Synthesis and in vitro evaluation of N-alkyl-3-hydroxy-3-(2-imino-3-methyl-5-oxoimidazolidin-4-yl)indolin-2-one analogs as potential anticancer agents.

PubWeight™: 1.05‹?› | Rank: Top 15%

🔗 View Article (PMC 3725999)

Published in Bioorg Med Chem Lett on June 10, 2010

Authors

Narsimha Reddy Penthala1, Thirupathi Reddy Yerramreddy, Nikhil Reddy Madadi, Peter A Crooks

Author Affiliations

1: Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, KY 40536, USA.

Articles cited by this

Noxious compounds activate TRPA1 ion channels through covalent modification of cysteines. Nature (2007) 7.12

Comparison of in vitro anticancer-drug-screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumor cell lines. J Natl Cancer Inst (1990) 4.08

Novel substituted (Z)-2-(N-benzylindol-3-ylmethylene)quinuclidin-3-one and (Z)-(+/-)-2-(N-benzylindol-3-ylmethylene)quinuclidin-3-ol derivatives as potent thermal sensitizing agents. Bioorg Med Chem Lett (2007) 3.14

In vitro cytotoxicity evaluation of some substituted isatin derivatives. Bioorg Med Chem (2006) 2.15

An investigation into the cytotoxicity and mode of action of some novel N-alkyl-substituted isatins. J Med Chem (2007) 1.57

N-phenethyl and N-naphthylmethyl isatins and analogues as in vitro cytotoxic agents. Bioorg Med Chem (2008) 1.56

3-(2-Amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-5-yl)-3-hydroxy-indolin-2-one monohydrate. Acta Crystallogr Sect E Struct Rep Online (2009) 1.29

Novel substituted (Z)-5-((N-benzyl-1H-indol-3-yl)methylene)imidazolidine-2,4-diones and 5-((N-benzyl-1H-indol-3-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-triones as potent radio-sensitizing agents. Bioorg Med Chem Lett (2009) 1.19

Synthesis, activity, and pharmacophore development for isatin-beta-thiosemicarbazones with selective activity toward multidrug-resistant cells. J Med Chem (2009) 1.17

Microwave assisted synthesis and in vitro cytotoxicities of substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones against human tumor cell lines. Bioorg Med Chem Lett (2009) 1.05

3-(2-Amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-5-yl)-5-fluoro-3-hydr-oxy-1-methyl-indolin-2-one methanol hemisolvate. Acta Crystallogr Sect E Struct Rep Online (2009) 1.04

Design, synthesis and in vivo anticonvulsant screening in mice of novel phenylacetamides. Eur J Med Chem (2006) 0.91

3-(2-Amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-5-yl)-3-hydr-oxy-1-phenyl-indolin-2-one ethanol solvate. Acta Crystallogr Sect E Struct Rep Online (2009) 0.88

Articles by these authors

Defunctionalized lobeline analogues: structure-activity of novel ligands for the vesicular monoamine transporter. J Med Chem (2005) 3.32

Novel substituted (Z)-2-(N-benzylindol-3-ylmethylene)quinuclidin-3-one and (Z)-(+/-)-2-(N-benzylindol-3-ylmethylene)quinuclidin-3-ol derivatives as potent thermal sensitizing agents. Bioorg Med Chem Lett (2007) 3.14

NADPH oxidase activity is essential for Keap1/Nrf2-mediated induction of GCLC in response to 2-indol-3-yl-methylenequinuclidin-3-ols. Cancer Res (2003) 3.02

Aminoparthenolides as novel anti-leukemic agents: Discovery of the NF-kappaB inhibitor, DMAPT (LC-1). Bioorg Med Chem Lett (2009) 2.77

A novel mechanism of action and potential use for lobeline as a treatment for psychostimulant abuse. Biochem Pharmacol (2002) 2.51

The NF-kappaB subunit Rel A is associated with in vitro survival and clinical disease progression in chronic lymphocytic leukemia and represents a promising therapeutic target. Blood (2008) 2.16

