当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY LETTERS期刊下所有文献 > Beta-keto-ester chemistry and ketolides. Synthesis and antibacterial activity of 2-halogeno, 2-methyl and 2,3 enol-ether ketolides.

Beta-keto-ester chemistry and ketolides. Synthesis and antibacterial activity of 2-halogeno, 2-methyl and 2,3 enol-ether ketolides.

Abstract：

:The effect of 2,3 modifications on the antibacterial activity of ketolides was evaluated by introducing substituents in position 2 and converting the C-1, C-2, C-3 beta-keto-ester into stable 2,3 enol-ether or 2,3 anhydro derivatives. Introduction of a fluorine in C-2 is beneficial with regard to the overall antibacterial spectrum whereas the enol-ether and 2,3 unsaturated compounds, as well as the bulky gem dimethyl or 2-chloro derivatives, are less active particularly against erythromycin resistant strains. A 2-fluoro ketolide derivative demonstrates good antibacterial activity and in vivo efficacy against multi-resistant Streptococcus pneumoniae. Compared to azithromycin against Haemophilus influenzae, this compound is equivalent in vitro and slightly more active in vivo. These results demonstrate that within the ketolide class, to retain good antibacterial activity, position 2 needs to remain tetrahedral and tolerates only very small substituents such as fluorine.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Denis A,Bretin F,Fromentin C,Bonnet A,Piltan G,Bonnefoy A,Agouridas C

doi

10.1016/s0960-894x(00)00392-9

subject

Has Abstract

pub_date

2000-09-04 00:00:00

pages

2019-22

issue

17

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(00)00392-9

journal_volume

10

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS文献大全
  • Investigations of the esterase, phosphatase, and sulfatase activities of the cytosolic mammalian carbonic anhydrase isoforms I, II, and XIII with 4-nitrophenyl esters as substrates.

    abstract：:The esterase, phosphatase, and sulfatase activities of carbonic anhydrase (CA, EC 4.2.1.1) isozymes, CA I, II, and XIII with 4-nitrophenyl esters as substrates was investigated. These enzymes show esterase activity with 4-nitrophenyl acetate as substrate, with second order rate constants in the range of 753-7706M(-1)s...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2008.03.012

    authors： Innocenti A,Scozzafava A,Parkkila S,Puccetti L,De Simone G,Supuran CT

    更新日期：2008-04-01 00:00:00

  • Inhibitors for expression of IgE receptor on human mast cell from Puerariae Flos.

    abstract：:Bioassay-guided separation of the extract of the medicinal plant, Puerariae Flos, disclosed the two isoflavones tectorigenin (1) and genistein (2) as the inhibitors for expression of IgE receptor (FcepsilonRI), the key molecule triggering the allergic reactions, on human mast cells. As a result of analysis of structur...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2010.05.038

    authors： Tamura S,Yoshihira K,Tokumaru M,Zisheng X,Murakami N

    更新日期：2010-07-01 00:00:00

  • Synthesis and immunological activity of an oligosaccharide-conjugate as a vaccine candidate against Group A Streptococcus.

    abstract：:The synthesis and immunogenicity of a tetanus toxoid (TT)-conjugate of the hexasaccharide portion of the cell-wall polysaccharide (CWPS) of the Group A Streptococcus (GAS) is described. The synthesis relies on the reaction of an allyl glycoside of the hexasaccharide with cysteamine, followed by the reaction of the res...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2013.09.042

    authors： Auzanneau FI,Borrelli S,Pinto BM

    更新日期：2013-11-15 00:00:00

  • Synthesis of conjugates between oxazolidinone antibiotics and a pyochelin analogue.

    abstract：:Pseudomonas aeruginosa is a Gram-negative pathogenic bacterium responsible for severe infections, and it is naturally resistant to many clinically approved antibiotic families. Oxazolidinone antibiotics are active against many Gram-positive bacteria, but are inactive against P. aeruginosa. Increasing the uptake of oxa...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2017.09.039

    authors： Paulen A,Hoegy F,Roche B,Schalk IJ,Mislin GLA

    更新日期：2017-11-01 00:00:00

  • Sensitivity of neuronal nicotinic acetylcholine receptors to the opiate antagonists naltrexone and naloxone: receptor blockade and up-regulation.

