Synthesis, Biological Properties and Anti-HIV-1 Activity of New Pyrimidine P<sub>1</sub>,P<sub>2</sub>-Dinucleotides

Miazga, Agnieszka; Ziemkowski, Przemysław; Siwecka, Maria A.; Lipniacki, Andrzej; Piasek, Andrzej; Kulikowski, Tadeusz

doi:10.1080/15257771003738642

Cited by 3 publications

(2 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the N-heterocyclic class of scaffolds, pyrimidine and its derivatives play a prominent role [ 11 ]. Being the main constituents of several natural products, these pyrimidines represent a significant class of molecules which have been of increased interest in recent years owing to their valuable pharmacological and biological applications in antimicrobial [ 12 ], antifungal [ 13 ], anti-tumor [ 14 ], anti-HIV [ 15 ], anti-tubercular [ 16 ], anti-inflammatory [ 17 ], and antimalarial [ 18 ] activities. Moreover, aryl-indenopyrimidines have been used as adenosine A2A receptor antagonists [ 19 ], which are useful, and many reports have dealt with the preparation of different types of pyrimidine derivatives via multicomponent reactions.…”

Section: Introductionmentioning

confidence: 99%

Ag2O on ZrO2 as a Recyclable Catalyst for Multicomponent Synthesis of Indenopyrimidine Derivatives

et al. 2018

View full text Add to dashboard Cite

We describe the synthesis of silver loaded on zirconia and its use as an efficient catalyst for a one-pot three-component reaction to synthesize 11 indenopyrimidine derivatives, of which 7 are new compounds. The procedure involves substituted benzaldehydes, indane-1,3-dione, and guanidinium hydrochloride, with ethanol as solvent. The proposed green protocol at room temperature is simple and efficient, giving excellent yields (90–96%) in short reaction times (<30 min). The protocol works well according to the green chemistry principles with respect to high atom economy, no need for column separation, and reusability of the catalyst, which are attractive features. XRD, TEM, SEM, and BET analysis were used to characterize the catalyst materials.

show abstract

Section: Introductionmentioning

confidence: 99%

Ag2O on ZrO2 as a Recyclable Catalyst for Multicomponent Synthesis of Indenopyrimidine Derivatives

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Thiosugars are carbohydrate analogues in which one or more oxygen atoms are substituted with sulfur in both furanoside and pyranoside structures. , Because of the unique conformational and electronic properties conferred by the presence of the sulfur atom, these compounds offer fascinating prospects for medicinal chemistry and have been shown to demonstrate potent biological activity as antiviral, , antidiabetic, and anticancer compounds. , The potent, naturally occurring α-glucosidase inhibitor salacinol ( 1 ) (Figure ) contains a 1-deoxy-4-thioarabinofuranosyl sulfonium cation, which is essential for the biological activity of the molecule. , The related family of sulfonium salts isolated from the Salacia species all contain an identical thioarabinofuranosyl core structure . The replacement of the furanose-ring oxygen with sulfur also confers potent biological activity on naturally occurring nucleosides. , Examples such as 4-thiothymidine ( 2 ) , and 2-deoxy-4-thiocytidine ( 3 ) (Figure ), in which a heterocyclic group is attached directly to C-1 of the thiofuranose ring, have been demonstrated to possess extremely potent antiviral and anticancer activity . The structurally related 4-thio analogues of C-nucleosides are also of considerable interest as potential glycosidase inhibitors, but currently there are a limited number of synthetic strategies available to access these compounds. , Recently, Haraguchi and co-workers developed a method for the synthesis of the β-anomer of 4-thio-C-ribonucleosides starting from a 3,5- O -(di- tert -butylsilylene)-4-thiofuranoid glycal .…”

Section: Introductionmentioning

confidence: 99%

Applications of 5-exo-trig Thiyl Radical Cyclizations for the Synthesis of Thiosugars

