AI Article Synopsis

  • The study involves a chemical reaction that creates isoxazolidine compounds by combining a specific nitrone with 6-bromo-2-vinyl-3-quinazolin-4-ones.
  • These newly formed isoxazolidines were tested for their ability to inhibit various DNA and RNA viruses, showing effectiveness against strains of varicella-zoster virus and human cytomegalovirus.
  • Some isoxazolidines also displayed moderate ability to inhibit the growth of human lymphocyte cells at certain concentrations.

Article Abstract

1,3-Dipolar cycloaddition of -methyl -(diethoxyphosphoryl) nitrone to N3-substituted 6-bromo-2-vinyl-3-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 EC in the 5.4⁻13.6 μΜ range, as well as human cytomegalovirus (EC = 8.9⁻12.5 μΜ). Isoxazolidines -, -, -, -/-, -, -, and -/- exhibited moderate cytostatic activity towards the human lymphocyte cell line CEM (IC = 9.6⁻17 μM).

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6222691PMC
http://dx.doi.org/10.3390/molecules23081889DOI Listing

Publication Analysis

Top Keywords

isoxazolidine conjugates
4
conjugates n3-substituted
4
n3-substituted 6-bromoquinazolinones-synthesis
4
6-bromoquinazolinones-synthesis anti-varizella-zoster
4
anti-varizella-zoster virus
4
virus anti-cytomegalovirus
4
anti-cytomegalovirus activity
4
activity 13-dipolar
4
13-dipolar cycloaddition
4
cycloaddition -methyl
4

Similar Publications

In this study, a new series of and 5-substituted-3-(dibenzyloxyphosphoryl)isoxazolidines - were synthesized by the 1,3-dipolar cycloaddition reaction of -benzyl--(dibenzyloxyphosphoryl)nitrone and selected -allyl--benzylquinazoline-2,4-diones. All the obtained -isoxazolidines - and the samples enriched in respective -isomers were evaluated for anticancer activity against three tumor cell lines. All the tested compounds exhibited high activity against the prostate cancer cell line (PC-3).

View Article and Find Full Text PDF

Characterization of an -Allylglyoxylamide-Based Bioorthogonal Nitrone Trap.

Bioconjug Chem

December 2023

Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.

Aldehydes are attractive bioorthogonal coupling partners. The ease of manipulation of aldehydes and their orthogonality to other classes of bioorthogonal reactions have inspired the exploration of chemistries, which generate irreversible conjugates. Similarly, nitrones have been shown to be potent 1,3-dipoles in bioorthogonal reactions when paired with strained alkynes.

View Article and Find Full Text PDF

Dipolar cycloaddition of the N-substituted -(diethoxyphosphonyl)nitrones with -allyl--benzylquinazoline-2,4-diones produced mixtures of diastereoisomeric 3-(diethoxyphosphonyl)isoxazolidines with a -benzylquinazoline-2,4-dione unit at C5. The obtained compounds were assessed for antiviral and antibacterial activities. Several compounds showed moderate inhibitory activities against VZV with EC values in the range of 12.

View Article and Find Full Text PDF

Functionalized polyhedral oligosilsesquioxanes (POSS) containing an isoxazolidine nucleus have been synthesized by microwave assisted 1,3-dipolar cycloaddition of -methyl--alkoxycarbonyl nitrone 1 with POSS containing olefin moieties. The results of cycloaddition processes were rationalized by computational studies at the DFT level. The covalent conjugation of chitosan with the cycloadduct 3a leads to composite material CS-POSS 7 which was gelified using genipin as cross linking agent.

View Article and Find Full Text PDF

DNA-Compatible [3 + 2] Nitrone-Olefin Cycloaddition Suitable for DEL Syntheses.

Org Lett

March 2019

Department of Chemistry and Chemical Biology , Harvard University, 12 Oxford Street , Cambridge , Massachusetts 02138 , United States.

The limited scope of DNA-compatible chemistry restricts the types of chemical features that can be incorporated into DNA-encoded libraries (DELs). Here, a method to synthesize DNA-conjugated polycyclic isoxazolidines via a [3 + 2] nitrone-olefin cycloaddition is described. The reaction is compatible with many olefin-containing substrates and diverse N-alkylhydroxylamines.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!