Design and one-pot synthesis of alpha-aminophosphonates and bis(alpha-aminophosphonates) by iron(III) chloride and cytotoxic activity.

Abstract:

:In this study, we used a solution of FeCl(3) in THF to facilitate the Mannich-type reaction of aldehyde, amine and phosphite compounds to form corresponding alpha-aminophosphonates in a one-pot, three-component reaction. Selected alpha-aminophosphonates were entered into a biological assay test and were studied by docking methods, using Autodock 3.0. The results showed that the reactions were carried out mildly and eco-friendly to form alpha-aminophosphonates in high yields. Some were found to have cytotoxic activity on the cell lines RAJI, JURKAT and MCF-7. An indole derived bis(alpha-aminophosphonates) showed maximum cytotoxic effect comparable to doxorubicin. Although the FDE (Final Docking Energy) for the most cytotoxic compound was of the most negative value, there is no correlation between FDE and cytotoxicity.

journal_name

Eur J Med Chem

authors

Rezaei Z,Firouzabadi H,Iranpoor N,Ghaderi A,Jafari MR,Jafari AA,Zare HR

doi

10.1016/j.ejmech.2009.07.009

subject

Has Abstract

pub_date

2009-11-01 00:00:00

pages

4266-75

issue

11

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(09)00389-4

journal_volume

44

pub_type

杂志文章
  • Design of nucleotide-mimetic and non-nucleotide inhibitors of the translation initiation factor eIF4E: Synthesis, structural and functional characterisation.

    abstract::Eukaryotic translation initiation factor 4E (eIF4E) is considered as the corner stone in the cap-dependent translation initiation machinery. Its role is to recruit mRNA to the ribosome through recognition of the 5'-terminal mRNA cap structure (m7GpppN, where G is guanosine, N is any nucleotide). eIF4E is implicated in...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.08.047

    authors: Soukarieh F,Nowicki MW,Bastide A,Pöyry T,Jones C,Dudek K,Patwardhan G,Meullenet F,Oldham NJ,Walkinshaw MD,Willis AE,Fischer PM

    更新日期:2016-11-29 00:00:00

  • Synthesis and in vitro Trichomonacidal activities of some new dialkylperoxides and 1,2,4-trioxanes.

    abstract::Two series of three trioxanes and 18 disubstituted peroxides were synthesised and evaluated for their in vitro trichomonacidal activity against Trichomonas vaginalis. The most active compound, 2-methylprop-2-yl 2-methoxyeth-1-yl peroxide exhibited an IC(50) value of 1.0+/-0.2 microM whereas other dialkyl peroxides had...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(01)01278-8

    authors: Camuzat-Dedenis B,Provot O,Cointeaux L,Peyrou V,Berrien JF,Bories C,Loiseau PM,Mayrargue J

    更新日期:2001-10-01 00:00:00

  • Tricyclononene carboxamide derivatives as novel anti-HIV-1 agents.

    abstract::By modifying the chemical structure of anti-orthopoxvirus compound ST-246, we designed and synthesized a series of tricyclononene carboxamide derivatives and tested their anti-HIV-1 activity and cytotoxicity. We found that benzoimidazol-containing compound 7g was highly effective in inhibiting HIV-1 R5 infection with ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.05.070

    authors: Dong MX,Zhang J,Peng XQ,Lu H,Yun LH,Jiang S,Dai QY

    更新日期:2010-09-01 00:00:00

  • Covalent and noncovalent constraints yield a figure eight-like conformation of a peptide inhibiting the menin-MLL interaction.

    abstract::The interaction between menin and mixed lineage leukemia (MLL) was identified as an interesting target for treating some cancers including acute leukemia. On the basis of the known crystal structure of the MBM1-menin complex (MBM - menin binding motif), several cyclic peptides were designed. Elaboration of the effecti...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112748

    authors: Fortuna P,Linhares BM,Purohit T,Pollock J,Cierpicki T,Grembecka J,Berlicki Ł

    更新日期:2020-12-01 00:00:00

  • Synthesis and biological evaluation of novel 2-arylamino-3-(arylsulfonyl)quinoxalines as PI3Kα inhibitors.

