1300713-25-0

Basic information

• Product Name: C₃₃H₃₃N₁₃O₂
• CAS NO: 1300713-25-0
• Molecular Weight: 643.711
• Mol File: 1300713-25-0.mol

Chemical Properties

• CAS DataBase Reference: C₃₃H₃₃N₁₃O₂(CAS DataBase Reference)
• NIST Chemistry Reference: C₃₃H₃₃N₁₃O₂(1300713-25-0)
• EPA Substance Registry System: C₃₃H₃₃N₁₃O₂(1300713-25-0)

Safety Data

• Hazardous Substances Data: 1300713-25-0(Hazardous Substances Data)

Upstream product

• 87156-40-9 1-amino-2-azidoethane 
• 1300713-24-9 C₂₉H₂₁N₅O₂ 
• 19718-49-1 4-amino-3-iodobenzoic acid methyl ester 
• 75867-46-8 2,6-diethynylpyridine 
• 1085359-41-6 C₂₃H₁₅N₃O₄ 
• 1050214-81-7 C₂₅H₁₉N₃O₄ 

Relevant articles and documents

Synthesis and binding studies of novel diethynyl-pyridine amides with genomic promoter DNA G-quadruplexes

Herein, we report the design, synthesis and biophysical evaluation of novel 1,2,3-triazole-linked diethynyl-pyridine amides and trisubstituted diethynyl-pyridine amides as promising G-quadruplex binding ligands. We have used a CuI-catalysed azide-alkyne cycloaddition click reaction to prepare the 1,2,3-triazole-linked diethynyl-pyridine amides. The G-quadruplex DNA binding properties of the ligands have been examined by using a Foerster resonance energy transfer (FRET) melting assay and surface plasmon resonance (SPR) experiments. The investigated compounds are conformationally flexible, having free rotation around the triple bond, and exhibit enhanced G-quadruplex binding stabilisation and specificity between intramolecular promoter G-quadruplex DNA motifs compared to the first generation of diarylethynyl amides (J. Am. Chem. Soc. 2008, 130, 15950-15956). The ligands show versatility in molecular recognition and promising G-quadruplex discrimination with 2-50-fold selectivity exhibited between different intramolecular promoter G-quadruplexes. Circular dichroism (CD) spectroscopic analysis suggested that at higher concentration these ligands disrupt the c-kit2 G-quadruplex structure. The studies validate the design concept of the 1,3-diethynyl-pyridine-based scaffold and demonstrate that these ligands exhibit not only significant selectivity over duplex DNA but also variation in G-quadruplex interaction properties based on small chemical changes in the scaffold, leading to unprecedented differential recognition of different DNA G-quadruplex sequences. Click side chains! Click chemistry has been used as a promising tool for side chain functionalisation of a diethynyl-pyridine carboxamide scaffold. The obtained ligands were screened by using structurally diverse genomic promoter G-quadruplex DNA sequences leading to enhanced specificity and differential recognition (see picture for an example).