1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-cyclopropaneacetaldehyde | 252556-34-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-cyclopropaneacetaldehyde
• 英文别名: 2-[1-(3,5,5,8,8-Pentamethyl-6,7-dihydronaphthalen-2-yl)cyclopropyl]acetaldehyde
• CAS: 252556-34-6
• 化学式: C₂₀H₂₈O
• 分子量: 284.442
• InChiKey: CVZXBEXIAWIPLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-cyclopropaneacetaldehyde 在 N,N-二甲基丙烯基脲 、 氢氧化钾 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (2E, 4E)-6-[(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl) cyclopropan-1-yl]-3-methyl hexadienoic acid
  参考文献：
  名称：

  Retinoic acid receptor ligands based on the 6-cyclopropyl-2,4-hexadienoic acid

  摘要：

  A series of novel cyclopropanyl methyl hexadienoic acid retinoids was designed and prepared. These compounds exhibited either selective activity as RXR agonists or pan-agonists on one or more of each of the RAR and RXR isoforms. The most potent pan-agonist 5a (RAR's EC50 = 17-59 nM; RXR's EC50 6-14 nM) showed good antiproliferative properties in the in vitro cancer cell lines, ME 180 and RPMI 8226. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00924-1
• 作为产物：
  描述：

  3,5,5,8,8-五甲基-5,6,7,8-四氢萘-2-硼酸 在 四(三苯基膦)钯 、 diethylzinc 、 sodium carbonate 、 pyridinium chlorochromate 作用下， 以 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 生成 1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-cyclopropaneacetaldehyde
  参考文献：
  名称：

  Retinoic acid receptor ligands based on the 6-cyclopropyl-2,4-hexadienoic acid

  摘要：

  A series of novel cyclopropanyl methyl hexadienoic acid retinoids was designed and prepared. These compounds exhibited either selective activity as RXR agonists or pan-agonists on one or more of each of the RAR and RXR isoforms. The most potent pan-agonist 5a (RAR's EC50 = 17-59 nM; RXR's EC50 6-14 nM) showed good antiproliferative properties in the in vitro cancer cell lines, ME 180 and RPMI 8226. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00924-1

文献信息

• US6005007A
  申请人：——

  公开号：US6005007A

  公开（公告）日：1999-12-21
• [EN] NOVEL RETINOIDS, METHODS FOR THEIR PRODUCTION AND USE<br/>[FR] NOUVEAUX RETINOIDES ET TECHNIQUES DE LEUR PRODUCTION ET UTILISATION
  申请人：LIGAND PHARM INC

  公开号：WO2000026173A1

  公开（公告）日：2000-05-11

  Dienoic retinoids having activity for retinoid X receptors or being panagonists on retinoic acid receptors and retinoid X receptors are provided. Also provided are pharmaceutical compositions incorporating such compounds and methods for their therapeutic use.
• Retinoic acid receptor ligands based on the 6-cyclopropyl-2,4-hexadienoic acid
  作者：Luc J. Farmer、Lin Zhi、Susan Jeong、William W. Lamph、Deborah L. Osburn、Glenn Croston、Karen S. Flatten、Rich A. Heyman、Alex M. Nadzan

  DOI：10.1016/s0960-894x(02)00924-1

  日期：2003.1

  A series of novel cyclopropanyl methyl hexadienoic acid retinoids was designed and prepared. These compounds exhibited either selective activity as RXR agonists or pan-agonists on one or more of each of the RAR and RXR isoforms. The most potent pan-agonist 5a (RAR's EC50 = 17-59 nM; RXR's EC50 6-14 nM) showed good antiproliferative properties in the in vitro cancer cell lines, ME 180 and RPMI 8226. (C) 2002 Elsevier Science Ltd. All rights reserved.