Cyclic urea derivatives as potent NK1 selective antagonists

Shue, Ho‐Jane; Chen, Xiao; Shih, Neng‐Yang; Blythin, David J.; Paliwal, Sunil; Li, Gang; Gu, Danlin; Schwerdt, John; Shah, Sapna; Reichard, Gregory A.; Piwinski, John J.; Duffy, Ruth A.; Lachowicz, Jean E.; Coffin, Vicki L.; Liu, Fei; Nomeir, Amin A.; Morgan, Cynthia A.; Varty, Geoffrey B.

doi:10.1016/j.bmcl.2005.05.111

Cited by 47 publications

(12 citation statements)

References 17 publications

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“…Among them, the imidazolidin-2-one motif is often found in both natural products 1,2 and pharmacologically interesting synthetic molecules. These five-membered heterocyclic compounds are P2X7, 3 neurokinin 1 (NK 1 ), 4 and muscarinic acetylcholine 5 receptor antagonists. Some of them inhibit various ferments, such as leucyl-tRNA synthetase, 6 -secretase, 7 HIV-1 protease, 8,9 and biotin biosynthesis, 10 and exhibit antimicrobial and antihepatitis С activity 11 (Figure 1).…”

Section: Published As Part Of the Special Topic Recent Advances In Ammentioning

confidence: 99%

Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones

et al. 2020

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Imidazolidin-2-one and 1,3-benzodiazepin-2-one scaffolds are structural motifs of many biologically active compounds. Herein, we report a highly regioselective acid-catalyzed intramolecular nucleophilic cyclization/intermolecular electrophilic substitution reaction sequence of (2,2-dialkoxyethyl)ureas. The reaction benefits from readily available starting materials, a simple workup procedure, moderate to high yields of target compounds, and provides a convenient entry to previously unknown 4-(het)arylimidazolidinones and 5-(het)arylbenzodiazepinones. The proposed mechanism of the reaction is also discussed.

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Section: Published As Part Of the Special Topic Recent Advances In Ammentioning

confidence: 99%

Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones

et al. 2020

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“…For example, several very potent HIV protease inhibitors contain cyclic urea moieties, 58 and these scaffolds are also displayed in 5-HT 3 -receptor antagonists 59 and NK1 antagonists. 60 In addition, imidazolidin-2-ones have been employed as chiral auxiliaries, 61 and as intermediates in the synthesis of amino acids and 1,2-diamines. 62…”

Section: Synthesis Of Imidazolidin-2-ones Via Palladium-catalyzed Carmentioning

confidence: 99%

Stereoselective Synthesis of Saturated Heterocycles via Palladium-Catalyzed Alkene Carboetherification and Carboamination Reactions

Wolfe¹

2008

Synlett

233

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The development of palladium-catalyzed carboetherification and carboamination reactions between aryl or alkenyl halides and alkenes bearing pendant heteroatoms is described. These transformations effect the stereoselective construction of useful heterocycles, such as tetrahydrofurans, pyrrolidines, imidazolidin-2-ones, isoxazolidines, and piperazines. The scope, limitations, and applications of these reactions are presented, and current stereochemical models are described. The mechanism of the product formation, which involves an unusual intramolecular syn-insertion of an alkene into a palladium-heteroatom bond, is also discussed in detail.

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“…In addition, organic chemists appreciate them for their use as chiral catalysts. Some of the imidazolidinones have either antiviral ( Figure 1), [1][2][3] anticancer, [5] or anti-inflammatory activities, [5] or act as NK 1 receptor antagonists, [6] Leishmania spp. inhibitors, [7] or b 3 adrenergic receptor agonists.…”

Section: Introductionmentioning

confidence: 99%

Imidazolidinones and Imidazolidine‐2,4‐diones as Antiviral Agents

Swain

Mohanty

2019

ChemMedChem

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Imidazolidinones and imidazolidine‐2,4‐diones are important classes of heterocyclic compounds that possess potent activities against several viruses such as dengue virus, enterovirus, hepatitis C virus (HCV), and human immunodeficiency virus (HIV). The first imidazolidinone derivative as an anti‐HIV agent was reported in 1996. Imidazolidinones inhibit HIV aspartic protease activity, and also act as CCR5 co‐receptor antagonists. Significant effort has been devoted to the design of various imidazolidinone analogues that are active against drug‐resistant HIV strains, with fewer side effects. Different scaffolds have been designed through both rational drug design strategies and computer‐aided drug design. Imidazolidinones have been found to be potent against HIV, and preclinical studies are currently in progress. There are some reports of imidazolidinones as having both anti‐HCV and anti‐dengue virus activity, and more research has yet to be done along these lines. These compounds inhibit NS3 serine protease of HCV, and NS2B‐NS3 protease of dengue virus. Pyridyl‐imidazolidinones possess very specific and potent activity against human enterovirus 71 (EV71) by targeting the EV71 capsid protein VP1, and inhibiting viral adsorption and/or viral RNA uncoating.

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Cyclic urea derivatives as potent NK1 selective antagonists

Cited by 47 publications

References 17 publications

Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones

Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones

Stereoselective Synthesis of Saturated Heterocycles via Palladium-Catalyzed Alkene Carboetherification and Carboamination Reactions

Imidazolidinones and Imidazolidine‐2,4‐diones as Antiviral Agents

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