    abstract::A series of novel 2-arylamino-3-(arylsulfonyl)quinoxalines was synthesized through a newly developed approach. All synthesized target compounds were screened for their cytotoxicities against cancer cell lines including PC3, A549, HCT116, HL60 and KB. Representative compounds with favorable cytotoxicities were tested f...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.09.015

    authors: Wu P,Su Y,Liu X,Zhang L,Ye Y,Xu J,Weng S,Li Y,Liu T,Huang S,Yang B,He Q,Hu Y

    更新日期:2011-11-01 00:00:00

  • 3D-QSAR analysis of human immunodeficiency virus entry-1 inhibitors by CoMFA and CoMSIA.

    abstract::3D-QSAR studies namely CoMFA, CoMFA region focusing and CoMSIA have been carried out on a series (36 compounds) of HIV-1 entry inhibitors. An alignment rule for the compounds was defined using Distill in SYBYL 7.3. Models were validated using a data set obtained by dividing the data set into a training set and test se...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.07.062

    authors: Pirhadi S,Ghasemi JB

    更新日期:2010-11-01 00:00:00

  • Plant-derived mPGES-1 inhibitors or suppressors: A new emerging trend in the search for small molecules to combat inflammation.

    abstract::Inflammation comprises the reaction of the body to injury, in which a series of changes of the terminal vascular bed, blood, and connective tissue tends to eliminate the injurious agent and to repair the damaged tissue. It is a complex process, which involves the release of diverse regulatory mediators. The current an...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2017.12.059

    authors: Khan H,Rengasamy KRR,Pervaiz A,Nabavi SM,Atanasov AG,Kamal MA

    更新日期:2018-06-10 00:00:00

  • Synthesis and in vitro evaluation of novel spiroketopyrazoles as acetyl-CoA carboxylase inhibitors and potential antitumor agents.

    abstract::Acetyl-CoA carboxylase (ACC) is a rate-limiting enzyme in de novo fatty acid synthesis, which plays a critical role in the growth and survival of cancer cells. In this study, a series of spiroketopyrazole derivatives bearing quinoline moieties were synthesized, and in vitro anticancer activities of these compounds as ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.113036

    authors: Huang T,Wu X,Yan S,Liu T,Yin X

    更新日期:2020-11-27 00:00:00

  • Synthesis, colon-targeted studies and pharmacological evaluation of an anti-ulcerative colitis drug 4-Aminosalicylic acid-β-O-glucoside.

    abstract::A glycoside prodrug of 4-aminosalicylic acid (4-ASA) with d-glucose was synthesized for targeted drug delivery to inflammatory bowel. The in vitro assessment of 4-aminosalicylic acid-β-O-glucoside (4-ASA-Glu) as a colon-specific prodrug was studied using colitis rat with the healthy one as control. The stability studi...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.12.021

    authors: Li F,Wu G,Zheng H,Wang L,Zhao Z

    更新日期:2016-01-27 00:00:00

  • Probing the antiamoebic and cytotoxicity potency of novel tetrazole and triazine derivatives.

    abstract::A series of compounds bearing a Tetrazole and Triazine ring motif conjugated with a SO(2)NH function were synthesized and investigated for their antiamoebic potency. Cytotoxicity of the compounds was checked on human hepatocellular carcinoma cell line HepG2. Incorporation of Triazine ring in place of tetrazole resulte...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.12.033

    authors: Wani MY,Bhat AR,Azam A,Choi I,Athar F

    更新日期:2012-02-01 00:00:00

  • Palladium(II) and platinum(II) complexes of a symmetric Schiff base derived from 2,6,diformyl-4-methylphenol with N-aminopyrimidine: synthesis, characterization and detection of DNA interaction by voltammetry.

    abstract::The two new mononuclear complexes were prepared by reacting symmetric Schiff base, containing pyrimidine rings and the metal chlorides of Pd(II) and Pt(II) in methanol. The mononuclear structure of the complexes was confirmed on the basis of elemental analyses, magnetic susceptibility, IR, UV-Vis, NMR, DTA/TGA and API...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.06.016

    authors: Sönmez M,Celebi M,Yardim Y,Sentürk Z

    更新日期:2010-09-01 00:00:00

  • Synthesis and biological evaluation of (1-aryl-1H-pyrazol-4-yl) (3,4,5-trimethoxyphenyl)methanone derivatives as tubulin inhibitors.

