1,3-Dipolar cycloaddition of nitrones: synthesis of multisubstituted, diverse range of heterocyclic compounds

2021 ◽  
Author(s):  
Seema Thakur ◽  
Arunima Das ◽  
Tapas Das
Keyword(s):  
Natural Products ◽  
Heterocyclic Compounds ◽  
Cycloaddition Reaction ◽  
Biologically Active ◽  
Dipolar Cycloaddition ◽  
Diverse Range

The 1,3-dipolar cycloaddition reaction of nitrone is one of the most important methods for the synthesis of different sizes of heterocycles which have enormous applications in natural products, biologically active molecules and pharmaceuticals.

Synthesis of New Hexakis-Heterocyclic Compounds and their Use in the Formation and Stabilization of Au and Ag Nanoparticles

2014 ◽  
Vol 976 ◽  
pp. 3-7
Author(s):  
María Isabel Montalvo-Sierra ◽  
Miriam A. Martins Alho ◽  
Ana María Herrera-Gonzalez ◽  
Jesús García-Serrano ◽  
Paola Belem Bocardo-Tovar
Keyword(s):  
Ir Spectroscopy ◽  
Ag Nanoparticles ◽  
Heterocyclic Compounds ◽  
Cyano Group ◽  
Cycloaddition Reaction ◽  
Aldehyde Group ◽  
Dipolar Cycloaddition ◽  
Vis Spectroscopy ◽  
Aldehyde Derivative

The stabilization of nanoparticles in solution is a challenge of major proportions, and avoiding the formation of aggregates and eventual coalescence of particles is directly linked to the conservation of its unique properties. In this work, we reported the synthesis of two hexakis-heterocyclic compounds, containing the tetrazole or 2-amino-1,3,4-thiadiazole group, respectively. The hexa-heterocyclic compounds were used in the synthesis and stabilization of Au and Ag nanoparticles. To obtain these molecules was used phosphonitrilic chloride trimer compound as core, which reacted with phenols properly substituted in theparaposition with either cyano or aldehyde group. The cyano group was successfully converted to the corresponding tetrazole using a 1,3-dipolar cycloaddition reaction with ammonium azide generatedin situ. In the case of aldehyde derivative, it was converted to the corresponding thiosemicarbazone, which was further cyclized using FeCl3. Compounds were characterized by RMN and IR spectroscopy. The UV-Vis spectroscopy was used for nanoparticles analysis.

scholarly journals Chemistry and Biological Activities of 1,2,4-Triazolethiones—Antiviral and Anti-Infective Drugs

Molecules ◽  
2020 ◽  
Vol 25 (13) ◽  
pp. 3036
Author(s):  
Ashraf A. Aly ◽  
Alaa A. Hassan ◽  
Maysa M. Makhlouf ◽  
Stefan Bräse
Keyword(s):  
Natural Products ◽  
Heterocyclic Compounds ◽  
Biological Activities ◽  
Biologically Active ◽  
Biological Applications ◽  
Active Moiety ◽  
Interesting Class

Mercapto-substituted 1,2,4-triazoles are very interesting compounds as they play an important role in chemopreventive and chemotherapeutic effects on cancer. In recent decades, literature has been enriched with sulfur- and nitrogen-containing heterocycles which are used as a basic nucleus of different heterocyclic compounds with various biological applications in medicine and also occupy a huge part of natural products. Therefore, we shed, herein, more light on the synthesis of this interesting class and its application as a biologically active moiety. They might also be suitable as antiviral and anti-infective drugs.

Recent Advances in the Transition Metal Catalyzed Addition of Carboxylic Acids to Alkynes

2021 ◽  
Vol 25 ◽  
Author(s):  
Victorio Cadierno
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Carboxylic Acids ◽  
Heterocyclic Compounds ◽  
Biologically Active ◽  
Recent Advances ◽  
Enol Esters ◽  
Cascade Processes ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

: Recent advances in the metal-catalyzed hydrofunctionalization of alkynes with carboxylic acids are comprehensively reviewed. Both inter- and intramolecular processes, leading respectively to enol esters and lactones, are discussed, as well as the involvement of these transformations in the synthesis of natural products and biologically active molecules, and the assembly of elaborated heterocyclic compounds though cascade processes. Literature published since 2011 is covered.

scholarly journals A Pseudoalteromonas clade with remarkable biosynthetic potential

2021 ◽  
Author(s):  
Rocky Chau ◽  
Leanne A. Pearson ◽  
Jesse Cain ◽  
John A. Kalaitzis ◽  
Brett A. Neilan
Keyword(s):  
Natural Products ◽  
Gene Cluster ◽  
Genome Mining ◽  
Gene Clusters ◽  
Average Density ◽  
Biologically Active ◽  
Biosynthesis Gene Cluster ◽  
Diverse Range ◽  
Siderophore Biosynthesis ◽  
Biosynthesis Gene

Pseudoalteromonas species produce a diverse range of biologically active compounds, including those biosynthesized by non-ribosomal peptide synthetases (NRPSs) and polyketide synthases (PKSs). Here we report the biochemical and genomic analysis of Pseudoalteromonas sp. HM-SA03, isolated from the blue-ringed octopus, Hapalochalaena sp. Genome mining for secondary metabolite pathways revealed seven putative NRPS/PKS biosynthesis gene clusters, including those for the biosynthesis of alterochromides, pseudoalterobactins, alteramides and four hitherto novel compounds. Among these was a novel siderophore biosynthesis gene cluster with unprecedented architecture (NRPS-PKS-NRPS-PKS-NRPS-PKS-NRPS). Alterochromide production in HM-SA03 was also confirmed by liquid chromatography-mass spectrometry. An investigation of the biosynthetic potential of 42 publicly available Pseudoalteromonas genomes indicated that some of these gene clusters are distributed throughout the genus. Through phylogenetic analysis, a particular subset of strains formed a clade with extraordinary biosynthetic potential, with an average density of ten biosynthesis gene clusters per genome. In contrast, the majority of Pseudoalteromonas strains outside this clade contained an average of three clusters encoding complex biosynthesis. These results highlight the under-explored potential of Pseudoalteromonas as a source of new natural products. Importance This study demonstrates that the Pseudoalteromonas strain, HM-SA03, isolated from the venomous blue-ringed octopus, Hapalochalaena sp., is a biosynthetically talented organism, capable of producing alterochromides and potentially six other specialized metabolites. We have identified a pseudoalterobactin biosynthesis gene cluster and proposed a pathway for the production of the associated siderophore. A novel siderophore biosynthesis gene cluster with unprecedented architecture was also identified in the HM-SA03 genome. Finally, we have demonstrated that HM-SA03 belongs to a phylogenetic clade of strains with extraordinary biosynthetic potential. While our results do not support a role of HM-SA03 in Hapalochalaena sp. venom (tetrodotoxin) production, they emphasize the untapped potential of Pseudoalteromonas as a source of novel natural products.

scholarly journals Synthesis of Bioactive Fluoropyrrolidines via Copper(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides

2021 ◽  
Author(s):  
Xiao Xu ◽  
Longzhu Bao ◽  
Lu Ran ◽  
Zhenyan Yang ◽  
Dingce Yan ◽  
...  
Keyword(s):  
Natural Products ◽  
Building Blocks ◽  
Biologically Active ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Active Natural

Chiral pyrrolidinyl units are important building blocks in biologically active natural products and drugs, and the develpment of efficient methods for the synthesis of diverse structured pyrrolidine derivatives is of...

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