DW22 | 1380681-81-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: DW22
• 英文别名: bexarotene hydroxamic acid；N-hydroxy-4-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzamide
• CAS: 1380681-81-1
• 化学式: C₂₄H₂₉NO₂
• 分子量: 363.5
• InChiKey: JGZNQNMCPDBAGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  27
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoyl chloride 在 盐酸羟胺 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以92%的产率得到DW22
  参考文献：
  名称：

  Discovery of a small molecular compound simultaneously targeting RXR and HADC: Design, synthesis, molecular docking and bioassay

  摘要：

  Retinoid X receptor (RXR) and Histone deacetylase (HDAC) are considered important targets for anti-cancer therapy due to their crucial roles in genetic or epigenetic regulations of cancer development and progression. Here, we have designed and synthesized a novel compound which targets both RXR and HADC. This dual-targeting agent is derived from bexarotene and suberoylanilide hydroxamic acid (SAHA), prototypical RXR agonist and HDAC inhibitor, respectively. Molecular docking studies demonstrate that this agent has a relatively strong affinity to RXR and HADC. Importantly, it presents the potentials of activation of RXR and inhibition of HDAC in both cell-free and whole-cell assays, and displays anti-proliferative effect on representative cancer cell lines and drug-resistant cancer cell lines. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.067

文献信息

• RXR AGONIST COMPOUNDS AND METHODS
  申请人：Case Western Reserve University

  公开号：US20140235676A1

  公开（公告）日：2014-08-21

  A method of treating a psychiatric or cognitive developmental disorder in a subject, includes administering to the subject a therapeutically effective amount of at least one RXR agonist.
• [EN] RXR AGONISTS COMPOUNDS AND METHODS<br/>[FR] COMPOSÉS AGONISTES DE RXR ET PROCÉDÉS ASSOCIÉS
  申请人：UNIV CASE WESTERN RESERVE

  公开号：WO2013056232A2

  公开（公告）日：2013-04-18
• Discovery of a small molecular compound simultaneously targeting RXR and HADC: Design, synthesis, molecular docking and bioassay
  作者：Guo-Liang Chen、Li-Hui Wang、Jian Wang、Kang Chen、Man Zhao、Zhao-Zhu Sun、Shuang Wang、Hong-Li Zheng、Jing-Yu Yang、Chun-Fu Wu

  DOI：10.1016/j.bmcl.2013.04.067

  日期：2013.7

  Retinoid X receptor (RXR) and Histone deacetylase (HDAC) are considered important targets for anti-cancer therapy due to their crucial roles in genetic or epigenetic regulations of cancer development and progression. Here, we have designed and synthesized a novel compound which targets both RXR and HADC. This dual-targeting agent is derived from bexarotene and suberoylanilide hydroxamic acid (SAHA), prototypical RXR agonist and HDAC inhibitor, respectively. Molecular docking studies demonstrate that this agent has a relatively strong affinity to RXR and HADC. Importantly, it presents the potentials of activation of RXR and inhibition of HDAC in both cell-free and whole-cell assays, and displays anti-proliferative effect on representative cancer cell lines and drug-resistant cancer cell lines. (c) 2013 Elsevier Ltd. All rights reserved.