    abstract::A series of (1-aryl-1H-pyrazol-4-yl) (3,4,5-trimethoxyphenyl)methanones (8a-p, 9a-p) and ketoxime (10c) derivatives were designed and synthesized as antitubulin agents. All of the target compounds were evaluated for the in vitro anti-proliferative activities against three tumor cell lines (A549, HT-1080, SGC-7901). Th...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.05.058

    authors: Zhai M,Wang L,Liu S,Wang L,Yan P,Wang J,Zhang J,Guo H,Guan Q,Bao K,Wu Y,Zhang W

    更新日期:2018-08-05 00:00:00

  • Synthesis and antiproliferative activity of novel selenoester derivatives.

    abstract::A series of 31 new selenoesters were synthesized and their cytotoxic activity was evaluated against a prostate cancer cell line (PC-3). The most active compounds were also tested against three tumoural cell lines (MCF-7, A-549 and HT-29) and one non-tumour prostate cell line (RWPE-1). Thirteen compounds showed signifi...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.11.034

    authors: Domínguez-Álvarez E,Plano D,Font M,Calvo A,Prior C,Jacob C,Palop JA,Sanmartín C

    更新日期:2014-02-12 00:00:00

  • Preparation and antitubercular activities in vitro and in vivo of novel Schiff bases of isoniazid.

    abstract::Structural modification of the frontline antitubercular isonicotinic acid hydrazide (INH) provides lipophilic adaptations (3-46) of the drug in which the hydrazine moiety of the parent compound has been chemically blocked from the deactivating process of N(2)-acetylation by N-arylaminoacetyl transferases. As a class, ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2009.05.009

    authors: Hearn MJ,Cynamon MH,Chen MF,Coppins R,Davis J,Joo-On Kang H,Noble A,Tu-Sekine B,Terrot MS,Trombino D,Thai M,Webster ER,Wilson R

    更新日期:2009-10-01 00:00:00

  • Synthesis, molecular docking and biological evaluation of Schiff base transition metal complexes as potential urease inhibitors.

    abstract::Six transition metal compounds of Schiff base ligands were evaluated for the inhibitory activity on jack bean urease, of which compounds 2-6 were determined by single crystal X-ray analysis. It was found that copper(II) complexes 1 and 4 showed strong inhibitory activity against jack bean urease (IC(50) = 0.52 and 0.4...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.07.007

    authors: Chen W,Li Y,Cui Y,Zhang X,Zhu HL,Zeng Q

    更新日期:2010-10-01 00:00:00

  • Synthesis of novel bioactive derivatives of 3-(4-chlorophenyl)-2-hydrazino-5,6,7,8-tetrahydrobenzo(b)thieno[2,3-d]pyrimidine-4(3H)-ones.

    abstract::A series of triazolo[4,3-a]tetrahydrobenzo(b)thieno[3,2-e]pyrimidine-5(4H)-ones (12a-n) were synthesized and evaluated for CNS depressant, skeletal muscle relaxant and anticonvulsant activities by photoactometer, Rotarod and pentylenetetrazole induced the convulsions method respectively in Swiss albino mice. Diazepam ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2009.05.027

    authors: Gupta SV,Baheti K,Bora R,Dekhane D,Chhabría M,Shingare M,Pawar S,Shishoo CJ,Thore SN

    更新日期:2009-11-01 00:00:00

  • Discovery of novel series of 2-substituted benzo[d]oxazol-5-amine derivatives as multi-target directed ligands for the treatment of Alzheimer's disease.

    abstract::Alzheimer's disease (AD) is associated with multifactorial neuropathological conditions, which include cholinergic deficit, amyloid-beta plaques formation, loss of neuronal plasticity and neuronal death. Treating such multifactorial conditions with a single target directed approach is considered to be inadequate. Acco...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.111613

    authors: Gutti G,Kakarla R,Kumar D,Beohar M,Ganeshpurkar A,Kumar A,Krishnamurthy S,Singh SK

    更新日期:2019-11-15 00:00:00

  • 2,2'-bipyridyl based copper complexes down regulate expression of pro-inflammatory cytokines and suppress MAPKs in mitogen induced Peripheral blood mononuclear cells.

