(Z)-4-(1,2-diphenyl-1-butenyl)phenol vinyl ether | 80234-19-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-4-(1,2-diphenyl-1-butenyl)phenol vinyl ether
• 英文别名: desdimethylamino-tamoxifen；1-[(Z)-1,2-diphenylbut-1-enyl]-4-ethenoxybenzene
• CAS: 80234-19-1
• 化学式: C₂₄H₂₂O
• 分子量: 326.438
• InChiKey: WXRBBQLOUUCAME-VHXPQNKSSA-N

物化性质

• 熔点：
  110.0-111.5 °C
• 沸点：
  429.3±24.0 °C(Predicted)
• 密度：
  1.049±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.58
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  1-(2-Bromo-ethoxy)-4-((Z)-1,2-diphenyl-but-1-enyl)-benzene 、 吡咯 生成 (Z)-4-(1,2-diphenyl-1-butenyl)phenol vinyl ether
  参考文献：
  名称：

  ROBERTSON, D. W.;KATZENELLENBOGEN, J. A.;HAYES, J. R.;KATZENELLENBOGEN, B+, J. MED. CHEM., 1982, 25, N 2, 167-171

  摘要：

  DOI：

文献信息

• Tamoxifen Stimulates Calcium Entry Into Human Platelets
  作者：Yuliya Dobrydneva、Ross V Weatherman、Joseph P Trebley、Melinda M Morrell、Megan C Fitzgerald、Craig E Fichandler、Nithiananda Chatterjie、Peter F Blackmore

  DOI：10.1097/fjc.0b013e31811ec748

  日期：2007.10

  also increased [Ca2+]i, but other tamoxifen metabolites and synthetic derivatives did not. Three hydroxylated derivatives of triphenylethylene (corresponding to the hydrophobic core of tamoxifen) which are transitional structures between tamoxifen (Ca agonist) and diethylstilbestrol (Ca antagonist) increased [Ca2+]i slightly (6% to 24%) and partially inhibited thrombin-induced [Ca2+]i elevation (68% to

  用于治疗和预防乳腺癌的抗雌激素药物他莫昔芬可导致血栓形成。我们发现他莫昔芬能迅速增加来自男性和女性供体的人血小板中的细胞内游离钙 [Ca2+]i。因此，10 microM 他莫昔芬使 [Ca2+] i 高于静息水平 197 +/- 19%。他莫昔芬与凝血酶、ADP 和加压素协同作用以增加 [Ca2+]i。抗雌激素 ICI 182780 没有减弱他莫昔芬增加 [Ca2+]i 的作用；然而，磷脂酶 C 抑制剂 U-73122 阻止了这种作用。他莫昔芬的主要代谢物 4-羟基他莫昔芬也增加了 [Ca2+]i，但其他他莫昔芬代谢物和合成衍生物没有增加。三苯乙烯的三种羟基化衍生物（对应于他莫昔芬的疏水核心）是他莫昔芬（Ca 激动剂）和己烯雌酚（Ca 拮抗剂）之间的过渡结构，使 [Ca2+]i 略微增加（6% 至 24%）并部分抑制凝血酶诱导的 [Ca2+] Ca2+]i 升高（68% 至 79%）。因此，二甲氨基乙基部分导致他莫昔芬成为
• Antiestrogen basicity-activity relationships: a comparison of the estrogen receptor binding and antiuterotrophic potencies of several analogs of (Z)-1,2-diphenyl-1-[4-[2-(dimethylamino)ethoxy]phenyl]-1-butene (Tamoxifen, Nolvadex) having altered basicity
  作者：David W. Robertson、John A. Katzenellenbogen、James R. Hayes、Benita S. Katzenellenbogen

  DOI：10.1021/jm00344a015

  日期：1982.2

  A series of N-substituted (Z)-1,2-diphenyl-1-[4-(2-aminoethoxy)phenyl]-1-butenes, analogues of the antiestrogen tamoxifen (Nolvadex), in which the side-chain basicity is varied over a wide range, has been prepared to probe the importance of basicity in evoking estrogen antagonism. All of the compounds, except the pyrrole analogue 14, were found to possess significant antiestrogenic activity in the rat, as measured by their ability to inhibit estrogen-induced uterine growth. This implies that in the tamoxifen series the level of side-chain basicity, at least in the Lowry-Brønsted sense, is not a determining factor in the estrogen antagonist potencies of these compounds.