17β-(N-t-butyloxycarbonylglycyl)aminoestra-1,3,5(10)-trien-3-ol | 136206-19-4

• 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: 17β-(N-t-butyloxycarbonylglycyl)aminoestra-1,3,5(10)-trien-3-ol
• 英文别名: tert-butyl N-[2-[[(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]amino]-2-oxoethyl]carbamate
• CAS: 136206-19-4
• 化学式: C₂₅H₃₆N₂O₄
• 分子量: 428.572
• InChiKey: JJSVYGNBSFJQJK-BHQAQYLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  17β-(N-t-butyloxycarbonylglycyl)aminoestra-1,3,5(10)-trien-3-ol 、 三氟乙酸 反应 2.0h， 以41%的产率得到
  参考文献：
  名称：

  Synthesis of new amino acid and peptide derivatives of estradiol and their binding affinities for the estrogen receptor

  摘要：

  A series of amino acid and peptide derivatives of estradiol have been synthesized by coupling 17 beta-aminoestra-1,3,5(10)-trien-3-ol, 17-hydrazonoestra-1,3,5(10)-trien-3-ol with amino acids or peptides, using tetrahydrothiazole-2-thione, N-hydroxy-1,4-epoxycyclohex-5-ene-2,3-dicarbonylimide, benzotriazolyloxy-tris(dimethylamino)phosphonium hexafluorophosphate, and p-nitrophenol as reagents. N-protected peptidyl steroids were deprotected by traditional methods. The relative binding affinities of the deprotected derivatives to the estrogen receptor were determined by competitive radioligand binding assay.

  DOI：

  10.1016/0039-128x(93)90015-f
• 作为产物：
  描述：

  3-hydroxy-estra-1,3,5(10)-trien-17-one oxime 在 sodium 作用下， 以 四氢呋喃 、 丙醇 为溶剂， 反应 6.0h， 生成 17β-(N-t-butyloxycarbonylglycyl)aminoestra-1,3,5(10)-trien-3-ol
  参考文献：
  名称：

  Synthesis of new amino acid and peptide derivatives of estradiol and their binding affinities for the estrogen receptor

  摘要：

  A series of amino acid and peptide derivatives of estradiol have been synthesized by coupling 17 beta-aminoestra-1,3,5(10)-trien-3-ol, 17-hydrazonoestra-1,3,5(10)-trien-3-ol with amino acids or peptides, using tetrahydrothiazole-2-thione, N-hydroxy-1,4-epoxycyclohex-5-ene-2,3-dicarbonylimide, benzotriazolyloxy-tris(dimethylamino)phosphonium hexafluorophosphate, and p-nitrophenol as reagents. N-protected peptidyl steroids were deprotected by traditional methods. The relative binding affinities of the deprotected derivatives to the estrogen receptor were determined by competitive radioligand binding assay.

  DOI：

  10.1016/0039-128x(93)90015-f