    abstract::2,2'-bipyridyl based copper complex I: [CuC24H22N6O10] at 10 nM and complex Ia: [Cu2C32H43N8O3](PF6)4 at 7 nM exhibited 50% inhibition of lymphocyte proliferation and less than 20% cytotoxicity in peripheral blood mononuclear cells (PBMCs). Further, pro-inflammatory cytokines such as TNF-alpha and IL-1beta and pro-inf...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.01.041

    authors: Rupesh KR,Priya AM,Sundarakrishnan B,Venkatesan R,Lakshmi BS,Jayachandran S

    更新日期:2010-06-01 00:00:00

  • Cardanol-derived AChE inhibitors: Towards the development of dual binding derivatives for Alzheimer's disease.

    abstract::Cardanol is a phenolic lipid component of cashew nut shell liquid (CNSL), obtained as the byproduct of cashew nut food processing. Being a waste product, it has attracted much attention as a precursor for the production of high-value chemicals, including drugs. On the basis of these findings and in connection with our...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.12.024

    authors: Lemes LFN,de Andrade Ramos G,de Oliveira AS,da Silva FMR,de Castro Couto G,da Silva Boni M,Guimarães MJR,Souza INO,Bartolini M,Andrisano V,do Nascimento Nogueira PC,Silveira ER,Brand GD,Soukup O,Korábečný J,Romeiro NC,Cas

    更新日期:2016-01-27 00:00:00

  • Pharmaceutical salts and cocrystals involving amino acids: a brief structural overview of the state-of-art.

    abstract::Salification of new drug substances in order to improve physico-chemical or solid-state properties (e.g. dissolution rate or solubility, appropriate workup process, storage for further industrial and marketing development) is a well-accepted procedure. Amino acids, like aspartic acid, lysine or arginine take a great p...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2013.11.045

    authors: Tilborg A,Norberg B,Wouters J

    更新日期:2014-03-03 00:00:00

  • Design of α7 nicotinic acetylcholine receptor ligands using the (het)Aryl-1,2,3-triazole core: Synthesis, in vitro evaluation and SAR studies.

    abstract::We report here the synthesis of a large library of 1,2,3-triazole derivatives which were in vitro tested as α7 nAchR ligands. The SAR study revealed that several crucial factors are involved in the affinity of these compounds for α7 nAchR such as a (R) quinuclidine configuration and a mono C-3 quinuclidine substitutio...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.11.001

    authors: Ouach A,Pin F,Bertrand E,Vercouillie J,Gulhan Z,Mothes C,Deloye JB,Guilloteau D,Suzenet F,Chalon S,Routier S

    更新日期:2016-01-01 00:00:00

  • Optimization of novel oxidative DIMs as Nur77 modulators of the Nur77-Bcl-2 apoptotic pathway.

    abstract::Nur77, an orphan nuclear receptor, is a member of the nuclear receptor superfamily. Nur77 plays important roles in various biological processes. Previously we reported that BI1071(DIM-C-pPhCF3+MeSO3-), an oxidized form and methanesulfonate salt of (4-CF3-Ph-C-DIM), can modulate Nur77's non-genomic apoptotic pathway th...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.113020

    authors: Tu X,Chen X,Zhang D,Gao M,Liang J,Bao G,Zhang J,Peng S,Zhang X,Zeng Z,Su Y

    更新日期:2021-02-05 00:00:00

  • Design and synthesis of aminothiazolyl norfloxacin analogues as potential antimicrobial agents and their biological evaluation.

    abstract::A series of aminothiazolyl norfloxacin analogues as a new type of potential antimicrobial agents were synthesized and screened for their antimicrobial activities. Most of the prepared compounds exhibited excellent inhibitory efficiencies. Especially, norfloxacin analogue II-c displayed superior antimicrobial activitie...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.01.072

    authors: Wang LL,Battini N,Bheemanaboina RRY,Zhang SL,Zhou CH

    更新日期:2019-04-01 00:00:00

  • Structure-activity relationship studies of acridones as potential antipsoriatic agents. 2. Synthesis and antiproliferative activity of 10-substituted hydroxy-10H-acridin-9-ones against human keratinocyte growth.

