Synthetic Studies on Enkephalin Analogs. III. A Highly Potent Enkephalin Analog, H-Tyr-D-Met (O)-Gly-Phe-NHNH-CO-CH_2CH_3

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概要

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• Thirty-five tetrapeptide acyl-hydrazide analogs of enkephalin substituted at position 2 were synthesized. Substitution of D-Ala at position 2 of H-Tyr-D-Ala-Gly-Phe-NHNH-CO-R (R=lower alkyl), by D-Met (O), D-Gln, D-Glu (NH-CH_3) or D-Thr enhanced the analgesic potency, but substitution by D-Glu or Ser resulted in an analog with no antinociceptive activity. Among the analogs synthesized, the D-Met (O)-analog was the most potent and H-Tyr-D-Met (O)-Gly-Phe-NHNH-CO-CH_2CH_3 exhibited analgesic activtiy four times more potent than that of morphine in mice following subcutaneous injection. Structure-activity relations for position 2 of the enkephalin-like tetrapeptide are discussed.

• 1981-12-25

著者

• 藤野 政彦

  Pharmaceutical Research Division Takeda Chemical Industries Ltd.

• 藤野 政彦

  武田薬品工業

• 藤野 政彦

  武田薬品中央研

• 藤野 政彦

  Central Research Division, Takeda Chemical Industries Ltd.

• 脇舛 光広

  Central Research Division, Takeda Chemical Industries, Ltd.

• 藤野 政彦

  武田薬品工業(株)

• 脇舛 光広

  Chemistry Laboratories, Central Research Division, Takeda Chemical Industries, Ltd.

• 品川 進

  Central Research Division, Takeda Chemical Industries, Ltd.

• 石井 治光

  Central Research Division, Takeda Chemical Industries, Ltd.

• 川井 清尚

  Central Research Division, Takeda Chemical Industries, Ltd.

• 脇舛 光広

  Chemistry Laboratories Central Research Division Takeda Chemical Industries Ltd.

• 石井 治光

  武田薬品工業株式会社中央研究所

• 川井 清尚

  Central Research Division Takeda Chemical Industries Ltd.

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