2-phenyl-3,3-bis(p-hydroxyphenyl)acrylonitrile | 66422-14-8

• 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-phenyl-3,3-bis(p-hydroxyphenyl)acrylonitrile
• 英文别名: 3,3-bis-(4-hydroxy-phenyl)-2-phenyl-acrylonitrile；3,3-Bis-(4-hydroxy-phenyl)-2-phenyl-acrylonitril；3,3-Bis-<4-hydroxy-phenyl>-2-phenyl-acrylnitril；3,3-Bis(4-hydroxyphenyl)-2-phenylprop-2-enenitrile
• CAS: 66422-14-8
• 化学式: C₂₁H₁₅NO₂
• 分子量: 313.356
• InChiKey: PMKMHLVHNOXPOY-UHFFFAOYSA-N

物化性质

• 熔点：
  249 °C
• 沸点：
  482.3±45.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-phenyl-3,3-bis(p-hydroxyphenyl)acrylonitrile 、 二异丙氨基乙基氯盐酸盐 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 22.0h， 以48%的产率得到3,3-Bis[4-[2-[di(propan-2-yl)amino]ethoxy]phenyl]-2-phenylprop-2-enenitrile
  参考文献：
  名称：

  Multivariate analysis by the minimum spanning tree method of the structural determinants of diphenylethylenes and triphenylacrylonitriles implicated in estrogen receptor binding, protein kinase C activity, and MCF7 cell proliferation

  摘要：

  The response profiles of 36 para-substituted diphenylethylenes (DPEs) and triphenylacrylonitriles (TPEs) have been compared by multivariate analysis. The responses measured were (a) relative binding affinity (RBA) for the cytosol estrogen receptor (ER), (b) ability to promote the growth of the human MCF7 breast cancer cell-line, (c) cytotoxicity in MCF7 cells, and (d) ability to stimulate or inhibit protein kinase C (PKC) III activity under three different conditions of enzyme activation. The prime object of the analysis was to observe the simultaneous influence of diverse combinations of substituents on all these in vitro responses. To do this, the minimum spanning tree (MST) method was used to organize the molecules into a network in which proximate molecules are closely related with regard to their responses whereas remote molecules are distinct. The MST of this population of molecules had four main branches. E2 and its TPE mime were located in a central position within the trunk whereas the tips of the branches tended toward molecules of different specificity, i.e., cytotoxic molecules that bind to ER and interfere with PKC, noncytotoxic molecules that also bind to ER and interfere with PKC but promote cell growth, molecules that also bind to ER and interfere with PKC but promote cell growth, molecules only active on PKC, and molecules active on all parameters except PKC stimulation. A parallel MST analysis of the relationships among the response parameters themselves confirmed previous conclusions: For this population of molecules, RBAs for ER are fairly closely related to ability to promote MCF7 cell growth and only little to cytotoxicity (Bignon et al. J. Med. Chem. 1989, 32, 2092). Cytotoxicity is much more clearly correlated with inhibition of diacylglcerol-stimulated PKC activity than with RBAs for ER. PKC inhibition differs substantially depending upon whether the substrate is H-1 histone or protamine sulfate.

  DOI：

  10.1021/jm00081a021
• 作为产物：
  描述：

  3,3-bis-(4-ethoxy-phenyl)-2-phenyl-acrylonitrile 在 吡啶盐酸盐 、 硝基苯 作用下， 生成 2-phenyl-3,3-bis(p-hydroxyphenyl)acrylonitrile
  参考文献：
  名称：

  3,4-DIARYLCOUMARINS

  摘要：

  DOI：

  10.1021/jo01373a025

文献信息

• Effect of triphenylacrylonitrile derivatives on estradiol-receptor binding and on human breast cancer cell growth
  作者：Eric Bignon、Michel Pons、Andre Crastes de Paulet、Jean Christophe Dore、Jacques Gilbert、Josephine Abecassis、Jean Francois Miquel、Tiiu Ojasoo、Jean Pierre Raynaud

  DOI：10.1021/jm00129a013

  日期：1989.9

  triphenylacrylonitrile derivatives (TPEs), we investigated the influence of several possibly interrelated factors on the proliferation of human breast cancer cell lines. (1) Chemical substituents: the test compounds were for the most part para-hydroxylated with increasingly bulky hydrophobic and/or basic side chains [isopropyloxy or (diethylamino)ethoxy] or standard reference compounds. (2) Relative binding affinities

