当前位置： SCI文献检索 > JOURNAL OF MEDICINAL CHEMISTRY期刊下所有文献 > Structure-taste correlations in sweet dihydrochalcone, sweet dihydroisocoumarin, and bitter flavone compounds.

Structure-taste correlations in sweet dihydrochalcone, sweet dihydroisocoumarin, and bitter flavone compounds.

Abstract：

:The dihydrochalcone derivatives of the bitter flavonoids naringin and neohesperedin are intensely sweet. Phyllodulcin is as sweet as the dihydrochalcones with similar taste properties although its structure apparently resembles that of bitter flavanone or flavone. Multifaceted approaches, including X-ray crystal structure analysis, energy calculation, and structure comparison, have been employed to clarify the structure-taste correlations in these classes of compounds. In the crystal, naringin dihydrochalcone assumes a 'J'-shaped conformation with a fully-extended dihydrochalcone moiety while neohesperidin dihydrochalcone assumes the same overall conformation but with a partially-extended moiety. A 2D conformational energy map of dihydrochalcone obtained using molecular mechanics revealed nine local minima. The pseudoequatorial and pseudoaxial forms of phyllodulcin have the same AM1 energies with a low energy barrier between them. The partially-extended form of dihydrochalcone and the pseudoequatorial form of phyllodulcin which are the maximally superposable conformers are proposed to be the active conformers. The major difference between the structures of flavone and phyllodulcin is not in the overall planarity but in the relative orientation of the pyrone and phenyl ring systems.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Shin W,Kim SJ,Shin JM,Kim SH

doi

10.1021/jm00021a022

subject

Has Abstract

pub_date

1995-10-13 00:00:00

pages

4325-31

issue

21

eissn

0022-2623

issn

1520-4804

journal_volume

38

pub_type

杂志文章

相关文献

JOURNAL OF MEDICINAL CHEMISTRY文献大全
  • Methylene-gem-difluorocyclopropane analogues of nucleosides: synthesis, cyclopropene-methylenecyclopropane rearrangement, and biological activity.

    abstract：:Alkylation-elimination of adenine and 2-amino-6-chloropurine with gem-difluorocyclopropane dibromide 10 gave E- and Z-methylene-gem-difluorocyclopropanes 11a, 11b, 12a, and 12b and gem-difluorocyclopropenes 13a and 13b. Debenzylation of intermediates 11a, 11b, 12a, and 12b afforded E- and Z-methylenecyclopropanes 4a, ...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm010191w

    authors： Wang R,Ksebati MB,Corbett TH,Kern ER,Drach JC,Zemlicka J

    更新日期：2001-11-08 00:00:00

  • Nontoxic Metal-Cyclam Complexes, a New Class of Compounds with Potency against Drug-Resistant Mycobacterium tuberculosis.

    abstract：:Tuberculosis (TB) accounted for 1.5 million deaths in 2014, and new classes of anti-TB drugs are required. We report a class of functionalized 1,8-disubstituted cyclam derivatives that display low micromolar activity against pathogenic mycobacteria. These compounds inhibit intracellular growth of Mycobacterium tubercu...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/acs.jmedchem.6b00432

    authors： Yu M,Nagalingam G,Ellis S,Martinez E,Sintchenko V,Spain M,Rutledge PJ,Todd MH,Triccas JA

    更新日期：2016-06-23 00:00:00

  • SAR Exploration of Tight-Binding Inhibitors of Influenza Virus PA Endonuclease.

    abstract：:Significant efforts have been reported on the development of influenza antivirals including inhibitors of the RNA-dependent RNA polymerase PA N-terminal (PAN) endonuclease. Based on recently identified, highly active metal-binding pharmacophores (MBPs) for PAN endonuclease inhibition, a fragment-based drug development...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/acs.jmedchem.9b00747

    authors： Credille CV,Morrison CN,Stokes RW,Dick BL,Feng Y,Sun J,Chen Y,Cohen SM

    更新日期：2019-11-14 00:00:00

  • Indanylacetic acid derivatives carrying 4-thiazolyl-phenoxy tail groups, a new class of potent PPAR alpha/gamma/delta pan agonists: synthesis, structure-activity relationship, and in vivo efficacy.

