1-chloro-10-phenoxydecane | 172174-16-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-chloro-10-phenoxydecane
• 英文别名: 10-Chlorodecoxybenzene
• CAS: 172174-16-2
• 化学式: C₁₆H₂₅ClO
• 分子量: 268.827
• InChiKey: SLNOXSVPWGAQLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-chloro-10-phenoxydecane 在 盐酸 、 正丁基锂 、 三氟乙酸酐 作用下， 以 乙醇 为溶剂， 反应 34.67h， 生成 (E)-1-{4-[(10-chlorodecyl)oxy]phenyl}-1-(4-iodophenyl)-2-phenyl-1-butene
  参考文献：
  名称：

  Homologs of Idoxifene:  Variation of Estrogen Receptor Binding and Calmodulin Antagonism with Chain Length

  摘要：

  A series of homologs of idoxifene [1a, (E)-1-[4-(N-pyrrolidinoethoxy)phenyl]-1-(4-iodophenyl)-2-phenyl-1-butene] and selected homologs of 4-iodotamoxifen [2a, (E)-1-[4-[N-dimethylamino)-ethoxy]phenyl]-1-(4-iodophenyl)-2-phenyl-1-butene] with the side chain (CH2)(n) varying in length from n = 3 (1b, 2b) to n = 10 (1i, 2i) have been synthesized and tested for antagonism of the calmodulin-dependent activity of cAMP phosphodiesterase and for binding affinity to rat uterine estrogen receptor. Compared with 1a (IC50 = 1.5 mu M), the homologs showed a progressive increase in calmodulin antagonism with a maximum inhibition at n = 7-9 (1f-h) (IC50 = 0.2 mu M), declining at n = 10 (1i) to IC50 = 1.6 mu M. In the pyrrolidino series, estrogen receptor binding affinity peaked at n = 3 (1b, RBA = 23; estradiol = 100), declining by n = 10 (1i) to RBA = 0.4, but the homolog n = 8 (1g, RBA = 3.5) was still comparable to tamoxifen (RBA = 3.9). A similar pattern of activity was seen for the dimethylamino counterparts. These compounds represent a new class of antiestrogens with potent calmodulin antagonism.

  DOI：

  10.1021/jm9505472
• 作为产物：
  描述：

  1,10-二氯癸烷 、 苯酚 在 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 反应 16.0h， 以69%的产率得到1-chloro-10-phenoxydecane
  参考文献：
  名称：

  Homologs of Idoxifene:  Variation of Estrogen Receptor Binding and Calmodulin Antagonism with Chain Length

  摘要：

  A series of homologs of idoxifene [1a, (E)-1-[4-(N-pyrrolidinoethoxy)phenyl]-1-(4-iodophenyl)-2-phenyl-1-butene] and selected homologs of 4-iodotamoxifen [2a, (E)-1-[4-[N-dimethylamino)-ethoxy]phenyl]-1-(4-iodophenyl)-2-phenyl-1-butene] with the side chain (CH2)(n) varying in length from n = 3 (1b, 2b) to n = 10 (1i, 2i) have been synthesized and tested for antagonism of the calmodulin-dependent activity of cAMP phosphodiesterase and for binding affinity to rat uterine estrogen receptor. Compared with 1a (IC50 = 1.5 mu M), the homologs showed a progressive increase in calmodulin antagonism with a maximum inhibition at n = 7-9 (1f-h) (IC50 = 0.2 mu M), declining at n = 10 (1i) to IC50 = 1.6 mu M. In the pyrrolidino series, estrogen receptor binding affinity peaked at n = 3 (1b, RBA = 23; estradiol = 100), declining by n = 10 (1i) to RBA = 0.4, but the homolog n = 8 (1g, RBA = 3.5) was still comparable to tamoxifen (RBA = 3.9). A similar pattern of activity was seen for the dimethylamino counterparts. These compounds represent a new class of antiestrogens with potent calmodulin antagonism.

  DOI：

  10.1021/jm9505472

文献信息

• Homologs of Idoxifene:  Variation of Estrogen Receptor Binding and Calmodulin Antagonism with Chain Length
  作者：Ian R. Hardcastle、Martin G. Rowlands、Rachel M. Grimshaw、John Houghton、Michael Jarman、Andrew Sharff、Stephen Neidle

  DOI：10.1021/jm9505472

  日期：1996.1.1

  A series of homologs of idoxifene [1a, (E)-1-[4-(N-pyrrolidinoethoxy)phenyl]-1-(4-iodophenyl)-2-phenyl-1-butene] and selected homologs of 4-iodotamoxifen [2a, (E)-1-[4-[N-dimethylamino)-ethoxy]phenyl]-1-(4-iodophenyl)-2-phenyl-1-butene] with the side chain (CH2)(n) varying in length from n = 3 (1b, 2b) to n = 10 (1i, 2i) have been synthesized and tested for antagonism of the calmodulin-dependent activity of cAMP phosphodiesterase and for binding affinity to rat uterine estrogen receptor. Compared with 1a (IC50 = 1.5 mu M), the homologs showed a progressive increase in calmodulin antagonism with a maximum inhibition at n = 7-9 (1f-h) (IC50 = 0.2 mu M), declining at n = 10 (1i) to IC50 = 1.6 mu M. In the pyrrolidino series, estrogen receptor binding affinity peaked at n = 3 (1b, RBA = 23; estradiol = 100), declining by n = 10 (1i) to RBA = 0.4, but the homolog n = 8 (1g, RBA = 3.5) was still comparable to tamoxifen (RBA = 3.9). A similar pattern of activity was seen for the dimethylamino counterparts. These compounds represent a new class of antiestrogens with potent calmodulin antagonism.