Malone

Scanlan

2013

J. Org. Chem.

View full text Add to dashboard Cite

The application of thiyl-radical-mediated 5-exo-trig cyclization reactions for the preparation of a series of C-linked 4-thiofuranoside sugars has been investigated. The cyclization reactions were found to proceed in high yield with complete regioselectivity and moderate to excellent diastereoselectivity for a number of benzyl-protected precursors. The diastereoselectivity of the radical cyclization was determined by a number of factors, primarily the stereochemistry at the C-2 position and the nature of the substituents attached to the olefin. The cyclization reactions proceed via transition-state intermediates that favor formation of the 1,2-trans products. For D-sugars, a chairlike transition state is proposed. For L-sugars, both chair- and boatlike transition states could be considered. Inversion of the stereochemistry at C-4 also induced a significant effect on the diastereoselectivity of the radical process. The synthetic route is general for both D- and L-sugars and offers a highly novel and efficient strategy for accessing C-linked 4-thiofuranosides. A fluorescently labeled thiosugar was prepared as a putative glycosidase inhibitor.

show abstract

Green Synthesis, Spectrofluorometric Characterization and Antibacterial Activity of Heterocyclic Compound from Chalcone on the Basis of in Vitro and Quantum Chemistry Calculation

Khan

2017

J Fluoresc

View full text Add to dashboard Cite

2-amino-4-(4-bromophenyl)-8-methoxy-5,6-dihydrobenzo[h]quinoline-3-carbonitrile (ABDC) was synthesized by the reaction of (2E)-2-(4 bromobenzylidene) - 6 -methoxy-3,4-dihydronaphthalen-1(2H)-one (Chalcone) with malononitrile and ammonium acetate under microwave irradiation. Chalcone was synthesised by the reaction 4-bromobenzaldehyd, 6-methoxy-1,2,3,4-tetrahydro-naphthalin-1-one under the same condition. Structure of ABDC was conformed by H andC NMR, FT-IR, EI-MS spectral studies and elemental analysis. The electronic absorption and fluorescence spectra of ABDC have been studied in solvents of different polarities, and the data were used to study the solvatochromic properties such as excitation coefficient, stokes shift, oscillator strength, transition dipole moment and fluorescence quantum yield. The absorption maximum and fluorescence emission maximum was observed red shift when increase solvent polarity n-Hexane to DMSO. ABDC undergoes solubilization in different micelles and may be used as a probe and quencher to determine the critical micelle concentration (CMC) of CTAB and SDS. The anti-bacterial activity of chalcone and its cyclized product ABDC was tested in vitro by the disk diffusion assay against two Gram-positive and two Gram-negative bacteria was determined with the reference of standard drug Tetracycline. Results showed that the ABDC is better anti-bacterial agent as compared to chalcone. The anti-bacterial activity was further supported by the quantum chemistry calculation.

show abstract

Synthesis, Biological Properties and Anti-HIV-1 Activity of New Pyrimidine P₁,P₂-Dinucleotides

Cited by 3 publications

References 4 publications

Ag2O on ZrO2 as a Recyclable Catalyst for Multicomponent Synthesis of Indenopyrimidine Derivatives

Ag2O on ZrO2 as a Recyclable Catalyst for Multicomponent Synthesis of Indenopyrimidine Derivatives

Applications of 5-exo-trig Thiyl Radical Cyclizations for the Synthesis of Thiosugars

Green Synthesis, Spectrofluorometric Characterization and Antibacterial Activity of Heterocyclic Compound from Chalcone on the Basis of in Vitro and Quantum Chemistry Calculation

Contact Info

Product

Resources

About

Synthesis, Biological Properties and Anti-HIV-1 Activity of New Pyrimidine P1,P2-Dinucleotides

Cited by 3 publications

References 4 publications

Ag2O on ZrO2 as a Recyclable Catalyst for Multicomponent Synthesis of Indenopyrimidine Derivatives

Ag2O on ZrO2 as a Recyclable Catalyst for Multicomponent Synthesis of Indenopyrimidine Derivatives

Applications of 5-exo-trig Thiyl Radical Cyclizations for the Synthesis of Thiosugars

Green Synthesis, Spectrofluorometric Characterization and Antibacterial Activity of Heterocyclic Compound from Chalcone on the Basis of in Vitro and Quantum Chemistry Calculation

Contact Info

Product

Resources

About

Synthesis, Biological Properties and Anti-HIV-1 Activity of New Pyrimidine P₁,P₂-Dinucleotides