Rhodium(II) acetate-catalyzed stereoselective synthesis, SAR and anti-HIV activity of novel oxindoles bearing cyclopropane ring.

Abstract:

:Novel oxindole derivatives bearing substituted cyclopropane ring have been designed on the basis of docking studies with HIV-1 RT using the software DS 2.5 and synthesized as probable NNRTIs against HIV-1 using rhodium(II) acetate-catalyzed stereoselective cyclopropanation reaction. The cyclopropane isomer, having trans relationship with respect to carbonyl of lactam moiety and functional group on the cyclopropane ring, was the major product in all cases along with a small amount of cis and methylene products. The trans isomers interacted well with HIV-1 RT through H-bonding with amino acids, like Lys101, Lys103, His235, Tyr318, constituting the non-nucleoside inhibitor binding pocket (NNIBP) during docking experiments. However, the compounds showed very little activity when subjected to in vitro anti-HIV-1 screening using β-galactosidase assay (TZM-bl cells) and GFP quantification (CEM-GFP cells). The very low level of in vitro HIV inhibition, in comparison to predicted EC(50) values on the basis of computational studies, during CEM-GFP screening using AZT as positive control indicated that probably the HIV RT is not the viral target and the molecules work through some different mechanism.

journal_name

Eur J Med Chem

authors

Kumari G,Nutan,Modi M,Gupta SK,Singh RK

doi

10.1016/j.ejmech.2011.01.037

subject

Has Abstract

pub_date

2011-04-01 00:00:00

pages

1181-8

issue

4

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(11)00059-6

journal_volume

46

pub_type

杂志文章
  • Targeting Eph/ephrin system in cancer therapy.

    abstract::It is well established that the Eph/ephrin system plays a central role in the embryonic development, with minor implications in the physiology of the adult. However, it is overexpressed and deregulated in a variety of tumors, with a primary involvement in tumorigenesis, tumor angiogenesis, metastasis development, and ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2017.07.029

    authors: Lodola A,Giorgio C,Incerti M,Zanotti I,Tognolini M

    更新日期:2017-12-15 00:00:00

  • New groups of antimycobacterial agents: 6-chloro-3-phenyl-4-thioxo-2H-1,3-benzoxazine-2(3H)-ones and 6-chloro-3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dithiones.

    abstract::A series of 6-chloro-3-phenyl-4-thioxo-2H-1,3-benzoxazine-2(3H)-ones 3 and a series of 6-chloro-3-phenyl-2H-1,3-benzoxazine-2, 4(3H)-dithiones 4 were synthesized by melting 6-chloro-3-phenyl-2H-1, 3-benzoxazine-2,4(3H)-dione and its derivatives substituted on the phenyl ring 2 with tetraphosphorus decasulfide. Compoun...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(00)00174-4

    authors: Waisser K,Gregor J,Kubicová L,Klimesová V,Kunes J,Machácek M,Kaustová J

    更新日期:2000-07-01 00:00:00

  • Thiazolidine-2,4-dione-based irreversible allosteric IKK-β kinase inhibitors: Optimization into in vivo active anti-inflammatory agents.

    abstract::Selective kinase inhibitors development is a cumbersome task because of ATP binding sites similarities across kinases. On contrast, irreversible allosteric covalent inhibition offers opportunity to develop novel selective kinase inhibitors. Previously, we reported thiazolidine-2,4-dione lead compounds eliciting in vit...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.111955

    authors: Elkamhawy A,Kim NY,Hassan AHE,Park JE,Paik S,Yang JE,Oh KS,Lee BH,Lee MY,Shin KJ,Pae AN,Lee KT,Roh EJ

    更新日期:2020-02-15 00:00:00

  • Non-chelating p-phenylidene-linked bis-imidazoline analogs of known influenza virus endonuclease inhibitors: Synthesis and anti-influenza activity.

