U23469 | 22845-55-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: U23469
• 英文别名: 3-{4-[(1S,2R)-6-methoxy-2-phenyl-1,2,3,4-tetrahydro-1-naphthalenyl]phenoxy}-1,2-propanediol；3-[4-[(1S,2R)-6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl]phenoxy]propane-1,2-diol
• CAS: 22845-55-2；22845-61-0；23979-05-7
• 化学式: C₂₆H₂₈O₄
• 分子量: 404.506
• InChiKey: YDDPQONJKPRFEC-HRFJKEBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-methoxy-2-[(trimethylsilyl)methyl]-4’-(methoxymethoxy)benzhydryl benzoate 在 potassium fluoride 、 18-冠醚-6 、 三甲基溴硅烷 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 83.0h， 生成 U23469
  参考文献：
  名称：

  Anortho-Quinodimethane Route to Lasofoxifene and U23469

  摘要：

  拉索昔芬是一种第三代选择性雌激素受体调节剂，可通过原位二甲烷和硼烷烃之间的[4 + 2]环加成反应进行区域和立体选择性合成。该方法也适用于合成抗雌激素 U23469。

  DOI：

  10.1246/cl.2011.1272

文献信息

• Compounds and process for preparing the same
  申请人：The Upjohn Company

  公开号：US03947520A1

  公开（公告）日：1976-03-30

  Cis and trans isomers of 1,2-diphenyl-1,2,3,4-tetrahydronaphthalenes, novel processes for the preparation thereof, and novel intermediates are disclosed herein. The novel 1,2-diphenyl-1,2,3,4-tetrahydronaphthalenes have utility as antifertility estrogenic, anti-estrogenic, anti-spermatogenic, cholesterol lowering and lipid normalizing agents.

  本文披露了1,2-二苯基-1,2,3,4-四氢萘烯的顺式和反式异构体，其制备的新方法以及新的中间体。这些新型的1,2-二苯基-1,2,3,4-四氢萘烯具有抗生育雌激素、抗雌激素、抗精子生成、降低胆固醇和正常化脂质的作用。
• Antiestrogens and antiestrogen metabolites: preparation of tritium-labeled (.+-.)-cis-3-[p-(1,2,3,4-tetrahydro-6-methoxy-2-phenyl-1-naphthyl)phenoxy]-1,2-propanediol and characterization and synthesis of a biologically important metabolite
  作者：Tochiro Tatee、Kathryn E. Carlson、John A. Katzenellenbogen、David W. Robertson、Benita S. Katzenellenbogen

  DOI：10.1021/jm00198a015

  日期：1979.12

  The Upjohn antiestrogen (+/-)-cis-3-[p-(1,2,3,4-tetrahydro-6-methoxy-2-phenyl-1-naphthyl)phenoxy]-1,2-propanediol (2b, U 23469) has been prepared in tritium-labeled form by reduction of an unsaturated dihydronaphthalene precursor with carrier-free tritium gas over a palladium catalyst followed by alkylation with 3-iodo-1,2-propanediol. After extensive chromatographic purification, the final material was obtained with a specific activity of 13 Ci/mmol and a radiochemical purity of 94%. In vivo studies with immature rats show that [3H]2b is slowly converted to a more polar metabolite that is selectively accumulated in the nuclear fraction of the uterus where it is bound to the estrogen receptor. Chromatographic comparisons indicate that this metabolite is the demethylated analogue 2c, a compound that has an affinity for estrogen receptor more than 300 times greater than that of 2b. These studies suggest that the demethylated analogue 2c may be a biologically important metabolite of 2b that is involved in the action of this antiestrogen.
• US3947520A
  申请人：——

  公开号：US3947520A

  公开（公告）日：1976-03-30