Ethyl 4-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl)benzoate | 107430-52-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Ethyl 4-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl)benzoate
• 英文别名: Ethyl 4-(5,5,8,8-tetramethyl-6,7-dihydroanthracen-2-yl)benzoate
• CAS: 107430-52-4
• 化学式: C₂₇H₃₀O₂
• 分子量: 386.534
• InChiKey: ZSRCJDLZXWWTCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Ethyl 4-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl)benzoate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以87%的产率得到4-(5,5,8,8-四甲基-6,7-二氢蒽-2-基)苯甲酸
  参考文献：
  名称：

  Effect of structural modifications in the C7-C11 region of the retinoid skeleton on biological activity in a series of aromatic retinoids

  摘要：

  A series of conformationally restricted analogues of (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)propenyl ] benzoic acid--(E)-4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2 - propenyl]benzoic acid, (E)-4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-bu ten- 2-yl]benzoic acid, trans-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl) cyclopropyl]benzoic acid, 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl)benzoic acid, 6-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2- naphthalenecarboxylic acid, 6-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-2- naphthalenecarboxylic acid and 6-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-5-methyl-2- naphthalenecarboxylic acid--were synthesized and screened for retinoid biological activity. Comparison of the conformers of these analogues generated by molecular mechanics calculations with the biological activity profiles of these compounds indicates that geometric constraints required for high biological activity are imposed on the bridge joining the two aromatic ring systems by the retinoid receptor.

  DOI：

  10.1021/jm00127a018
• 作为产物：
  描述：

  4-溴苯甲酸乙酯 在 三氯化铝 作用下， 以 二硫化碳 为溶剂， 反应 0.5h， 生成 Ethyl 4-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl)benzoate
  参考文献：
  名称：

  Effect of structural modifications in the C7-C11 region of the retinoid skeleton on biological activity in a series of aromatic retinoids

  摘要：

  A series of conformationally restricted analogues of (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)propenyl ] benzoic acid--(E)-4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2 - propenyl]benzoic acid, (E)-4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-bu ten- 2-yl]benzoic acid, trans-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl) cyclopropyl]benzoic acid, 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl)benzoic acid, 6-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2- naphthalenecarboxylic acid, 6-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-2- naphthalenecarboxylic acid and 6-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-5-methyl-2- naphthalenecarboxylic acid--were synthesized and screened for retinoid biological activity. Comparison of the conformers of these analogues generated by molecular mechanics calculations with the biological activity profiles of these compounds indicates that geometric constraints required for high biological activity are imposed on the bridge joining the two aromatic ring systems by the retinoid receptor.

  DOI：

  10.1021/jm00127a018

文献信息

• DAWSON, MARCIA I.;HOBBS, PETER D.;DERDZINSKI, KRZYSZTOF A.;CHAO, WAN-RU;F+, J. MED. CHEM., 32,(1989) N, C. 1504-1517
  作者：DAWSON, MARCIA I.、HOBBS, PETER D.、DERDZINSKI, KRZYSZTOF A.、CHAO, WAN-RU、F+

  DOI：——

  日期：——
• [EN] NOVEL COMPOUNDS USEFUL IN MODULATING GENE EXPRESSION OF RETINOID RESPONSIVE GENES AND/OR HAVING ANTI-AP-1 ACTIVITY<br/>[FR] NOUVEAUX COMPOSES UTILES POUR MODULER L'EXPRESSION DE GENES SENSIBLES AUX RETINOIDES ET/OU PRESENTANT UNE ACTIVITE ANTI AP-1
  申请人：SRI INTERNATIONAL

  公开号：WO1995033745A2

  公开（公告）日：1995-12-14

  (EN) Novel compounds are provided which are useful for the regulation of gene expression by retinoids; these compounds are represented by structural formula (I), wherein the substituents R1 through R5 are as defined herein. Additional compounds are provided which are useful for selectively inhibiting AP-1 or an AP-1 component; one group of such compounds is exemplified by structural formula (II), wherein the substituents R1, R2, R20, R21, R22 and R23 are defined herein. Pharmaceutical compositions are provided as well, as are methods of using the compounds in a variety of contexts.(FR) L'invention concerne de nouveaux composés utiles pour réguler l'expression de gènes par les rétinoïdes; ces composés sont structurés selon la formule (I) dans laquelle les substituants R1 à R5 ont la notation mentionnée dans la description. L'invention concerne également des composés utiles pour inhiber de façon sélective l'AP-1 ou un constituant de l'AP-1; un groupe de ces composés est structuré selon la formule (II) dans laquelle les substituants R1, R2, R20, R21, R22 et R23 ont la notation mentionnée dans la description. L'invention concerne enfin des compositions pharmaceutiques ainsi que des procédés d'utilisation de ces composés dans différents contextes.
• Effect of structural modifications in the C7-C11 region of the retinoid skeleton on biological activity in a series of aromatic retinoids
  作者：Marcia I. Dawson、Peter D. Hobbs、Krzysztof A. Derdzinski、Wan Ru Chao、Gernot Frenking、Gilda H. Loew、Anton M. Jetten、Joseph L. Napoli、John B. Williams

  DOI：10.1021/jm00127a018

  日期：1989.7

  A series of conformationally restricted analogues of (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)propenyl ] benzoic acid--(E)-4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2 - propenyl]benzoic acid, (E)-4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-bu ten- 2-yl]benzoic acid, trans-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl) cyclopropyl]benzoic acid, 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl)benzoic acid, 6-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2- naphthalenecarboxylic acid, 6-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-2- naphthalenecarboxylic acid and 6-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-5-methyl-2- naphthalenecarboxylic acid--were synthesized and screened for retinoid biological activity. Comparison of the conformers of these analogues generated by molecular mechanics calculations with the biological activity profiles of these compounds indicates that geometric constraints required for high biological activity are imposed on the bridge joining the two aromatic ring systems by the retinoid receptor.