    abstract::A novel chemotype topologically similar to known influenza virus PA endonuclease inhibitors has been designed. It was aimed to reproduce the extended topology of the known metal-chelating ligands with a p-phenylidene-linked bis-imidazoline scaffold. It was envisioned that aromatic groups introduced to this scaffolds v...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.10.063

    authors: Dar'in D,Zarubaev V,Galochkina A,Gureev M,Krasavin M

    更新日期:2019-01-01 00:00:00

  • Structure-activity relationships of new Organotin(IV) anticancer agents and their cytotoxicity profile on HL-60, MCF-7 and HeLa human cancer cell lines.

    abstract::There is a growing interest in the cancer cell growth inhibitory effects of organotin (IV) compounds and, accordingly, a new series of dimethyl-, di-(n-butyl)-, diphenyl- and chloro-phenyl tin(IV) complexes with a Schiff base core were prepared. Their binding to DNA was assessed by UV thermal denaturation showing no i...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.07.047

    authors: Ullah H,Previtali V,Mihigo HB,Twamley B,Rauf MK,Javed F,Waseem A,Baker RJ,Rozas I

    更新日期:2019-11-01 00:00:00

  • Inhibition of 17β-HSD1: SAR of bicyclic substituted hydroxyphenylmethanones and discovery of new potent inhibitors with thioether linker.

    abstract::Estradiol is the most potent estrogen in humans. It is known to be involved in the development and proliferation of estrogen dependent diseases such as breast cancer and endometriosis. The last step of its biosynthesis is catalyzed by 17β-hydroxysteroid dehydrogenase type 1 (17β- HSD1) which consequently is a promisin...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.05.074

    authors: Abdelsamie AS,Bey E,Hanke N,Empting M,Hartmann RW,Frotscher M

    更新日期:2014-07-23 00:00:00

  • Discovery of novel triazolo[4,3-b]pyridazin-3-yl-quinoline derivatives as PIM inhibitors.

    abstract::PIM kinase family (PIM-1, PIM-2 and PIM-3) is an appealing target for the discovery and development of selective inhibitors, useful in various disease conditions in which these proteins are highly expressed, such as cancer. The significant effort put, in the recent years, towards the development of small molecules exh...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.02.022

    authors: Martínez-González S,Rodríguez-Arístegui S,Gómez de la Oliva CA,Hernández AI,González Cantalapiedra E,Varela C,García AB,Rabal O,Oyarzabal J,Bischoff JR,Klett J,Albarrán MI,Cebriá A,Ajenjo N,García-Serelde B,Gómez-Casero E,

    更新日期:2019-04-15 00:00:00

  • Synthesis and biological evaluation of geniposide derivatives as potent and selective PTPlB inhibitors.

    abstract::Herein a series of Geniposide derivatives were designed, synthesized and evaluated as protein tyrosine phosphatase 1B (PTPlB) inhibitors. Most of these compounds exhibited potent in vitro PTP1B inhibitory activities, the representative 7a and 17f were found to be the most potent inhibitors against the enzyme with IC50...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112508

    authors: Lei S,Zhang D,Qi Y,Chowdhury SR,Sun R,Wang J,Du Y,Fu L,Jiang F

    更新日期:2020-11-01 00:00:00

  • Discovery of 5-bromo-4-phenoxy-N-phenylpyrimidin-2-amine derivatives as novel ULK1 inhibitors that block autophagy and induce apoptosis in non-small cell lung cancer.

    abstract::UNC51-like kinase1 (ULK1) recruits its binding partners and initiates the autophagy process in cancer. ULK1 is significantly overexpressed in Non-small cell lung cancer (NSCLC) and negatively correlated with clinical prognosis in NSCLC patients. Based upon the binding features of ULK1, we explored the pharmacophore mo...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112782

    authors: Sun D,Yang Z,Zhen Y,Yang Y,Chen Y,Yuan Y,Zhang L,Zeng X,Chen L

    更新日期:2020-12-15 00:00:00

  • Discovery of fast-acting dual-stage antimalarial agents by profiling pyridylvinylquinoline chemical space via copper catalyzed azide-alkyne cycloadditions.

    abstract::To identity fast-acting, multistage antimalarial agents, a series of pyridylvinylquinoline-triazole analogues have been synthesized via CuAAC. Most of the compounds display significant inhibitory effect on the drug-resistant malarial Dd2 strain at low submicromolar concentrations. Among the tested analogues, compound ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112889

    authors: Huang G,Solano CM,Melendez J,Yu-Alfonzo S,Boonhok R,Min H,Miao J,Chakrabarti D,Yuan Y