An orally bioavailable parthenolide analog selectively eradicates acute myelogenous leukemia stem and progenitor cells. Blood (2007) 2.14

Chemical genomic screening reveals synergism between parthenolide and inhibitors of the PI-3 kinase and mTOR pathways. Blood (2010) 1.92

Lobeline analogs with enhanced affinity and selectivity for plasmalemma and vesicular monoamine transporters. J Pharmacol Exp Ther (2004) 1.83

Lobelane decreases methamphetamine self-administration in rats. Eur J Pharmacol (2007) 1.82

Vesicular monoamine transporter 2: role as a novel target for drug development. AAPS J (2006) 1.78

Lobelane inhibits methamphetamine-evoked dopamine release via inhibition of the vesicular monoamine transporter-2. J Pharmacol Exp Ther (2009) 1.49

N,N'-Alkane-diyl-bis-3-picoliniums as nicotinic receptor antagonists: inhibition of nicotine-evoked dopamine release and hyperactivity. J Pharmacol Exp Ther (2008) 1.44

Melampomagnolide B: a new antileukemic sesquiterpene. Bioorg Med Chem (2011) 1.40

Lobelane analogues as novel ligands for the vesicular monoamine transporter-2. Bioorg Med Chem (2005) 1.38

Subtype-selective nicotinic receptor antagonists: potential as tobacco use cessation agents. Bioorg Med Chem Lett (2004) 1.36

The effects of a novel nicotinic receptor antagonist N,N-dodecane-1,12-diyl-bis-3-picolinium dibromide (bPiDDB) on acute and repeated nicotine-induced increases in extracellular dopamine in rat nucleus accumbens. Neuropharmacology (2006) 1.32

Novel chemical enhancers of heat shock increase thermal radiosensitization through a mitotic catastrophe pathway. Cancer Res (2007) 1.32

Pyrrolidine analogues of lobelane: relationship of affinity for the dihydrotetrabenazine binding site with function of the vesicular monoamine transporter 2 (VMAT2). J Med Chem (2009) 1.30

3-(2-Amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-5-yl)-3-hydroxy-indolin-2-one monohydrate. Acta Crystallogr Sect E Struct Rep Online (2009) 1.29

Extending the analysis of nicotinic receptor antagonists with the study of alpha6 nicotinic receptor subunit chimeras. Neuropharmacology (2008) 1.25

Targeting aberrant glutathione metabolism to eradicate human acute myelogenous leukemia cells. J Biol Chem (2013) 1.25

(Z)-3-(Benzo[b]thiophen-2-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile and (E)-3-(benzo[b]thiophen-2-yl)-2-(3,4-dimethoxyphenyl)acrylonitrile. [corrected]. Acta Crystallogr C (2007) 1.23

Novel substituted (Z)-5-((N-benzyl-1H-indol-3-yl)methylene)imidazolidine-2,4-diones and 5-((N-benzyl-1H-indol-3-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-triones as potent radio-sensitizing agents. Bioorg Med Chem Lett (2009) 1.19

A NADPH oxidase-dependent redox signaling pathway mediates the selective radiosensitization effect of parthenolide in prostate cancer cells. Cancer Res (2010) 1.18

The pharmacological activity of nicotine and nornicotine on nAChRs subtypes: relevance to nicotine dependence and drug discovery. J Neurochem (2007) 1.18

Molecular pathway for thymoquinone-induced cell-cycle arrest and apoptosis in neoplastic keratinocytes. Anticancer Drugs (2004) 1.17

bis-Azaaromatic quaternary ammonium analogues: ligands for alpha4beta2* and alpha7* subtypes of neuronal nicotinic receptors. Bioorg Med Chem Lett (2002) 1.17

Synthesis and evaluation of a series of benzothiophene acrylonitrile analogs as anticancer agents. Medchemcomm (2013) 1.17

Antileukemic activity of aminoparthenolide analogs. Bioorg Med Chem Lett (2008) 1.14

