Synthesis and biological evaluation of novel aliphatic amido-quaternary ammonium salts for anticancer chemotherapy: part II.

Abstract:

:A series of novel aliphatic amido-quaternary ammonium salts were synthesized and evaluated for their anticancer effects involving induction of RhoB. Most of these compounds, featuring open-ring forms of aliphatic amido-quaternary ammonium salts, exhibited potent anti-proliferative activities in human cancer cell lines, including PC-3, NUGC-3, MDA-MB-231, ACHN, HCT-15, and NCI-H23. In further evaluation, the representative compound N,N-diethyl-N-(2-(N-methyltetradecanamido)ethyl)prop-2-en-1-aminium bromide (3b) exhibited potent pro-apoptotic activity, through RhoB activation, in HeLa cells.

journal_name

Eur J Med Chem

authors

Yang JS,Song D,Ko WJ,Kim B,Kim BK,Park SK,Won M,Lee K,Lee K,Kim HM,Han G

doi

10.1016/j.ejmech.2012.12.063

subject

Has Abstract

pub_date

2013-05-01 00:00:00

pages

621-8

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(13)00122-0

journal_volume

63

pub_type

杂志文章
  • Angiotensin II--AT1 receptor antagonists: design, synthesis and evaluation of substituted carboxamido benzimidazole derivatives.

    abstract::A series of 5-(alkyl and aryl)carboxamido benzimidazole derivatives had been designed, synthesized and evaluated for in vitro angiotensin II--AT1 receptor antagonism and in vivo antihypertensive activities. The pharmacological activities were inversely related to the size of alkyl and aryl substituents. It can be sugg...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2007.11.008

    authors: Shah DI,Sharma M,Bansal Y,Bansal G,Singh M

    更新日期:2008-09-01 00:00:00

  • Microwave assisted synthesis of unsaturated jasmone heterocyclic analogues as new fragrant substances.

    abstract::Taking the rising interest in jasmone structure based fragrant compounds into account it has been decided to take up an attempt to synthesize the new heterocyclic derivatives of this 2,3-disubstituted cyclopentenone, which could be characterized by the ability of interaction with the same receptors with which jasmone ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.07.028

    authors: Pawełczyk A,Zaprutko L

    更新日期:2009-07-01 00:00:00

  • Nitrogen-containing ecdysteroid derivatives vs. multi-drug resistance in cancer: Preparation and antitumor activity of oximes, oxime ethers and a lactam.

    abstract::Multidrug resistance is a widespread problem among various diseases and cancer is no exception. We had previously described the chemo-sensitizing activity of ecdysteroid derivatives with low polarity on drug susceptible and multi-drug resistant (MDR) cancer cells. We have also shown that these molecules have a marked ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.12.032

    authors: Vágvölgyi M,Martins A,Kulmány Á,Zupkó I,Gáti T,Simon A,Tóth G,Hunyadi A

    更新日期:2018-01-20 00:00:00

  • Synthesis and biological evaluation of α-santonin derivatives as anti-hepatoma agents.

    abstract::A series of α-santonin-derived compounds as potentially anti-hepatoma agents were designed and synthesized in an effort to find novel therapeutic agents. Among them, derivative 5h was more potent than the positive control 5-fluorouracil (5-Fu) on HepG-2, QGY-7703 and SMMC-7721 with IC50 values of 7.51, 3.06 and 4.08 μ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.02.073

    authors: Chen H,Yang X,Yu Z,Cheng Z,Yuan H,Zhao Z,Wu G,Xie N,Yuan X,Sun Q,Zhang W

    更新日期:2018-04-10 00:00:00

  • Decision trees to characterise the roles of permeability and solubility on the prediction of oral absorption.

    abstract::Oral absorption of compounds depends on many physiological, physiochemical and formulation factors. Two important properties that govern oral absorption are in vitro permeability and solubility, which are commonly used as indicators of human intestinal absorption. Despite this, the nature and exact characteristics of ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.12.006

    authors: Newby D,Freitas AA,Ghafourian T

    更新日期:2015-01-27 00:00:00

  • Structure-based design of N-substituted 1-hydroxy-4-sulfamoyl-2-naphthoates as selective inhibitors of the Mcl-1 oncoprotein.