    更新日期:2021-01-01 00:00:00

  • Novel benzopsoralen analogues: synthesis, biological activity and molecular docking studies.

    abstract::New benzopsoralen analogues were synthesized and their inhibitory effect on the growth of tumourtumour cell lines (MDA MB231 and TCC-SUP) was evaluated. The in vitro antitumour activity of the new benzopsoralen analogues was discussed in terms of structure-activity relationship. Molecular docking studies with human-CY...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.09.066

    authors: Francisco CS,Rodrigues LR,Cerqueira NM,Oliveira-Campos AM,Esteves AP

    更新日期:2014-11-24 00:00:00

  • Reversal of P-gp and BCRP-mediated MDR by tariquidar derivatives.

    abstract::With an aim to generate non-toxic, specific and highly potent multidrug resistance (MDR) modulators, a novel series of anthranilic acid amide-substituted tariquidar derivatives were synthesized. The new compounds were evaluated for their cytotoxicity toward normal human colon fibroblasts (CCD18-Co), human gastric epit...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.06.049

    authors: Li XQ,Wang L,Lei Y,Hu T,Zhang FL,Cho CH,To KK

    更新日期:2015-08-28 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

  • Hybrid compounds with two redox centres: modular synthesis of chalcogen-containing lapachones and studies on their antitumor activity.

    abstract::Chalcogen-containing β-lapachone derivatives were synthesized using a straightforward methodology and evaluated against several cancer cell lines (leukaemia, human colon carcinoma, prostate, human metastatic prostate, ovarian, central nervous system and breast), showing, in some cases, IC50 values below 1 μM. The cyto...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.06.044

    authors: Vieira AA,Brandão IR,Valença WO,de Simone CA,Cavalcanti BC,Pessoa C,Carneiro TR,Braga AL,da Silva EN

    更新日期:2015-08-28 00:00:00

  • Monoamine oxidase inhibition by selected anilide derivatives.

    abstract::A series of anilide derivatives were synthesized and evaluated as inhibitors of recombinant human monoamine oxidase (MAO) A and B. The most potent inhibitors among the derivatives that were initially evaluated were (2E)-N-(3-chlorophenyl)-3-phenylprop-2-enamide (2c) and (2E)-N-(3-bromophenyl)-3-phenylprop-2-enamide (2...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.08.036

    authors: Legoabe L,Kruger J,Petzer A,Bergh JJ,Petzer JP

    更新日期:2011-10-01 00:00:00

  • Homology modeling in tandem with 3D-QSAR analyses: a computational approach to depict the agonist binding site of the human CB2 receptor.

    abstract::CB2 receptor belongs to the large family of G-protein coupled receptors (GPCRs) controlling a wide variety of signal transduction. The recent crystallographic determination of human β2 adrenoreceptor and its high sequence similarity with human CB2 receptor (hCB2) prompted us to compute a theoretical model of hCB2 base...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.07.023

    authors: Cichero E,Ligresti A,Allarà M,di Marzo V,Lazzati Z,D'Ursi P,Marabotti A,Milanesi L,Spallarossa A,Ranise A,Fossa P

    更新日期:2011-09-01 00:00:00

  • Synthesis and anti-tuberculosis activity of new hetero(Mn, Co, Ni)trinuclear iron(III) furoates.

    abstract::New hetero(micro(3)-oxo)trinuclear iron(III) furoates with the general formulas [Fe(2)MO(alpha-Fur)(6)(L)(H(2)O)(2)], where L = THF (1-3), DMF (4-5), M = Mn(2+) (1, 4), Co(2+) (2, 5), Ni(2+) (3, 6) and [Fe(2)MO(alpha-Fur)(6)(3Cl-Py)(3)], where M = Mn(2+) (7), Co(2+) (8), Ni(2+) (9); have been synthesised and investiga...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2009.12.053

    authors: Melnic S,Prodius D,Stoeckli-Evans H,Shova S,Turta C

    更新日期:2010-04-01 00:00:00

  • Lignopurines: a new family of hybrids between cyclolignans and purines. Synthesis and biological evaluation.

