L,Castillo I,López-Vallejo F,Soria-Arteche O,Hernández-Campos A,Castillo R,Hernández-Luis F

    更新日期：2011-01-15 00:00:00

  • Synthesis and structure-activity data of some new epibatidine analogues.

    abstract：:The high-pressure Diels-Alder reaction of N-carbomethyoxypyrroles and phenyl vinyl sulfone affords versatile intermediates for the palladium-catalyzed preparation of new epibatidine analogues. Structure-activity relationships of new epibatidine analogues are presented. High affinities of Ki = 0.81 and 2.6 nM for the [...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(98)00163-1

    authors： Seerden JP,Tulp MT,Scheeren HW,Kruse CG

    更新日期：1998-11-01 00:00:00

  • Design and synthesis of 6-fluoro-2-naphthyl derivatives as novel CCR3 antagonists with reduced CYP2D6 inhibition.

    abstract：:In our previous study on discovering novel types of CCR3 antagonists, we found a fluoronaphthalene derivative (1) that exhibited potent CCR3 inhibitory activity with an IC(50) value of 20 nM. However, compound 1 also inhibited human cytochrome P450 2D6 (CYP2D6) with an IC(50) value of 400 nM. In order to reduce its CY...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.08.006

    authors： Sato I,Morihira K,Inami H,Kubota H,Morokata T,Suzuki K,Iura Y,Nitta A,Imaoka T,Takahashi T,Takeuchi M,Ohta M,Tsukamoto S

    更新日期：2008-09-15 00:00:00

  • Synthesis and preliminary cytotoxicity study of glucuronide derivatives of CC-1065 analogues.

    abstract：:Glucuronide derivatives of CBI-bearing CC-1065 analogues have been synthesized, and their cytotoxicities tested against U937 leukemia cells. The new compounds show potent antitumor activity in vitro. Compounds 1 and 2, and their corresponding glucuronides 3 and 4 have IC(50) values of 0.6, 0.1, 1.4 and 0.6 nM, respect...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(02)00603-x

    authors： Wang Y,Yuan H,Wright SC,Wang H,Larrick JW

    更新日期：2003-04-03 00:00:00

  • Soft drugs--XIV. Synthesis and anticholinergic activity of soft phenylsuccinic analogs of methatropine.

    abstract：:Three soft drug analogs and a metabolite of methatropine based on phenylsuccinic structural moiety were synthesized and tested for activity. In an in vivo assay, the soft drugs were found to be two orders of magnitude less potent than methatropine while the carboxylate metabolite was found to be one order of magnitude...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(00)82119-7

    authors： Hammer RH,Gunes E,Kumar GN,Wu WM,Srinivasan V,Bodor NS

    更新日期：1993-09-01 00:00:00

  • Identification of 4-(2-furanyl)pyrimidin-2-amines as Janus kinase 2 inhibitors.

    abstract：:Janus kinases inhibitor is considered to have therapeutic potential for the treatment of oncology and immune-inflammatory diseases. Two series of 4-(2-benzofuranyl)pyrimidin-2-amine and 4-(4,5,6,7-tetrahydrofuro[3,2-c]pyridin-2-yl)pyrimidin-2-amine derivatives have been designed and synthesized. Primary SAR studies re...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2016.10.011

    authors： Wang Y,Huang W,Xin M,Chen P,Gui L,Zhao X,Tang F,Wang J,Liu F

    更新日期：2017-01-01 00:00:00

  • Mechanism-based inhibitors of serine proteases with high selectivity through optimization of S' subsite binding.

    abstract：:A series of mechanism-based inhibitors designed to interact with the S' subsites of serine proteases was synthesized and their inhibitory activity toward the closely-related serine proteases human neutrophil elastase (HNE) and proteinase 3 (PR 3) was investigated. The compounds were found to be time-dependent inhibito...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.04.011

    authors： Li Y,Dou D,He G,Lushington GH,Groutas WC

    更新日期：2009-05-15 00:00:00

  • Synthesis and insecticidal activity of chromanone and chromone analogues of diacylhydrazines.