    abstract：:Compounds that simultaneously activate the three peroxisome proliferator-activated receptor (PPAR) subtypes alpha, gamma, and delta hold potential to address the adverse metabolic and cardiovascular conditions associated with diabetes and the metabolic syndrome. We recently identified the indanylacetic acid moiety as ...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm061299k

    authors： Rudolph J,Chen L,Majumdar D,Bullock WH,Burns M,Claus T,Dela Cruz FE,Daly M,Ehrgott FJ,Johnson JS,Livingston JN,Schoenleber RW,Shapiro J,Yang L,Tsutsumi M,Ma X

    更新日期：2007-03-08 00:00:00

  • Synthesis and biological evaluation of chiral alpha-aminoanilides with central antinociceptive activity.

    abstract：:Tocainide and related optically active chiral alpha-aminoanilides were synthesized and tested in vivo via the hot plate test to evaluate their central analgesic action. The aims of the study were to verify if a) the increase in lipophilicity, obtained by the introduction of an alkyl group on the steric center (3f-i), ...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm061078e

    authors： Corbo F,Franchini C,Lentini G,Muraglia M,Ghelardini C,Matucci R,Galeotti N,Vivoli E,Tortorella V

    更新日期：2007-04-19 00:00:00

  • Identification and characterization of small molecule inhibitors of a class I histone deacetylase from Plasmodium falciparum.

    abstract：:A library of approximately 2000 small molecules biased toward inhibition of histone deacetylases was assayed for antimalarial activity in a high-throughput P. falciparum viability assay. Active compounds were cross-analyzed for induction of histone hyperacetylation in a human myeloma cell line to identify HDAC inhibit...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm801654y

    authors： Patel V,Mazitschek R,Coleman B,Nguyen C,Urgaonkar S,Cortese J,Barker RH,Greenberg E,Tang W,Bradner JE,Schreiber SL,Duraisingh MT,Wirth DF,Clardy J

    更新日期：2009-04-23 00:00:00

  • Optical resolution of (+/-)-2,5-dimethyl-2'-hydroxy-9alpha- and -9beta-propyl-6,7-benzomorphans and their pharmacological properties.

    abstract：:The levo and dextro isomers of 2,5-dimethyl-2'-hydroxy-9alpha- and -9beta-propyl-6,7-benzomorphans have been prepared. The analgesic potency and physical dependence capacity of the optical isomers and their racemic parents were determined. The 9alpha-propyl levo isomer was analgesically equipotent with morphine; the 9...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm00225a021

    authors： Rice KC,Jacobson AE

    更新日期：1976-03-01 00:00:00

  • Conjugates of gadolinium complexes to bile acids as hepatocyte-directed contrast agents for magnetic resonance imaging.

    abstract：:A series of structurally different Gd(III) conjugates incorporating a bile acid moiety have been prepared. Polyaminopolycarboxylic ligands such as diethylenetriaminepentaacetic acid (DTPA) and 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetracetic acid (DOTA) have been selected as chelating subunit for the Gd(III) ion. Ch...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm0310683

    authors： Anelli PL,Lattuada L,Lorusso V,Lux G,Morisetti A,Morosini P,Serleti M,Uggeri F

    更新日期：2004-07-01 00:00:00

  • Effect of reductive alkylation of lysine in positions 6 and/or 8 on the histamine-releasing activity of luteinizing hormone-releasing hormone antagonists.

    abstract：:The solid-phase reductive alkylation of the Lys side chain in positions 6 (D) and 8 (L) and position 8 alone of the LH-RH antagonist [N-Ac-D-Nal,D-Ph2,3,D-Arg6,Phe7,D-Ala10]LH-RH was investigated in an attempt to reduce the histamine-releasing activity inherent to most potent antagonists while retaining high antiovula...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm00393a038

    authors： Hocart SJ,Nekola MV,Coy DH

    更新日期：1987-10-01 00:00:00

  • Synthesis and antiarrhythmic activity of novel 3-alkyl-1-[omega-[4-[(alkylsulfonyl)amino]phenyl]-omega- hydroxyalkyl]-1H-imidazolium salts and related compounds. 2.

    abstract：:Novel analogues of the class III antiarrhythmic agent 1-[2-hydroxy-2-[4-[(methylsulfonyl)amino]phenyl]ethyl]-3-methyl-1H- imidazolium chloride, 1 (CK-1649), were prepared and investigated for their class III electrophysiological activity on isolated canine cardiac Purkinje fibers and ventricular muscle tissue. Structu...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm00395a021

    authors： Lis R,Davey DD,Morgan TK Jr,Lumma WC Jr,Wohl RA,Jain VK,Wan CN,Argentieri TM,Sullivan ME,Cantor EH

