2-[(E)-2-(5,5,8,8-四甲基-6,7-二氢萘并醛烯-2-基)丙-1-烯基]苯甲酸 | 112642-02-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 2-[(E)-2-(5,5,8,8-四甲基-6,7-二氢萘并醛烯-2-基)丙-1-烯基]苯甲酸
• 英文名称: 2-[(E)-2-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-propenyl]-benzoic acid
• 英文别名: 2-[(E)-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-enyl]benzoic acid
• CAS: 112642-02-1
• 化学式: C₂₄H₂₈O₂
• 分子量: 348.485
• InChiKey: NKHXGKGXOLIAEA-JQIJEIRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  <1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-ethyl>-triphenylphosphonium bromide 在 lithium hydroxide 、 正丁基锂 作用下， 以 乙醚 为溶剂， 生成 2-[(E)-2-(5,5,8,8-四甲基-6,7-二氢萘并醛烯-2-基)丙-1-烯基]苯甲酸
  参考文献：
  名称：

  Programmed cell death (PCD) associated with the stilbene motif of arotinoids: discovery of novel apoptosis inducer agents possessing activity on multidrug resistant tumor cells

  摘要：

  Considering that the stereochemistry of the C9-C10 alkenyl portion of natural 9-cis-RA, as the one of the olefinic moiety of the previously described isoxazole retinoid 4, seems of particular importance for their apoptotic activity, we prepared a novel class of TTNPB analogues bearing both the cis or trans configuration of the alkenyl portion. The compounds were evaluated in vitro for their cytotoxic and apoptotic activities. We discovered that the cis-TTNPB 9c possesses apoptotic activity comparable with that of the retinoid 4. Moreover, the amino arotinoid 16c showed potent apoptotic activity in HL60 promyelocytic leukemia cells. Interestingly, 16c proved to be a particularly potent apoptosis-inducing agent active in multidrug resistant (MDR) cell lines. Therefore, to the best of our knowledge, 16c may represent the first known aminoarotinoid endowed with potent apoptotic activity in MDR cells. Taken together, these results seem to point out that the cis-stilbene motif of arotinoids may be at least an important feature in conferring cytotoxic and apoptotic activity to this class of compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00547-3

文献信息

• US6110485A
  申请人：——

  公开号：US6110485A

  公开（公告）日：2000-08-29
• Programmed cell death (PCD) associated with the stilbene motif of arotinoids: discovery of novel apoptosis inducer agents possessing activity on multidrug resistant tumor cells
  作者：Daniele Simoni、Marinella Roberti、Francesco Paolo Invidiata、Riccardo Rondanin、Riccardo Baruchello、Cinzia Malagutti、Angelica Mazzali、Marcello Rossi、Stefania Grimaudo、Luisa Dusonchet、Maria Meli、Maria Valeria Raimondi、Natale D'Alessandro、Manlio Tolomeo

  DOI：10.1016/s0960-894x(00)00547-3

  日期：2000.12

  Considering that the stereochemistry of the C9-C10 alkenyl portion of natural 9-cis-RA, as the one of the olefinic moiety of the previously described isoxazole retinoid 4, seems of particular importance for their apoptotic activity, we prepared a novel class of TTNPB analogues bearing both the cis or trans configuration of the alkenyl portion. The compounds were evaluated in vitro for their cytotoxic and apoptotic activities. We discovered that the cis-TTNPB 9c possesses apoptotic activity comparable with that of the retinoid 4. Moreover, the amino arotinoid 16c showed potent apoptotic activity in HL60 promyelocytic leukemia cells. Interestingly, 16c proved to be a particularly potent apoptosis-inducing agent active in multidrug resistant (MDR) cell lines. Therefore, to the best of our knowledge, 16c may represent the first known aminoarotinoid endowed with potent apoptotic activity in MDR cells. Taken together, these results seem to point out that the cis-stilbene motif of arotinoids may be at least an important feature in conferring cytotoxic and apoptotic activity to this class of compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.