Pyrrolo[2,3-d]pyrimidine β-L-Nucleosides Containing 7-Deazaadenine, 2-Amino-7-deazaadenine, 7-Deazaguanine, 7-Deazaisoguanine, and 7-Deazaxanthine

2006 ◽  
Vol 71 (7) ◽  
pp. 956-977 ◽  
Author(s):  
Frank Seela ◽  
Xiaohua Peng

The synthesis and properties of 7-deazapurine β-L-nucleosides are described. The stereoselective glycosylation of the anions of 2-amino-6-chloro-7-deazapurines 9a, 9b or 6-chloro-7-deazapurines 13a, 13d with 3,5-di-O-(4-methylbenzoyl)-2-deoxy-α-L-erythro-pentofuranosyl chloride (8) furnished the β-L-2'-deoxyribonucleosides 1-4. The synthesis of β-L-ribonucleosides 5-7 used the Silyl-Hilbert-Johnson reaction (TMSOTf/BSA/MeCN) performed under Vorbrüggen conditions for the glycosylation of 7-halogenated 6-chloro-2-pivalamido-7-deazapurines 17b-17d with 1-O-acetyl-2,3,5-tri-O-benzoyl-L-ribofuranose (16). Single-crystal X-ray analyses were performed and CD spectra were measured to assign the configuration. The antiviral activity against selected DNA and RNA viruses is reported.

2015 ◽  
Vol 23 (17) ◽  
pp. 5345-5351 ◽  
Author(s):  
Giorgia Botta ◽  
Bruno Mattia Bizzarri ◽  
Adriana Garozzo ◽  
Rossella Timpanaro ◽  
Benedetta Bisignano ◽  
...  

Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 1889 ◽  
Author(s):  
Magdalena Grabkowska-Drużyc ◽  
Graciela Andrei ◽  
Dominique Schols ◽  
Robert Snoeck ◽  
Dorota Piotrowska

1,3-Dipolar cycloaddition of N-methyl C-(diethoxyphosphoryl) nitrone to N3-substituted 6-bromo-2-vinyl-3H-quinazolin-4-ones gave (3-diethoxyphosphoryl) isoxazolidines substituted at C5 with quinazolinones modified at N3. All isoxazolidine cycloadducts were screened for antiviral activity against a broad spectrum of DNA and RNA viruses. Several isoxazolidines inhibited the replication of both thymidine kinase wild-type and deficient (TK+ and TK−) varicella-zoster virus strains at EC50 in the 5.4–13.6 μΜ range, as well as human cytomegalovirus (EC50 = 8.9–12.5 μΜ). Isoxazolidines trans-11b, trans-11c, trans-11e, trans-11f/cis-11f, trans-11g, trans-11h, and trans-11i/cis-11i exhibited moderate cytostatic activity towards the human lymphocyte cell line CEM (IC50 = 9.6–17 μM).


2020 ◽  
Vol 14 (1) ◽  
pp. 83-98
Author(s):  
Paola Corona ◽  
Sandra Piras ◽  
Roberta Ibba ◽  
Federico Riu ◽  
Gabriele Murineddu ◽  
...  

Background: For the last thirty years, the benzotriazole scaffold has been the object of our group interest and we have already presented some results on the antiviral activity of our compounds. Objective: In this article, we conclude the exploration of N-(4-(R-2H-benzo[d][1,2,3]triazol-2-yl)phenyl)-4-R’-benzamides and 1-(4-(R-2H-benzo[d][1,2,3]triazol-2-yl)phenyl)-3-R’-ureas by synthesizing further modified derivatives, in order to have more elements for SARs evaluation. Methods: Here, we reported the synthesis and the antiviral screening results of 38 newly synthesized benzotriazole derivatives against a panel of DNA and RNA viruses. We also analyse SARs in comparing these compounds with previously published benzotriazole analogues, taking stock of the situation. Results: Among the newly presented derivatives, compounds 17 and 18 were the most active with EC50 6.9 and 5.5 µM, respectively against Coxsackievirus B5 (CV-B5) and 20.5 and 17.5 µM against Poliovirus (Sb-1). Conclusion: we can conclude that N-(4-(2H-benzo[d] [1 - 3] triazol-2-yl)phenyl-R-amide is a good chemical scaffold for the development of new antiviral molecules.


2014 ◽  
Vol 2014 ◽  
pp. 1-12 ◽  
Author(s):  
Paolo Quadrelli ◽  
Naiara Vazquez Martinez ◽  
Roberto Scrocchi ◽  
Antonino Corsaro ◽  
Venerando Pistarà

The current synthesis of racemic purine and pyrimidine isoxazoline-carbocyclic nucleosides is reported, detailing the key-steps for standard and reliable preparations. Improved yields were obtained by the proper tuning of the single synthetic steps, opening the way for the preparation of a variety of novel compounds. Some of the obtained compounds were also evaluated against a wide variety of DNA and RNA viruses including HIV. No specific antiviral activity was observed in the cases at hand. Novel compounds were prepared for future biological tests.


1985 ◽  
Vol 38 (11) ◽  
pp. 1581-1587 ◽  
Author(s):  
MASAHIDE HASOBE ◽  
MINEO SANEYOSHI ◽  
KIYOSHI ISONO

Molecules ◽  
2021 ◽  
Vol 26 (3) ◽  
pp. 536
Author(s):  
Jing Li ◽  
Ying Han ◽  
Chuan-Feng Chen

Starting from the enantiopure precursors, a pair of chiral macrocyclic arenes named helic[1]triptycene[3]arenes were conveniently synthesized. The circular dichroism (CD) spectra of the enantiomeric macrocyclic arenes exhibited mirror images, and the X-ray single crystal structures confirmed their absolute conformations as well. Moreover, the macrocyclic arenes showed strong complexation with secondary ammonium and primary ammonium salts containing aminoindan groups. In particular, the chiral macrocyclic arenes exhibited enantioselective recognition ability towards the chiral secondary ammonium salts containing aminoindan groups with an enantioselective ratio up to 3.89.


2004 ◽  
Vol 61 (1) ◽  
pp. 57-62 ◽  
Author(s):  
V BUCKWOLD ◽  
R WILSON ◽  
A NALCA ◽  
B BEER ◽  
T VOSS ◽  
...  

Author(s):  
J. M. Galbraith ◽  
L. E. Murr ◽  
A. L. Stevens

Uniaxial compression tests and hydrostatic tests at pressures up to 27 kbars have been performed to determine operating slip systems in single crystal and polycrystal1ine beryllium. A recent study has been made of wave propagation in single crystal beryllium by shock loading to selectively activate various slip systems, and this has been followed by a study of wave propagation and spallation in textured, polycrystal1ine beryllium. An alteration in the X-ray diffraction pattern has been noted after shock loading, but this alteration has not yet been correlated with any structural change occurring during shock loading of polycrystal1ine beryllium.This study is being conducted in an effort to characterize the effects of shock loading on textured, polycrystal1ine beryllium. Samples were fabricated from a billet of Kawecki-Berylco hot pressed HP-10 beryllium.


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