当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY期刊下所有文献 > Anthranilic diamides derivatives as potential ryanodine receptor modulators: Synthesis, biological evaluation and structure activity relationship.

Anthranilic diamides derivatives as potential ryanodine receptor modulators: Synthesis, biological evaluation and structure activity relationship.

Abstract：

:A series of novel anthranilic diamides derivatives (7a-s) containing halogen, trifluoromethyl group and cyano group were designed, synthesized, and characterized by melting point, 1H NMR, 13C NMR and elemental analyses. The bioactivity revealed that most of them showed moderate to excellent activities against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella). Above all, the larvicidal activity of 7o against oriental armyworm was 100% and 40% at 0.25 and 0.1 mg L-1, comparable to that of the standard chlorantraniliprole (100%, 0.25 mg L-1 and 20%, 0.1 mg L-1). What is more, 7o against diamondback moth displayed 90% insecticidal activity at 0.01 mg L-1, superior to chlorantraniliprole (45%, 0.01 mg L-1). The experiments 7o on the American cockroach (Periplaneta Americana) heart beating rates (Dorsal vessel) and contractile force were compared with chlorantraniliprole. In addition, 7o could affect the calcium homeostasis in the central neurons of the third larvae of oriental armyworm, which revealed that the ryanodine receptor is the potential target of 7o. The density functional theory (DFT) calculation results revealed the amide bridge, the benzene ring of anthraniloyl moiety and pyrazole ring might play an important role in the insecticidal activity through hydrophobic interactions and π-π conjugations.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Liu JB,Li FY,Dong JY,Li YX,Zhang XL,Wang YH,Xiong LX,Li ZM

doi

10.1016/j.bmc.2018.05.028

subject

Has Abstract

pub_date

2018-07-23 00:00:00

pages

3541-3550

issue

12

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(18)30483-8

journal_volume

26

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY文献大全
  • 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 biological research of novel azaacridine derivatives as potent DNA-binding ligands and topoisomerase II inhibitors.

    abstract：:DNA and DNA-related enzymes are one of the most effective and common used intracellular anticancer targets in clinic and laboratory studies, however, most of DNA-targeting drugs suffered from toxic side effects. Development of new molecules with good antitumor activity and low side effects is important. Based on compu...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.04.030

    authors： Li D,Yuan Z,Chen S,Zhang C,Song L,Gao C,Chen Y,Tan C,Jiang Y

    更新日期：2017-07-01 00:00:00

  • Novel designed enediynes: molecular design, chemical synthesis, mode of cycloaromatization and guanine-specific DNA cleavage.

    abstract：:The molecular design and chemical synthesis of novel enediyne molecules related to the neocarzinostatin chromophore (1), and their chemical and DNA cleaving properties are described. The 10-membered enediyne triols 16-18 were effectively synthesized from xylitol (10) in a short step, and found to be quite stable when ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/0968-0896(95)00170-0

    authors： Toshima K,Ohta K,Kano T,Nakamura T,Nakata M,Kinoshita M,Matsumura S

    更新日期：1996-01-01 00:00:00

  • Large scale preparation of chiral building blocks for the P3 site of renin inhibitors.

    abstract：:Racemic ethyl 2-benzyl-3-(tert-butylsulfonyl)propionate (1) and racemic ethyl 2-benzyl-3-[[1-methyl-1-((morpholin-4-yl)carbonyl)ethyl]sulfonyl] propionate (3) were enantioselectively hydrolyzed by subtilisin Carlsberg generating the respective (S)-acids used as building blocks for renin inhibitors. The esters were rea...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/0968-0896(94)80007-3

    authors： Doswald S,Estermann H,Kupfer E,Stadler H,Walther W,Weisbrod T,Wirz B,Wostl W

    更新日期：1994-06-01 00:00:00

  • 3'-Hydroxy-3,4'-dimethoxyflavone blocks tubulin polymerization and is a potent apoptotic inducer in human SK-MEL-1 melanoma cells.