    abstract::Structure-based drug design was utilized to develop novel, 1-hydroxy-2-naphthoate-based small-molecule inhibitors of Mcl-1. Ligand design was driven by exploiting a salt bridge with R263 and interactions with the p2 pocket of the protein. Significantly, target molecules were accessed in just two synthetic steps, sugge...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.02.006

    authors: Lanning ME,Yu W,Yap JL,Chauhan J,Chen L,Whiting E,Pidugu LS,Atkinson T,Bailey H,Li W,Roth BM,Hynicka L,Chesko K,Toth EA,Shapiro P,MacKerell AD Jr,Wilder PT,Fletcher S

    更新日期:2016-05-04 00:00:00

  • Estrogen signaling: An emanating therapeutic target for breast cancer treatment.

    abstract::Breast cancer, a most common malignancy in women, was known to be associated with steroid hormone estrogen. The discovery of estrogen receptor (ER) gave us not only a powerful predictive and prognostic marker, but also an efficient target for the treatment of hormone-dependent breast cancer with various estrogen ligan...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2019.05.023

    authors: Saha T,Makar S,Swetha R,Gutti G,Singh SK

    更新日期:2019-09-01 00:00:00

  • Design and synthesis of chloroquine analogs with anti-breast cancer property.

    abstract::A series of chloroquine (CQ) analogs were designed and synthesized in a repositioning approach to develop compounds with high anti-breast cancer property. The compounds were then examined for their antiproliferative effects on two human breast tumor cell lines and a matching non-cancer cell line. Although many of them...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.05.046

    authors: Solomon VR,Hu C,Lee H

    更新日期:2010-09-01 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

  • Design and synthesis of azolopyrimidoquinolines, pyrimidoquinazolines as anti-oxidant, anti-inflammatory and analgesic activities.

    abstract::The 5,10-dihydro-2-thioxo-pyrimido[4,5-b]quinolines (2a-c) and its oxidized form 3 were prepared and used as key intermediates for the synthesis of thiazolo[3',2':1,2]pyrimido[4,5-b]-quinolines (5a-c), isoxazolo[5'',4'':4',5']thiazolo[3',2':1,2]pyrimido[4,5-b]quinolines (6a-c), 4-chloro-2-methylthio-pyrimido[4,5-b]qui...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.03.022

    authors: El-Gazzar AB,Youssef MM,Youssef AM,Abu-Hashem AA,Badria FA

    更新日期:2009-02-01 00:00:00

  • 10-Boronic acid substituted camptothecin as prodrug of SN-38.

    abstract::Malignant tumor cells have been found to have high levels of reactive oxygen species such as hydrogen peroxide (H2O2), supporting the hypothesis that a prodrug could be activated by intracellular H2O2 and lead to a potential antitumor therapy. In this study, the 7-ethyl-10-boronic acid camptothecin (B1) was synthesize...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.03.063

    authors: Wang L,Xie S,Ma L,Chen Y,Lu W

    更新日期:2016-06-30 00:00:00

  • Synthesis and anticancer activity of 6-heteroarylcoumarins.

    abstract::A series of novel 7-hydroxy-8-methyl-coumarins with indole, pyrimidine, pyrazole, pyran, tetrazolo[1,5-a]pyrimidine, pyrimido[1,2-a]benzimidazol, 2-oxo-1,2-dihydropyridine and dihydropyrazolo[3,4-b]pyridine moieties at C6 position of heterocyclic core have been synthesized. Anticancer activity screening on NCI60 cell ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.10.021

    authors: Galayev O,Garazd Y,Garazd M,Lesyk R

    更新日期:2015-11-13 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

  • A novel series of 6-substituted 3-(pyrrolidin-1-ylmethyl)chromen-2-ones as selective monoamine oxidase (MAO) A inhibitors.

    abstract::A series of 6-substituted 3-(pyrrolidin-1-ylmethyl)chromen-2-ones (coumarins) have been synthesized and their inhibitory activity to human monoamine oxidase A (MAO A) and B (MAO B) determined. Incorporation of a basic amino function in the C3 position together with substitution at the C6 position produced novel coumar...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.11.035

    authors: Mattsson C,Svensson P,Sonesson C

    更新日期:2014-02-12 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

  • Synthesis and preliminary evaluation of peptidomimetic inhibitors of human beta-secretase.