    abstract：:In HEK293 cells stably expressing alpha4beta2 nAChRs, naltrexone, but not naloxone, blocked alpha4beta2 nAChRs via an open-channel blocking mechanism. In primary hippocampal cultures, naltrexone inhibited alpha7 nAChRs up-regulated by nicotine, and in organotypic hippocampal cultures naltrexone caused a time-dependent...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2004.01.004

    authors： Almeida LE,Pereira EF,Camara AL,Maelicke A,Albuquerque EX

    更新日期：2004-04-19 00:00:00

  • New antibacterial isocoumarin glycosides from a wetland soil derived fungal strain Metarhizium anisopliae.

    abstract：:Eight new isocoumarin glycosides (1-8) were obtained from the solid culture of the wetland soil-derived fungus Metarhizium anisopliae (No. DTH12-10). Their chemical structures were elucidated by analyses of HR ESI-TOF MS, (1)H, (13)C NMR, (1)H-(1)H COSY, HSQC, and HMBC spectra. The absolute configurations were determi...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2016.01.074

    authors： Tian JF,Li PJ,Li XX,Sun PH,Gao H,Liu XZ,Huang P,Tang JS,Yao XS

    更新日期：2016-03-01 00:00:00

  • Structure-activity relationship in two series of aminoalkyl substituted coumarin inhibitors of gyrase B.

    abstract：:Two series of aminosubstituted coumarins were synthesised and evaluated in vitro as inhibitors of DNA gyrase and as potential antibacterials. Novel novobiocin-like coumarins, 4-(dialkylamino)methylcoumarins and 4-((2-alkylamino)ethoxy)coumarins, were discovered as gyrase B inhibitors with promising antibacterial activ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(99)00492-8

    authors： Laurin P,Ferroud D,Schio L,Klich M,Dupuis-Hamelin C,Mauvais P,Lassaigne P,Bonnefoy A,Musicki B

    更新日期：1999-10-04 00:00:00

  • Solid-phase synthesis of endothelin receptor antagonists.

    abstract：:A new solid-phase synthesis for ET receptor antagonists suitable for automation is presented. A support bound 2-hydroxybutyric acid derivative was converted to the corresponding ether derivatives using 4-halo-2-methylsulfonylpyrimidines. Subsequent Suzuki coupling with various aryl boronic acids gave the desired antag...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(03)00236-1

    authors： Lange UE,Braje WM,Amberg W,Kettschau G

    更新日期：2003-05-19 00:00:00

  • Flavonoids from Woodfordia fruticosa as potential SmltD inhibitors in the alternative biosynthetic pathway of peptidoglycan.

    abstract：:SmltD is an ATP-dependent ligase that catalyzes the condensation of UDP-MurNAc-l-Ala and l-Glu to form UDP-MurNAc-l-Ala-l-Glu, in the newly discovered peptidoglycan biosynthesis pathway of a Gram-negative multiple-drug-resistant pathogen, Stenotrophomonas maltophilia. Phytochemical investigation of the 70% ethanol ext...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2021.127787

    authors： Lee YE,Kodama T,Win NN,Ki DW,Hoang NN,Wong CP,Lae KZW,Ngwe H,Dairi T,Morita H

    更新日期：2021-01-15 00:00:00

  • Synthesis and antimicrobial activity of some new pyrazole derivatives containing a ferrocene unit.

    abstract：:A series of new imines and amines have been synthesized by condensation of 1H-3-ferrocenyl-1-phenylpyrazole-4-carboxaldehyde with the corresponding amines, followed by reduction with sodium borohydride. The synthesized compounds have been screened for their in vitro antimicrobial activity against 11 bacteria and three...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2009.01.006

    authors： Damljanović I,Vukićević M,Radulović N,Palić R,Ellmerer E,Ratković Z,Joksović MD,Vukićević RD

    更新日期：2009-02-15 00:00:00

  • Tri-substituted acylhydrazines as tertiary amide bioisosteres: HCV NS5B polymerase inhibitors.

    abstract：:The use of a tri-substituted acylhydrazine as an isostere of a tertiary amide was explored in a series of HCV NS5B thumb site II inhibitors. Direct replacement generated an analog with similar conformational and physicochemical properties. The series was extended to produce compounds with potent binding affinities and...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2012.05.025

    authors： Canales E,Carlson JS,Appleby T,Fenaux M,Lee J,Tian Y,Tirunagari N,Wong M,Watkins WJ

