当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY期刊下所有文献 > Design, synthesis and herbicidal activity of new iron chelating motifs for HPPD-inhibitors.

Design, synthesis and herbicidal activity of new iron chelating motifs for HPPD-inhibitors.

Abstract：

:HPPD (p-hydroxyphenylpyruvate dioxygenase) is a herbicidal target that all major companies active in plant protection research have worked on intensely in the last decade. Several modern herbicides with this mode of action have been introduced recently, or are currently in development. The activity of all commercialized HPPD-inhibitors is based on a chelating functionality, which binds to the redoxactive iron center in the enzyme. In the course of our research, leading to the new broad spectrum corn herbicide topramezone by BASF, this chelating functionality has been examined thoroughly, and many new chelating motifs have been synthesized. The chelating motif N-O in combination with C=O, which is known for its iron-binding potential from many natural siderophores, was especially promising. Examination of several different motifs of this type resulted in the identification of benzoyl-N-hydroxyimidazoles, which inhibited the HPPD-enzyme with potency comparable to the best known systems. Significant herbicidal activity in the greenhouse could also be identified for some of these compounds, but this activity was weaker than for the analogous benzoylpyrazolones of the topramezone-type.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Witschel M

doi

10.1016/j.bmc.2008.11.006

subject

Has Abstract

pub_date

2009-06-15 00:00:00

pages

4221-9

issue

12

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(08)01060-2

journal_volume

17

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY文献大全
  • 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

  • Syntheses, biochemical and biological evaluation of staurosporine analogues from the microbial metabolite rebeccamycin.

    abstract：:The indolocarbazole antibiotics staurosporine and rebeccamycin (1) are potent antitumor drugs targeting protein kinase C and topoisomerase I, respectively. To obtain staurosporine analogues from rebeccamycin, different structural modifications were performed: coupling of the sugar moiety to the second indole nitrogen,...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(98)00096-0

    authors： Anizon F,Moreau P,Sancelme M,Voldoire A,Prudhomme M,Ollier M,Sevère D,Riou JF,Bailly C,Fabbro D,Meyer T,Aubertin AM

    更新日期：1998-09-01 00:00:00

  • Alkylation potency and protein specificity of aromatic urea derivatives and bioisosteres as potential irreversible antagonists of the colchicine-binding site.

    abstract：:A number of N-phenyl-N'-(2-chloroethyl)ureas (CEUs) have been shown to be potent antimitotics through their covalent binding to the colchicine-binding site on intracellular beta-tubulin. The present communication aimed to evaluate the role of the electrophilic 2-chloroethyl amino moiety of CEU on cell growth inhibitio...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.04.028

    authors： Fortin JS,Lacroix J,Desjardins M,Patenaude A,Petitclerc E,C-Gaudreault R

    更新日期：2007-07-01 00:00:00

  • Identification of sortase substrates by specificity profiling.

    abstract：:Sortases catalyze the attachment of surface proteins to the peptidoglycan layer of gram-positive bacteria and further represent powerful tools of protein chemistry. During catalysis sortases cleave a donor substrate containing the LPxTG (x=any amino acid) sorting motif under formation of an enzyme-bound thioester and ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.06.033

    authors： Schmohl L,Bierlmeier J,von Kügelgen N,Kurz L,Reis P,Barthels F,Mach P,Schutkowski M,Freund C,Schwarzer D

    更新日期：2017-09-15 00:00:00

  • Thieno[2,3-d]pyrimidine-2-carboxamides bearing a carboxybenzene group at 5-position: highly potent, selective, and orally available MMP-13 inhibitors interacting with the S1″ binding site.

    abstract：:On the basis of X-ray co-crystal structures of matrix metalloproteinase-13 (MMP-13) in complex with its inhibitors, our structure-based drug design (SBDD) strategy was directed to achieving high affinity through optimal protein-ligand interaction with the unique S1″ hydrophobic specificity pocket. This report details ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2014.07.025

    authors： Nara H,Sato K,Naito T,Mototani H,Oki H,Yamamoto Y,Kuno H,Santou T,Kanzaki N,Terauchi J,Uchikawa O,Kori M