    abstract：:Flavonoids are naturally occurring polyphenolic compounds and are among the most promising anticancer agents. A series of flavonols and their 3-methyl ether derivatives were synthesized and assessed for cytotoxicity. It was found that 3'-hydroxy-3,4'-dimethoxyflavone (flavonoid 7a) displayed strong cytotoxicity agains...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.09.043

    authors： Estévez-Sarmiento F,Said M,Brouard I,León F,García C,Quintana J,Estévez F

    更新日期：2017-11-01 00:00:00

  • Design and synthesis of novel HDAC8 inhibitory 2,5-disubstituted-1,3,4-oxadiazoles containing glycine and alanine hybrids with anti cancer activity.

    abstract：:Oxadiazole is a heterocyclic compound containing an oxygen atom and two nitrogen atoms in a five-membered ring. Of the four oxadiazoles known, 1,3,4-oxadiazole has become an important structural motif for the development of new drugs and the compounds containing 1,3,4-oxadiazole cores have a broad spectrum of biologic...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2016.09.022

    authors： Pidugu VR,Yarla NS,Pedada SR,Kalle AM,Satya AK

    更新日期：2016-11-01 00:00:00

  • Radical scavenging and cytochrome P450 3A4 inhibitory activity of bergaptol and geranylcoumarin from grapefruit.

    abstract：:Grapefruit juice has been shown to increase the oral bioavailability of several clinically important drugs by inhibiting first pass metabolism. Several compounds in grapefruit juice have shown different biological activities. Unique among them are furocoumarins with potent inhibitory activity against cytochrome P450 e...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.03.047

    authors： Girennavar B,Jayaprakasha GK,Jadegoud Y,Nagana Gowda GA,Patil BS

    更新日期：2007-06-01 00:00:00

  • Synthesis of substituted diphenyl sulfones and their structure-activity relationship with the antagonism of 5-НТ6 receptors.

    abstract：:Substituted diphenyl sulfones (10a-n) were synthesised, and the structures were confirmed by NMR, LC-MS and X-ray crystallography. Their antagonistic activities towards 5-HT₆ receptor were assessed in a cell-based functional assay. Diphenyl sulfone 10a, in spite of being the smallest and simplest known sulfonyl-contai...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2013.05.040

    authors： Ivachtchenko A,Golovina E,Kadieva M,Mitkin O,Tkachenko S,Okun I

    更新日期：2013-08-01 00:00:00

  • Prospects of PASylation® for the design of protein and peptide therapeutics with extended half-life and enhanced action.

    abstract：:Pharmacokinetic (PK) extension is no longer just a means to create improved second generation biologics (so-called biobetters), but constitutes an accepted strategy in biopharmaceutical drug development today. Although PEGylation has become a widely applied methodology to furnish therapeutic proteins and peptides with...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.09.016

    authors： Gebauer M,Skerra A

    更新日期：2018-06-01 00:00:00

  • Fine tuning of agonistic/antagonistic activity for vitamin D receptor by 22-alkyl chain length of ligands: 22S-Hexyl compound unexpectedly restored agonistic activity.

    abstract：:1α,25-Dihydroxyvitamin D3 exerts its actions by binding to vitamin D receptor (VDR). We are continuing the study related to the alteration of pocket structure of VDR by 22-alkyl substituent of ligands and the relationships between the alteration and agonistic/antagonistic activity. Previously we reported that compound...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.10.026

    authors： Anami Y,Sakamaki Y,Itoh T,Inaba Y,Nakabayashi M,Ikura T,Ito N,Yamamoto K

    更新日期：2015-11-15 00:00:00

  • Acetyl analogs of combretastatin A-4: synthesis and biological studies.