    abstract::A new family of hybrids between cyclolignans related to podophyllic aldehyde, a non-lactonic cyclolignan, and purines were prepared and evaluated against several human tumour cell lines. Both fragments, cyclolignan and purine, were linked through aliphatic and aromatic chains. The influence on the cytotoxicity of the ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.10.026

    authors: Castro MÁ,Miguel del Corral JM,García PA,Rojo MV,Bento AC,Mollinedo F,Francesch AM,San Feliciano A

    更新日期:2012-12-01 00:00:00

  • Design, synthesis, and in vitro cancer cell growth inhibition evaluation and antimalarial testing of trioxanes installed in cyclic 2-enoate substructures.

    abstract::A novel series of 1,2,4-trioxanes were synthesized from 2H-pyrans via photooxidation, and their antiproliferative and growth factor inhibitory activity has been investigated across a variety of human cancer cell lines. Compounds 5k, 5l, 5s, 7a and 7c exhibited the highest activity and selectivity against a human leuke...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.08.008

    authors: Hossain MI,Świtalska M,Peng W,Takashima M,Wang N,Kaiser M,Wietrzyk J,Dan S,Yamori T,Inokuchi T

    更新日期:2013-11-01 00:00:00

  • Post-docking virtual screening of diverse binding pockets: comparative study using DOCK, AMMOS, X-Score and FRED scoring functions.

    abstract::Most of the benchmark studies on docking-scoring methods reported in the last decade conclude that no single scoring function performs well across different protein targets. In this study a comparison of thirteen commonly used force field and empirical scoring functions as implemented in DOCK, AMMOS, X-Score and FRED ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2009.12.025

    authors: Pencheva T,Soumana OS,Pajeva I,Miteva MA

    更新日期:2010-06-01 00:00:00

  • Synthesis, structure, toxicological and pharmacological investigations of 4-hydroxycoumarin derivatives.

    abstract::Twenty 4-hydroxycoumarin derivatives were synthesized. Five of them are described for the first time. The X-ray crystal structure analysis of 3,3'-(2,3,4-trimethoxyphenylmethylene)bis-(4-hydroxy-2H-1-benzopyran-2-one) (7) and 3,3'-(3,5-dimethoxy-4-hydroxyphenylmethylene)bis-(4-hydroxy-2H-1-benzopyran-2-one) (9) confir...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2006.03.007

    authors: Manolov I,Maichle-Moessmer C,Danchev N

    更新日期:2006-07-01 00:00:00

  • Synthesis and anti-cancer activity evaluation of 5-(2-carboxyethenyl)-isatin derivatives.

    abstract::A series of novel di- or trisubstituted isatin derivatives were designed and synthesized in 5-6 steps in 25-45% overall yields. Their structures were confirmed by 1H NMR and 13C NMR as well as LC-MS. The anticancer activity of the fourty-three new isatin derivatives against human T lymphocyte cells Jurkat was evaluate...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.12.050

    authors: Teng YO,Zhao HY,Wang J,Liu H,Gao ML,Zhou Y,Han KL,Fan ZC,Zhang YM,Sun H,Yu P

    更新日期:2016-04-13 00:00:00

  • Regioselective chemical and rapid enzymatic synthesis of a novel redox – Antiproliferative molecular hybrid.

    abstract::Recent science evidenced the interlinkage of oxidative stress and cancer. Due to the inherent complexity of cancer and its accompanying effect of oxidative stress, novel molecules, containing combinatorial functionalities should be targeted. Herein, we synthesized gemcitabine-5'-O-lipoate derived from a regioselective...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.03.064

    authors: Geromichalou E,Sayyad N,Kyriakou E,Chatzikonstantinou AV,Giannopoulou E,Vrbjar N,Kalofonos HP,Stamatis H,Tzakos AG

    更新日期:2015-01-01 00:00:00

  • Design and studies of multiple mechanism of anti-Candida activity of a new potent Trp-rich peptide dendrimers.