    更新日期：1987-12-01 00:00:00

  • Subtlety of the structure-affinity and structure-efficacy relationships around a nonpeptide oxytocin receptor agonist.

    abstract：:Very few nonpeptide oxytocin agonists have currently been reported, and none of them seem suitable for the in vivo investigation of the oxytocin mediated functions. In an attempt to rationalize the design of better tools, we have systematically studied the structural determinants of the affinity and efficacy of repres...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm901084f

    authors： Frantz MC,Rodrigo J,Boudier L,Durroux T,Mouillac B,Hibert M

    更新日期：2010-02-25 00:00:00

  • Biophysical mapping of the adenosine A2A receptor.

    abstract：:A new approach to generating information on ligand receptor interactions within the binding pocket of G protein-coupled receptors has been developed, called Biophysical Mapping (BPM). Starting from a stabilized receptor (StaR), minimally engineered for thermostability, additional single mutations are then added at pos...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm2003798

    authors： Zhukov A,Andrews SP,Errey JC,Robertson N,Tehan B,Mason JS,Marshall FH,Weir M,Congreve M

    更新日期：2011-07-14 00:00:00

  • 3-Amino-beta-carboline derivatives and the benzodiazepine receptor. Synthesis of a selective antagonist of the sedative action of diazepam.

    abstract：:Seven 3-N-substituted derivatives of 3-amino-beta-carboline were synthesized and their affinities for the benzodiazepine receptor were assessed in vitro. Two compounds, 3-(ethylamino)-beta-carboline and 3-[(methoxycarbonyl)amino]-beta-carboline (beta-CMC), showing IC50 values of 460 and 71 nM, respectively, were selec...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm00383a024

    authors： Dodd RH,Ouannès C,de Carvalho LP,Valin A,Venault P,Chapouthier G,Rossier J,Potier P

    更新日期：1985-06-01 00:00:00

  • Iron-mediated generation of the neurotoxin 6-hydroxydopamine quinone by reaction of fatty acid hydroperoxides with dopamine: a possible contributory mechanism for neuronal degeneration in Parkinson's disease.

    abstract：:Exposure of dopamine to an excess of linoleic acid 13-hydroperoxide (13-hydroperoxyoctadecadienoic acid) in the presence of ferrous ions in Tris buffer, pH 7.4, resulted in a relatively fast, oxygen-independent reaction exhibiting first-order kinetics with respect to both catecholamine and metal concentrations. Produc...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm970099t

    authors： Pezzella A,d'Ischia M,Napolitano A,Misuraca G,Prota G

    更新日期：1997-07-04 00:00:00

  • Targeting the MKK7-JNK (Mitogen-Activated Protein Kinase Kinase 7-c-Jun N-Terminal Kinase) Pathway with Covalent Inhibitors.

    abstract：:The protein kinase MKK7 is linked to neuronal development and the onset of cancer. The field, however, lacks high-quality functional probes that would allow for the dissection of its detailed functions. Against this background, we describe an effective covalent inhibitor of MKK7 based on the pyrazolopyrimidine scaffol...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/acs.jmedchem.9b00102

    authors： Wolle P,Hardick J,Cronin SJF,Engel J,Baumann M,Lategahn J,Penninger JM,Rauh D

    更新日期：2019-03-14 00:00:00

  • Modulating retinoid X receptor with a series of (E)-3-[4-hydroxy-3-(3-alkoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)phenyl]acrylic acids and their 4-alkoxy isomers.

    abstract：:Rexinoids are ligands for the retinoid X receptor (RXR) that have great promise for both the prevention and treatment of cancer and metabolic diseases. In this regard, synthetic, functional, and structural investigations into the structure-activity relationships of derivatives of the potent RXR agonist (E)-3-[3-(3,5,5...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm900096q

    authors： Pérez Santín E,Germain P,Quillard F,Khanwalkar H,Rodríguez-Barrios F,Gronemeyer H,de Lera AR,Bourguet W

    更新日期：2009-05-28 00:00:00

  • Inhibition of MIF bioactivity by rational design of pharmacological inhibitors of MIF tautomerase activity.

    abstract：:The pro-inflammatory mediator macrophage migration inhibitory factor (MIF) is produced by immune and endocrine cells and inhibits the antiinflammatory activities of glucocorticoids. MIF also catalyzes the tautomerization of the non-naturally occurring D-isomer of dopachrome, phenylpyruvate, and certain catecholamines,...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm010534q

    authors： Dios A,Mitchell RA,Aljabari B,Lubetsky J,O'Connor K,Liao H,Senter PD,Manogue KR,Lolis E,Metz C,Bucala R,Callaway DJ,Al-Abed Y

