当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY期刊下所有文献 > 000Synthesis of new α-aminophosphonates: Evaluation as anti-inflammatory agents and QSAR studies.

000Synthesis of new α-aminophosphonates: Evaluation as anti-inflammatory agents and QSAR studies.

Abstract：

:In this paper, we report the synthesis of a new series of α-aminophosphonates derivatives based in an efficient three-component reaction. All compounds prepared showed significant anti-inflammatory activity, being the compounds 1a, 1c, 1d, 1f, 2b and 2c the most promising ones, in terms of maximal efficacy (over 95%), potency (ED50 range between 0.7 and 10.1 mg/ear) and relative potency (range from 0.04 to 0.67). Compounds 1a, 1c, 1d and 1f significantly decrease the number of neutrophils (range from 46.7 to 63.0%) and monocytes (18.9-34.1%) in blood samples from the orbital sinus. Additionally, QSAR model revealed that the spherical molecular shape and the location of the HOMO on the phenyl ring improves the anti-inflammatory activity of the compounds. The values of R2, Q2, s and F statistical parameters and the QUIK, asymptotic Q2 and Overfitting rules validate the descriptive and predictive ability of the QSAR model. Altogether these results suggest that these new α-aminophosphonates are potential agents for the treatment of inflammation.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Romero-Estudillo I,Viveros-Ceballos JL,Cazares-Carreño O,González-Morales A,de Jesús BF,López-Castillo M,Razo-Hernández RS,Castañeda-Corral G,Ordóñez M

doi

10.1016/j.bmc.2018.12.041

subject

Has Abstract

pub_date

2019-06-15 00:00:00

pages

2376-2386

issue

12

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(18)31938-2

journal_volume

27

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY文献大全
  • 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

  • Studies on 3'-quaternary ammonium cephalosporins--IV. Synthesis and antibacterial activity of 3'-(2-alkyl-3-aminopyrazolium) cephalosporins related to FK037.

    abstract：:The synthesis and in vitro antibacterial activity of 7 beta-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido] cephalosporins bearing various 2-alkyl-3-aminopyrazolium groups at the 3-position are described. Antibacterial activity against MRSA was affected by the nature of the substituent at the 2-position on the 3...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(97)00092-8

    authors： Ohki H,Kawabata K,Inamoto Y,Okuda S,Kamimura T,Sakane K

    更新日期：1997-08-01 00:00:00

  • Imidazolone-amide bridges and their effects on tubulin polymerization in cis-locked vinylogous combretastatin-A4 analogues: synthesis and biological evaluation.

    abstract：:A series of novel combretastatin-A4 analogues in which the cis-olefinic bridge is replaced by an imidazolone-amide were synthesized, and their cytotoxicity and tubulin-polymerization inhibitory activities were evaluated. These compounds appear to be potential tubulin-polymerization inhibitors. Compounds 10, 9b and 9c,...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2011.03.068

    authors： Li YW,Liu J,Liu N,Shi D,Zhou XT,Lv JG,Zhu J,Zheng CH,Zhou YJ

    更新日期：2011-06-01 00:00:00

  • Tessaric acid derivatives induce G2/M cell cycle arrest in human solid tumor cell lines.

    abstract：:A series of analogs were synthesized in a straightforward manner from naturally available sesquiterpenes ilicic acid and tessaric acid. The in vitro antiproliferative activities were examined in the human solid tumor cell lines A2780, HBL-100, HeLa, SW1573, T-47D and WiDr. The most potent analog induced considerably g...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.07.053

    authors： León LG,Donadel OJ,Tonn CE,Padrón JM

    更新日期：2009-09-01 00:00:00

  • The synthesis of (R)-(+)-lipoic acid using a monooxygenase-catalysed biotransformation as the key step.

    abstract：:2-(2-Acetoxyethyl)cyclohexanone (4) was converted into the lactone (-)-(5) regio- and enantioselectively using 2-oxo-delta 3-4,5,5-trimethylcyclopentenyl acetyl-CoA monooxygenase, an NADPH-dependent Baeyer-Villiger monooxygenase from camphor grown Pseudomonas putida NCIMB 10007. The lactone (-)-(5) was converted into ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(96)00234-9

    authors： Adger B,Bes MT,Grogan G,McCague R,Pedragosa-Moreau S,Roberts SM,Villa R,Wan PW,Willetts AJ

    更新日期：1997-02-01 00:00:00

  • Synthesis and anticancer activity of benzyloxybenzaldehyde derivatives against HL-60 cells.

