Steering the azido–tetrazole equilibrium of 4-azidopyrimidines via substituent variation – implications for drug design and azide–alkyne cycloadditions-Reference-Cited by-同舟云学术

Steering the azido–tetrazole equilibrium of 4-azidopyrimidines via substituent variation – implications for drug design and azide–alkyne cycloadditions

Published:2015 Issue:43 Volume:13 Page:10620-10630
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Thomann A.¹²³⁴,Zapp J.⁵⁶³⁴,Hutter M.⁵⁷³⁴,Empting M.¹²³⁴,Hartmann R. W.¹²³⁴⁵

Affiliation:

1. Helmholtz Institute for Pharmaceutical Research Saarland (HIPS)

2. Department for Drug Design and Optimization (DDOP)

3. 66123 Saarbrücken

4. Germany

5. Saarland University

6. Department of Pharmaceutical Biology

7. Center for Bioinformatics

Abstract

Variations of substituents at 2-substituted 4-azidopyrimidines allowed us to shift the azido–tetrazole equilibrium to either of the two constitutional isomers. This can be exploited for click chemistry and fragment-based drug design.

Funder

Bundesministerium für Bildung und Forschung

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2015/OB/C5OB01006C

Reference86 articles.

1. Synthesis and Structure–Activity Relationship Study of Triazine-Based Inhibitors of the DNA Binding of NF-κB

2. Synthesis, molecular modeling and biological activity of methyl and thiomethyl substituted pyrimidines as corticotropin releasing hormone type 1 antagonists

3. Synthesis and structure-activity study of fungicidal anilinopyrimidines leading to mepanipyrim (KIF-3535) as an anti-Botrytis agent

4. Palladium Complexes with Pyrimidine-Functionalized N-Heterocyclic Carbene Ligands: Synthesis, Structure and Catalytic Activity

Cited by 24 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Synthesis of 2-azido-4-chloro-6-phenylpyrimidine-5-carbaldehyde and its transformations in DMSO;Russian Chemical Bulletin;2024-07

2. Synthesis and Study of Steering of Azido-tetrazole Behavior in Tetrazolo[1,5-c]pyrimidin-5-amine-Based Energetic Materials;The Journal of Organic Chemistry;2024-04-25

3. Design, Synthesis, and Biological Evaluation of Pyrimidine Dihydroquinoxalinone Derivatives as Tubulin Colchicine Site-Binding Agents That Displayed Potent Anticancer Activity Both In Vitro and In Vivo;ACS Pharmacology & Translational Science;2023-03-22

4. Destabilizing Predictive Copper‐Catalyzed Click Reactions by Remote Interactions with a Zinc‐Porphyrin Backbone;Helvetica Chimica Acta;2023-02-07

5. Quo vadis quorum sensing? Advances in disrupting the Pseudomonas quinolone signal (PQS);New Approaches Towards Novel Antibacterial Agents;2023