    更新日期：2002-06-06 00:00:00

  • Novel arylsulfoanilide-oxindole hybrid as an anticancer agent that inhibits translation initiation.

    abstract：:Structure-activity relationship studies of substituted arylsulfoanilides as antiproliferatives, which are mediated by the partial depletion of intracellular Ca(2+) stores, resulted in the identification of compounds with micromolar activity against lung cancer cells in a growth inhibition assay. Incorporating the subs...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm0496234

    authors： Natarajan A,Guo Y,Harbinski F,Fan YH,Chen H,Luus L,Diercks J,Aktas H,Chorev M,Halperin JA

    更新日期：2004-10-07 00:00:00

  • Chemically stable N-methyl-4-(alkylthio)cyclophosphamide derivatives as prodrugs of 4-hydroxycyclophosphamide.

    abstract：:Two prototype N-methyl-4-thio-substituted cyclophosphamide (CP) derivatives (5 and 6), prodrugs of 4-hydroxycyclophosphamide (4-HO-CP), were designed to undergo oxidative N-demethylation to release the active alkylating agent. These prodrugs were chemically stable until oxidatively N-demethylated in the presence of he...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm00005a012

    authors： Moon KY,Shirota FN,Baturay N,Kwon CH

    更新日期：1995-03-03 00:00:00

  • 3-Phenyl-substituted imidazo[1,5-alpha]quinoxalin-4-ones and imidazo[1,5-alpha]quinoxaline ureas that have high affinity at the GABAA/benzodiazepine receptor complex.

    abstract：:A series of imidazo[1,5-alpha]quinoxalin-4-ones and imidazo[1,5-alpha]quinoxaline ureas containing substituted phenyl groups at the 3-position was developed. Compounds within the imidazo[1,5-alpha]quinoxaline urea series had high affinity for the GABAA/benzodiazepine receptor complex with varying in vitro efficacy, al...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm960070+

    authors： Jacobsen EJ,Stelzer LS,Belonga KL,Carter DB,Im WB,Sethy VH,Tang AH,VonVoigtlander PF,Petke JD

    更新日期：1996-09-13 00:00:00

  • A Computer Vision Approach to Align and Compare Protein Cavities: Application to Fragment-Based Drug Design.

    abstract：:Identifying local similarities in binding sites from distant proteins is a major hurdle to rational drug design. We herewith present a novel method, borrowed from computer vision, adapted to mine fragment subpockets and compare them to whole ligand-binding sites. Pockets are represented by pharmacophore-annotated poin...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/acs.jmedchem.0c00422

    authors： Eguida M,Rognan D

    更新日期：2020-07-09 00:00:00

  • Substituted 5,5'-diphenyl-2-thioxoimidazolidin-4-one as CB1 cannabinoid receptor ligands: synthesis and pharmacological evaluation.

    abstract：:A set of 30 substituted 5,5'-diphenyl-2-thioxoimidazolidin-4-one (thiohydantoins) derivatives was synthesized, and their affinity for the human CB(1) cannabinoid receptor has been evaluated. These compounds are derived from the previously described cannabinoid ligands 5,5'-diphenylimidazolidine-2,4-dione (hydantoins)....

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm049263k

    authors： Muccioli GG,Martin D,Scriba GK,Poppitz W,Poupaert JH,Wouters J,Lambert DM

    更新日期：2005-04-07 00:00:00

  • Design, synthesis, and structure--activity relationship studies for a new imidazole series of J774 macrophage specific acyl-CoA:cholesterol acyltransferase (ACAT) inhibitors.

    abstract：:Acyl-CoA:cholesterol acyltransferase (ACAT) is the primary enzyme involved in intracellular cholesterol esterification. Arterial wall infiltration by macrophages and subsequent uncontrolled esterification of cholesterol leading to foam cell formation is believed to be an important process which leads to the developmen...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm00007a004

    authors： Maduskuie TP Jr,Wilde RG,Billheimer JT,Cromley DA,Germain S,Gillies PJ,Higley CA,Johnson AL,Pennev P,Shimshick EJ

    更新日期：1995-03-31 00:00:00

  • Design and synthesis of orally bioavailable aminopyrrolidinone histone deacetylase 6 inhibitors.

