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Search for "peptidomimetics" in Full Text gives 62 result(s) in Beilstein Journal of Organic Chemistry.

Synthesis of acylhydrazino-peptomers, a new class of peptidomimetics, by consecutive Ugi and hydrazino-Ugi reactions

  • Angélica de Fátima S. Barreto,
  • Veronica Alves dos Santos and
  • Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2016, 12, 2865–2872, doi:10.3762/bjoc.12.285

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  • for the synthesis of acylhydrazino-peptomers, a new class of peptidomimetics. The key idea in this approach is based on a simple route using a one-pot hydrazino-Ugi four-component reaction followed by a hydrazinolysis or hydrolysis reaction and subsequent hydrazino-Ugi reaction or classical Ugi
  • peptidomimetics with potential biological activity. Keywords: acylhydrazino-peptomers; consecutive Ugi reactions; peptide-peptoid hybrid; peptomer; Introduction In the last decades, increasing efforts have been extensively carried out to improve the pharmacological properties of natural peptides by structural
  • modification of the amino acids [1][2][3][4][5][6][7][8]. These modifications allowed the obtention of molecules that mimic the properties of peptides (peptidomimetics) but usually exhibit greater proteolytic stability, increased cellular permeabilities and avoid stereochemical constraints. Figure 1 represents
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Published 27 Dec 2016

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

  • Mohammad Haji

Beilstein J. Org. Chem. 2016, 12, 1269–1301, doi:10.3762/bjoc.12.121

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  • peptidomimetics possessing phosphonate groups by MCR-based strategies would significantly extend the synthetic potential of MCRs towards heterocyclic phosphonates. The Biginelli condensation. The Biginelli reaction of β-ketophosphonates catalyzed by ytterbium triflate. Trimethylchlorosilane-mediated Biginelli
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Published 21 Jun 2016

Diastereoselective Ugi reaction of chiral 1,3-aminoalcohols derived from an organocatalytic Mannich reaction

  • Samantha Caputo,
  • Andrea Basso,
  • Lisa Moni,
  • Renata Riva,
  • Valeria Rocca and
  • Luca Banfi

Beilstein J. Org. Chem. 2016, 12, 139–143, doi:10.3762/bjoc.12.15

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  • subjected to an Ugi multicomponent reaction under classical or Lewis acid-promoted conditions with diastereoselectivities ranging from moderate to good. This approach represents a step-economical path to enantiomerically pure, polyfunctionalized peptidomimetics endowed with three stereogenic centers
  • , allowing the introduction of five diversity inputs. Keywords: aminoalcohols; isocyanides; multicomponent reactions; peptidomimetics; Ugi reaction; Findings Isocyanide-based multicomponent reactions [1][2][3], such as the Ugi reaction, were demonstrated to be very useful in the rapid assembly of complex
  • poor stereochemical control that is typically achieved [8][9], which hampers its utilization in the diversity-oriented or target-oriented synthesis of complex chiral peptidomimetics. No efficient asymmetric catalytic classic Ugi reaction has been reported to date (whereas some success was obtained on
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Published 26 Jan 2016

Synthesis of constrained analogues of tryptophan

  • Elisabetta Rossi,
  • Valentina Pirovano,
  • Marco Negrato,
  • Giorgio Abbiati and
  • Monica Dell’Acqua

Beilstein J. Org. Chem. 2015, 11, 1997–2006, doi:10.3762/bjoc.11.216

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  • products and biochemical studies. In recent years, both pharmaceutical companies and academics became interested in the design and synthesis of peptidomimetics and peptide analogues as new therapeutic drugs [2][3]. Medicinal chemistry progress in these fields was probably inspired by the biochemical
  • interactions and reduced oral absorption that prevent their use in therapy [4]. On the other hand, peptidomimetics offer the advantage of nearly countless manipulations in order to control the biological functions, stability, potency, and ADME parameters [5]. In particular, the inclusion of the amino acidic
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Published 27 Oct 2015

Regulation of integrin and growth factor signaling in biomaterials for osteodifferentiation

  • Qiang Wei,
  • Theresa L. M. Pohl,
  • Anja Seckinger,
  • Joachim P. Spatz and
  • Elisabetta A. Cavalcanti-Adam

