2,3-Bis(4-methoxyphenyl)valeronitril | 79568-15-3

• 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: 2,3-Bis(4-methoxyphenyl)valeronitril
• 英文别名: (+/-)-erythro-2,3-bis-(4-methoxy-phenyl)-valeronitrile；(2R,3S)-2,3-bis(4-methoxyphenyl)pentanenitrile
• CAS: 79568-15-3
• 化学式: C₁₉H₂₁NO₂
• 分子量: 295.381
• InChiKey: JHXQMIVRDWRWDV-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-Bis(4-methoxyphenyl)valeronitril 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 120.0h， 生成 2,2'-imino>diethanol
  参考文献：
  名称：

  Potential Antineoplastics, 6th edition. 1) 具有烷基化侧链的己雌醇衍生物的合成

  摘要：

  芥子化合物 9 和三氮烯 19 是完全合成的。

  DOI：

  10.1002/ardp.19833160316
• 作为产物：
  描述：

  对甲氧基苯乙腈 在 sodium ethanolate 、 magnesium 作用下， 以 乙醇 为溶剂， 反应 28.0h， 生成 2,3-Bis(4-methoxyphenyl)valeronitril
  参考文献：
  名称：

  Potential Antineoplastics, 6th edition. 1) 具有烷基化侧链的己雌醇衍生物的合成

  摘要：

  芥子化合物 9 和三氮烯 19 是完全合成的。

  DOI：

  10.1002/ardp.19833160316

文献信息

• Estrogen Receptor-β Potency-Selective Ligands:  Structure−Activity Relationship Studies of Diarylpropionitriles and Their Acetylene and Polar Analogues
  作者：Marvin J. Meyers、Jun Sun、Kathryn E. Carlson、Gwendolyn A. Marriner、Benita S. Katzenellenbogen、John A. Katzenellenbogen

  DOI：10.1021/jm010254a

  日期：2001.11.1

  than their nitrile counterparts. The polar analogues have lower affinities, and only the fluorinated polar analogues have substantial affinity selectivities. This study suggests that, in this series of ligands, the nitrile functionality is critical to ERbeta selectivity because it provides the optimal combination of linear geometry and polarity. Furthermore, the addition of a second nitrile group beta

  通过努力开发对雌激素受体α（ERalpha）和β（ERbeta）具有亚型选择性的新型配体，我们发现2,3-双（4-羟苯基）丙腈（DPN）在两种ER上均充当激动剂亚型，但在与ERalpha相比，用ERbeta进行转录测定时，其相对结合亲和力和相对效价分别高70倍和170倍。为了进一步研究该DPN的ERbeta亲和力和效能选择特性，我们制备了一系列DPN类似物，其中配体核心和芳环均通过酚羟基的重新定位以及烷基取代基和腈基。我们还准备了其他系列的DPN类似物，其中腈官能团被乙炔基或极性官能团取代，分别模拟腈的线性几何形状或极性。在不同程度上，所有类似物均显示出对ERbeta的优先结合亲和力（即，它们对ERbeta亲和力具有选择性），并且许多（但不是全部）与通过ERalpha相比，它们通过ERbeta激活转录的能力更强（即，它们是ERbeta效能选择）。meso-2,3-双（4-羟苯基）琥珀腈和dl-2
• Estrogenic affinity labels: synthesis, irreversible receptor binding, and bioactivity of aziridine-substituted hexestrol derivatives
  作者：Jeffery A. Zablocki、John A. Katzenellenbogen、Kathryn E. Carlson、M. J. Norman、Benita S. Katzenellenbogen

  DOI：10.1021/jm00388a015

  日期：1987.5

  To develop an affinity label for the estrogen receptor that would be an estrogen agonist, rather than antagonist, we prepared several aziridine derivatives of the potent nonsteroidal estrogen hexestrol [3R,4S)-3,4-bis(4-hydroxyphenyl)hexane) bearing an aziridine function on the side chain. Three functional groups link the hexestrol ligand and the aziridine: a carbonyl group (ketone or ester), a thioether, or a methylene chain. The apparent competitive binding affinity of these derivatives for the estrogen receptor ranges from 1.8% to 25% that of estradiol, and most of them bind in a time-dependent, irreversible manner with the receptor, although the rate and efficiency of this binding vary widely, often with relatively small changes in structure. This is consistent with the irreversible attachment requiring a precise alignment of activating and reacting residues in the binding site of the receptor. The estrogenic and antiestrogenic activity of these aziridine derivatives was investigated in MCF-7 human breast cancer cells. Most of the compounds are agonists, with one being an antagonist. The derivative (6R,7S)-1-N-aziridinyl-6,7-bis(4-hydroxyphenyl)-5-nonanone (keto-nonestrol aziridine 3) appears to have the most ideal behavior of the estrogenic affinity labeling agents prepared: It is an agonist, and it binds to receptor irreversibly, efficiently, and quite rapidly.
• alpha, beta-(polyhydroxyaryl)-alkanamides and methods for their producton
  申请人：SEARLE & CO

  公开号：US02666789A1

  公开（公告）日：1954-01-19
• Collins; Hobbs, Australian Journal of Chemistry, 1970, vol. 23, p. 1605,1607, 1617
  作者：Collins、Hobbs

  DOI：——

  日期：——
• Nuclearly hydroxylated derivatives of alpha, beta-diphenylalkanonitriles
  申请人：SEARLE &

  公开号：US02740806A1

  公开（公告）日：1956-04-03