    abstract：:Histone deacetylase 6 (HDAC6) removes the acetyl group from lysine residues in a number of non-histone substrates and plays important roles in microtubule dynamics and chaperone activities. There is growing interest in identifying HDAC6-selective inhibitors as chemical biology tools and ultimately as new therapeutic a...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm502011f

    authors： Lin X,Chen W,Qiu Z,Guo L,Zhu W,Li W,Wang Z,Zhang W,Zhang Z,Rong Y,Zhang M,Yu L,Zhong S,Zhao R,Wu X,Wong JC,Tang G

    更新日期：2015-03-26 00:00:00

  • Impact of the nature of the substituent at the 3-position of 4H-1,2,4-benzothiadiazine 1,1-dioxides on their opening activity toward ATP-sensitive potassium channels.

    abstract：:The synthesis of diversely substituted 3-isopropoxy-, 3-isopropylsulfanyl-, 3-isopropylsulfinyl-, and 3-isobutyl-4H-1,2,4-benzothiadiazine 1,1-dioxides is described. Their activity on pancreatic β-cells (inhibitory effect on the insulin releasing process) and on vascular and uterine smooth muscle tissues (myorelaxant ...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm200100c

    authors： Pirotte B,de Tullio P,Boverie S,Michaux C,Lebrun P

    更新日期：2011-05-12 00:00:00

  • Synthesis, structure-activity relationships, and biological profiles of a quinazolinone class of histamine H3 receptor inverse agonists.

    abstract：:A new series of quinazolinone derivatives was synthesized and evaluated as nonimidazole H 3 receptor inverse agonists. 2-Methyl-3-(4-[[3-(1-pyrrolidinyl)propyl]oxy]phenyl)-5-(trifluoromethyl)-4(3 H)-quinazolinone ( 1) was identified as a promising derivative for further evaluation following optimization of key paramet...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm8003834

    authors： Nagase T,Mizutani T,Ishikawa S,Sekino E,Sasaki T,Fujimura T,Ito S,Mitobe Y,Miyamoto Y,Yoshimoto R,Tanaka T,Ishihara A,Takenaga N,Tokita S,Fukami T,Sato N

    更新日期：2008-08-14 00:00:00

  • 6beta-Acyloxy(nor)tropanes: affinities for antagonist/agonist binding sites on transfected and native muscarinic receptors.

    abstract：:A series of esters of 6beta-hydroxynortropane and the N-methyl analogue 6beta-tropanol were synthesized and screened versus binding of an antagonist (quinuclidinyl benzilate) and an agonist (oxotremorine-M) at sites on human m(1)-, m(2)-, m(3)-, and m(4)-muscarinic receptors in transfected cell membranes and on native...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm9904001

    authors： Daly JW,Gupta TH,Padgett WL,Pei XF

    更新日期：2000-06-29 00:00:00

  • Nonsymmetrical bipiperidyls as inhibitors of vesicular acetylcholine storage.

    abstract：:Introduction of a nitrogen atom into the cyclohexane ring of 2-(4-phenylpiperidinyl)cyclohexanol (vesamicol, AH5183) yielded two positional isomers, 5-azavesamicol (5, prezamicol) and 4-azavesamicol (6, trozamicol). As inhibitors of vesicular acetylcholine transport, 5 and 6 were found to be 147 and 85 times less pote...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm00060a005

    authors： Efange SM,Khare A,Parsons SM,Bau R,Metzenthin T

    更新日期：1993-04-16 00:00:00

  • Bisphosphonate inhibition of phosphoglycerate kinase: quantitative structure-activity relationship and pharmacophore modeling investigation.

    abstract：:We report the results of a three-dimensional quantitative structure-activity relationship (3D-QSAR) and pharmacophore modeling investigation of the interaction of the enzyme 3-phosphoglycerate kinase (PGK) with aryl and alkyl bisphosphonates. For the human enzyme, the IC50 values are predicted within a factor of 2 ove...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm0604833

    authors： Kotsikorou E,Sahota G,Oldfield E

    更新日期：2006-11-16 00:00:00

  • Self-organizing maps for identification of new inhibitors of P-glycoprotein.

    abstract：:Self-organizing maps were trained to separate high- and low-active propafenone-type inhibitors of P-glycoprotein. The trained maps were subsequently used to identify highly active compounds in a virtual screen of the SPECS compound library. ...

    journal_title：Journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1021/jm060604z

    authors： Kaiser D,Terfloth L,Kopp S,Schulz J,de Laet R,Chiba P,Ecker GF,Gasteiger J

    更新日期：2007-04-05 00:00:00