    更新日期：2012-07-01 00:00:00

  • Discovery of phenyl acetamides as potent and selective GPR119 agonists.

    abstract：:The paper describes the SAR/SPR studies that led to the discovery of phenoxy cyclopropyl phenyl acetamide derivatives as potent and selective GPR119 agonists. Based on a cis cyclopropane scaffold discovered previously, phenyl acetamides such as compound 17 were found to have excellent GPR119 potency and improved physi...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2017.01.091

    authors： Zhu C,Wang L,Zhu Y,Guo ZZ,Liu P,Hu Z,Szewczyk JW,Kang L,Chicchi G,Ehrhardt A,Woods A,Seo T,Woods M,van Heek M,Dingley KH,Pang J,Salituro GM,Powell J,Terebetski JL,Hornak V,Campeau LC,Orr RK,Ujjainwalla F,Mil

    更新日期：2017-03-01 00:00:00

  • Neamphamide B, new cyclic depsipeptide, as an anti-dormant mycobacterial substance from a Japanese marine sponge of Neamphius sp.

    abstract：:A new cyclic depsipeptide, designated neamphamide B (1), was isolated from a marine sponge of Neamphius sp. collected at Okinawa, Japan in 1993 as an anti-mycobacterial substance against active and dormant bacilli. The planar structure of neamphamide B (1) was determined on the basis of spectroscopic analysis, and ste...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2012.05.071

    authors： Yamano Y,Arai M,Kobayashi M

    更新日期：2012-07-15 00:00:00

  • Promoting the formation of tetramolecular G-quadruplexes under freezing condition.

    abstract：:In the study, we demonstrated that freezing was able to facilitate the short DNA strand T(4)G(4) to self-assemble into a tetramolecular G-quadruplex with a low DNA concentration in the absence of any ligand, providing a fast approach to configure intermolecular G-quadruplexes. The fast formation of intermolecular G-qu...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2011.11.099

    authors： Zhai Q,Deng M,Xu L,Zhang X,Zhou X

    更新日期：2012-01-15 00:00:00

  • Solid-phase synthesis and pharmacological evaluation of novel nucleoside-tethered dinuclear platinum(II) complexes.

    abstract：:Three novel inosine-based dinuclear platinum complexes have been synthesized via a solid-phase strategy. In these compounds, the metal is linked both to the N-7 of the purine nucleus and to the terminal amine group of a hexylamine side chain installed on N-1. Cis- or trans- diamine as well as ethylenediamine ligands a...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2011.07.104

    authors： D'Errico S,Oliviero G,Piccialli V,Amato J,Borbone N,D'Atri V,D'Alessio F,Di Noto R,Ruffo F,Salvatore F,Piccialli G

    更新日期：2011-10-01 00:00:00

  • 2,7-Pyrrolo[2,1-f][1,2,4]triazines as JAK2 inhibitors: modification of target structure to minimize reactive metabolite formation.

    abstract：:The JAK2/STAT pathway has important roles in hematopoiesis. With the discovery of the JAK2 V617F mutation and its presence in many patients with myeloproliferative neoplasms, research in the JAK2 inhibitor arena has dramatically increased. We report a novel series of potent JAK2 inhibitors containing a 2,7-pyrrolotria...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2011.10.032

    authors： Weinberg LR,Albom MS,Angeles TS,Breslin HJ,Gingrich DE,Huang Z,Lisko JG,Mason JL,Milkiewicz KL,Thieu TV,Underiner TL,Wells GJ,Wells-Knecht KJ,Dorsey BD

    更新日期：2011-12-15 00:00:00

  • Aryl sulfonamido indane inhibitors of the Kv1.5 ion channel.

    abstract：:A collection of aryl sulfonamido indanes based on the lead compound 1 was synthesized and evaluated for Kv1.5 inhibitory activity. Kv1.5 inhibitors have the potential to be atrium-selective agents for treatment of atrial fibrillation. (1R,2R)-1 has an IC(50) of 0.033microM against Kv1.5 and is selective against other ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2007.02.052

    authors： Gross MF,Beaudoin S,McNaughton-Smith G,Amato GS,Castle NA,Huang C,Zou A,Yu W