    abstract：:The combretastatins have received significant attention because of their simple chemical structures, excellent antitumor efficacy and novel antivascular mechanisms of action. Herein, we report the synthesis of 20 novel acetyl analogs of CA-4 (1), synthesized from 3,4,5-trimethoxyphenylacetone that comprises the A ring...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2011.02.018

    authors： Babu B,Lee M,Lee L,Strobel R,Brockway O,Nickols A,Sjoholm R,Tzou S,Chavda S,Desta D,Fraley G,Siegfried A,Pennington W,Hartley RM,Westbrook C,Mooberry SL,Kiakos K,Hartley JA,Lee M

    更新日期：2011-04-01 00:00:00

  • A novel series of complexones with bis- or biazole structure as mixed ligands of paramagnetic contrast agents for MRI.

    abstract：:We describe the syntheses, physicochemical properties and biological evaluation of a novel series of complexones containing bis- or biazoles moieties and two iminodiacetic acid units as novel ligands for paramagnetic lanthanides. The complexones were prepared by reaction of the corresponding 1,1'-bishaloethylbi- or bi...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2003.07.002

    authors： Mayoral EP,García-Amo M,López P,Soriano E,Cerdán S,Ballesteros P

    更新日期：2003-12-01 00:00:00

  • Biaryl diacid inhibitors of human s-PLA2 with anti-inflammatory activity.

    abstract：:Twenty-four hydrophobic dicarboxylic acids are described which were evaluated as inhibitors of 14 kDa human platelet phospholipase A2 (HP-PLA2). In general, biarylacetic acid derivatives were found to be more active than biaryl acids or biarylpropanoic acids. More potent inhibitors were obtained when hydrophobic group...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(00)00047-x

    authors： Springer DM,Luh BY,Bronson JJ,McElhone KE,Mansuri MM,Gregor KR,Nettleton DO,Stanley PL,Tramposch KM

    更新日期：2000-05-01 00:00:00

  • Synthesis and antiprotozoal activity of dicationic 2,6-diphenylpyrazines and aza-analogues.

    abstract：:Dicationic 2,6-diphenylpyrazines, aza-analogues and prodrugs were synthesized; evaluated for DNA affinity, activity against Trypanosoma brucei rhodesiense (T. b. r.) and Plasmodium falciparum (P. f.) in vitro, efficacy in T. b. r. STIB900 acute and T. b. brucei GVR35 CNS mouse models. Most diamidines gave poly(dA-dT)2...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2013.08.006

    authors： Hu L,Patel A,Bondada L,Yang S,Wang MZ,Munde M,Wilson WD,Wenzler T,Brun R,Boykin DW

    更新日期：2013-11-01 00:00:00

  • The phytoalexins brassilexin and camalexin inhibit cyclobrassinin hydrolase, a unique enzyme from the fungal pathogen Alternaria brassicicola.

    abstract：:Alternaria brassicicola is a fungal pathogen of many agriculturally important cruciferous crops. Cyclobrassinin hydrolase (CH) is an enzyme produced by A. brassicicola that catalyzes the transformation of the cruciferous phytoalexin cyclobrassinin into S-methyl[(2-sulfanyl-1H-indolyl-3)methyl]carbamothioate. The purif...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2013.11.005

    authors： Pedras MS,Minic Z

    更新日期：2014-01-01 00:00:00

  • Synthesis of phenserine analogues and evaluation of their cholinesterase inhibitory activities.

    abstract：:Phenserine is a potentially attractive drug for Alzheimer's disease. In order to further expand SAR study for inhibitions of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), the methyl group at the 3a-position of phenserine was replaced with an alkyl or alkenyl group, and its phenylcarbamoyl moiety was s...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2012.06.048

    authors： Shinada M,Narumi F,Osada Y,Matsumoto K,Yoshida T,Higuchi K,Kawasaki T,Tanaka H,Satoh M

    更新日期：2012-08-15 00:00:00

  • Synthesis and biological evaluation of 1,1-dichloro-2,3-diarylcyclopropanes as antitubulin and anti-breast cancer agents.