    更新日期：2014-10-01 00:00:00

  • ORL1 and opioid receptor preferences of nociceptin and dynorphin A analogues with Dmp substituted for N-terminal aromatic residues.

    abstract：:Nociceptin (NOC) and dynorphin A (DYN) analogues containing 2',6'-dimethylphenylalanine (Dmp) in place of Phe or Tyr in position 1 and/or 4 were synthesized and their metabolic stability and receptor-binding properties were investigated. [Dmp1]NOC(1-13)-NH2 (1) possessed high ORL1 receptor affinity comparable to that ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2005.11.021

    authors： Sasaki Y,Kawano S,Kohara H,Watanabe H,Ambo A

    更新日期：2006-04-01 00:00:00

  • Discovery of INT131: a selective PPARγ modulator that enhances insulin sensitivity.

    abstract：:PPARγ is a member of the nuclear hormone receptor family and plays a key role in the regulation of glucose homeostasis. This Letter describes the discovery of a novel chemical class of diarylsulfonamide partial agonists that act as selective PPARγ modulators (SPPARγMs) and display a unique pharmacological profile comp...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2012.11.058

    authors： Taygerly JP,McGee LR,Rubenstein SM,Houze JB,Cushing TD,Li Y,Motani A,Chen JL,Frankmoelle W,Ye G,Learned MR,Jaen J,Miao S,Timmermans PB,Thoolen M,Kearney P,Flygare J,Beckmann H,Weiszmann J,Lindstrom M,Walker N,Li

    更新日期：2013-02-15 00:00:00

  • Molecular design of N-linked tetravalent glycosides bearing N-acetylglucosamine, N,N'-diacetylchitobiose and N-acetyllactosamine: Analysis of cross-linking activities with WGA and ECA lectins.

    abstract：:Two types of nonspacer- and spacer-N-linked tetravalent glycosides bearing N-acetylglucosamine (GlcNAc), N,N'-diacetylchitobiose [(GlcNAc)(2)] and N-acetyllactosamine (LacNAc) were designed and prepared as glycomimetics. The interactions of wheat germ (Triticum vulgaris) agglutinin (WGA) and coral tree (Erythrina cris...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.12.006

    authors： Masaka R,Ogata M,Misawa Y,Yano M,Hashimoto C,Murata T,Kawagishi H,Usui T

    更新日期：2010-01-15 00:00:00

  • Design, synthesis and biological assessment of novel N-substituted 3-(phthalimidin-2-yl)-2,6-dioxopiperidines and 3-substituted 2,6-dioxopiperidines for TNF-α inhibitory activity.

    abstract：:Eight novel 2-(2,6-dioxopiperidin-3-yl)phthalimidine EM-12 dithiocarbamates 9 and 10, N-substituted 3-(phthalimidin-2-yl)-2,6-dioxopiperidines 11-14 and 3-substituted 2,6-dioxopiperidines 16 and 18 were synthesized as tumor necrosis factor-α (TNF-α) synthesis inhibitors. Synthesis involved utilization of a novel conde...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2011.05.029

    authors： Luo W,Yu QS,Salcedo I,Holloway HW,Lahiri DK,Brossi A,Tweedie D,Greig NH

    更新日期：2011-07-01 00:00:00

  • Identification of an achiral analogue of J-113397 as potent nociceptin/orphanin FQ receptor antagonist.

    abstract：:To date, J-113397 represents the most potent and selective non peptide NOP receptor antagonist widely used in pharmacological studies. However, the synthesis, purification, and enantiomer separation of this molecule, which contains two chiral centers, is rather difficult and low-yielding. Here, we synthesized and test...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2005.08.049

    authors： Trapella C,Guerrini R,Piccagli L,Calo' G,Carra' G,Spagnolo B,Rubini S,Fanton G,Hebbes C,McDonald J,Lambert DG,Regoli D,Salvadori S

    更新日期：2006-02-01 00:00:00

  • Astersedifolioside A-C, three new oleane-type saponins with antiproliferative activity.