    abstract::Based on the structure of OM99-2 and the X-ray crystal structure of its complex with beta-secretase, a series of compounds containing the Leu*Ala hydroxyethylene isostere as a scissile bond substitution were designed. 31 compounds were synthesized and their beta-secretase inhibition activities were measured. It was fo...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.01.044

    authors: Niu Y,Wang Y,Zou X,Yang X,Ma C,Lü Y,Zhou B,Yuan Y,Du G,Xu P

    更新日期:2010-05-01 00:00:00

  • The chemical diversity and structure-based evolution of non-peptide CXCR4 antagonists with diverse therapeutic potential.

    abstract::The CXC chemokine receptor 4 (CXCR4) is a highly reserved G-protein coupled 7-transmembrane (TM) chemokine receptor which consists of 352 amino acids. CXCR4 has only one endogenous chemokine ligand of CXCL12, besides several other natural nonchemokine ligands such as extracellular ubiquitin and noncognate ligand of MI...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2018.02.043

    authors: Peng D,Cao B,Zhou YJ,Long YQ

    更新日期:2018-04-10 00:00:00

  • Synthesis and cancer cell growth inhibitory activity of icaritin derivatives.

    abstract::A series of icaritin derivatives bearing carboxylic acid or carboxylic ester groups are synthesized, and their in vitro cytotoxic activity against three cancer cell lines, MCF-7, MDA-MB-435s, and A549, are evaluated by MTT assay. Several derivatives including 2h, 2j, 5b and 5d show higher cytotoxic activity than the p...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.06.006

    authors: Wang C,Wu P,Shi JF,Jiang ZH,Wei XY

    更新日期:2015-07-15 00:00:00

  • Synthesis, beta-adrenoceptor pharmacology and toxicology of S-(-)-1-(4-(2-ethoxyethoxy)phenoxy)-2-hydroxy-3-(2-(3,4-dimethoxyphenyl)ethylamino)propane hydrochloride, a short acting beta(1)-specific antagonist.

    abstract::The synthesis of S-(-)-1-(4-(2-ethoxyethoxy)phenoxy)-2-hydroxy-3-(2-(3,4-dimethoxyphenyl)ethylamino)propane hydrochloride (D140S.HCl 6), a novel short acting beta(1)-specific adrenoceptor antagonist, has been described. The antagonist potency for D140S.HCl 6 has been compared with esmolol, another short acting agent, ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(02)01399-5

    authors: Jackman GP,Iakovidis D,Nero TL,Anavekar NS,Rezmann-Vitti LA,Louis SN,Mori M,Drummer OH,Louis WJ

    更新日期:2002-09-01 00:00:00

  • Discovery of methoxy-naphthyl linked N-(1-benzylpiperidine) benzamide as a blood-brain permeable dual inhibitor of acetylcholinesterase and butyrylcholinesterase.

    abstract::The cholinesterase enzymes play a vital role in maintaining balanced levels of the neurotransmitter acetylcholine in the central nervous system. However, the overexpression of these enzymes results in hampered neurotransmission. Both the major forms of cholinesterase enzymes viz. acetylcholinesterase (AChE) and butyry...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112761

    authors: Abdullaha M,Nuthakki VK,Bharate SB

    更新日期:2020-12-01 00:00:00

  • SPF32629A and SPF32629B: enantioselective synthesis, determination of absolute configuration, cytotoxicity and antibacterial evaluation.

    abstract::We report herein an efficient enantioselective synthesis of SPF32629A and SPF32629B through one-pot enantioselective reduction and protecting-group-free regioselective O-acylation strategy. The absolute configuration of the enantiomerically pure isomers was established by Mosher ester analysis. The inhibitory potencie...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.02.039

    authors: Vegi SR,Boovanahalli SK,Patro B,Mukkanti K

    更新日期:2011-05-01 00:00:00

  • Synthesis and biological screening for cytotoxic activity of N-substituted indolines and morpholines.

    abstract::Development of novel anticancer drugs is inevitable to improve treatment of cancers. In this study, novel derivatives of indoline and morpholine were synthesized and tested for their cytotoxic effects on osteosarcoma and Human Embryonic Kidney cells. To characterize cytotoxicity and the mechanism of cell death, we use...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.05.024

    authors: Doan P,Karjalainen A,Chandraseelan JG,Sandberg O,Yli-Harja O,Rosholm T,Franzen R,Candeias NR,Kandhavelu M

    更新日期:2016-09-14 00:00:00

  • Antifungal activities of novel non-azole molecules against S. cerevisiae and C. albicans.

