1-<4-<(5-chloropentyl)oxy>phenyl>-2-phenyl-1-butanone | 172174-17-3

• 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: 1-<4-<(5-chloropentyl)oxy>phenyl>-2-phenyl-1-butanone
• 英文别名: 1-[4-(5-Chloropentyloxy)phenyl]-2-phenyl-butan-1-one；1-[4-(5-chloropentoxy)phenyl]-2-phenylbutan-1-one
• CAS: 172174-17-3
• 化学式: C₂₁H₂₅ClO₂
• 分子量: 344.881
• InChiKey: XFTVBTUCLKIXDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-<4-<(5-chloropentyl)oxy>phenyl>-2-phenyl-1-butanone 在 盐酸 、 正丁基锂 作用下， 以 乙醇 为溶剂， 反应 18.67h， 生成 (E)-1-{4-[(5-chloropentyl)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-chloro-5-phenoxypentane 、 2-苯基丁酸 在 三氟乙酸酐 作用下， 反应 16.0h， 以80%的产率得到1-<4-<(5-chloropentyl)oxy>phenyl>-2-phenyl-1-butanone
  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

• Triphenylethylenes, process for their production, pharmaceutical
  申请人：Schering Aktiengesellschaft

  公开号：US05807899A1

  公开（公告）日：1998-09-15

  This invention describes the new triphenylethylenes of general formula I ##STR1## in which n means an integer from 1 to 10, R' means a sulfur-containing organic radical, R" means a hydrogen atom, an iodine atom or a hydroxy groups, E means a hydrogen atom, G means a hydrogen atom or E and G together mean a methylene bridge. The new compounds have strong antiestrogenic properties and are suitable for the production of pharmaceutical agents, for example for treating breast cancer.

  本发明描述了一种新的三苯乙烯化合物，其通式为I ##STR1## 其中n表示1至10的整数，R'表示含硫有机基团，R"表示氢原子、碘原子或羟基，E表示氢原子，G表示氢原子或E和G一起表示亚甲基桥。这些新化合物具有强烈的抗雌激素作用，适用于制备药物，例如用于治疗乳腺癌。
• [DE] TRIPHENYLETHYLENE MIT ANTIESTROGENEN EIGENSCHAFTEN<br/>[EN] TRIPHENYL ETHYLENES WITH ANTI-OESTROGENIC PROPERTIES<br/>[FR] ETHYLENES DE TRIPHENYLE A PROPRIETES ANTI-OESTROGENIQUES
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：WO1997003046A1

  公开（公告）日：1997-01-30

  (DE) Die vorliegende Erfindung beschreibt die neuen Triphenylethylene der allgemeinen Formel (I), worin n eine ganze Zahl von 1 bis 10, R' einen schwefelhaltigen organischen Rest, R' ein Wasserstoffatom, ein Jodatom oder eine Hydroxygruppe, E ein Wasserstoffatom, G ein Wasserstoffatom oder E und G gemeinsam eine Methylenbrücke bedeuten. Die neuen Verbindungen besitzen starke antiestrogene Eigenschaften und sind zur Herstellung von Arzneimitteln, beispielsweise zur Behandlung des Mammacarcinoms, geeignet.(EN) New triphenyl ethylenes have the general formula (I), in which n is an integer from 1 to 10, R' is a sulphur-containing organic rest, R'' is a hydrogen atom, an iodine atom or a hydroxyl group, E is a hydrogen atom, G is a hydrogen atom, or E and G form together a methylene bridge. These new compounds have strong anti-oestrogenic properties and are suitable for producing medicaments, for example for treating mammary carcinoma.(FR) L'invention concerne des éthylènes de triphényle de formule générale (I), dans laquelle n est un nombre entier de 1 à 10, R' est un reste organique contenant du soufre, R'' est un atome d'hydrogène, un atome d'iode ou un groupe hydroxyle, E est un atome d'hydrogène, G est un atome d'hydrogène, ou E et G forment ensemble un pont méthylène. Ces nouveaux composés ont de fortes propriétés anti-oestrogéniques et permettent de produire des médicaments, par exemple pour la thérapie du carcinome mammaire.

  (中) 本发明涉及一类三苯乙烯物质，其通用分子式为(I)，其中，n为 1至10的整数，R'为含一个硫元素的有机基团，R''为一个氢原子、一个碘原子或一个羟基，E为一个氢原子，G为一个氢原子，或E和G共同构成一个甲基桥。这些新化合物具较强的雌激素抑制作用，可用于合成药品，例如用于治疗乳腺癌。
• TRIPHENYLETHYLENE MIT ANTIESTROGENEN EIGENSCHAFTEN
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0839130A1

  公开（公告）日：1998-05-06
• US5807899A
  申请人：——

  公开号：US5807899A

  公开（公告）日：1998-09-15
• 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.