    abstract：:A phytochemical analysis of Aster sedifolius has led to the isolation of three novel triterpenoid saponins, based on an oleane-type skeleton and named astersedifolioside A (1), B (2) and C (3). On the basis of chemical, and 2D NMR and mass spectrometry data, the structures of the new compounds were elucidated as 3-O-[...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.06.042

    authors： Corea G,Iorizzi M,Lanzotti V,Cammareri M,Conicella C,Laezza C,Bifulco M

    更新日期：2004-09-15 00:00:00

  • Synthesis and receptor binding affinity of new selective GluR5 ligands.

    abstract：:Two hybrid analogues of the kainic acid receptor agonists, 2-amino-3-(5-tert-butyl-3-hydroxy-4-isoxazolyl)propionic acid (ATPA) and (2S,4R)-4-methylglutamic acid ((2S,4R)-4-Me-Glu), were designed, synthesized, and characterized in radioligand binding assays using cloned ionotropic and metabotropic glutamic acid recept...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(00)00304-7

    authors： Bunch L,Johansen TH,Bräuner-Osborne H,Stensbøl TB,Johansen TN,Krogsgaard-Larsen P,Madsen U

    更新日期：2001-04-01 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

  • 2-Amino diphenylsulfides as inhibitors of trypanothione reductase: modification of the side chain.

    abstract：:A molecular modeling study meant to detect pharmacophore-like patterns in the active site of trypanothione reductase (TR) offered hints about the opportunity of synthesizing and testing diphenylsulfide derivatives with prolonged or branched polyamino side chains as putative TR inhibitors. The inhibition results within...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/0968-0896(96)00083-1

    authors： Baillet S,Buisine E,Horvath D,Maes L,Bonnet B,Sergheraert C

    更新日期：1996-06-01 00:00:00

  • meso-Dihydroguaiaretic acid derivatives with antibacterial and antimycobacterial activity.

    abstract：:Thirty-three meso-dihydroguaiaretic acid (meso-DGA) derivatives bearing esters, ethers, and amino-ethers were synthesized. All derivatives were tested against twelve drug-resistant clinical isolates of Gram-positive and Gram-negative bacteria, including sensitive (H37Rv) and multidrug-resistant Mycobacterium tuberculo...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.07.047

    authors： Reyes-Melo K,García A,Romo-Mancillas A,Garza-González E,Rivas-Galindo VM,Miranda LD,Vargas-Villarreal J,Favela-Hernández JMJ,Camacho-Corona MDR

    更新日期：2017-10-15 00:00:00

  • Modeling and synthesis of novel tight-binding inhibitors of cytochrome P450 2C9.

    abstract：:Cytochrome P450 2C9 (2C9) is one of the three major drug metabolizing cytochrome P450 enzymes in human liver. Although the crystal structure of 2C9 has been solved, the important physicochemical properties of substrate-enzyme interactions remain difficult to be determined. This is due in part to the conformational fle...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.01.021

    authors： Peng CC,Rushmore T,Crouch GJ,Jones JP

    更新日期：2008-04-01 00:00:00

  • Structural insights into the hot spot amino acid residues of mushroom tyrosinase for the bindings of thujaplicins.

    abstract：:Tyrosinase inhibitors are important agents for cosmetic products. We examined here the inhibitory effects of three isomers of thujaplicins (α, β and γ) on mushroom tyrosinase and analyzed their binding modes using a homology model from the crystal structure of Streptomyces castaneoglobisporus tyrosinase (PDB ID: 1wx2)...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.08.056

    authors： Takahashi S,Kamiya T,Saeki K,Nezu T,Takeuchi S,Takasawa R,Sunaga S,Yoshimori A,Ebizuka S,Abe T,Tanuma S

    更新日期：2010-11-15 00:00:00

  • Synthesis and structure-activity relationships of benzyloxyphenyl derivatives as a novel class of NCX inhibitors: effects on heart failure.

