scholarly journals Ugi reaction-derived prolyl peptide catalysts grafted on the renewable polymer polyfurfuryl alcohol for applications in heterogeneous enamine catalysis

2019 ◽  
Vol 15 ◽  
pp. 1210-1216 ◽  
Author(s):  
Alexander F de la Torre ◽  
Gabriel S Scatena ◽  
Oscar Valdés ◽  
Daniel G Rivera ◽  
Márcio W Paixão
Keyword(s):  
Multicomponent Reactions ◽  
Supported Catalysts ◽  
Ugi Reaction ◽  
Multicomponent Synthesis ◽  
Polyfurfuryl Alcohol ◽  
Peptide Catalysts ◽  
Asymmetric Michael Addition ◽  
Enamine Catalysis ◽  
Work Supports ◽  
Peptide Catalyst

The multicomponent synthesis of prolyl pseudo-peptide catalysts using the Ugi reaction with furfurylamines or isocyanides is described. The incorporation of such a polymerizable furan handle enabled the subsequent polymerization of the peptide catalyst with furfuryl alcohol, thus rendering polyfurfuryl alcohol-supported catalysts for applications in heterogeneous enamine catalysis. The utilization of the polymer-supported catalysts in both batch and continuous-flow organocatalytic procedures proved moderate catalytic efficacy and enantioselectivity, but excellent diastereoselectivity in the asymmetric Michael addition of n-butanal to β-nitrostyrene that was used as a model reaction. This work supports the potential of multicomponent reactions towards the assembly of catalysts and their simultaneous functionalization for immobilization.

In situ generation and protonation of the isocyanide/acetylene adduct: a powerful catalyst-free strategy for multicomponent synthesis of ketenimines, aza-dienes, and heterocycles

RSC Advances ◽  
2015 ◽  
Vol 5 (117) ◽  
pp. 97044-97065 ◽  
Author(s):  
Sadegh Rostamnia
Keyword(s):  
Multicomponent Reactions ◽  
Multicomponent Synthesis ◽  
New Class ◽  
Catalyst Free ◽  
In Situ Generation

In addition to isocyanide-based Ugi, Passerini, van Leusen, and Orru multicomponent reactions, a new class of isocyanide/acetylene-based multicomponent reactions, using zwitterionic adducts, have emerged as powerful methods to synthesize biologically interesting molecules.

Chiral β3-isocyanopropionates for multicomponent synthesis of peptides and depsipeptides containing a β-amino acid fragment

2018 ◽  
Vol 16 (33) ◽  
pp. 5987-5998 ◽  
Author(s):  
Danil P. Zarezin ◽  
Olga I. Shmatova ◽  
Valentine G. Nenajdenko
Keyword(s):  
Amino Acid ◽  
Multicomponent Reactions ◽  
Short Peptides ◽  
Multicomponent Synthesis ◽  
Acid Moiety ◽  
Amino Acid Fragment ◽  
Acid Fragment ◽  
Amino Acid Moiety ◽  
New Type

Chiral β3-isocyanopropionic acids derivatives is a new type of isocyanides for multicomponent reactions. The use of these isocyanides in Ugi and Passerini reactions allows to prepare short peptides and depsipeptides with β-amino acid moiety in the structure.

Polypeptide-catalyzed Biosilicification of Dentin Surfaces

2009 ◽  
Vol 88 (4) ◽  
pp. 377-381 ◽  
Author(s):  
A.J. Goldberg ◽  
M.C. Advincula ◽  
T. Komabayashi ◽  
P.A. Patel ◽  
P.T. Mather ◽  
...  
Keyword(s):  
Photoelectron Spectroscopy ◽  
Treatment Strategies ◽  
Marine Species ◽  
X Ray ◽  
Mineral Particles ◽  
Peptide Catalysts ◽  
Wide Range ◽  
Negative Controls ◽  
Peptide Catalyst

In situ formation of mineral particles by biocatalysis would be advantageous for occluding dentin tubules to reduce permeability or for sealing of material-tooth interfaces. One approach would require that the peptide-catalyst remain functional on the dentin surface. Based on recent observations of retained activity on other surfaces, we hypothesized that poly(L-lysine) (PLL), an analog of the protein catalyst responsible for silica formation in primitive marine species, would remain functional on dentin. PLL was applied to dentin discs along with a pre-hydrolyzed silica precursor, tetramethyl orthosilicate (TMOS). Discs were analyzed microscopically (scanning electron microscopy, SEM) and chemically (x-ray photoelectron spectroscopy, XPS). The treated discs, but not the negative controls, exhibited partial distinct coating whose XPS survey was consistent with that of silica, demonstrating that the polypeptide was required and retained its mediating activity. Peptide-catalysts that mediate mineral formation can retain functionality on dentin, suggesting a wide range of preventive and treatment strategies.

