4-[2-(4-Hydroxy-2,3-dimethyl-benzoylamino)-phenoxy]-butyric acid ethyl ester | 187675-70-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[2-(4-Hydroxy-2,3-dimethyl-benzoylamino)-phenoxy]-butyric acid ethyl ester
• CAS: 187675-70-3
• 化学式: C₂₁H₂₅NO₅
• 分子量: 371.433
• InChiKey: UJNVWPWCPLUGMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.86
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-[2-(4-Hydroxy-2,3-dimethyl-benzoylamino)-phenoxy]-butyric acid ethyl ester 在 sodium hydroxide 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 25.0h， 生成 (+/-)-ONO-3805
  参考文献：
  名称：

  Steroid 5α-Reductase: Comparative Study of Mechanism of Inhibition by Nonsteroids ONO-3805 and LY191704

  摘要：

  Two nonsteroids, ONO-3805 and LY191704, were evaluated as inhibitors of the human and rat 5 alpha-reductases (5 alpha R). ONO-3805 was prepared in a 12-step convergent synthesis. This compound is a potent inhibitor of the human and rat 5 alpha Rs, with more potent inhibition seen against the rat enzymes. The inhibition patterns of this compound were best fit to an uncompetitive model which suggests binding in a ternary complex with enzyme and NADP(+). Apparent K-i values of 27, 31, 1, and 0.5 nM versus testosterone were obtained with human type 1, human type 2, rat type 1, and rat type 2 5 alpha R, respectively. Multiple inhibition studies with ONO-3805 and NADP(+) support synergistic binding of these two inhibitors with all isozymes. LY191704 was also evaluated as an inhibitor of the human and rat 5 alpha Rs. This compound is a selective, competitive inhibitor of human type 1 5 alpha R. Poor inhibition was observed with human type 2 and rat types 1 and 2 5 alpha R. (C) 1996 Academic Press, Inc.

  DOI：

  10.1006/bioo.1996.0033
• 作为产物：
  描述：

  4-甲氧基-2,3-二甲基苯甲酸 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 草酰氯 、 硫酸 、 氢气 、 三溴化硼 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 丙酮 为溶剂， -70.0~25.0 ℃ 、275.79 kPa 条件下， 反应 1.5h， 生成 4-[2-(4-Hydroxy-2,3-dimethyl-benzoylamino)-phenoxy]-butyric acid ethyl ester
  参考文献：
  名称：

  Steroid 5α-Reductase: Comparative Study of Mechanism of Inhibition by Nonsteroids ONO-3805 and LY191704

  摘要：

  Two nonsteroids, ONO-3805 and LY191704, were evaluated as inhibitors of the human and rat 5 alpha-reductases (5 alpha R). ONO-3805 was prepared in a 12-step convergent synthesis. This compound is a potent inhibitor of the human and rat 5 alpha Rs, with more potent inhibition seen against the rat enzymes. The inhibition patterns of this compound were best fit to an uncompetitive model which suggests binding in a ternary complex with enzyme and NADP(+). Apparent K-i values of 27, 31, 1, and 0.5 nM versus testosterone were obtained with human type 1, human type 2, rat type 1, and rat type 2 5 alpha R, respectively. Multiple inhibition studies with ONO-3805 and NADP(+) support synergistic binding of these two inhibitors with all isozymes. LY191704 was also evaluated as an inhibitor of the human and rat 5 alpha Rs. This compound is a selective, competitive inhibitor of human type 1 5 alpha R. Poor inhibition was observed with human type 2 and rat types 1 and 2 5 alpha R. (C) 1996 Academic Press, Inc.

  DOI：

  10.1006/bioo.1996.0033