3-(3,5-Di-t-butylphenyl)but-2-enal | 178688-26-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: 3-(3,5-Di-t-butylphenyl)but-2-enal
• 英文别名: (Z)-3-(3,5-ditert-butylphenyl)but-2-enal
• CAS: 178688-26-1
• 化学式: C₁₈H₂₆O
• 分子量: 258.404
• InChiKey: OLQFOEXVMZZPJH-JYRVWZFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(3,5-Di-t-butylphenyl)but-2-enal 在 sodium hydroxide 、 正丁基锂 作用下， 以 甲醇 为溶剂， 反应 0.42h， 生成 LG100567
  参考文献：
  名称：

  Discovery of Novel Retinoic Acid Receptor Agonists Having Potent Antiproliferative Activity in Cervical Cancer Cells

  摘要：

  Retinoic acid receptor (RAR) active retinoids have proven therapeutically useful for treating certain cancers and dermatological diseases. Herein, we describe the discovery of two new RAR active trienoic acid retinoids, (2E,4E,6E)-7-(3,5-di-tert-butylphenyl)-3-methylocta-2,4,6-trienoic acid (10a, ALRT1550) and (2E,4E,6Z)-7-(3,5-di-tert-butylphenyl)-3-methylocta-2,4,6-trienoic acid (10b, LG100567). ALRT1550 is a RAR selective retinoid which exhibits exceptional potency in both competitive binding and cotransfection assays. Moreover, it is the most potent antiproliferative retinoid described to date and thus has implications for the treatment of certain cancers. LG100567 is a potent panagonist which activates both RARs and retinoid X receptors.

  DOI：

  10.1021/jm960285j
• 作为产物：
  描述：

  1-(3,5-二叔丁基苯基)乙酮 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.75h， 生成 3-(3,5-Di-t-butylphenyl)but-2-enal
  参考文献：
  名称：

  Discovery of Novel Retinoic Acid Receptor Agonists Having Potent Antiproliferative Activity in Cervical Cancer Cells

  摘要：

  Retinoic acid receptor (RAR) active retinoids have proven therapeutically useful for treating certain cancers and dermatological diseases. Herein, we describe the discovery of two new RAR active trienoic acid retinoids, (2E,4E,6E)-7-(3,5-di-tert-butylphenyl)-3-methylocta-2,4,6-trienoic acid (10a, ALRT1550) and (2E,4E,6Z)-7-(3,5-di-tert-butylphenyl)-3-methylocta-2,4,6-trienoic acid (10b, LG100567). ALRT1550 is a RAR selective retinoid which exhibits exceptional potency in both competitive binding and cotransfection assays. Moreover, it is the most potent antiproliferative retinoid described to date and thus has implications for the treatment of certain cancers. LG100567 is a potent panagonist which activates both RARs and retinoid X receptors.

  DOI：

  10.1021/jm960285j

文献信息

• [EN] NOVEL TRIENOIC RETINOID COMPOUNDS AND METHODS<br/>[FR] NOUVEAUX COMPOSES DE RETINOIDE TRIENOIQUE ET METHODES D'UTILISATION
  申请人：LIGAND PHARMACEUTICALS INCORPORATED

  公开号：WO1996020913A1

  公开（公告）日：1996-07-11

  (EN) Novel trienoic retinoid compounds having activity for retinoic acid receptors and retinoid X receptors are provided. Also provided are pharmaceutical compositions incorporating such compounds and methods for their use.(FR) L'invention porte sur des composés de rétinoïde triénoïque faisant preuve d'activité à l'égard de récepteurs d'acide rétinoïque et de récepteurs de rétinoïde X. Elle porte également sur des préparations pharmaceutiques contenant ces composés ainsi que sur leurs méthodes d'utilisation.

  (中文) 提供了具有对视黄酸受体和维甲酸X受体活性的新型三烯酸类维甲酸化合物。还提供了包含这些化合物的药物组合物和它们的使用方法。
• NOVEL TRIENOIC RETINOID COMPOUNDS AND METHODS
  申请人：LIGAND PHARMACEUTICALS, INC.

  公开号：EP0800503B1

  公开（公告）日：2000-05-10
• US5721103A
  申请人：——

  公开号：US5721103A

  公开（公告）日：1998-02-24
• US6083977A
  申请人：——

  公开号：US6083977A

  公开（公告）日：2000-07-04
• Discovery of Novel Retinoic Acid Receptor Agonists Having Potent Antiproliferative Activity in Cervical Cancer Cells
  作者：Lin Zhang、Alex M. Nadzan、Richard A. Heyman、Deborah L. Love、Dale E. Mais、Glenn Croston、William W. Lamph、Marcus F. Boehm

  DOI：10.1021/jm960285j

  日期：1996.1.1

  Retinoic acid receptor (RAR) active retinoids have proven therapeutically useful for treating certain cancers and dermatological diseases. Herein, we describe the discovery of two new RAR active trienoic acid retinoids, (2E,4E,6E)-7-(3,5-di-tert-butylphenyl)-3-methylocta-2,4,6-trienoic acid (10a, ALRT1550) and (2E,4E,6Z)-7-(3,5-di-tert-butylphenyl)-3-methylocta-2,4,6-trienoic acid (10b, LG100567). ALRT1550 is a RAR selective retinoid which exhibits exceptional potency in both competitive binding and cotransfection assays. Moreover, it is the most potent antiproliferative retinoid described to date and thus has implications for the treatment of certain cancers. LG100567 is a potent panagonist which activates both RARs and retinoid X receptors.