    abstract：:In the context of heart failure and myocardial ischemia reperfusion, the activity of the sodium-calcium exchanger can lead to calcium overload, which in turn can lead to contractile dysfunction and arrhythmia. Therefore, NCX is an attractive target for treatment of heart failure and myocardial ischemia reperfusion. We...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.10.048

    authors： Kuramochi T,Kakefuda A,Yamada H,Ogiyama T,Taguchi T,Sakamoto S

    更新日期：2005-02-01 00:00:00

  • The case for configurational stability of H-phosphonate diesters in the presence of diazabicyclo[5.4.0]undec-7-ene (DBU).

    abstract：:Configurational stability of dinucleoside H-phosphonates and the stereochemical course of their sulfurisation in the presence of diazabicyclo[5.4.0]undec-7-ene (DBU) were investigated using 31P NMR spectroscopy. It was found that under the reaction conditions and irrespective of the type of protecting groups present i...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(01)00140-7

    authors： Johansson T,Stawinski J

    更新日期：2001-09-01 00:00:00

  • Induction of enantio-selective apoptosis in human leukemia HL-60 cells by (S)-erypoegin K, an isoflavone isolated from Erythrina poeppigiana.

    abstract：:Erypoegin K, an isoflavone isolated from the stem bark of Erythrina poeppigiana, has potent apoptosis-inducing effect on human leukemia HL-60 cells. Erypoegin K has a chiral carbon at the C-2'' position of its furan ring and naturally occurs as a racemic mixture of (S)- and (R)-isomers. In the present study, we semi-s...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2020.115490

    authors： Hikita K,Saigusa S,Takeuchi Y,Matsuyama H,Nagai R,Kato K,Murata T,Tanaka H,Wagh YS,Asao N,Kaneda N

    更新日期：2020-06-01 00:00:00

  • Synthesis of benzoxazole derivatives as interleukin-6 antagonists.

    abstract：:A growing number of studies have demonstrated that interleukin (IL)-6 plays pathological roles in the development of chronic inflammatory disease and autoimmune disease by activating innate immune cells and by stimulating adaptive inflammatory T cells. So, suppression of IL-6 function may be beneficial for prevention ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.03.072

    authors： Kim D,Won HY,Hwang ES,Kim YK,Choo HP

    更新日期：2017-06-15 00:00:00

  • Design, synthesis and biological evaluation of novel hydroxamic acid based histone deacetylase 6 selective inhibitors bearing phenylpyrazol scaffold as surface recognition motif.

    abstract：:In recent years, inhibition of HDAC6 became a promising therapeutic strategy for the treatment of cancer and HDAC6 inhibitors were considered to be potent anti-cancer agents. In this work, celecoxib showed moderate degree of HDAC6 inhibition activity and selectivity in preliminary enzyme inhibition activity assay. A s...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.08.029

    authors： Yang J,Cheng G,Xu Q,Luan S,Wang S,Liu D,Zhao L

    更新日期：2018-05-01 00:00:00

  • Efficient sequential synthesis of PET Probes of the COX-2 inhibitor [11C]celecoxib and its major metabolite [11C]SC-62807 and in vivo PET evaluation.

    abstract：:Synthesis of [(11)C]celecoxib, a selective COX-2 inhibitor, and [(11)C]SC-62807, a major metabolite of celecoxib, were achieved and the potential of these PET probes for assessing the function of drug transporter in biliary excretion was evaluated. The synthesis of [(11)C]celecoxib was achieved in one-pot by reacting ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2011.03.020

    authors： Takashima-Hirano M,Takashima T,Katayama Y,Wada Y,Sugiyama Y,Watanabe Y,Doi H,Suzuki M

    更新日期：2011-05-01 00:00:00

  • Synthesis, structural investigations and biological evaluation of novel hexahydropyridazine-1-carboximidamides, -carbothioamides and -carbothioimidic acid esters as inducible nitric oxide synthase inhibitors.

    abstract：:Local excess of nitric oxide (NO) has been implicated in beta-cell damage, thus, a possible approach to the treatment of autoimmune IDDM is the selective inhibition of inducible nitric oxide synthase (iNOS). A series of variously substituted hexahydropyridazine-1-carbothioamides, -carbothioimidic acid esters and -carb...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2003.12.007

    authors： Morgenstern O,Wanka H,Röser I,Steveling A,Kuttler B

    更新日期：2004-03-01 00:00:00

  • Design, synthesis, and in vitro evaluation of new naphthylnitrobutadienes with potential antiproliferative activity: toward a structure/activity correlation.