    abstract::A series of 10-substituted hydroxy-10H-acridin-9-ones were synthesized and studied as potential antipsoriatic agents. The antiproliferative activity of the novel derivatives, which can be considered as aza-analogues of the antipsoriatic drug anthralin, was determined using the human keratinocyte cell line HaCaT. Struc...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.08.059

    authors: Putic A,Stecher L,Prinz H,Müller K

    更新日期:2010-11-01 00:00:00

  • Synthesis, antiarrhythmic and anticoagulant activities of novel thiazolo derivatives from methyl 2-(thiazol-2-ylcarbamoyl)acetate.

    abstract::A series of novel thiazolo derivatives were synthesized by initial condensation of methyl 2-(thiazol-2-ylcarbamoyl)acetate with phenyl isothiocyanate and further reactions using different organic reagents. The structures of newly synthesized compounds were confirmed by IR, 1H NMR, EIMS spectral data and elemental anal...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.05.004

    authors: Amr Ael-G,Sabrry NM,Abdalla MM,Abdel-Wahab BF

    更新日期:2009-02-01 00:00:00

  • Substitution at the indole 3 position yields highly potent indolecombretastatins against human tumor cells.

    abstract::Resistance to combretastatin A-4 is mediated by metabolic modification of the phenolic hydroxyl and ether groups of the 3-hydroxy-4-methoxyphenyl (B ring). Replacement of the B ring of combretastatin A-4 by a N-methyl-5-indolyl reduces tubulin polymerization inhibition (TPI) and cytotoxicity against human cancer cell ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.08.078

    authors: Álvarez R,Gajate C,Puebla P,Mollinedo F,Medarde M,Peláez R

    更新日期:2018-10-05 00:00:00

  • Discovery of target based novel pyrrolyl phenoxy derivatives as antimycobacterial agents: an in silico approach.

    abstract::A new series of pyrrolyl phenoxy derivatives bearing alkoxy linker were synthesized and evaluated for anti-tubercular activity (anti-TB) against Mycobacterium tuberculosis. Molecular modeling, pharmacophore constructed using GALAHAD to produce an effective alignment of data set and evaluated by Pareto ranking. The pha...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.03.013

    authors: More UA,Joshi SD,Aminabhavi TM,Kulkarni VH,Badiger AM,Lherbet C

    更新日期:2015-04-13 00:00:00

  • Hydroxymethyl bioisosteres of phenolic GluN2B-selective NMDA receptor antagonists: Design, synthesis and pharmacological evaluation.

    abstract::Antagonists addressing selectively NMDA receptors containing the GluN2B subunit are of particular interest for the treatment of various neurological disorders including neurodegenerative diseases. With the aim to bioisosterically replace the metabolically labile phenol of 7-amino-6,7,8,9-tetrahydro-5H-benzo[7]annulen-...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.12.054

    authors: Temme L,Frehland B,Schepmann D,Robaa D,Sippl W,Wünsch B

    更新日期:2018-01-20 00:00:00

  • Small molecule therapeutics for tauopathy in Alzheimer's disease: Walking on the path of most resistance.

    abstract::Alzheimer's disease (AD) is the most common form of dementia characterized by presence of extracellular amyloid plaques and intracellular neurofibrillary tangles composed of tau protein. Currently there are close to 50 million people living with dementia and this figure is expected to increase to 75 million by 2030 pu...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2020.112915

    authors: Wang L,Bharti,Kumar R,Pavlov PF,Winblad B

    更新日期:2021-01-01 00:00:00

  • Synthesis of isatin based N1-alkylated 3-β-C-glycoconjugated-oxopropylidene oxindoles as potent antiplasmodial agents.

    abstract::In an attempt to develop new antimalarial drugs, we have synthesized a new class of N-alkylated 3-glycoconjugated-oxopropylidene oxindoles starting from substituted isatins and glucopyranosyl propanone via a well-known cross-aldol reaction followed by dehydration. The newly synthesized compounds were screened for thei...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.11.008

    authors: Thakur RK,Joshi P,Upadhyaya K,Singh K,Sharma G,Shukla SK,Tripathi R,Tripathi RP

    更新日期:2019-01-15 00:00:00