    abstract：:Diacylhydrazine derivatives have been identified as one of the most important insect growth regulators. A variety of diacylhydrazine derivatives were designed and synthesized in recent years due to their unique action mechanism, simple structure, and environmental benign character. This paper describes the molecular d...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.01.008

    authors： Zhao PL,Li J,Yang GF

    更新日期：2007-03-01 00:00:00

  • Synthesis and in vivo evaluation of [O-methyl-11C] N-[3,5-dichloro-2-(methoxy)phenyl]-4-(methoxy)-3-(1-piperazinyl)benzenesulfonamide as an imaging probe for 5-HT6 receptors.

    abstract：:The serotonin receptor 6 (5-HT(6)) is implicated in the pathophysiology of cognitive diseases, schizophrenia, anxiety and obesity and in vivo studies of this receptor would be of value for studying the pathophysiology of these disorders. Therefore, N-[3,5-dichloro-2-(methoxy)phenyl]-4-(methoxy)-3-(1-piperazinyl)benzen...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2011.06.090

    authors： Liu F,Majo VJ,Prabhakaran J,Milak MS,John Mann J,Parsey RV,Kumar JS

    更新日期：2011-09-01 00:00:00

  • Covalent inhibition of SUMO and ubiquitin-specific cysteine proteases by an in situ thiol-alkyne addition.

    abstract：:Posttranslational modification of proteins with ubiquitin and ubiquitin-like modifiers such as SUMO can be reverted by specific proteases, also referred to as deubiquitinases and isopeptidases, most of which are cysteine-dependent. We have found that the replacement of the conserved C-terminal glycine with propargylam...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2013.02.039

    authors： Sommer S,Weikart ND,Linne U,Mootz HD

    更新日期：2013-05-01 00:00:00

  • Zinc(II) complexes of the second-generation quinolone antibacterial drug enrofloxacin: Structure and DNA or albumin interaction.

    abstract：:Zinc mononuclear complexes with the second-generation quinolone antibacterial drug enrofloxacin in the absence or presence of a nitrogen donor heterocyclic ligand 1,10-phenanthroline or 2,2'-bipyridine have been synthesized and characterized. Enrofloxacin is on deprotonated mode acting as a bidentate ligand coordinate...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.02.021

    authors： Tarushi A,Raptopoulou CP,Psycharis V,Terzis A,Psomas G,Kessissoglou DP

    更新日期：2010-04-01 00:00:00

  • Inhibitory effects of flavonol glycosides from Cinnamomum osmophloeum on inflammatory mediators in LPS/IFN-gamma-activated murine macrophages.

    abstract：:Four kaempferol glycosides were isolated from the leaves of Cinnamomum osmophloeum Kaneh, a Taiwan endemic tree. These compounds namely, kaempferitrin (1), kaempferol 3-O-beta-D-glucopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-7-O-alpha-L-rhamnopyranoside (2), kaempferol 3-O-beta-D-apiofuranosyl-(1-->2)-alpha-L-arabinof...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2005.01.050

    authors： Fang SH,Rao YK,Tzeng YM

    更新日期：2005-04-01 00:00:00

  • Synthesis and structure-activity relationships of potent 4-fluoro-2-cyanopyrrolidine dipeptidyl peptidase IV inhibitors.

    abstract：:Dipeptidyl peptidase IV (DPP-IV) inhibitors are promising antidiabetic drugs, and several drugs are in the developmental stage. We previously reported that the introduction of fluorine to the 4-position of 2-cyanopyrrolidine enhanced the DPP-IV inhibitory effect. In the present report, we examined the structure-activi...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.01.016

    authors： Fukushima H,Hiratate A,Takahashi M,Mikami A,Saito-Hori M,Munetomo E,Kitano K,Chonan S,Saito H,Suzuki A,Takaoka Y,Yamamoto K

    更新日期：2008-04-01 00:00:00

  • Effect of the complexation with cyclodextrins on the in vitro antiviral activity of ganciclovir against human cytomegalovirus.