    abstract：:On the grounds of previous encouraging results on the antitumor activity of (1E,3E)-1,4-bis(1-naphthyl)-2,3-dinitro-1,3-butadiene (1), we have designed and synthesized two new molecules [(1E,3E)-1,4-bis(4-carboxy-1-naphthyl)-2,3-dinitro-1,3-butadiene (2) and methyl (2Z,4E)-2-methylsulfanyl-5-(1-naphthyl)-4-nitro-2,4-p...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.09.042

    authors： Petrillo G,Mariggiò MA,Aiello C,Cordazzo C,Fenoglio C,Morganti S,Croce M,Rizzato E,Spinelli D,Maccagno M,Bianchi L,Prevosto C,Tavani C,Viale M

    更新日期：2008-01-01 00:00:00

  • Synthesis and evaluation of verticipyrone analogues as mitochondrial complex I inhibitors.

    abstract：:Verticipyrone has recently been isolated from the culture broth of Verticillium sp. and shown to inhibit NADH fumarate reductase, as well as NADH oxidoreductase (complex I) of the mitochondrial electron transport chain. In order to assess the structural elements in verticipyrone essential for complex I inhibitor, 15 s...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.03.070

    authors： Leiris SJ,Khdour OM,Segerman ZJ,Tsosie KS,Chapuis JC,Hecht SM

    更新日期：2010-05-15 00:00:00

  • Structure-activity relationships for analogs of the tuberculosis drug bedaquiline with the naphthalene unit replaced by bicyclic heterocycles.

    abstract：:Replacing the naphthalene C-unit of the anti-tuberculosis drug bedaquiline with a range of bicyclic heterocycles of widely differing lipophilicity gave analogs with a 4.5-fold range in clogP values. The biological results for these compounds indicate on average a lower clogP limit of about 5.0 in this series for reten...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2018.02.026

    authors： Sutherland HS,Tong AST,Choi PJ,Conole D,Blaser A,Franzblau SG,Cooper CB,Upton AM,Lotlikar MU,Denny WA,Palmer BD

    更新日期：2018-05-01 00:00:00

  • Polymer supported synthesis of a natural product-inspired oxepane library.

    abstract：:Natural product inspired compound collections are prevalidated due to the evolutionary selection of the natural product scaffolds. Their synthesis requires the development of novel strategies amenable to formats suitable for library build-up. We describe a method for the synthesis of an oxepane library inspired by the...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2014.05.039

    authors： Basu S,Waldmann H

    更新日期：2014-08-15 00:00:00

  • Discovery of 1H-benzo[d][1,2,3]triazol-1-yl 3,4,5-trimethoxybenzoate as a potential antiproliferative agent by inhibiting histone deacetylase.

    abstract：:Twenty-one benzotriazoles (3-16 and 18-24) were synthesized and half of them (5, 8-16, 20, and 21) were reported for the first time. Their antiproliferative activities against three human cancer cells were assayed. It revealed that 1H-benzo[d][1,2,3]triazol-1-yl 3,4,5-trimethoxybenzoate (9) showed considerable activit...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.10.049

    authors： Fu J,Yang Y,Zhang XW,Mao WJ,Zhang ZM,Zhu HL

    更新日期：2010-12-15 00:00:00

  • Synthesis and antimicrobial activity of dermaseptin S1 analogues.

    abstract：:Dermaseptins are peptides found in the skin secretions of Phyllomedusinae frogs. These peptides exert lytic action on some microorganisms without substantial haemolysis. In an attempt to understand the antimicrobial activity of these peptides we designed several dermaseptin S1 (ALWKTMLKKLGTMALHAGKAALGAAADTISQGTQ) (DS1...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.07.032

    authors： Savoia D,Guerrini R,Marzola E,Salvadori S

    更新日期：2008-09-01 00:00:00