    更新日期：2007-05-15 00:00:00

  • Inhibition of NaV1.6 sodium channel currents by a novel series of 1,4-disubstituted-triazole derivatives obtained via copper-catalyzed click chemistry.

    abstract：:We have synthesized and evaluated a series of 1,4-disubstituted-triazole derivatives for inhibition of the rat Na(V)1.6 sodium channel isoform, an isoform thought to play an important role in controlling neuronal firing. Starting from a series of 2,4(1H)-diarylimidazoles previously published, we decided to extend the ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2012.08.067

    authors： Rivara M,Patel MK,Amori L,Zuliani V

    更新日期：2012-10-15 00:00:00

  • Sequence selective naked-eye detection of DNA harnessing extension of oligonucleotide-modified nucleotides.

    abstract：:DNA polymerases can efficiently and sequence selectively incorporate oligonucleotide (ODN)-modified nucleotides and the incorporated oligonucleotide strand can be employed as primer in rolling circle amplification (RCA). The effective amplification of the DNA primer by Φ29 DNA polymerase allows the sequence-selective ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2015.12.082

    authors： Verga D,Welter M,Marx A

    更新日期：2016-02-01 00:00:00

  • Discovery of potent and selective matrix metalloprotease 12 inhibitors for the potential treatment of chronic obstructive pulmonary disease (COPD).

    abstract：:Chronic obstructive pulmonary disease (COPD) is an inflammatory lung disease associated with irreversible progressive airflow limitation. Matrix metalloproteinase-12 (MMP-12) has been characterized to be one of the major proteolytic enzymes to induce airway remodeling, destruction of elastin and the aberrant remodelin...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2011.11.046

    authors： Wu Y,Li J,Wu J,Morgan P,Xu X,Rancati F,Vallese S,Raveglia L,Hotchandani R,Fuller N,Bard J,Cunningham K,Fish S,Krykbaev R,Tam S,Goldman SJ,Williams C,Mansour TS,Saiah E,Sypek J,Li W

    更新日期：2012-01-01 00:00:00

  • Discovery of new diphenyloxazole derivatives containing a pyrrolidine ring: orally active prostacyclin mimetics. Part 2.

    abstract：:Synthetic and biological evaluation of novel diphenyloxazole derivatives containing a pyrrolidine ring, as a prostacyclin mimetic without the PG skeleton, are described. Asymmetric reduction of a ketone using a chiral Ru complex and reductive amination by NaBH(4) produces four isomers of the tetrahydronaphthalene ring...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2005.04.042

    authors： Hattori K,Okitsu O,Tabuchi S,Taniguchi K,Nishio M,Koyama S,Seki J,Sakane K

    更新日期：2005-07-01 00:00:00

  • Use of parallel-synthesis combinatorial libraries for rapid identification of potent FKBP12 inhibitors.

    abstract：:Using simple, inexpensive equipment, we have used solution-phase parallel synthesis to rapidly prepare hundreds of sulfonamide- and urea-containing FKBP inhibitors, resulting in rapid identification of extremely potent compounds in these series. ...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(02)00147-6

    authors： Choi C,Li JH,Vaal M,Thomas C,Limburg D,Wu YQ,Chen Y,Soni R,Scott C,Ross DT,Guo H,Howorth P,Valentine H,Liang S,Spicer D,Fuller M,Steiner J,Hamilton GS

    更新日期：2002-05-20 00:00:00

  • Diamino benzo[b]thiophene derivatives as a novel class of active site directed thrombin inhibitors. Part 6: further focus on the contracted C4'-side chain analogues.

    abstract：:Novel benzo[b]thiophene diamine thrombin inhibitors were investigated, focusing on a contracted C4'-side chain series. SAR studies identified compounds with either a pyrrolidino or morpholino group as potent, active site directed thrombin inhibitors when the amino group was connected to the C3-phenyl ring with a methy...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/s0960-894x(00)00211-0

    authors： Takeuchi K,Kohn TJ,Harper RW,Lin HS,Gifford-Moore DS,Richett ME,Sall DJ,Smith GF,Zhang M

    更新日期：2000-06-05 00:00:00

  • Design and synthesis of new 2-substituted-5-(2-benzylthiophenyl)-1,3,4-oxadiazoles as benzodiazepine receptor agonists.