(Z)-2-(1-Phenylsulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one and (Z)-(S)-2-(1-phenylsulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-ol. Acta Crystallogr C (2004) 1.13

N-n-alkylnicotinium analogs, a novel class of nicotinic receptor antagonists: interaction with alpha4beta2* and alpha7* neuronal nicotinic receptors. J Pharmacol Exp Ther (2003) 1.13

N-n-alkylpyridinium analogs, a novel class of nicotinic receptor antagonists: selective inhibition of nicotine-evoked [3H] dopamine overflow from superfused rat striatal slices. J Pharmacol Exp Ther (2003) 1.12

(Z)-3-(1H-Indol-3-yl)-2-(3-thienyl)acrylonitrile and (Z)-3-[1-(4-tert-butylbenzyl)-1H-indol-3-yl]-2-(3-thienyl)acrylonitrile. Acta Crystallogr C (2005) 1.11

Synthesis and evaluation of a series of homologues of lobelane at the vesicular monoamine transporter-2. Bioorg Med Chem Lett (2008) 1.11

Novel N-1,2-dihydroxypropyl analogs of lobelane inhibit vesicular monoamine transporter-2 function and methamphetamine-evoked dopamine release. J Pharmacol Exp Ther (2011) 1.10

(Z)-2-[(1-Phenylsulfonyl-1H-indol-3-yl)methylene]-1-azabicyclo[2.2.2]octan-3-one semicarbazone. Acta Crystallogr C (2007) 1.10

A pilot study of plasma caffeine concentrations in a US sample of smoker and nonsmoker volunteers. Prog Neuropsychopharmacol Biol Psychiatry (2003) 1.09

Nicotinic receptor-based therapeutics and candidates for smoking cessation. Biochem Pharmacol (2009) 1.09

Transdermal delivery of naltrexol and skin permeability lifetime after microneedle treatment in hairless guinea pigs. J Pharm Sci (2010) 1.09

The effect of a novel VMAT2 inhibitor, GZ-793A, on methamphetamine reward in rats. Psychopharmacology (Berl) (2011) 1.08

Pharmacokinetics of the novel nicotinic receptor antagonist N,N'-dodecane-1,12-diyl-bis-3-picolinium dibromide in the rat. Drug Metab Dispos (2008) 1.07

Synthesis and evaluation of a series of tropane analogues as novel vesicular monoamine transporter-2 ligands. Bioorg Med Chem Lett (2005) 1.06

rac-2-(2-Amino-4-oxo-4,5-dihydro-1,3-thia-zol-5-yl)-2-hydroxy-indane-1,3-dione. Acta Crystallogr Sect E Struct Rep Online (2009) 1.06

Carrier-mediated transport of the quaternary ammonium neuronal nicotinic receptor antagonist n,n'-dodecylbispicolinium dibromide at the blood-brain barrier. J Pharmacol Exp Ther (2007) 1.06

N-n-alkylnicotinium analogs, a novel class of nicotinic receptor antagonist: inhibition of S(-)-nicotine-evoked [(3)H]dopamine overflow from superfused rat striatal slices. J Pharmacol Exp Ther (2002) 1.05

Modeling multiple species of nicotine and deschloroepibatidine interacting with alpha4beta2 nicotinic acetylcholine receptor: from microscopic binding to phenomenological binding affinity. J Am Chem Soc (2005) 1.05

Microwave assisted synthesis and in vitro cytotoxicities of substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones against human tumor cell lines. Bioorg Med Chem Lett (2009) 1.05

(Z)-4-[3-(2,5-Dioxoimidazolidin-4-ylidenemeth-yl)-1H-indol-1-ylmeth-yl]benzonitrile. Acta Crystallogr Sect E Struct Rep Online (2008) 1.04

3-(2-Amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-5-yl)-5-fluoro-3-hydr-oxy-1-methyl-indolin-2-one methanol hemisolvate. Acta Crystallogr Sect E Struct Rep Online (2009) 1.04

