Mechanism‐Driven Bioactive Indazole Frameworks: Photoinitiated Demethylation–Aromatization Synthesis and Biosensing Applications

Y Yi‐Feng Ou (State Key Laboratory of Chemo and Biosensing College of Chemistry and Chemical Engineering Hunan University Changsha P.R. China) S Songhua Chen (State Key laboratory of Chemo and Biosensing College of Chemistry and Chemical Engineering Hunan University Changsha 410082 P.R. China) Q Qian Lei (Department of Pulmonary and Critical Care Medicine, State Key Laboratory of Respiratory Health and Multimorbidity, West China Hospital) Y Yang Shen (Beijing National Laboratory for Condensed Matter Physics, Institute of Physics) N Niu Tang (State Key Laboratory of Chemo and Biosensing, College of Chemistry and Chemical Engineering Hunan University Changsha Hunan 410082 P.R. China) Y Yongbo Zhou S Shuang‐Feng Yin (College of Materials and Energy Central South University of Forestry and Technology Changsha People's Republic of China) N Nobuaki Kambe (State Key laboratory of Chemo and Biosensing College of Chemistry and Chemical Engineering Hunan University Changsha 410082 P.R. China) L Lin Yuan (State Key Laboratory of Chemo and Biosensing, College of Chemistry and Chemical Engineering) R Renhua Qiu (State Key Laboratory of Chemo and Biosensing, College of Chemistry and Chemical Engineering Hunan University Changsha Hunan 410082 P.R. China)

Abstract

Abstract Indazole frameworks are pivotal in medicinal chemistry and fluorescent conjugate design. Herein, we reported a photochemical strategy enabling efficient N ‐demethylation and aromatic cyclization of N ‐methyl amines via UV‐induced nitroso intermediates, offering an environmentally benign route to structurally diverse 2 H ‐indazole scaffolds. Diverging from conventional methods, this protocol demonstrates exceptional substrate compatibility with various alkyl/aryl amines, facilitating streamlined assembly of functionalized 2 H ‐indazole modules. The methodology has been successfully applied to synthesize modified drugs and tumor‐specific fluorescent probes targeting G‐quadruplexes. Preliminary evaluations of physiological toxicity and cellular fluorescence imaging highlight their biomedical potential, establishing these strategies as potential tools for pharmacological development and bioimaging research.

Article Details

Volume / Issue Vol. 64, Issue 32
Published August 04, 2025
ISSN 1433-7851
Publisher Wiley

Journal Info

Angewandte Chemie International Edition

Wiley

ISSN: 1433-7851 Physical Sciences

Authors (10)

Y

Yi‐Feng Ou

State Key Laboratory of Chemo and Biosensing College of Chemistry and Chemical Engineering Hunan University Changsha P.R. China

S

Songhua Chen

State Key laboratory of Chemo and Biosensing College of Chemistry and Chemical Engineering Hunan University Changsha 410082 P.R. China

Q

Qian Lei

Department of Pulmonary and Critical Care Medicine, State Key Laboratory of Respiratory Health and Multimorbidity, West China Hospital

Y

Yang Shen

Beijing National Laboratory for Condensed Matter Physics, Institute of Physics

N

Niu Tang

State Key Laboratory of Chemo and Biosensing, College of Chemistry and Chemical Engineering Hunan University Changsha Hunan 410082 P.R. China

Y

Yongbo Zhou

S

Shuang‐Feng Yin

College of Materials and Energy Central South University of Forestry and Technology Changsha People's Republic of China

N

Nobuaki Kambe

State Key laboratory of Chemo and Biosensing College of Chemistry and Chemical Engineering Hunan University Changsha 410082 P.R. China

L

Lin Yuan

State Key Laboratory of Chemo and Biosensing, College of Chemistry and Chemical Engineering

R

Renhua Qiu

State Key Laboratory of Chemo and Biosensing, College of Chemistry and Chemical Engineering Hunan University Changsha Hunan 410082 P.R. China