    abstract：:A series of new 2-substituted-5-(2-benzylthiophenyl)-1,3,4-oxadiazoles was designed and synthesized as anticonvulsant agents. Conformational analysis and superimposition of energy minima conformers of the designed molecules on estazolam, a known benzodiazepine receptor agonist, revealed that the main proposed benzodia...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2005.04.018

    authors： Zarghi A,Faizi M,Shafaghi B,Ahadian A,Khojastehpoor HR,Zanganeh V,Tabatabai SA,Shafiee A

    更新日期：2005-06-15 00:00:00

  • Carbonic anhydrase activators: the first X-ray crystallographic study of an adduct of isoform I.

    abstract：:The X-ray crystallographic structure for the adduct of an activator with human carbonic anhydrase isozyme I (hCA I) is reported. L-Histidine binds deep within the enzyme active site, participating in a network of hydrogen bonds involving its carboxylate moiety and the zinc-bound water molecule, as well as the imidazol...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2006.07.021

    authors： Temperini C,Scozzafava A,Supuran CT

    更新日期：2006-10-01 00:00:00

  • Dual function inhibitors of relevance to chronic obstructive pulmonary disease.

    abstract：:The general strategy and rationale underlying the design of COPD therapeutics that possess protease inhibitory activity and are also capable of releasing a species that attenuates inflammation by inhibiting caspase-1, are described. The synthesis and in vitro biochemical evaluation of a dual function molecule that seq...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2010.12.033

    authors： Dou D,He G,Alliston KR,Groutas WC

    更新日期：2011-05-15 00:00:00

  • Progress in discovery of small-molecule modulators of protein-protein interactions via fragment screening.

    abstract：:Protein-protein interactions (PPIs) present a formidable challenge to medicinal chemistry. The extended and open nature of many binding sites at protein interfaces has made it difficult to find useful chemical matter by traditional screening methods using standard screening libraries. This Digest focuses on the progre...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章,评审

    doi：10.1016/j.bmcl.2015.04.089

    authors： Magee TV

    更新日期：2015-06-15 00:00:00

  • A comparative protease stability study of synthetic macrocyclic peptides that mimic two endocrine hormones.

    abstract：:Peptide therapeutics have traditionally faced many challenges including low bioavailability, poor proteolytic stability and difficult cellular uptake. Conformationally constraining the backbone of a peptide into a macrocyclic ring often ameliorates these problems and allows for the development of a variety of new drug...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2012.12.041

    authors： Ferrie JJ,Gruskos JJ,Goldwaser AL,Decker ME,Guarracino DA

    更新日期：2013-02-15 00:00:00

  • 1,2,3-Triazoles as inhibitors of indoleamine 2,3-dioxygenase 2 (IDO2).

    abstract：:Indoleamine 2,3-dioxygenase 2 (IDO2) is a potential therapeutic target for the treatment of diseases that involve immune escape such as cancer. In contrast to IDO1, only a very limited number of inhibitors have been described for IDO2 due to inherent difficulties in expressing and purifying a functionally active, solu...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2016.07.031

    authors： Röhrig UF,Majjigapu SR,Caldelari D,Dilek N,Reichenbach P,Ascencao K,Irving M,Coukos G,Vogel P,Zoete V,Michielin O

    更新日期：2016-09-01 00:00:00

  • C29 sterols with a cyclopropane ring at C-25 and 26 from the Vietnamese marine sponge Ianthella sp. and their anticancer properties.

    abstract：:Two new C(29) sterols with a cyclopropane ring at C-25 and C-26, petrosterol-3,6-dione (1) and 5alpha,6alpha-epoxy-petrosterol (2), along with petrosterol (3), were isolated from the Vietnamese marine sponge Ianthella sp. The structures of the new compounds were elucidated by comprehensive spectroscopic analyses. Comp...

    journal_title：Bioorganic & medicinal chemistry letters

    pub_type： 杂志文章

    doi：10.1016/j.bmcl.2009.06.097

    authors： Nguyen HT,Chau VM,Tran TH,Phan VK,Hoang TH,Nguyen TD,Nguyen XN,Tai BH,Hyun JH,Kang HK,Kim YH

    更新日期：2009-08-15 00:00:00