Methyl 3-((6-Methoxy-1,4-dihydroindeno[1,2-<i>c</i>]pyrazol-3-yl)amino)benzoate (GN39482) as a Tubulin Polymerization Inhibitor Identified by MorphoBase and ChemProteoBase Profiling Methods

DOI Web Site PubMed 被引用文献8件 参考文献30件
  • Hidemitsu Minegishi
    Chemical Resources Laboratory, Tokyo Institute of Technology, Nagatsuta-cho, Midori-ku, Yokohama 226-8503, Japan
  • Yushi Futamura
    Chemical Biology Research Group, RIKEN Center for Sustainable Resource Center, Hirosawa, Wako, Saitama 351-0198, Japan
  • Shinji Fukashiro
    Department of Life Science, Faculty of Science, Gakushuin University, Mejiro, Toshima-ku, Tokyo 171-8588, Japan
  • Makoto Muroi
    Chemical Biology Research Group, RIKEN Center for Sustainable Resource Center, Hirosawa, Wako, Saitama 351-0198, Japan
  • Makoto Kawatani
    Chemical Biology Research Group, RIKEN Center for Sustainable Resource Center, Hirosawa, Wako, Saitama 351-0198, Japan
  • Hiroyuki Osada
    Chemical Biology Research Group, RIKEN Center for Sustainable Resource Center, Hirosawa, Wako, Saitama 351-0198, Japan
  • Hiroyuki Nakamura
    Chemical Resources Laboratory, Tokyo Institute of Technology, Nagatsuta-cho, Midori-ku, Yokohama 226-8503, Japan

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説明

A series of indenopyrazoles was synthesized from the corresponding indanones and phenyl isothiocyanates in two steps. Among the compounds synthesized, methyl 3-((6-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)amino)benzoate 6m (GN39482) was found to possess a promising antiproliferative activity toward human cancer cells without affecting any antimicrobial and antimalarial activities at 100 nM. Both a methoxy group at R(1) position and a methoxycarbonyl group at R(2) position of the anilinoquinazoline framework are essential for the high cell growth inhibition. Both MorphoBase and ChemProteoBase profiling analyses suggested that compound 6m was classified as a tubulin inhibitor. Indeed, compound 6m inhibited the acetylated tubulin accumulation and the microtubule formation and induced G2/M cell cycle arrest in HeLa cells, revealing that a promising antiproliferative activity of compound 6m toward human cancer cells is probably caused by the tubulin polymerization inhibition.

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