On water synthesis of pyran–chromenes via a multicomponent reactions catalyzed by fluorescent t-ZrO2nanoparticles

RSC Advances ◽  
2015 ◽  
Vol 5 (123) ◽  
pp. 101664-101671 ◽  
Author(s):  
Arijit Saha ◽  
Soumen Payra ◽  
Subhash Banerjee
Keyword(s):  
Multicomponent Reactions ◽  
Reusable Catalyst ◽  
Multicomponent Synthesis

Here, we have reported multicomponent synthesis of diverse pyran fused chromenes namely 2-aminochromene, dihydropyrano[3,2-c]chromene, and chromeno[4,3-b]chromene derivatives using fluorescentt-ZrO2nanoparticles as reusable catalyst in water.

scholarly journals Ecofriendly and Facile One-Pot Multicomponent Synthesis of Thiopyrimidines under Microwave Irradiation

2013 ◽  
Vol 2013 ◽  
pp. 1-6 ◽  
Author(s):  
Biswa Mohan Sahoo ◽  
B. V. V. Ravi Kumar ◽  
Jnyanaranjan Panda ◽  
S. C. Dinda
Keyword(s):  
Reaction Time ◽  
Microwave Irradiation ◽  
Spectral Data ◽  
Multicomponent Reaction ◽  
Multicomponent Reactions ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
Heating Method ◽  
Green Protocol ◽  
Drug Molecules

A rapid, improved, and ecofriendly synthesis of thiopyrimidines is carried out via one-pot multicomponent reaction of ethylcyanoacetate, substituted benzaldehydes, and thiourea in presence of ethanolic K2CO3 using microwave irradiation heating method. Excellent yields, shorter reaction time, and easy workup are the major advantageous features of this green protocol. So the application of multicomponent reactions involves the combination of multiple starting materials with different functional groups leading to the highly efficient and environmentally friendly construction of multifunctional drug molecules. The structures of the newly synthesized products were assigned on the basis of IR and 1HNMR spectral data.

scholarly journals Isonitrile-Based Multicomponent Synthesis of β-Amino Boronic Acids as β-Lactamase Inhibitors

Antibiotics ◽  
2020 ◽  
Vol 9 (5) ◽  
pp. 249 ◽  
Author(s):  
Emanuele Bassini ◽  
Stefano Gazzotti ◽  
Filomena Sannio ◽  
Leonardo Lo Presti ◽  
Jacopo Sgrignani ◽  
...  
Keyword(s):  
Multicomponent Reactions ◽  
Inhibitory Concentration ◽  
Binding Mode ◽  
Antimicrobial Activities ◽  
X Ray Diffraction ◽  
Multicomponent Synthesis ◽  
X Ray ◽  
Class D ◽  
11B Nmr ◽  
Van Leusen Reaction

The application of various isonitrile-based multicomponent reactions to protected (2-oxoethyl)boronic acid (as the carbonyl component) is described. The Ugi reaction, both in the four components and in the four centers–three components versions, and the van Leusen reaction, proved effective at providing small libraries of MIDA-protected β-aminoboronic acids. The corresponding free β-aminoboronic acids, quantitatively recovered through basic mild deprotection, were found to be quite stable and were fully characterized, including by 11B-NMR spectroscopy. Single-crystal X-ray diffraction analysis, applied both to a MIDA-protected and a free β-aminoboronic acid derivative, provided evidence for different conformations in the solid-state. Finally, the antimicrobial activities of selected compounds were evaluated by measuring their minimal inhibitory concentration (MIC) values, and the binding mode of the most promising derivative on OXA-23 class D β-lactamase was predicted by a molecular modeling study.

scholarly journals Facile Synthesis of Chrysin-derivatives with Promising Activities as Aromatase Inhibitors†

2011 ◽  
Vol 6 (1) ◽  
pp. 1934578X1100600 ◽  
Author(s):  
Hamdoon A. Mohammed ◽  
Lalla A. Ba ◽  
Torsten Burkholz ◽  
Elena Schumann ◽  
Britta Diesel ◽  
...  
Keyword(s):  
Aromatase Inhibitors ◽  
Anticancer Agents ◽  
Multicomponent Reactions ◽  
Multicomponent Synthesis ◽  
Facile Synthesis ◽  
Functional Elements ◽  
Lead Structure ◽  
New Class ◽  
Flavone Derivatives ◽  
Human Aromatase

Flavones such as chrysin show structural similarities to androgens, the substrates of human aromatase, which converts androgens to estrogens. Aromatase is a key target in the treatment of hormone-dependent tumors, including breast cancer. Flavone-based aromatase inhibitors are of growing interest, and chrysin in particular provides a (natural) lead structure. This paper reports multicomponent synthesis as a means for facile modification of the chrysin core structure in order to add functional elements. A Mannich-type reaction was used to synthesize a range of mono- and disubstituted chrysin derivatives, some of which are more effective aromatase inhibitors than the benchmark compound, aminoglutethimide. Similarly, the reaction of chrysin with various isonitriles and acetylene dicarboxylates results in a new class of flavone derivatives, tricyclic pyrano-flavones which also inhibit human aromatase. Multicomponent reactions involving flavones therefore enable the synthesis of a variety of derivatives, some of which may be useful as anticancer agents.

ChemInform Abstract: Multicomponent Synthesis of Cyclic Depsipeptide Mimics by Ugi Reaction Including Cyclic Hemiacetals Derived from Asymmetric Organocatalysis.

ChemInform ◽  
2016 ◽  
Vol 47 (25) ◽  
Author(s):  
Alexander F. de la Torre ◽  
Daniel G. Rivera ◽  
Odette Concepcion ◽  
Radell Echemendia ◽  
Arlene G. Correa ◽  
...  
Keyword(s):  
Ugi Reaction ◽  
Multicomponent Synthesis ◽  
Cyclic Depsipeptide ◽  
Asymmetric Organocatalysis
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