ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Rapid synthesis and bioactivities of 3-(nitromethylene)indolin-2-one analogues

Gang Chen, Xiao-Jiang Hao, Qian-Yun Sun, and Jian Ding

College of Chemistry & Chemical Engineering, Xi’an Shiyou University, Xi’an, Shaanxi, 710065 China

E-mail: gangchen@xsyu.edu.cn

Abstract: A new synthesis method of 3-(nitromethylene)indolin-2-one analogues is described, using the Henry reaction of isatin and N-substituted isatins with nitromethane followed by dehydration of the nitroaldol adduct with mesyl chloride. The use of diethylamine (rather than DBU) as the base catalyst in a solvent-free Henry reaction gave the nitroaldol adduct in sufficient purity as to allow its direct dehydration to nitroalkene. Overall yields for this two-step synthesis are satisfactory (typically 50–77 % after chromatographic purification). 3-(Nitromethylene)indolin-2-one analogues are valued protective agents against H₂O₂-induced apoptosis using PC12 cells, and for their cytotoxicity against the A549 and P388 lung cancer cell lines. One compound, (E)-1-benzyl-3-(nitromethylene)indolin-2-one (VIII), exhibited potent activity in the latter assay.

Keywords: 3-(nitromethylene)indolin-2-one - diethylamine - antitumor neuroprotection - catalyst

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-010-0047-1

Chemical Papers 64 (5) 673–677 (2010)