Solid‐phase synthesis of C‐terminal azapeptides

Doan, Ngoc-Duc; Traoré, Mariam; Kamdem, Winnie; Lubell, William D.

doi:10.1002/psc.2711

Cited by 20 publications

(10 citation statements)

References 24 publications

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“…Clearly, this alkylation can proceed only via formation of a conjugate base of the starting material. Various base/solvent combinations for deprotonation of semicarbazones (e.g., MeONa/DMF [25,26], Et4NOH/THF [27][28][29], NaOH/EtOH-H2O [30], t-BuOK/THF [5,[31][32][33], NaH/DMF [34], K2CO3/DMF [35][36][37], Cs2CO3/MeCN [38], tert-butylimino-tri(pyrrolidino)phosphorane/THF [39]), followed by treatment with alkylating reagents, were reported. We tested some base/solvent combinations for the alkylation of semicarbazones of aromatic aldehydes (E)-1a-c as model compounds (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

A New Efficient Route to 2-Alkylsemicarbazides

Fesenko

Trafimova²,

Zimin³

et al. 2019

The 23rd International Electronic Conference on Synthetic Organic Chemistry

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Section: Resultsmentioning

confidence: 99%

A New Efficient Route to 2-Alkylsemicarbazides

Fesenko

Trafimova²,

Zimin³

et al. 2019

The 23rd International Electronic Conference on Synthetic Organic Chemistry

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“…Aza-lysine GHRP-6 analogues were synthesized using two different submonomer procedures. Alkylation of semicarbazones (e.g., 39) was used to install aza-amino acids with chloroalkyl and propargyl side chains [33][34][35]. Chloride 40 was employed in different S N 2 displacement reactions with a variety of amines and sodium azide to prepare various aza-ornithine, aza-arginine and aza-lysine derivatives (e.g., 44-47) [33,34].…”

Section: Aza-lysine Ghrp-6 Analoguesmentioning

confidence: 99%

“…Alkylation of semicarbazones (e.g., 39) was used to install aza-amino acids with chloroalkyl and propargyl side chains [33][34][35]. Chloride 40 was employed in different S N 2 displacement reactions with a variety of amines and sodium azide to prepare various aza-ornithine, aza-arginine and aza-lysine derivatives (e.g., 44-47) [33,34]. Alternatively, aza-propargylglycine (azaPra) residues 42 were employed in copper-catalyzed A 3 -coupling reactions, between alkyne, aldehyde, and amine components, to prepare aminobutynylglycine peptides (e.g., 48-50) [35].…”

Section: Aza-lysine Ghrp-6 Analoguesmentioning

confidence: 99%

Synthesis and Biomedical Potential of Azapeptide Modulators of the Cluster of Differentiation 36 Receptor (CD36)

et al. 2020

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The innovative development of azapeptide analogues of growth hormone releasing peptide-6 (GHRP-6) has produced selective modulators of the cluster of differentiation 36 receptor (CD36). The azapeptide CD36 modulators curb macrophage-driven inflammation and mitigate atherosclerotic and angiogenic pathology. In macrophages activated with Toll-like receptor-2 heterodimer agonist, they reduced nitric oxide production and proinflammatory cytokine release. In a mouse choroidal explant microvascular sprouting model, they inhibited neovascularization. In murine models of cardiovascular injury, CD36-selective azapeptide modulators exhibited cardioprotective and anti-atherosclerotic effects. In subretinal inflammation models, they altered activated mononuclear phagocyte metabolism and decreased immune responses to alleviate subsequent inflammation-dependent neuronal injury associated with retinitis pigmentosa, diabetic retinopathy and age-related macular degeneration. The translation of GHRP-6 to potent and selective linear and cyclic azapeptide modulators of CD36 is outlined in this review which highlights the relevance of turn geometry for activity and the biomedical potential of prototypes for the beneficial treatment of a wide range of cardiovascular, metabolic and immunological disorders.

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“…The synthesis of C-terminal GHRP-6 was communicated by application of benzhydrylidene-aza-glycinamide rink resin [102]. In addition, the utility of this method has been demonstrated by the synthesis of [aza-Lys 6 ] GHRP-6 derivatives by a protocol featuring regioselective alkylation of benzhydrylidene aza-glycinamide [103].…”

Section: Various Azapeptide Scaffolds As Peptidomimeticsmentioning

confidence: 99%

A Review on Azapeptides: The Promising Peptidomimetics

Begum¹,

Sujatha²,

Prasad³

et al. 2017

Asian J. Chem.

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Peptidomimetics, the mimics of natural peptides are considered as promising therapeutics with potential applications in modern medicine. Among the various structural variants of peptidomimetics that have been designed and synthesized, the azapeptides serve as the interesting peptide backbone modifications owing to their diversified biological and pharmacokinetic properties. The aim of this review is to highlight the significance of azapeptide in enhancement of stability and bioavailability, represent the various scaffolds of azapeptides as peptidomimetics, notify their significance as cysteine and serine protease inhibitors, provide an insight on the various biologically significant azapeptides and emphasize the main features on the conventional to modified synthetic strategies of azapeptides.

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Solid‐phase synthesis of C‐terminal azapeptides

Abstract: The solid-phase synthesis of azapeptides possessing a C-terminal aza-residue has been accomplished by a protocol featuring regioselective alkylation of benzhydrylidene-aza-glycinamide and illustrated by the syntheses of [aza-Lys(6)] growth-hormone-releasing peptide-6 analogs.

Cited by 20 publications

References 24 publications

A New Efficient Route to 2-Alkylsemicarbazides

A New Efficient Route to 2-Alkylsemicarbazides

Synthesis and Biomedical Potential of Azapeptide Modulators of the Cluster of Differentiation 36 Receptor (CD36)

A Review on Azapeptides: The Promising Peptidomimetics

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