6ξ-bromonorgestrel 17β-cyclopentanecarboxylate | 110606-05-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 6ξ-bromonorgestrel 17β-cyclopentanecarboxylate
• CAS: 110606-05-8
• 化学式: C₂₇H₃₅BrO₃
• 分子量: 487.477
• InChiKey: BBPHHKOEGVWTJN-RPHBQAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.0
• 重原子数：
  31.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6ξ-bromonorgestrel 17β-cyclopentanecarboxylate 在 氢氧化钾 、 N,N'-羰基二咪唑 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 D-6α-carboxymethylmercaptonorgestrel 17β-cyclopentanecarboxylate histamine conjugate
  参考文献：
  名称：

  Development and use of a radioimmunoassay for D-(-)-norgestrel 17β-cyclopentane-carboxylate

  摘要：

  The synthesis of the 6 alpha-carboxymethylmercapto BSA and homologous histamine conjugate of D-(-)-norgestrel 17 beta-cyclopentanecarboxylate is reported. Using the BSA conjugate as an immunogen for the development of antibody in the rabbit and the 125I-histamine conjugate as the radioligand, a radioimmunoassay (RIA) for the ester was developed. Serum profiles of the free alcohol and ester were determined following IV or IM injection in macaques. Peak values for the ester (about 12 ng/mL) were observed 2 min following an IV bolus of 0.5 mg in one rhesus monkey. Blood levels dropped rapidly within the first 30 min and were barely detectable at 24 h. Serum levels of the free alcohol rose to a peak at 30 min and then declined slowly to very low values by 24 h. Following IM injection of 20 mg in cynomolgus monkeys, peak levels of the ester were observed within a few days while the free alcohol reached a maximum about day 30. Serum concentrations of D-(-)-norgestrel had fallen to about 0.4 ng/mL 160 days post-injection when levels of the ester fell below 0.2 ng/mL.

  DOI：

  10.1016/0039-128x(86)90039-5
• 作为产物：
  描述：

  苯丁酸,b-氨基-2,4-二氯-,盐酸(1:1),(bR)- 在 N-溴代丁二酰亚胺(NBS) 、 对甲苯磺酸 作用下， 以 吡啶 、 乙醇 、 水 、 溶剂黄146 、 丙酮 、 苯 为溶剂， 反应 3.25h， 生成 6ξ-bromonorgestrel 17β-cyclopentanecarboxylate
  参考文献：
  名称：

  Development and use of a radioimmunoassay for D-(-)-norgestrel 17β-cyclopentane-carboxylate

  摘要：

  The synthesis of the 6 alpha-carboxymethylmercapto BSA and homologous histamine conjugate of D-(-)-norgestrel 17 beta-cyclopentanecarboxylate is reported. Using the BSA conjugate as an immunogen for the development of antibody in the rabbit and the 125I-histamine conjugate as the radioligand, a radioimmunoassay (RIA) for the ester was developed. Serum profiles of the free alcohol and ester were determined following IV or IM injection in macaques. Peak values for the ester (about 12 ng/mL) were observed 2 min following an IV bolus of 0.5 mg in one rhesus monkey. Blood levels dropped rapidly within the first 30 min and were barely detectable at 24 h. Serum levels of the free alcohol rose to a peak at 30 min and then declined slowly to very low values by 24 h. Following IM injection of 20 mg in cynomolgus monkeys, peak levels of the ester were observed within a few days while the free alcohol reached a maximum about day 30. Serum concentrations of D-(-)-norgestrel had fallen to about 0.4 ng/mL 160 days post-injection when levels of the ester fell below 0.2 ng/mL.

  DOI：

  10.1016/0039-128x(86)90039-5