    abstract：:The toxicity of the molecules currently used in the treatment of human cytomegalovirus (HCMV) in immunocompromised hosts often causes interruption of the therapy. Cyclodextrins (Cds), oligosaccharides possessing a hydrophobic cavity, have the property of forming inclusion complexes with a great number of molecules, im...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(00)00247-9

    authors： Nicolazzi C,Abdou S,Collomb J,Marsura A,Finance C

    更新日期：2001-02-01 00:00:00

  • Phosphoenolpyruvate as a dual purpose reagent for integrated nucleotide/nicotinamide cofactor recycling.

    abstract：:An efficient technique is presented which integrates cofactor dependent enzymic phosphorylation and dehydrogenation into a single, closed-loop system by employing phosphoenolpyruvate as the sacrificial reagent for sequential ATP and NAD+ recycling steps. Exemplary applications are developed for the synthesis of 6-phos...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/0968-0896(94)85012-7

    authors： Fessner WD,Sinerius G

    更新日期：1994-07-01 00:00:00

  • Pyrrolomycins as antimicrobial agents. Microwave-assisted organic synthesis and insights into their antimicrobial mechanism of action.

    abstract：:New compounds able to counteract staphylococcal biofilm formation are needed. In this study we investigate the mechanism of action of pyrrolomycins, whose potential as antimicrobial agents has been demonstrated. We performed a new efficient and easy method to use microwave organic synthesis suitable for obtaining pyrr...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2019.01.010

    authors： Raimondi MV,Listro R,Cusimano MG,La Franca M,Faddetta T,Gallo G,Schillaci D,Collina S,Leonchiks A,Barone G

    更新日期：2019-03-01 00:00:00

  • 1,2,3-Selenadiazole thioacetanilides: synthesis and anti-HIV activity evaluation.

    abstract：:The development of new HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) offers the possibility of generating novel structures of increased potency. Based on the bioisosteric principle, novel series of 1,2,3-selenadiazole thioacetanilide derivatives were designed, and synthesized using an original synthet...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.07.027

    authors： Zhan P,Liu X,Fang Z,Pannecouque C,De Clercq E

    更新日期：2009-09-01 00:00:00

  • Allosteric kidney-type glutaminase (GLS) inhibitors with a mercaptoethyl linker.

    abstract：:A series of allosteric kidney-type glutaminase (GLS) inhibitors possessing a mercaptoethyl (SCH2CH2) linker were synthesized in an effort to further expand the structural diversity of chemotypes derived from bis-2-(5-phenylacetamido-1,3,4-thiadiazol-2-yl)ethyl sulfide (BPTES), a prototype allosteric inhibitor of GLS. ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2020.115698

    authors： Duvall B,Zimmermann SC,Gao RD,Thomas AG,Kalčic F,Veeravalli V,Elgogary A,Rais R,Rojas C,Le A,Slusher BS,Tsukamoto T

    更新日期：2020-10-15 00:00:00

  • Discovery and structural characterization of peficitinib (ASP015K) as a novel and potent JAK inhibitor.

    abstract：:Janus kinases (JAKs) are considered promising targets for the treatment of autoimmune diseases including rheumatoid arthritis (RA) due to their important role in multiple cytokine receptor signaling pathways. Recently, several JAK inhibitors have been developed for the treatment of RA. Here, we describe the identifica...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2018.08.005

    authors： Hamaguchi H,Amano Y,Moritomo A,Shirakami S,Nakajima Y,Nakai K,Nomura N,Ito M,Higashi Y,Inoue T

    更新日期：2018-10-01 00:00:00

  • Synthesis and preliminary biological evaluation of radiolabeled 5-BDBD analogs as new candidate PET radioligands for P2X4 receptor.

    abstract：:P2X4 receptor has become an interesting molecular target for treatment and PET imaging of neuroinflammation and associated brain diseases such as Alzheimer's disease. This study reports the first design, synthesis, radiolabeling and biological evaluation of new candidate PET P2X4 receptor radioligands using 5-BDBD, a ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.05.031

    authors： Wang M,Gao M,Meyer JA,Peters JS,Zarrinmayeh H,Territo PR,Hutchins GD,Zheng QH

    更新日期：2017-07-15 00:00:00

  • Synthesis and biological evaluation of nonpeptide mimetics of omega-conotoxin GVIA.