    abstract::Because of the increasing number of immunocompromised patients and due to problems with antifungal treatment, especially with the most widely used antifungals, azoles, there is an urgent need for new, potent and safe antifungals with fewer cytochrome P450 (CYP)-mediated interactions with other drugs. In the present st...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.10.053

    authors: Tani N,Rahnasto-Rilla M,Wittekindt C,Salminen KA,Ritvanen A,Ollakka R,Koskiranta J,Raunio H,Juvonen RO

    更新日期:2012-01-01 00:00:00

  • High anticancer potency on tumor cells of dehydroabietylamine Schiff-base derivatives and a copper(II) complex.

    abstract::Five bioactive dehydroabietylamine Schiff-base derivatives (L1-L5) had been synthesized from Dehydroabietylamine (L0), and the complex Cu(L1)2 had been obtained from the compound L1 and copper(II) acetate. Their activities against Hela (cervix), MCF-7 (breast), A549 (lung), HepG2 (liver) and HUVEC (umbilical vein, nor...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.01.041

    authors: Zhao F,Wang W,Lu W,Xu L,Yang S,Cai XM,Zhou M,Lei M,Ma M,Xu HJ,Cao F

    更新日期:2018-02-25 00:00:00

  • Design, synthesis and antiviral activity of novel quinazolinones.

    abstract::HIV-1 integrase (IN) is a validated therapeutic target for antiviral drug design. However, the emergence of viral strains resistant to clinically studied IN inhibitors demands the discovery of novel inhibitors that are structurally as well as mechanistically different. Herein, a series of quinazolinones were designed ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.04.010

    authors: Wang Z,Wang M,Yao X,Li Y,Tan J,Wang L,Qiao W,Geng Y,Liu Y,Wang Q

    更新日期:2012-07-01 00:00:00

  • Bioactive fused heterocycles: Nucleoside analogs with an additional ring.

    abstract::The following mini-review summarizes the basic literature data regarding synthesis, biological activity, structure-activity relationship, and discussion of the mechanisms of action of two major classes of nucleoside analogs with fused heterocyclic rings: (i) the ethenonucleosides and their related derivatives of the 5...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2014.12.026

    authors: Jahnz-Wechmann Z,Framski G,Januszczyk P,Boryski J

    更新日期:2015-06-05 00:00:00

  • Structural modifications at the 6-position of thieno[2,3-d]pyrimidines and their effects on potency at FLT3 for treatment of acute myeloid leukemia.

    abstract::Fms-like tyrosine kinase 3 (FLT3) is a well-known and important target for the treatment of acute myeloid leukemia (AML). A series of thieno[2,3-d]pyrimidine derivatives from a modification at the 6-position were synthesized to identify effective FLT3 inhibitors. Although compounds 1 and 2 emerged as promising FLT3 in...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.05.022

    authors: Kim H,Lee C,Yang JS,Choi S,Park CH,Kang JS,Oh SJ,Yun J,Kim MH,Han G

    更新日期:2016-09-14 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

  • Chalcogen containing heterocyclic scaffolds: New hybrids with antitumoral activity.

    abstract::In this work, 27 novel hybrid derivatives containing diverse substituents with chalcogen atoms (selenium or sulfur) and several active heterocyclic scaffolds have been synthesized. Compounds were tested against two human cancer cells lines (MCF7 and PC-3) and a normal human mammary epithelial cell line (184B5) in orde...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.07.042

    authors: Alcolea V,Plano D,Encío I,Palop JA,Sharma AK,Sanmartín C

    更新日期:2016-11-10 00:00:00

  • Synthesis and study of cytotoxic activity of 1,2,4-trioxane- and egonol-derived hybrid molecules against Plasmodium falciparum and multidrug-resistant human leukemia cells.

    abstract::Malaria and cancer cause the death of millions of people every year. To combat these two diseases, it is important that new pharmaceutically active compounds have the ability to overcome multidrug resistance in cancer and Plasmodium falciparum strains. In search of effective anti-cancer and anti-malaria hybrids that p...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.01.043

    authors: Reiter C,Capcı Karagöz A,Fröhlich T,Klein V,Zeino M,Viertel K,Held J,Mordmüller B,Emirdağ Öztürk S,Anıl H,Efferth T,Tsogoeva SB

    更新日期:2014-03-21 00:00:00