5-Dimethylamino-naphthalene-1-sulfonic acid {3-[5-{(1R,2S)-1-ethyl-2-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-butyl}-2-(tetrahydro-pyran-2-yloxy)-phenyl]-propyl}-amide | 104946-91-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-Dimethylamino-naphthalene-1-sulfonic acid {3-[5-{(1R,2S)-1-ethyl-2-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-butyl}-2-(tetrahydro-pyran-2-yloxy)-phenyl]-propyl}-amide
• CAS: 104946-91-0
• 化学式: C₄₃H₅₆N₂O₆S
• 分子量: 728.993
• InChiKey: HGBQHSBYKBUFMH-QTUGRXLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.32
• 重原子数：
  52.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  86.33
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-Dimethylamino-naphthalene-1-sulfonic acid {3-[5-{(1R,2S)-1-ethyl-2-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-butyl}-2-(tetrahydro-pyran-2-yloxy)-phenyl]-propyl}-amide 在 对甲苯磺酸 作用下， 以81%的产率得到(3R*,4S*)-3-<3-<3-<5-(N,N-dimethylamino)naphthalene-1-sulfonamido>propyl>-4-hydroxyphenyl>-4-(4-hydroxyphenyl)hexane
  参考文献：
  名称：

  Preparation, receptor binding, and fluorescence properties of hexestrol-fluorophore conjugates: evaluation of site of attachment, fluorophore structure, and fluorophore-ligand spacing

  摘要：

  We have undertaken a staged development of certain estrogen-fluorophore conjugates, in order to prepare a fluorescent estrogen suitable for determination of the estrogen receptor content of individual cells. Since non-steroidal estrogens with bulky substituents are often more readily bound by receptor than their steroidal counterparts, we have investigated fluorophore conjugates with derivatives of the non-steroidal estrogen hexestrol [3R*, 4S*)-3,4-bis(4-hydroxyphenyl)hexane). On the basis of the receptor-binding affinity of model compounds, we prepared a prototypical set of three ring- and side-chain-substituted fluorescent hexestrol derivatives, whose binding and fluorescence properties ultimately led to the preparation of a series of side-chain-substituted nitrobenzoxadiazole derivatives. The compounds prepared have binding affinities for the estrogen receptors that range from ca. 1% to 5% that of estradiol, and they have very favorable fluorescence characteristics, similar to those of fluorescein.

  DOI：

  10.1021/jm00384a026
• 作为产物：
  描述：

  (3R*,4S*)-3-<3-(3-phthalimidopropyl)-4-(2-tetrahydropyranyloxy)phenyl>-4-<4-(2-tetrahydropyranyloxy)phenyl>hexane 在 一水合肼 、 三乙胺 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 61.0h， 生成 5-Dimethylamino-naphthalene-1-sulfonic acid {3-[5-{(1R,2S)-1-ethyl-2-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-butyl}-2-(tetrahydro-pyran-2-yloxy)-phenyl]-propyl}-amide
  参考文献：
  名称：

  Preparation, receptor binding, and fluorescence properties of hexestrol-fluorophore conjugates: evaluation of site of attachment, fluorophore structure, and fluorophore-ligand spacing

  摘要：

  We have undertaken a staged development of certain estrogen-fluorophore conjugates, in order to prepare a fluorescent estrogen suitable for determination of the estrogen receptor content of individual cells. Since non-steroidal estrogens with bulky substituents are often more readily bound by receptor than their steroidal counterparts, we have investigated fluorophore conjugates with derivatives of the non-steroidal estrogen hexestrol [3R*, 4S*)-3,4-bis(4-hydroxyphenyl)hexane). On the basis of the receptor-binding affinity of model compounds, we prepared a prototypical set of three ring- and side-chain-substituted fluorescent hexestrol derivatives, whose binding and fluorescence properties ultimately led to the preparation of a series of side-chain-substituted nitrobenzoxadiazole derivatives. The compounds prepared have binding affinities for the estrogen receptors that range from ca. 1% to 5% that of estradiol, and they have very favorable fluorescence characteristics, similar to those of fluorescein.

  DOI：

  10.1021/jm00384a026