Enhancement of transdermal delivery of 6-beta-naltrexol via a codrug linked to hydroxybupropion. J Control Release (2006) 1.03

The radiosensitization effect of parthenolide in prostate cancer cells is mediated by nuclear factor-kappaB inhibition and enhanced by the presence of PTEN. Mol Cancer Ther (2007) 1.03

Transdermal delivery of naltrexone and its active metabolite 6-beta-naltrexol in human skin in vitro and guinea pigs in vivo. J Pharm Sci (2005) 1.03

Active transport of high-affinity choline and nicotine analogs into the central nervous system by the blood-brain barrier choline transporter. J Pharmacol Exp Ther (2003) 1.02

Effects of norketamine enantiomers in rodent models of persistent pain. Pharmacol Biochem Behav (2008) 1.02

Flux across [corrected] microneedle-treated skin is increased by increasing charge of naltrexone and naltrexol in vitro. Pharm Res (2008) 1.01

In vitro permeation of a pegylated naltrexone prodrug across microneedle-treated skin. J Control Release (2010) 1.00

Tris-azaaromatic quaternary ammonium salts: Novel templates as antagonists at nicotinic receptors mediating nicotine-evoked dopamine release. Bioorg Med Chem Lett (2007) 1.00

The novel pyrrolidine nor-lobelane analog UKCP-110 [cis-2,5-di-(2-phenethyl)-pyrrolidine hydrochloride] inhibits VMAT2 function, methamphetamine-evoked dopamine release, and methamphetamine self-administration in rats. J Pharmacol Exp Ther (2010) 1.00

Mecamylamine, dihydro-beta-erythroidine, and dextromethorphan block conditioned responding evoked by the conditional stimulus effects of nicotine. Pharmacol Biochem Behav (2009) 1.00

Targeting reward-relevant nicotinic receptors in the discovery of novel pharmacotherapeutic agents to treat tobacco dependence. Nebr Symp Motiv (2009) 1.00

Discovery of non-peptide, small molecule antagonists of α9α10 nicotinic acetylcholine receptors as novel analgesics for the treatment of neuropathic and tonic inflammatory pain. Bioorg Med Chem Lett (2011) 0.99

Synthesis and antitubercular activity of a series of hydrazone and nitrovinyl analogs derived from heterocyclic aldehydes. J Enzyme Inhib Med Chem (2009) 0.99

(Z)-2-(1H-Indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one. Acta Crystallogr C (2003) 0.99

Human skin permeation of branched-chain 3-0-alkyl ester and carbonate prodrugs of naltrexone. Pharm Res (2005) 0.98

In vivo evaluation of 3-O-alkyl ester transdermal prodrugs of naltrexone in hairless guinea pigs. J Control Release (2005) 0.98

Modeling subtype-selective agonists binding with alpha4beta2 and alpha7 nicotinic acetylcholine receptors: effects of local binding and long-range electrostatic interactions. J Med Chem (2006) 0.98

Suppression of pancreatic tumor growth by combination chemotherapy with sulindac and LC-1 is associated with cyclin D1 inhibition in vivo. Mol Cancer Ther (2007) 0.97

3D-QSAR study of bis-azaaromatic quaternary ammonium analogs at the blood-brain barrier choline transporter. Bioorg Med Chem (2005) 0.96

Transdermal delivery of bupropion and its active metabolite, hydroxybupropion: a prodrug strategy as an alternative approach. J Pharm Sci (2009) 0.96

Novel small molecule α9α10 nicotinic receptor antagonist prevents and reverses chemotherapy-evoked neuropathic pain in rats. Anesth Analg (2012) 0.96

Selective inhibition of acetylcholine-evoked responses of alpha7 neuronal nicotinic acetylcholine receptors by novel tris- and tetrakis-azaaromatic quaternary ammonium antagonists. Mol Pharmacol (2009) 0.94

Indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline: application to the synthesis of (-)-sedamine. J Org Chem (2004) 0.94

Indolyl-quinuclidinols inhibit ENOX activity and endothelial cell morphogenesis while enhancing radiation-mediated control of tumor vasculature. FASEB J (2009) 0.94