    abstract:PURPOSE:Eight peptide dendrimers were designed as structural mimics of natural cationic amphiphilic peptides with antifungal activity and evaluated for their anti-Candida potential against the wild type strains and mutants. METHODS:Dendrimer 14 containing four Trp residues and dodecyl tail and a slightly smaller dendr...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.10.013

    authors: Zielińska P,Staniszewska M,Bondaryk M,Koronkiewicz M,Urbańczyk-Lipkowska Z

    更新日期:2015-11-13 00:00:00

  • Synthesis and characterization of novel phosphonocarboxylate inhibitors of RGGT.

    abstract::Phosphonocarboxylate (PC) analogs of the anti-osteoporotic drugs, bisphosphonates, represent the first class of selective inhibitors of Rab geranylgeranyl transferase (RabGGTase, RGGT), an enzyme implicated in several diseases including ovarian, breast and skin cancer. Here we present the synthesis and biological char...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.06.062

    authors: Coxon FP,Joachimiak L,Najumudeen AK,Breen G,Gmach J,Oetken-Lindholm C,Way R,Dunford JE,Abankwa D,Błażewska KM

    更新日期:2014-09-12 00:00:00

  • [1,2,4]Triazolo[1,5-c]pyrimidines as adenosine receptor antagonists: Modifications at the 8 position to reach selectivity towards A3 adenosine receptor subtype.

    abstract::[1,2,4]Triazolo[1,5-c]pyrimidine is a promising platform to develop adenosine receptor antagonists. Here, we tried to investigate the effect of the substituent at the 8 position of [1,2,4]triazolo[1,5-c]pyrimidine derivatives on affinity and selectivity at the human A3 adenosine receptor subtype. In particular, we hav...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.08.042

    authors: Federico S,Margiotta E,Salmaso V,Pastorin G,Kachler S,Klotz KN,Moro S,Spalluto G

    更新日期:2018-09-05 00:00:00

  • Synthesis, in vitro anticancer and antibacterial activities and in silico studies of new 4-substituted 1,2,3-triazole-coumarin hybrids.

    abstract::The 4-substituted 1,2,3-triazole core in designed coumarin hybrids (4-35) with diverse physicochemical properties was introduced by eco-friendly copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition under microwave irradiation. Coumarin-1,2,3-triazole-benzofused heterocycle hybrids emerged as the class of compounds ex...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.08.062

    authors: Kraljević TG,Harej A,Sedić M,Pavelić SK,Stepanić V,Drenjančević D,Talapko J,Raić-Malić S

    更新日期:2016-11-29 00:00:00

  • Synthetic studies on cyclic octapeptides: Yunnanin F and Hymenistatin.

    abstract::Two biologically active cyclic peptides, Yunnanin F 8 and Hymenistatin 16 were synthesized and the structures were established on the basis of analytical, IR, NMR and mass spectral data. The newly synthesized compounds were screened for their antimicrobial and pharmacological activities. These cyclic octapeptides have...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2004.11.013

    authors: Poojary B,Belagali SL

    更新日期:2005-04-01 00:00:00

  • Synthesis and antitumor activity of emodin quaternary ammonium salt derivatives.

    abstract::A series of new emodin derivatives modified at the C-3 and the C-6 positions were synthesized, and evaluated for their anticancer activities in vitro and in vivo. Among them, Compounds 5g and 5h had more significant antiproliferative ability against HepG2, BGC-823, AGS cancer cell lines and low cytotoxicity to HELF no...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.07.047

    authors: Shao J,Zhang F,Bai Z,Wang C,Yuan Y,Wang W

    更新日期:2012-10-01 00:00:00

  • Design, synthesis and evaluation of diarylpiperazine derivatives as potent anti-tubercular agents.

    abstract::Molecular hybridization is an emerging approach to design novel ligands by combination of two or more pharmacophoric subunits of known bioactive compounds. In the present study, we have designed a novel series of diarylpiperazine analogues, synthesized, characterized using FTIR, (1)H NMR, Mass, Elemental analysis and ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.10.024

    authors: Penta A,Franzblau S,Wan B,Murugesan S

    更新日期:2015-11-13 00:00:00