Design, synthesis and biological evaluation of 3-fluoroalkenyloxindole ring-fused 3-trifluoromethyloxindoles obtained from indoline-2,3-diones and difluoromethylene phosphabetaine

GRAPHICAL ABSTRACT

ABSTRACT

A wide variety of multi-substituted 3-fluoroalkenyloxindole ring-fused 3-trifluoromethyloxindoles were obtained in good yields by the reaction of indoline-2,3-diones with difluoromethylene phosphabetaine. Their biological activities against human prostate cancer cells PC-3 and human Breast cancer cells MCF-7 have been preliminarily demonstrated, using MTT-based assays with the commercially available standard drug Paclitaxel as a positive control. Several compounds exhibited comparable in vitro inhibitory activities against human prostate cancer cells PC-3 and human Breast cancer cells MCF-7 to Paclitaxel. These results indicate that 3-fluoroalkenyloxindole ring-fused 3-trifluoromethyloxindoles may be potential lead compounds for further biological screening.

KEYWORDS:

• Difluoromethylene phosphabetaine
• 2-Oxindoles
• Biological evaluation
• anticancer agents

Acknowledgments

We thank Science and Technology Department of Sichuan Province (No. 2016JY0246), the National Natural Science Foundation of China (21502131), Sichuan University of Science & Engineering (No. 2014RC07; 2016RCL07), Zigong Science and Technology Bureau (No. 2015SF02; 2015SF01), Education Department of Sichuan Province (No. 16ZB0247; 15ZB0211), Key Laboratory of Green Catalysis of Higher Education Institutes of Sichuan (No. LZJ1505; LYJ1505), Undergraduate Training Programs for Innovation and Entrepreneurship (No. 201510622003; 201610622003) and Opening Project of Sichuan Province Key Laboratory of Natural Products and Small Molecule Synthesis (No. TRCWYXFZCH2016005) are also greatly acknowledged for funding this work.

Funding

Science and Technology Department of Sichuan Province (No. 2016JY0246). National Natural Science Foundation of China (21502131). Sichuan University of Science & Engineering (2014RC07; 2016RCL07). Zigong Science and Technology Bureau (2015SF02; 2015SF01). Education Department of Sichuan Province (16ZB0247; 15ZB0211). Key Laboratory of Green Catalysis of Higher Education Institutes of Sichuan, (LZJ1505; LYJ1505). Undergraduate Training Programs for Innovation and Entrepreneurship (201510622003; 201610622003). Opening Project of Sichuan Province Key Laboratory of Natural Products and Small molecule Synthesis (TRCWYXFZCH2016005).

Additional information

Funding

Key Laboratory of Green Chemistry of Sichuan Institutes of Higher Education(LZJ1505, LYJ1505), Opening Project of Sichuan Province Key Laboratory of Natural Ptoducts and Small molecule Synthesis(TRCWYXFZCH2016005)