  在对一系列26种三苯基丙烯腈衍生物（TPE）的研究中，我们研究了几种可能相关的因素对人乳腺癌细胞系增殖的影响。（1）化学取代基：测试化合物大部分被对羟基羟基化的羟基和/或碱性侧链[异丙氧基或（二乙氨基）乙氧基]或标准参考化合物所取代。（2）相对结合亲和力（RBA）：它们竞争[3H]雌二醇（E2）与小牛子宫细胞质的结合，几乎不竞争与[3H]他莫昔芬标记的抗雌激素结合位点（AEBS）的结合。低速上清液。对小腿，大鼠，小鼠子宫内溶质雌激素受体（ER）揭示了物种特异性受体构象和/或环境对结合的可能影响。（3）雌激素/抗雌激素能力：测量它们对ER阳性人乳腺癌细胞系（MCF7）的刺激和抑制作用。仅具有羟基取代基的化合物比甲基化衍生物更明显地刺激增殖，并且在10（-11）-10（-6）M时具有最大作用。刺激与ER的RBA有关。具有异丙氧基或（二乙氨基）乙氧基侧链的化合物仅弱刺激MCF7细胞生长，而更强烈
• BIGNON, ERIC;PONS, MICHEL;DE, PAULET ANDRE CRASTES;DORE, JEAN-CHRISTOPHE;+, J. MED. CHEM., 32,(1989) N, C. 2092-2103
  作者：BIGNON, ERIC、PONS, MICHEL、DE, PAULET ANDRE CRASTES、DORE, JEAN-CHRISTOPHE、+

  DOI：——

  日期：——
• 3,4-DIARYLCOUMARINS
  作者：NG. PH. BUU-HOÏ、BERNARD ECKERT

  DOI：10.1021/jo01373a025

  日期：1954.8
• Multivariate analysis by the minimum spanning tree method of the structural determinants of diphenylethylenes and triphenylacrylonitriles implicated in estrogen receptor binding, protein kinase C activity, and MCF7 cell proliferation
  作者：Jean Christophe Dore、Jacques Gilbert、Eric Bignon、Andre Crastes de Paulet、Tiiu Ojasoo、Michel Pons、Jean Pierre Raynaud、Jean Francois Miquel

  DOI：10.1021/jm00081a021

  日期：1992.2

  The response profiles of 36 para-substituted diphenylethylenes (DPEs) and triphenylacrylonitriles (TPEs) have been compared by multivariate analysis. The responses measured were (a) relative binding affinity (RBA) for the cytosol estrogen receptor (ER), (b) ability to promote the growth of the human MCF7 breast cancer cell-line, (c) cytotoxicity in MCF7 cells, and (d) ability to stimulate or inhibit protein kinase C (PKC) III activity under three different conditions of enzyme activation. The prime object of the analysis was to observe the simultaneous influence of diverse combinations of substituents on all these in vitro responses. To do this, the minimum spanning tree (MST) method was used to organize the molecules into a network in which proximate molecules are closely related with regard to their responses whereas remote molecules are distinct. The MST of this population of molecules had four main branches. E2 and its TPE mime were located in a central position within the trunk whereas the tips of the branches tended toward molecules of different specificity, i.e., cytotoxic molecules that bind to ER and interfere with PKC, noncytotoxic molecules that also bind to ER and interfere with PKC but promote cell growth, molecules that also bind to ER and interfere with PKC but promote cell growth, molecules only active on PKC, and molecules active on all parameters except PKC stimulation. A parallel MST analysis of the relationships among the response parameters themselves confirmed previous conclusions: For this population of molecules, RBAs for ER are fairly closely related to ability to promote MCF7 cell growth and only little to cytotoxicity (Bignon et al. J. Med. Chem. 1989, 32, 2092). Cytotoxicity is much more clearly correlated with inhibition of diacylglcerol-stimulated PKC activity than with RBAs for ER. PKC inhibition differs substantially depending upon whether the substrate is H-1 histone or protamine sulfate.