    abstract：:Z-1,1-Dichloro-2,3-diphenylcyclopropane (1) is an effective anti-breast cancer agent in rodents and in cell culture. We recently determined that 1 inhibits tubulin assembly in vitro and causes microtubule loss in breast cancer cells, leading to accumulation in the G2/M portion of the cell cycle. Aryl ring-halogenated,...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(97)00014-x

    authors： Jonnalagadda SS,ter Haar E,Hamel E,Lin CM,Magarian RA,Day BW

    更新日期：1997-04-01 00:00:00

  • An efficient substitution reaction for the preparation of thyroid hormone analogues.

    abstract：:The substitution of the sterically hindered carbon of the potent thyroid hormone agonist, GC-1, was effected by a reaction based on the solvolysis of the benzylic hydroxyl group. The reaction was found to proceed in high yield with a variety of nucleophiles including alcohols, thiols, allyl silanes and electron-rich a...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(98)00085-6

    authors： Yoshihara HA,Chiellini G,Mitchison TJ,Scanlan TS

    更新日期：1998-08-01 00:00:00

  • Mapping of possible binding sequences of two beta-sheet breaker peptides on beta amyloid peptide of Alzheimer's disease.

    abstract：:Aggregation of amyloid peptide (Abeta) has been identified as a major feature of the pathogenesis of Alzheimer's disease. Increased risk for disease is associated with increased formation of polymerized Abeta. Inhibition of formation of toxic (aggregated) form of Abeta is one of the therapeutic possibilities. Beta she...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(01)00424-2

    authors： Hetényi C,Körtvélyesi T,Penke B

    更新日期：2002-05-01 00:00:00

  • Synthesis and monoamine transporter binding properties of 2beta-[3'-(substituted benzyl)isoxazol-5-yl]- and 2beta-[3'-methyl-4'-(substituted phenyl)isoxazol-5-yl]-3beta-(substituted phenyl)tropanes.

    abstract：:A series of 2beta-[3'-(substituted benzyl)isoxazol-5-yl]- and 2beta-[3'-methyl-4'-(substituted phenyl)isoxazol-5-yl]-3beta-(substituted phenyl)tropanes were prepared and evaluated for affinities at dopamine, serotonin, and norepinephrine transporters using competitive radioligand binding assays. The 2beta-[3'-(substit...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.05.073

    authors： Jin C,Navarro HA,Page K,Carroll FI

    更新日期：2008-07-15 00:00:00

  • Synthesis and biological evaluation of cis-restrained carbocyclic combretastatin A-4 analogs: Influence of the ring size and saturation on cytotoxic properties.

    abstract：:Combretastatin A-4 (CA-4) is a highly cytotoxic natural product and several derivatives have been prepared which underwent clinical trial. These investigations revealed that the cis-stilbene moiety of the natural product is prone to undergo cis/trans isomerization under physiological conditions, reducing the overall a...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2019.07.048

    authors： Nowikow C,Fuerst R,Kauderer M,Dank C,Schmid W,Hajduch M,Rehulka J,Gurska S,Mokshyna O,Polishchuk P,Zupkó I,Dzubak P,Rinner U

    更新日期：2019-10-01 00:00:00

  • Synthesis and characterizations of novel quinoline derivatives having mixed ligand activities at the kappa and mu receptors: Potential therapeutic efficacy against morphine dependence.

    abstract：:Based on an established 3D pharmacophore, a series of quinoline derivatives were synthesized. The opioidergic properties of these compounds were determined by a competitive binding assay using (125)I-Dynorphine, (3)H-DAMGO and (125)I-DADLE for kappa, mu, and delta receptors, respectively. Results showed varying degree...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.07.024

    authors： Deb I,Paira P,Hazra A,Banerjee S,Dutta PK,Mondal NB,Das S

    更新日期：2009-08-15 00:00:00

  • Synthesis of chlorogenic acid derivatives with promising antifungal activity.