    abstract：:A series of benzyloxybenzaldehyde derivatives were prepared and tested against the HL-60 cell line for anticancer activity. Preliminary structure-activity relationships were established. It was discovered that 2-(benzyloxy)benzaldehyde (17), 2-(benzyloxy)-4-methoxybenzaldehyde (26), 2-(benzyloxy)-5-methoxybenzaldehyde...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.12.026

    authors： Lin CF,Yang JS,Chang CY,Kuo SC,Lee MR,Huang LJ

    更新日期：2005-03-01 00:00:00

  • Design, synthesis and biological evaluation of a series of pyrano chalcone derivatives containing indole moiety as novel anti-tubulin agents.

    abstract：:A new series of pyrano chalcone derivatives containing indole moiety (3-42, 49a-49r) were synthesized and evaluated for their antiproliferative activities. Among all the compounds, compound 49b with a propionyloxy group at the 4-position of the left phenyl ring and N-methyl-5-indoly on the right ring displayed the mos...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2014.02.028

    authors： Wang G,Li C,He L,Lei K,Wang F,Pu Y,Yang Z,Cao D,Ma L,Chen J,Sang Y,Liang X,Xiang M,Peng A,Wei Y,Chen L

    更新日期：2014-04-01 00:00:00

  • Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages.

    abstract：:Caffeic acid esters, one of the components of propolis, are known to show a variety of biological effects such as anti-tumor, anti-oxidant, and anti-inflammatory activities. Although, the anti-inflammatory activities of caffeic acid esters have been studied by analyzing their structure, the detailed mechanisms of thei...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.07.006

    authors： Uwai K,Osanai Y,Imaizumi T,Kanno S,Takeshita M,Ishikawa M

    更新日期：2008-08-15 00:00:00

  • Sulfonamide-1,2,4-triazole derivatives as antifungal and antibacterial agents: synthesis, biological evaluation, lipophilicity, and conformational studies.

    abstract：:A series of 10 new 5-[2-(substituted sulfamoyl)-4,5-dimethoxy-benzyl]-4aryl-s-triazole-3-thiones were synthesized and evaluated for in vitro antifungal and antibacterial activity. All compounds tested showed significant antifungal activity against all the micromycetes, compared to the commercial fungicide bifonazole. ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.10.082

    authors： Ezabadi IR,Camoutsis C,Zoumpoulakis P,Geronikaki A,Soković M,Glamocilija J,Cirić A

    更新日期：2008-02-01 00:00:00

  • Simple molecular engineering of glycol nucleic acid: progression from self-pairing to cross-pairing with cDNA and RNA.

    abstract：:The acyclic chiral nucleic acid analogue, Glycol Nucleic Acid (GNA), displayed exceptional structural simplicity and atom economy while forming self-paired duplexes, using canonical Watson-Crick base pairing. We disclose here that the replacement of phosphodiester linker in GNA with somewhat rigid and shorter carbamat...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2014.08.022

    authors： Bose T,Kumar VA

    更新日期：2014-11-01 00:00:00

  • Neurotrophic and antileukemic daphnane diterpenoids from Synaptolepis kirkii.

    abstract：:Biological assay guided fractionation of a dichloromethane extract of Synaptolepis kirkii led to the isolation of four new and five known daphnane-type diterpene orthoesters, whose structure was established by spectroscopic data. Full spectroscopic data of the new and known natural products are reported here for the f...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(02)00163-3

    authors： He W,Cik M,Van Puyvelde L,Van Dun J,Appendino G,Lesage A,Van der Lindin I,Leysen JE,Wouters W,Mathenge SG,Mudida FP,De Kimpe N

    更新日期：2002-10-01 00:00:00

  • Synthesis and anti-inflammatory activity of isoquebecol.

    abstract：:We report here the synthesis of isoquebecol, an unprecedented constitutional isomer of quebecol, a polyphenolic compound discovered in maple syrup. The methodology used to prepare isoquebecol involves, as key steps, the formation of a dibromoalkene from an α-ketoester precursor, followed by a double Suzuki-Miyaura rea...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.01.050

    authors： Cardinal S,Paquet-Côté PA,Azelmat J,Bouchard C,Grenier D,Voyer N

    更新日期：2017-04-01 00:00:00

  • Design, synthesis, and docking studies of quinazoline analogues bearing aryl semicarbazone scaffolds as potent EGFR inhibitors.

    abstract：:Two series of quinazoline derivatives bearing aryl semicarbazone scaffolds (9a-o and 10a-o) were designed, synthesized and evaluated for the IC50 values against four cancer cell lines (A549, HepG2, MCF-7 and PC-3). The selected compound 9o was further evaluated for the inhibitory activity against EGFR kinases. Four of...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.04.001

    authors： Tu Y,Wang C,Xu S,Lan Z,Li W,Han J,Zhou Y,Zheng P,Zhu W

    更新日期：2017-06-15 00:00:00

  • Discovery of a series of novel compounds with moderate anti-hepatitis C virus NS3 protease activity in vitro.

