67823-52-3Relevant articles and documents
Transient resonance Raman and density functional theory investigation of the 2-fluorenylnitrenium ion
Zhu,Shing Yau Ong,Pik Ying Chan,King Hung Leung,Phillips
, p. 2645 - 2649 (2001)
We report a transient resonance Raman spectrum for the 2-fluorenylnitrenium ion obtained after photolysis of 2-azidofluorene. The 10 experimental Raman band frequencies of the transient spectrum show very good agreement with the computed frequencies from BPW91/cc-PVDZ density functional theory calculations for the 2-fluorenylnitrenium ion. Our results confirm the assignment of the ～-460 nm transient absorption band formed after photolysis of 2-azidofluorene in water/acetonitrile or water solution to the singlet ground electronic state 2-fluorenylnitrenium ion. Our study indicates the 2-fluorenylnitrenium has a large degree of iminocyclohexadienyl cation character with significant delocalization of the charge over both phenyl rings of the fluorene moiety. We compare our results for the 2-fluoreneylnitrenium ion to those previously reported for several other arylnitrenium ions.
Synthesis and studies on the photophysical/biophysical properties of triazolylfluorene-labeled 2′-deoxyuridines
Bag, Subhendu Sekhar,Gogoi, Hiranya,Sinha, Sayantan
supporting information, (2021/11/18)
The planar structure, attractive photophysical property, and scarcity of electronically conjugated fluorene-containing biomolecular building blocks have attracted recent research interest on synthesizing triazolylfluorene decorated nucleosides with modulated photophysical features. Herein, we report the synthesis of few fluorescent nucleosides wherein the C5 of 2′-deoxyuridine is electronically conjugated with fluorene analogues via Sonogashira cross-coupling and copper-catalyzed click reaction. The study of photophysical properties of the synthesized nucleosides shows that two of the synthesized nucleosides show interesting dual emission properties in various organic solvents. The dual emitting fluorene nucleosides might impact significantly in nucleic acid research for monitoring the DNA microenvironment. Furthermore, we evaluated the interaction of cyanofluorenyl 2′-deoxyuridine with Calf thymus DNA (ctDNA) and observed that this nucleoside could sense ctDNA via the generation of an enhanced fluorescence signal.
Stereospecific photochemistry of Δ2-1,2,3-triazolines in solution and in the solid state: Scope and mechanistic studies
Chung, Tim S.,Xue, Yang,Carranza, Alberto,Garcia-Garibay, Miguel A.
, p. 1458 - 1463 (2017/09/23)
The stereospecific photochemistry of ten N-aryl-substituted cis- or trans-Δ2-1,2,3-triazolines to form the corresponding cis- or trans-aziridines was investigated both in solution and in the solid-state. We found that photochemical reactions in the solid state are more stereospecific than in solution for the 8 crystalline Δ2-1,2,3-triazolines. Additionally, triplet sensitization for some triazolines results in triplet biradicals, which provide the more thermodynamically favored trans-aziridine regardless of the starting triazoline stereochemistry. Product analyses as a function of temperature and solvent polarity suggest that the electronic excitation of the Δ2-1,2,3-triazolines results in the formation of a 1,3-biradical intermediate.
Using click chemistry toward novel 1,2,3-triazole-linked dopamine D3 receptor ligands
Keck, Thomas M.,Banala, Ashwini K.,Slack, Rachel D.,Burzynski, Caitlin,Bonifazi, Alessandro,Okunola-Bakare, Oluyomi M.,Moore, Martin,Deschamps, Jeffrey R.,Rais, Rana,Slusher, Barbara S.,Newman, Amy Hauck
, p. 4000 - 4012 (2015/02/19)
The dopamine D3 receptor (D3R) is a target of pharmacotherapeutic interest in a variety of neurological disorders including schizophrenia, Parkinson's disease, restless leg syndrome, and drug addiction. A common molecular template used in the development of D3R-selective antagonists and partial agonists incorporates a butylamide linker between two pharmacophores, a phenylpiperazine moiety and an extended aryl ring system. The series of compounds described herein incorporates a change to that chemical template, replacing the amide functional group in the linker chain with a 1,2,3-triazole group. Although the amide linker in the 4-phenylpiperazine class of D3R ligands has been previously deemed critical for high D3R affinity and selectivity, the 1,2,3-triazole moiety serves as a suitable bioisosteric replacement and maintains desired D3R-binding functionality of the compounds. Additionally, using mouse liver microsomes to evaluate CYP450-mediated phase I metabolism, we determined that novel 1,2,3-triazole-containing compounds modestly improves metabolic stability compared to amide-containing analogues. The 1,2,3-triazole moiety allows for the modular attachment of chemical subunit libraries using copper-catalyzed azide-alkyne cycloaddition click chemistry, increasing the range of chemical entities that can be designed, synthesized, and developed toward D3R-selective therapeutic agents.
