Synthesis of Substituted Imidazolidin-2-ones as Aminoacyl-tRNA Synthase Inhibitors

Eum, Heesung; Lee, Yuno; Kim, Songmi; Baek, Ayoung; Son, Maeng-Hyun; Lee, Keun Woo; Ko, Seung Whan; Kim, Sung Hoon; Yun, Sae Young; Lee, Won Koo; Ha, Hyun‐Joon

doi:10.5012/bkcs.2010.31.03.611

Cited by 8 publications

(5 citation statements)

References 12 publications

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“…The ring expansion of aziridines to obtain imidazolidin-2-one derivatives may be also carried out using triphosgene and sodium hydride. This methodology has been recently applied with good results by Lee et al to obtain precursors of aminoacyl-tRNA synthase inhibitors (Scheme 59) [175]. A wide array of enantiomerically pure imidazolidin-2-one-4-carboxylates can be obtained in a one-step, simple, and highly efficient manner using a Lewis acid-catalyzed ring expansion reaction of the commercially available chiral aziridines with isocyanates.…”

Section: Non-catalytic Aziridine Ring-expansion Reactionsmentioning

confidence: 99%

Recent Advances in the Catalytic Synthesis of Imidazolidin-2-ones and Benzimidazolidin-2-ones

et al. 2019

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2-Imidazolidinone and its analogues are omnipresent structural motifs of pharmaceuticals, natural products, chiral auxiliaries, and intermediates in organic syntheses. Over the years, continuous efforts have been addressed to the development of sustainable and more efficient protocols for the synthesis of these heterocycles. This review gives a summary of the catalytic strategies to access imidazolidin-2-ones and benzimidazolidin-2-ones that have appeared in the literature from 2010 to 2018. Particularly important contributions beyond the timespan will be mentioned. The review is organized in four main chapters that identify the most common approaches to imidazolidin-2-one derivatives: (1) the direct incorporation of the carbonyl group into 1,2-diamines, (2) the diamination of olefins, (3) the intramolecular hydroamination of linear urea derivatives and (4) aziridine ring expansion. Methods not included in this classification will be addressed in the miscellaneous section.

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Section: Non-catalytic Aziridine Ring-expansion Reactionsmentioning

confidence: 99%

Recent Advances in the Catalytic Synthesis of Imidazolidin-2-ones and Benzimidazolidin-2-ones

et al. 2019

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“…Substituted imidazolin-2-ones are of interest as potential aminoacyl-tRNA synthase inhibitors. When the aziridine-aldehyde (2 R ,1' R )- 6 was subjected to the reductive amination with 4 dipeptides secondary amines 172 ( a R' = iBu, R''= sec -Bu; b R' = R'' = iBu; c R' = sec -Bu, R'' = iBu; d R' = R'' = sec -Bu) were produced (Scheme 44) [101]. In the presence of triphosgene a series of imidazolin-2-ones having a 2-chloromethyl substituent 173 was formed.…”

Section: Reviewmentioning

confidence: 99%

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

Głowacka¹,

Trocha²,

Wróblewski³

et al. 2019

Beilstein J. Org. Chem.

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Since Garner’s aldehyde has several drawbacks, first of all is prone to racemization, alternative three-carbon chirons would be of great value in enantioselective syntheses of natural compounds and/or drugs. This review article summarizes applications of N-(1-phenylethyl)aziridine-2-carboxylates, -carbaldehydes and -methanols in syntheses of approved drugs and potential medications as well as of natural products mostly alkaloids but also sphingoids and ceramides and their 1- and 3-deoxy analogues and several hydroxy amino acids and their precursors. Designed strategies provided new procedures to several drugs and alternative approaches to natural products and proved efficiency of a 2-substituted N-(1-phenylethyl)aziridine framework as chiron bearing a chiral auxiliary.

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“…In particular, the latter have been utilized as structural elements in peptidomimetic inhibitors of HIV protease and HIV replication, antibacterial MurB inhibitors, dopamine D4 and CGRP receptor antagonists, angiotensin converting enzyme (ACE) inhibitors, serine protease inhibitors, and integrin inhibitors . In the literature, cyclic ureas are most commonly constructed via treatment of 1,2-diamine precursors with carbonyldiimidazole, or by intramolecular diamination of alkenes, via rearrangement of Asn, , via ring expansion of aziridine derivatives, by cyclization of aza-propargylglycinamides, by alkylation of the urea nitrogen of semicarbazone residues, by Pd-catalyzed urea carboamination reactions, and so on. Although a number of synthetic methods are available, many are not feasible in peptide chemistry.…”

Section: Introductionmentioning

confidence: 99%

In-Peptide Synthesis of Imidazolidin-2-one Scaffolds, Equippable with Proteinogenic or Taggable/Linkable Side Chains, General Promoters of Unusual Secondary Structures

et al. 2019

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Peptidomimetics containing (S)- or (R)-imidazolidin-2-one-4-carboxylate (Imi) have been obtained by the expedient in-peptide cyclization of (S)- or (R)-α,β-diaminopropionic acid (Dap) residues. These Imi scaffolds behave as proline analogues characterized by a flat structure and a trans-restricted geometry of the preceding peptide bond and induce well-defined secondary structures in a biomimetic environment. While (S)-Imi peptides adopted a γ′-turn conformation, (R)-Imi induced the contemporary formation of a γ-turn and a rare 11-membered H-bonded structure in the 2→4 opposite direction of the sequence, identified as a ε-turn. In order to exploit these Imi scaffolds as general promoters of unusual secondary structures, proteinaceous side chains have been introduced at the N1 position of the five-membered ring, potentially mimicking any residues. Finally, the Imi rings have been equipped with unnatural side chains or with functionalized substituents, which can be utilized as linkers to chemoselectively bind the Imi-peptides onto nanoparticles, biomaterials, or diagnostic probes.

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Synthesis of Substituted Imidazolidin-2-ones as Aminoacyl-tRNA Synthase Inhibitors

Cited by 8 publications

References 12 publications

Recent Advances in the Catalytic Synthesis of Imidazolidin-2-ones and Benzimidazolidin-2-ones

Recent Advances in the Catalytic Synthesis of Imidazolidin-2-ones and Benzimidazolidin-2-ones

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

In-Peptide Synthesis of Imidazolidin-2-one Scaffolds, Equippable with Proteinogenic or Taggable/Linkable Side Chains, General Promoters of Unusual Secondary Structures

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