    abstract：:The hepatitis C virus (HCV) NS3/4A protease that plays an important role in the viral life cycle has been proven to be an excellent target for the discovery of anti-HCV drugs. Enlightened by some P2-triazole and amide compounds, which had been found as HCV NS3 protease inhibitors, we designed and synthesized a series ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.07.032

    authors： Shi F,Zhang Y,Xu W

    更新日期：2015-09-01 00:00:00

  • Design, synthesis and biological evaluation of N-phenylthieno[2,3-d]pyrimidin-4-amines as inhibitors of FGFR1.

    abstract：:Fibroblast grow factor receptor 1 (FGFR1) is an important anti-cancer target that plays crucial role in oncogenesis and oncogenic angiogenesis. The structure-activity relationship (SAR) of N-phenylthieno[2,3-d]pyrimidin-4-amines was investigated. Binding of active compounds with FGFR1 kinase was analyzed by molecular ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2014.12.044

    authors： Gryshchenko AA,Bdzhola VG,Balanda AO,Briukhovetska NV,Kotey IM,Golub AG,Ruban TP,Lukash LL,Yarmoluk SM

    更新日期：2015-05-01 00:00:00

  • Toward the development of chemoprevention agents. Part 1: Design, synthesis, and anti-inflammatory activities of a new class of 2,5-disubstituted-dioxacycloalkanes.

    abstract：:A new class of 2,5-disubstituted-dioxacycloalkanes were designed and synthesized via stereoselective synthetic method as cancer chemoprevention agents. The anti-inflammatory activities of these compounds were tested using the xylene-induced mouse ear edema model. Some of these compounds exhibited comparable or better ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.05.013

    authors： Gu K,Bi L,Zhao M,Wang C,Ju J,Peng S

    更新日期：2007-07-15 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

  • 6-Hydrophobic aromatic substituent pyrimethamine analogues as potential antimalarials for pyrimethamine-resistant Plasmodium falciparum.

    abstract：:The series of des-Cl (unsubstituted) and m-Cl phenyl analogues of PYR with various flexible 6-substituents were synthesized and studied for the binding affinities with highly resistant quadruple mutant (QM) DHFR. The derivatives carrying 4 atoms linker with a terminal carboxyl substituted on the aromatic ring exhibite...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2019.115158

    authors： Saepua S,Sadorn K,Vanichtanankul J,Anukunwithaya T,Rattanajak R,Vitsupakorn D,Kamchonwongpaisan S,Yuthavong Y,Thongpanchang C

    更新日期：2019-12-15 00:00:00

  • Discovery of novel 4-(2-fluorophenoxy)quinoline derivatives bearing 4-oxo-1,4-dihydrocinnoline-3-carboxamide moiety as c-Met kinase inhibitors.

    abstract：:A series of novel 4-(2-fluorophenoxy)quinoline derivatives containing 4-oxo-1,4-dihydrocinnoline-3-carboxamide moiety were designed, synthesized and evaluated for their in vitro biological activities against c-Met kinase and six typical cancer cell lines (A549, H460, HT-29, MKN-45, U87MG and SMMC-7721). All the prepar...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2013.04.013

    authors： Li S,Zhao Y,Wang K,Gao Y,Han J,Cui B,Gong P

    更新日期：2013-06-01 00:00:00

  • Substituted thiophene-anthranilamides as potent inhibitors of human factor Xa.

    abstract：:A series of thiophene-containing non-amidine factor Xa inhibitors is described. Simple methyl-substituted thiophene analogs were relatively weak inhibitors. However, introduction of hydrophilic substituents at C-4 or C-5 of the thiophene afforded inhibitors with low nanomolar potency. Optimization of the thiophene sub...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2006.12.019

    authors： Kochanny MJ,Adler M,Ewing J,Griedel BD,Ho E,Karanjawala R,Lee W,Lentz D,Liang AM,Morrissey MM,Phillips GB,Post J,Sacchi KL,Sakata ST,Subramanyam B,Vergona R,Walters J,White KA,Whitlow M,Ye B,Zhao Z,Shaw KJ

    更新日期：2007-03-01 00:00:00

  • Synthesis and characterization of some atypical sphingoid bases.

    abstract：:Sphingolipids are ubiquitous and abundant components of all eukaryotic and some prokaryotic organisms. Sphingolipids show a large structural variety not only between the different species, but also within an individual cell. This variety is not limited to alterations in the polar headgroups of e.g. glycosphingolipids,...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2018.06.031

    authors： Saied EM,Le TL,Hornemann T,Arenz C

    更新日期：2018-08-07 00:00:00

  • Synthesis of both enantiomers of hydroxypipecolic acid derivatives equivalent to 5-azapyranuronic acids and evaluation of their inhibitory activities against glycosidases.