    abstract：:Derivatives of chlorogenic acid or its analogues were synthesized by coupling protected chlorogenic acid or its analogues with p-octyloxyaniline and selected amino acids. Most of the compounds exhibited significant potency against Cryptococcus neoformans and Candida species with low toxicity to brine shrimps. The 4,5-...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.07.038

    authors： Ma CM,Kully M,Khan JK,Hattori M,Daneshtalab M

    更新日期：2007-11-01 00:00:00

  • Dose dependent actions of LCL521 on acid ceramidase and key sphingolipid metabolites.

    abstract：:The function of acid ceramidase (ACDase), whose congenital deficiency leads to Farber disease, has been recognized to be vital to tumor cell biology, and inhibition of its activity may be beneficial in cancer therapy. Therefore, manipulation of the activity of this enzyme may have significant effect, especially on can...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2018.11.012

    authors： Bai A,Bielawska A,Rahmaniyan M,Kraveka JM,Bielawski J,Hannun YA

    更新日期：2018-12-15 00:00:00

  • Construction of a chemically and conformationally self-replicating system of amyloid-like fibrils.

    abstract：:The amyloid-like fibril is considered to be a macromolecular self-assemblage with a highly-ordered quaternary structure, in which numerous beta-stranded polypeptide chains align regularly. Therefore, this kind of fibril has the potential to be engineered into proteinaceous materials, although conformational alteration...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2003.11.022

    authors： Takahashi Y,Mihara H

    更新日期：2004-02-15 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

  • Preparation and biological properties of biotinylated PhTX derivatives.

    abstract：:We report the synthesis of several highly functionalized biotinylated philanthotoxin (PhTX) analogues (7, 8, 10, 13-16) designed on the basis of earlier structure-activity relationship studies. Despite the extensive modifications, the binding to nicotinic acetylcholine receptor (nAChR) is in the low micromolar range a...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(99)00054-1

    authors： Hashimoto M,Liu Y,Fang K,Li HY,Campiani G,Nakanishi K

    更新日期：1999-06-01 00:00:00

  • Novel azalides derived from 16-membered macrolides. Part II: Isolation of the linear 9-formylcarboxylic acid and its sequential macrocyclization with an amino alcohol or an azidoamine.

    abstract：:The design and synthesis of novel 14- to 16-membered 11-azalides starting from 16-membered macrolides are reported. A linear 9-formylcarboxylic acid was isolated via a mobile dialdehyde previously reported. Sequential macrocyclization of the formylcarboxylic acid with amino alcohol followed by deprotection afforded co...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.09.054

    authors： Miura T,Kanemoto K,Natsume S,Atsumi K,Fushimi H,Yoshida T,Ajito K

    更新日期：2008-12-01 00:00:00

  • Binding to delta and mu opioid receptors by deltorphin I/II analogues modified at the Phe3 and Asp4/Glu4 side chains: a report of 32 new analogues and a QSAR study.

    abstract：:The synthesis and binding affinities of 32 X3Gly4 dual-substitution analogues of the natural opioid heptapeptides deltorphin I and II are reported. A multiple regression QSAR analysis was performed using those results along with literature data for the X3Asp4 and Phe3X4 side chain analogues. Fitting to a three-term po...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(97)00163-6

    authors： Schullery SE,Mohammedshah T,Makhlouf H,Marks EL,Wilenkin BS,Escobar S,Mousigian C,Heyl DL

    更新日期：1997-12-01 00:00:00

  • Comparison in antioxidant action between α-chitosan and β-chitosan at a wide range of molecular weight and chitosan concentration.

    abstract：:Antioxidant activity in α- and β-chitosan at a wide range of molecular weight (Mw) and chitosan concentration (CS) was determined by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity, reducing ability, chelating ability, and hydroxyl radical scavenging activity. The form of chitosan (FC) had significant...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2012.03.020

    authors： Jung J,Zhao Y

    更新日期：2012-05-01 00:00:00