QSAR modeling of mono- and bis-quaternary ammonium salts that act as antagonists at neuronal nicotinic acetylcholine receptors mediating dopamine release. Bioorg Med Chem (2006) 0.93

Bis-azaaromatic quaternary ammonium salts as antagonists at nicotinic receptors mediating nicotine-evoked dopamine release: An investigation of binding conformation. Bioorg Med Chem Lett (2007) 0.93

The antiproliferative and immunotoxic effects of L-canavanine and L-canaline. Anticancer Drugs (2002) 0.93

The effect of VMAT2 inhibitor GZ-793A on the reinstatement of methamphetamine-seeking in rats. Psychopharmacology (Berl) (2012) 0.93

Synthesis and hydrolytic behavior of two novel tripartate codrugs of naltrexone and 6beta-naltrexol with hydroxybupropion as potential alcohol abuse and smoking cessation agents. Bioorg Med Chem (2006) 0.91

meso-Transdiene analogs inhibit vesicular monoamine transporter-2 function and methamphetamine-evoked dopamine release. J Pharmacol Exp Ther (2010) 0.91

(Z)-3-(1-Methyl-1H-indol-3-yl)-2-(thiophen-3-yl)acrylonitrile. Acta Crystallogr C (2004) 0.91

Elimination of alkaloids from plant-derived human monoclonal antibody. J Immunol Methods (2004) 0.91

A duplex "Gemini" prodrug of naltrexone for transdermal delivery. J Control Release (2004) 0.91

bPiDI: a novel selective α6β2* nicotinic receptor antagonist and preclinical candidate treatment for nicotine abuse. Br J Pharmacol (2011) 0.91

Effect of celecoxib and the novel anti-cancer agent, dimethylamino-parthenolide, in a developmental model of pancreatic cancer. Pancreas (2008) 0.90

In vitro/in vivo correlation of transdermal naltrexone prodrugs in hairless guinea pigs. Pharm Res (2005) 0.90

Total cotinine in plasma: a stable biomarker for exposure to tobacco smoke. J Clin Psychopharmacol (2002) 0.90

KEAP1 is a redox sensitive target that arbitrates the opposing radiosensitive effects of parthenolide in normal and cancer cells. Cancer Res (2013) 0.90

(Z)-3-(1-Benzofuran-2-yl)-2-(3,4,5-tri-meth-oxy-phen-yl)acrylonitrile. Acta Crystallogr Sect E Struct Rep Online (2012) 0.89

Repeated nicotine administration robustly increases bPiDDB inhibitory potency at alpha6beta2-containing nicotinic receptors mediating nicotine-evoked dopamine release. Biochem Pharmacol (2010) 0.89

Pyrrolidine analogs of GZ-793A: synthesis and evaluation as inhibitors of the vesicular monoamine transporter-2 (VMAT2). Bioorg Med Chem Lett (2013) 0.89

Physicochemical evaluation, in vitro human skin diffusion, and concurrent biotransformation of 3-O-alkyl carbonate prodrugs of naltrexone. Pharm Res (2004) 0.89

Bioconversion of naltrexone and its 3-O-alkyl-ester prodrugs in a human skin equivalent. J Pharm Sci (2005) 0.89

Phenyl ring-substituted lobelane analogs: inhibition of [³H]dopamine uptake at the vesicular monoamine transporter-2. J Pharmacol Exp Ther (2010) 0.89

Tetrakis-azaaromatic quaternary ammonium salts: novel subtype-selective antagonists at neuronal nicotinic receptors that mediate nicotine-evoked dopamine release. Bioorg Med Chem Lett (2008) 0.89

Antiangiogenic properties of substituted (Z)-(±)-2-(N-benzylindol-3-ylmethylene)quinuclidin-3-ol/one analogs and their derivatives. Bioorg Med Chem Lett (2010) 0.89

Toxicity of dipyridyl compounds and related compounds. Crit Rev Toxicol (2004) 0.89