    abstract：:We have synthesized 3-hydroxy- and 3,4,5-trihydroxypipecolic acid derivatives corresponding to 5-aza derivatives of uronic acids and evaluated their inhibitory activities against various glycosidases including beta-glucuronidase. Compounds 4 and 5 were chosen as common intermediates for the synthesis of 3,4,5-trihydro...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.06.016

    authors： Yoshimura Y,Ohara C,Imahori T,Saito Y,Kato A,Miyauchi S,Adachi I,Takahata H

    更新日期：2008-09-01 00:00:00

  • Conformational control of cyclosporin through substitution of the N-5 position. A new class of cyclosporin antagonists.

    abstract：:Cyclosporin A (CsA) can be regiospecifically alkylated at the NH of Val-5 with reactive bromides in the presence of phosphazene-base P4-t-Bu to yield derivatives 2-5. These are devoid of immunosuppressive activity in vitro but they have binding affinity for cyclophilin A (CypA) similar to that of CsA and thus represen...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(96)00204-0

    authors： Papageorgiou C,Kallen J,France J,French R

    更新日期：1997-01-01 00:00:00

  • Elaboration of a fragment library hit produces potent and selective aspartate semialdehyde dehydrogenase inhibitors.

    abstract：:Aspartate-β-semialdehyde dehydrogenase (ASADH) lies at the first branch point in the aspartate metabolic pathway which leads to the biosynthesis of several essential amino acids and some important metabolites. This pathway is crucial for many metabolic processes in plants and microbes like bacteria and fungi, but is a...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.09.017

    authors： Thangavelu B,Bhansali P,Viola RE

    更新日期：2015-10-15 00:00:00

  • Click synthesis of estradiol-cyclodextrin conjugates as cell compartment selective estrogens.

    abstract：:Cyclodextrin (CD) is a well known drug carrier and excipient for enhancing aqueous solubility. CDs themselves are anticipated to have low membrane permeability because of relatively high hydrophilicity and molecular weight. CD derivatization with 17-beta estradiol (E(2)) was explored extensively using a number of diff...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.11.046

    authors： Kim HY,Sohn J,Wijewickrama GT,Edirisinghe P,Gherezghiher T,Hemachandra M,Lu PY,Chandrasena RE,Molloy ME,Tonetti DA,Thatcher GR

    更新日期：2010-01-15 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

  • New, stronger nucleophiles for nucleic acid-templated chemistry: Synthesis and application in fluorescence detection of cellular RNA.

    abstract：:Nucleic acid-templated chemistry is a promising strategy for imaging genetic sequences in living cells. Here we describe the synthesis of two new nucleophiles for use in templated nucleophilic displacements with DNA probes. The nucleophilic groups are phosphorodithioate and phosphorotrithioate; we report on synthetic ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.04.051

    authors： Miller GP,Silverman AP,Kool ET

    更新日期：2008-01-01 00:00:00

  • Discovery and synthesis of novel luteolin derivatives as DAT agonists.

    abstract：:Luteolin, 5,7-dihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one, has been proposed and proved to be a novel dopamine transporter (DAT) activator. In order to develop this potential of luteolin, a series of novel luteolin derivatives were designed, synthesized, and evaluated for their DAT agonistic activities, utilizi...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.09.049

    authors： Zhang J,Liu X,Lei X,Wang L,Guo L,Zhao G,Lin G

    更新日期：2010-11-15 00:00:00

  • Syntheses and evaluation of antioxidant activity of sydnonyl substituted thiazolidinone and thiazoline derivatives.

    abstract：:3-Aryl-4-formylsydnone 4'-phenylthiosemicarbazones (3a-d) and 3-aryl-4-formylsydnone thiosemicarbazones (3e-h), which are precursors of 3-aryl-4-heterocyclic sydnones, are prepared by the condensation of 3-aryl-4-formylsydnones (1a-d) with 4'-phenylthiosemicarbazide (2a) and thiosemicarbazide (2b), respectively. The t...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.06.033

    authors： Shih MH,Ke FY

    更新日期：2004-09-01 00:00:00

  • Synthesis and structure-activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents.

    abstract：:KPU-105 (4), a potent anti-microtubule agent that contains a benzophenone was derived from the diketopiperazine-type vascular disrupting agent (VDA) plinabulin 3, which displays colchicine-like tubulin depolymerization activity. To develop derivatives with more potent anti-microtubule and cytotoxic activities, we furt...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2012.05.059

    authors： Yamazaki Y,Sumikura M,Masuda Y,Hayashi Y,Yasui H,Kiso Y,Chinen T,Usui T,Yakushiji F,Potts B,Neuteboom S,Palladino M,Lloyd GK,Hayashi Y

    更新日期：2012-07-15 00:00:00