Beilstein J. Org. Chem. 2015, 11, 773–783, doi:10.3762/bjoc.11.87

Graphical Abstract
  • , peptidomimetics of the α5β1 antagonist and the αvβ3 antagonist were synthesized, respectively (Figure 3). Both peptidomimetics can selectively mediate cell adhesion by binding with the relative single integrin subtype without losing activity, while avoiding unspecific adhesion and integrin binding. This
  • -selective (right) peptidomimetics. Reprinted with permission from [22]. Copyright 2013 Wiley. When the distance between two neighboring integrin ligands is <70 nm, the focal adhesions and contractile actin cytoskeletal stress fibres allow cell spreading (a). When the distance is >70 nm, the formation of
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Published 13 May 2015

Synthesis of antibacterial 1,3-diyne-linked peptoids from an Ugi-4CR/Glaser coupling approach

  • Martin C. N. Brauer,
  • Ricardo A. W. Neves Filho,
  • Bernhard Westermann,
  • Ramona Heinke and
  • Ludger A. Wessjohann

Beilstein J. Org. Chem. 2015, 11, 25–30, doi:10.3762/bjoc.11.4

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  • increasing interest to synthesize dimerized peptidomimetics with pharmacological properties through a step-efficient protocol that allows rapid access to highly diverse dimer libraries, we set out to develop a strategy based on an U-4CR/Glaser-type homocoupling sequence [34]. In comparison to popular cross
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Published 07 Jan 2015

The Shono-type electroorganic oxidation of unfunctionalised amides. Carbon–carbon bond formation via electrogenerated N-acyliminium ions

  • Alan M. Jones and
  • Craig E. Banks

Beilstein J. Org. Chem. 2014, 10, 3056–3072, doi:10.3762/bjoc.10.323

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  • electroorganic techniques and future directions. Keywords: anodic oxidation; electrochemistry; electroorganic, electrosynthesis, N-acyliminium ions; natural products; non-Kolbe oxidation; peptidomimetics; Shono oxidation; synthesis; Review N-Acyliminium ions are synthetically versatile N-Acyliminium ions [1][2
  • into the synthesis of functionalised peptides and peptidomimetics using the anode oxidation strategy [91][92][93][94][95]. The anodic oxidation of pyrrolidine derivatives and silylated peptides afforded a variety of bicyclic lactam peptidomimetics and functionalised peptides (Scheme 22) [91][92][94
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Published 18 Dec 2014

Recent advances in the electrochemical construction of heterocycles

  • Robert Francke

Beilstein J. Org. Chem. 2014, 10, 2858–2873, doi:10.3762/bjoc.10.303

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  • research on functionalized peptidomimetics, Moeller and co-workers found that the amide unit provides an excellent opportunity for oxidative modification of the peptide framework [50][51]. In order to construct constrained peptidomimetics, several electrochemical protocols for generation and cyclization of
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Published 03 Dec 2014

Facile synthesis of 1H-imidazo[1,2-b]pyrazoles via a sequential one-pot synthetic approach

  • András Demjén,
  • Márió Gyuris,
  • János Wölfling,
  • László G. Puskás and
  • Iván Kanizsai

Beilstein J. Org. Chem. 2014, 10, 2338–2344, doi:10.3762/bjoc.10.243

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  • -component reaction (U-4CR), can be adopted. The sequential combination of four species (amines, aldehydes, isocyanides and carboxylic acids) in a single-pot synthetic operation permits access to bisamide peptidomimetics through a highly electrophilic nitrilium intermediate [1][2][3][4]. Modification of the
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Published 08 Oct 2014

Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

  • Thilo Focken and
  • Stephen Hanessian

Beilstein J. Org. Chem. 2014, 10, 1848–1877, doi:10.3762/bjoc.10.195

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  • MMP inhibitors by Hanessian and co-workers, trans- and cis-aziridines scaffolds were used as peptidomimetics to construct a series of hydroxamic acids analogs such as 17 (Scheme 17) [63]. While the trans-aziridines were prepared by conjugate addition of O-benzylhydroxylamine to α,β-unsaturated amides
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Published 13 Aug 2014

Asymmetric Ugi 3CR on isatin-derived ketimine: synthesis of chiral 3,3-disubstituted 3-aminooxindole derivatives

  • Giordano Lesma,
  • Fiorella Meneghetti,
  • Alessandro Sacchetti,
  • Mattia Stucchi and
  • Alessandra Silvani

