3815-80-3Relevant articles and documents
Water-Involved Ring-Opening of 4-Phenyl-1,2,4-triazoline-3,5-dione for “Photo-Clicked” Access to Carbamoyl Formazan Photoswitches In Situ
Zheng, Yuanqin,Zhou, Yuqiao,Zhang, Yan,Deng, Pengchi,Zhao, Xiaohu,Jiang, Shichao,Du, Guangxi,Shen, Xin,Xie, Xinyu,Su, Zhishan,Yu, Zhipeng
, (2021/12/22)
Cyclic azodicarbonyl derivatives, particularly 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), commonly serve as arenophile, dienophile, enophile and electrophile. Perplexed by its instability in aqueous environment, there are few studies focused on the transient intermediate produced by hydrolysis of PTAD to achieve synthetic significance. Herein, we describe a “photo-click” method that involves nitrile imine (NI) from diarylsydnone to capture the diazenecarbonyl-phenyl-carbamic acid (DACPA) generated by water-promoted ring-opening of PTAD. DFT calculation reveal that H-bonding interactions between PTAD and water are vital to form DACPA which exhibited an umpolung effect during ligation by nature bond orbit (NBO) analysis. The ultra-fast ligation resulted in carbamoyl formazans, as a unique Z?E photo-switchable linker on target molecules, including peptide and drugs, with excellent anti-fatigue performance. This strategy is showcased to construct highly functionalized carbamoyl formazans in situ for photo-pharmacology and material studies, which also expands the chemistry of PTAD in aqueous media.
Synthesis and evaluation of photo-activatable β-diarylsydnone-L-alanines for fluorogenic photo-click cyclization of peptides
Yao, Zhuojun,Wu, Xueting,Zhang, Xiaocui,Xiong, Qin,Jiang, Shichao,Yu, Zhipeng
, p. 6777 - 6781 (2019/07/22)
Herein, we design and synthesize a series of photoactivatable β-diarylsydnone-l-alanines (DASAs), which have excellent photo-reactivity with high fluorescence turn-on toward alkenes in a biocompatible environment. The environmental sensing properties of t
Discovery of Fluorogenic Diarylsydnone-Alkene Photoligation: Conversion of ortho-Dual-Twisted Diarylsydnones into Planar Pyrazolines
Zhang, Linmeng,Zhang, Xiaocui,Yao, Zhuojun,Jiang, Shichao,Deng, Jiajie,Li, Bo,Yu, Zhipeng
, p. 7390 - 7394 (2018/06/13)
A small library of diarylsydnones (DASyds) was constructed based on aryl-pairing combinations and subjected to click reaction toward alkenes under photoirradiation with high efficiency. We were able to demonstrate the utility of DASyds for highly fluorescent turn-on ligation targeting the trans-cyclooct-4-en-1-ol moieties on protein.