2-(5-Benzyloxy-2-hydroxy-phenylsulfanyl)-2-(4-benzyloxy-phenyl)-1-(4-iodo-phenyl)-ethanone | 744256-23-3

• 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: 2-(5-Benzyloxy-2-hydroxy-phenylsulfanyl)-2-(4-benzyloxy-phenyl)-1-(4-iodo-phenyl)-ethanone
• CAS: 744256-23-3
• 化学式: C₃₄H₂₇IO₄S
• 分子量: 658.556
• InChiKey: DVKTVIXSZNBAOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.87
• 重原子数：
  40.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(5-Benzyloxy-2-hydroxy-phenylsulfanyl)-2-(4-benzyloxy-phenyl)-1-(4-iodo-phenyl)-ethanone 在 三乙基硅烷 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3-{4-[(2S,3R)-6-Benzyloxy-3-(4-benzyloxy-phenyl)-2,3-dihydro-benzo[1,4]oxathiin-2-yl]-phenyl}-prop-2-yn-1-ol
  参考文献：
  名称：

  Estrogen receptor ligands. Part 5: The SAR of dihydrobenzoxathiins containing modified basic side chains

  摘要：

  Dihydrobenzoxathiin analogs (1-11) with modifications on the basic side chain region were prepared and evaluated for estrogen/anti-estrogen activity in both in vitro and in vivo models. The compounds generally maintained a high degree of selectivity for ERalpha over ERbeta, similar to the original lead compound I. Many of the compounds also maintained high potency in the inhibition of human carcinoma MCF-7 cell growth. However, all were less potent in the inhibition of estradiol-triggered uterine growth. This work demonstrates the sensitive nature of modification to the antagonist basic side chain region. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.100
• 作为产物：
  描述：

  4-Iodo-benzoic acid 4-benzyloxy-2-(4-benzyloxy-benzylsulfanyl)-phenyl ester 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 2-(5-Benzyloxy-2-hydroxy-phenylsulfanyl)-2-(4-benzyloxy-phenyl)-1-(4-iodo-phenyl)-ethanone
  参考文献：
  名称：

  Estrogen receptor ligands. Part 5: The SAR of dihydrobenzoxathiins containing modified basic side chains

  摘要：

  Dihydrobenzoxathiin analogs (1-11) with modifications on the basic side chain region were prepared and evaluated for estrogen/anti-estrogen activity in both in vitro and in vivo models. The compounds generally maintained a high degree of selectivity for ERalpha over ERbeta, similar to the original lead compound I. Many of the compounds also maintained high potency in the inhibition of human carcinoma MCF-7 cell growth. However, all were less potent in the inhibition of estradiol-triggered uterine growth. This work demonstrates the sensitive nature of modification to the antagonist basic side chain region. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.100