Synthesis and Antitumor Activity of Novel Pyrimidinyl Pyrazole Derivatives(3)Synthesis and Antitumor Activity of 3-Phenylpiperazinyl-1-trans-propenes

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  • Naito Hiroyuki
    Medicinal Chemistry Research Laboratory, Daiichi Pharmaceutical Co. Ltd.
  • Ohsuki Satoru
    Medicinal Chemistry Research Laboratory, Daiichi Pharmaceutical Co. Ltd.
  • Atsumi Ryo
    Drug Metabolism & Physicochemical Property Research Laboratory, Daiichi Pharmaceutical Co. Ltd.
  • Minami Megumi
    New Product Research Laboratories III, Daiichi Pharmaceutical Co. Ltd.
  • Mochizuki Mineko
    New Product Research Laboratories III, Daiichi Pharmaceutical Co. Ltd.
  • Hirotani Kenji
    Discovery Research Laboratory, Daiichi Pharmaceutical Co. Ltd.
  • Kumazawa Eiji
    New Product Research Laboratories III, Daiichi Pharmaceutical Co. Ltd.
  • Ejima Akio
    Medicinal Chemistry Research Laboratory, Daiichi Pharmaceutical Co. Ltd.

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  • Synthesis and Antitumor Activity of Novel Pyrimidinyl Pyrazole Derivatives. III. Synthesis and Antitumor Activity of 3-Phenylpiperazinyl-1-trans-propenes

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A series of novel 3-[4-phenyl-1-piperazinyl]-1-[5-methyl-1-(2-pyrimidinyl)-4-pyrazolyl]-1-trans-propenes and related compounds were synthesized and evaluated by their cytotoxic activity against several tumor cell lines in vitro and in vivo antitumor activity against some tumor models when administered both intraperitoneally and orally. Compounds with the 3-chloropyridin-2-yl group (9g) and the 3-fluoro-5-substituted phenylpiperazinyl group (29b, c, and e) showed significantly potent cytotoxicity by in vitro testing. Among them, the 3-cyano-5-fluorophenyl derivative (29b) exhibited potent antitumor activity against several tumor cells including human carcinoma without causing undesirable effects in mice.

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