Beilstein J. Org. Chem. 2014, 10, 1383–1389, doi:10.3762/bjoc.10.141

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  • subjected to post-Ugi transformations, paving the way to application as peptidomimetics. Keywords: isatin; multicomponent; oxindole; peptidomimetics; Ugi; Introduction Isatin and its derivatives have drawn considerable and renewed interest due to their peculiar chemistry and wide range of bioactivities
  • interest was also the product 10, derived from a reaction of isocyanide 2d (Table 2, entry 7), since it can be easily converted into the correspondent primary amide derivative (vide infra). To explore potential applications of the Ugi reaction products in the field of peptidomimetics, we also tested the
  • pharmacologically active peptidomimetics [41][42][43]. The reaction proceeded smoothly in methanol under reflux in the presence of excess TEA to give the product 18 by a regioselective six-exo-trig cyclization. Conclusion We have developed a novel approach to the synthesis of optically active 3,3-disubstituted 3
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Published 18 Jun 2014

Automated solid-phase peptide synthesis to obtain therapeutic peptides

  • Veronika Mäde,
  • Sylvia Els-Heindl and
  • Annette G. Beck-Sickinger

Beilstein J. Org. Chem. 2014, 10, 1197–1212, doi:10.3762/bjoc.10.118

Graphical Abstract
  • produce these peptides in order to develop chemically engineered peptidomimetics or to uncover their distinct binding modes. Figure 4 illustrates possible strategies and Figure 5 feasible moieties for chemical modifications, which can be incorporated by semi-automated Fmoc/t-Bu-based SPPS. Amino acid
  • generated more potent and stable peptidomimetics as compared to the wild types. Most steps within the synthesis of those analogs can be performed automatically by a peptide synthesizer, providing a fast and straightforward access to the peptides. SPPS can also be used to introduce specific tools into the
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Published 22 May 2014

Stereocontrolled synthesis of 5-azaspiro[2.3]hexane derivatives as conformationally “frozen” analogues of L-glutamic acid

  • Beatrice Bechi,
  • David Amantini,
  • Cristina Tintori,
  • Maurizio Botta and
  • Romano di Fabio

Beilstein J. Org. Chem. 2014, 10, 1114–1120, doi:10.3762/bjoc.10.110

Graphical Abstract
  • bioactive conformations [19]. Following the latter approach, Ib, shown in Figure 1, was designed as a novel potential ligand of the L-Glu receptors and building block for peptidomimetics. To the best of our knowledge, few structurally related azetidine derivatives 10a,b,11a,b and Ia [20][21][22], have been
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Published 14 May 2014

Molecular architecture with carbohydrate functionalized β-peptides adopting 314-helical conformation

  • Nitin J. Pawar,
  • Navdeep S. Sidhu,
  • George M. Sheldrick,
  • Dilip D. Dhavale and
  • Ulf Diederichsen

Beilstein J. Org. Chem. 2014, 10, 948–955, doi:10.3762/bjoc.10.93

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  • attracted interest due to their use as structural elements as peptidomimetics [38][39], oligosaccharide mimetics [40][41] and induction of secondary structures [42][43][44][45][46]. Carbohydrate-derived β-amino acids used in this study were obtained by conjugate addition (Michael addition) of ammonia to a
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Published 28 Apr 2014

Conformation of dehydropentapeptides containing four achiral amino acid residues – controlling the role of L-valine

  • Michał Jewgiński,
  • Joanna Krzciuk-Gula,
  • Maciej Makowski,
  • Rafał Latajka and
  • Paweł Kafarski

Beilstein J. Org. Chem. 2014, 10, 660–666, doi:10.3762/bjoc.10.58

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  • this group of compounds. These peptidomimetics and natural peptides are characterized by a double bond between the Cα and Cβ atoms [2]. This modification entails a lot of structural consequences in the conformation of the peptides. The presence of a Cα–Cβ double bond together with two flanking peptide
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Published 14 Mar 2014

Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

  • Gijs Koopmanschap,
  • Eelco Ruijter and
  • Romano V.A. Orru

Beilstein J. Org. Chem. 2014, 10, 544–598, doi:10.3762/bjoc.10.50

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  • and synthesis of peptide mimics (peptidomimetics) has received much attention. This because they have shown in many cases enhanced pharmacological properties over their natural peptide analogues. In particular, the incorporation of cyclic constructs into peptides is of high interest as they reduce the
  • peptidomimetics usually a sequence of multiple reactions has been applied, which makes it difficult to easily introduce structural diversity necessary for fine tuning the biological activity. A promising approach to tackle this problem is the use of multicomponent reactions (MCRs), because they can introduce both
  • structural diversity and molecular complexity in only one step. Among the MCRs, the isocyanide-based multicomponent reactions (IMCRs) are most relevant for the synthesis of peptidomimetics because they provide peptide-like products. However, these IMCRs usually give linear products and in order to obtain
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Published 04 Mar 2014

Concise, stereodivergent and highly stereoselective synthesis of cis- and trans-2-substituted 3-hydroxypiperidines – development of a phosphite-driven cyclodehydration

  • Peter H. Huy,
  • Julia C. Westphal and
  • Ari M. P. Koskinen

Beilstein J. Org. Chem. 2014, 10, 369–383, doi:10.3762/bjoc.10.35

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  • (commercial trade names Halocur® (lactate salt) and Stenorol® (hydrobromide salt)) [22]. Other relevant examples are 3-hydroxypipecolic acids, which serve as (conformationally restricted) substitutes of proline and serine [23][24] and have been incorporated into diverse bioactive peptidomimetics [25][26], and
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Published 11 Feb 2014

Synthesis of the reported structure of piperazirum using a nitro-Mannich reaction as the key stereochemical determining step

  • James C. Anderson,
  • Andreas S. Kalogirou,
  • Michael J. Porter and
  • Graham J. Tizzard

Beilstein J. Org. Chem. 2013, 9, 1737–1744, doi:10.3762/bjoc.9.200

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  • ]. They have been used to synthesise many nitrogen-containing functional groups including α-amino carbonyls [2][3], peptidomimetics [4], natural products [5][6][7][8][9][10] and many heterocyclic small molecules [11][12][13][14][15][16][17][18][19][20][21][22][23][24] of importance to drug discovery
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Published 23 Aug 2013

Development of peptidomimetic ligands of Pro-Leu-Gly-NH2 as allosteric modulators of the dopamine D2 receptor

  • Swapna Bhagwanth,
  • Ram K. Mishra and
  • Rodney L. Johnson

Beilstein J. Org. Chem. 2013, 9, 204–214, doi:10.3762/bjoc.9.24

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  • /bjoc.9.24 Abstract A variety of stable, small-molecule peptidomimetic ligands have been developed to elucidate the mechanism by which the neuropeptide Pro-Leu-Gly-NH2 (PLG) modulates dopaminergic neurotransmission. Photoaffinity labeling ligands based upon PLG peptidomimetics have been used to
  • establish that PLG binds to the D2 dopamine receptor at a site that is different from the orthosteric site, thus making PLG and its peptidomimetics allosteric modulators of the dopamine receptor. Through the design, synthesis and pharmacological evaluation of conformationally constrained peptidomimetics
  • containing lactam, bicyclic, and spiro-bicyclic scaffolds, support was provided for the hypothesis that the bioactive conformation of PLG is a type II β-turn. In addition, studies with peptidomimetics designed to mimic either a type VI β-turn or polyproline II helix conformation yielded molecules that were
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Published 30 Jan 2013

The diketopiperazine-fused tetrahydro-β-carboline scaffold as a model peptidomimetic with an unusual α-turn secondary structure

  • Francesco Airaghi,
  • Andrea Fiorati,
  • Giordano Lesma,
  • Manuele Musolino,
  • Alessandro Sacchetti and
  • Alessandra Silvani

Beilstein J. Org. Chem. 2013, 9, 147–154, doi:10.3762/bjoc.9.17

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  • that characterizes the α-turn structure is confirmed by 1H NMR conformational studies. To the best of our knowledge, this scaffold represents one of the rare examples of a designed constrained α-turn mimic. Keywords: α-turn; conformational analysis; diketopiperazine; peptidomimetics; tetrahydro-β
  • -HIV compounds [38]. Other examples of α-turn conformations are described in synthetic peptidomimetics [36][39][40][41][42]. Despite the growing interest in this kind of reverse turn and the need for all kinds of conformationally constrained mimics as tools for medicinal chemistry, the development of
  • /EM conformational analysis for peptidomimetics 1a and 1b. The + symbol indicates the presence in the global minimum.
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Published 22 Jan 2013

Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry

  • Daniel Fürniss,
  • Timo Mack,
  • Frank Hahn,
  • Sidonie B. L. Vollrath,
  • Katarzyna Koroniak,
  • Ute Schepers and
  • Stefan Bräse

Beilstein J. Org. Chem. 2013, 9, 56–63, doi:10.3762/bjoc.9.7

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  • ][24][25], have emerged as powerful tools in the context of drug delivery [26][27][28][29], peptidomimetics and other biologically relevant applications [28][30][31][32] as well as materials science [33][34]. During the last decade the synthesis of polyamines and peptoids has been well established on
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Published 10 Jan 2013

Modulating the activity of short arginine-tryptophan containing antibacterial peptides with N-terminal metallocenoyl groups

  • H. Bauke Albada,
  • Alina-Iulia Chiriac,
  • Michaela Wenzel,
  • Maya Penkova,
  • Julia E. Bandow,
  • Hans-Georg Sahl and
  • Nils Metzler-Nolte

Beilstein J. Org. Chem. 2012, 8, 1753–1764, doi:10.3762/bjoc.8.200

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  • innate immune system, the name “antimicrobial peptides” (abbreviated as AMPs) defines a larger group of peptides that also encompasses synthetic peptides, and peptidomimetics, for example. Among these, synthetic peptide-based antimicrobial agents are especially interesting because isolation and/or
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Published 15 Oct 2012

Similarity analysis, synthesis, and bioassay of antibacterial cyclic peptidomimetics

  • Workalemahu M. Berhanu,
  • Mohamed A. Ibrahim,
  • Girinath G. Pillai,
  • Alexander A. Oliferenko,
  • Levan Khelashvili,
  • Farukh Jabeen,
  • Bushra Mirza,
  • Farzana Latif Ansari,
  • Ihsan ul-Haq,
  • Said A. El-Feky and
  • Alan R. Katritzky

Beilstein J. Org. Chem. 2012, 8, 1146–1160, doi:10.3762/bjoc.8.128

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  • University, Islamabad 45320, Pakistan Department of Biochemistry, Quaid i Azam University, Islamabad 45320, Pakistan Department of Chemistry, King Abdulaziz University, Jeddah 21589, Saudi Arabia 10.3762/bjoc.8.128 Abstract The chemical similarity of antibacterial cyclic peptides and peptidomimetics was
  • . Some of the synthesized compounds were tested against an array of microorganisms and showed antibacterial activity against Bordetella bronchistepica, Micrococcus luteus, and Salmonella typhimurium. Keywords: antibacterial; cluster analysis; N-acylbenzotriazoles; peptidomimetics; similarity
  • peptides are more stable to proteolysis due to the lack of free N- and C-termini, as well as reduced conformational freedom. Stability can also be achieved by modifying peptides into “peptidomimetics” that mimic and/or stabilize the secondary structure that modifies associated biological processes, thus
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Published 24 Jul 2012

Antibiotic and cytotoxic peptides

  • Norbert Sewald

Beilstein J. Org. Chem. 2012, 8, 1144–1145, doi:10.3762/bjoc.8.127

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  • in Medicinal Chemistry [2]. This Thematic Series on “Antibiotic and cytotoxic peptides” presents contributions from synthetic chemists active in the fields of peptides, peptidomimetics, drug design, and method development, in order to promote the research area further and to disseminate the
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Published 24 Jul 2012

Parallel solid-phase synthesis of diaryltriazoles

  • Matthias Wrobel,
  • Jeffrey Aubé and
  • Burkhard König

Beilstein J. Org. Chem. 2012, 8, 1027–1036, doi:10.3762/bjoc.8.115

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  • protein–protein interactions. Keywords: chemical diversity; Huisgen cycloaddition; library synthesis; peptidomimetics; solid phase synthesis; triazole; Introduction The α-helix was the first-described secondary structure of peptides discovered by Linus Pauling in 1951 [1]. With about 30% of the amino
  • is another successful strategy [11]. Horwell pioneered this type of peptidomimetics and showed that 1,6-disubstituted indanes can imitate the helix residues i and i+1 [12][13]. Hamilton reported a 3,2′,2″-substituted terphenyl scaffold with a spatial orientation that mimics the i, i+3 and i+7
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Published 06 Jul 2012
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