    abstract：:A benzothiazole-derived compound (4a) designed to mimic the C(alpha)-C(beta) bond vectors and terminal functionalities of Lys2, Tyr13 and Arg17 in omega-conotoxin GVIA was synthesised, together with analogues (4b-d), which had each side-chain mimic systematically truncated or eliminated. The affinity of these compound...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.05.040

    authors： Baell JB,Duggan PJ,Forsyth SA,Lewis RJ,Lok YP,Schroeder CI

    更新日期：2004-08-01 00:00:00

  • N-Alkenyl and cycloalkyl carbamates as dual acting histamine H3 and H4 receptor ligands.

    abstract：:Previous studies have shown that several imidazole derivatives possess affinity to histamine H(3) and H(4) receptors. Continuing our study on structural requirements responsible for affinity and selectivity for H(3)/H(4) receptor subtypes, two series of 3-(1H-imidazol-4-yl)propyl carbamates were prepared: a series of ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2011.03.046

    authors： Więcek M,Kottke T,Ligneau X,Schunack W,Seifert R,Stark H,Handzlik J,Kieć-Kononowicz K

    更新日期：2011-05-01 00:00:00

  • Synthesis and DNA binding studies of a new asymmetric cyanine dye binding in the minor groove of [poly(dA-dT)]2.

    abstract：:A new asymmetric cyanine dye has been synthesised and its interaction with different DNA has been investigated. In this dye, BEBO, the structure of the known intercalating cyanine dye BO has been extended with a benzothiazole substituent. The resulting crescent-shape of the molecule is similar to that of the well-know...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(02)00463-7

    authors： Karlsson HJ,Lincoln P,Westman G

    更新日期：2003-03-20 00:00:00

  • Three-dimensional molecular-field analyses of octopaminergic agonists for the cockroach neuronal octopamine receptor.

    abstract：:The quantitative structure-activity relationship of a set of 40 octopaminergic agonists against receptor 2 in cockroach nervous tissue, was analyzed using molecular-field analysis (MFA). MFA on the study set of those compounds evaluated effectively the energy between a probe and a molecular model at a series of points...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(03)00313-4

    authors： Hirashima A,Morimoto M,Kuwano E,Eto M

    更新日期：2003-08-15 00:00:00

  • Novel BACE1 inhibitors with a non-acidic heterocycle at the P1' position.

    abstract：:We have reported potent peptidic and non-peptidic BACE1 inhibitors with a hydroxymethylcarbonyl (HMC) isostere as a substrate transition-state mimic. However, our potent inhibitors possess a tetrazole ring at the P1' position. It is desirable that central nervous system (CNS) drugs do not possess an acidic moiety. In ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2013.08.016

    authors： Suzuki K,Hamada Y,Nguyen JT,Kiso Y

    更新日期：2013-11-01 00:00:00

  • Discovery of potent and selective PARP-1 and PARP-2 inhibitors: SBDD analysis via a combination of X-ray structural study and homology modeling.

    abstract：:We disclose herein our efforts aimed at discovery of selective PARP-1 and PARP-2 inhibitors. We have recently discovered several novel classes of quinazolinones, quinazolidinones, and quinoxalines as potent PARP-1 inhibitors, which may represent attractive therapeutic candidates. In PARP enzyme assays using recombinan...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2005.09.061

    authors： Ishida J,Yamamoto H,Kido Y,Kamijo K,Murano K,Miyake H,Ohkubo M,Kinoshita T,Warizaya M,Iwashita A,Mihara K,Matsuoka N,Hattori K

    更新日期：2006-03-01 00:00:00

  • Antimalarial and antiproliferative evaluation of bis-steroidal tetraoxanes.

    abstract：:Several cis and trans bis-steroidal 1,2,4,5-tetraoxanes possessing amide terminus were synthesised and evaluated as antimalarials and antiproliferatives. The compounds exhibited submicromolar antimalarial activity against Plasmodium falciparum D6 and W2 strains. The existence of HN-C(O) moiety was found necessary for ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(03)00224-4

    authors： Opsenica D,Angelovski G,Pocsfalvi G,Juranić Z,Zizak Z,Kyle D,Milhous WK,Solaja BA

    更新日期：2003-07-03 00:00:00