N-tert-butyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxamide | 1580483-23-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-tert-butyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxamide
• 英文别名: N-tert-butyl-5,5,8,8-tetramethyl-6,7-dihydronaphthalene-2-carboxamide
• CAS: 1580483-23-3
• 化学式: C₁₉H₂₉NO
• 分子量: 287.445
• InChiKey: OGXWUVIYVLVYOY-UHFFFAOYSA-N

物化性质

• 沸点：
  381.1±31.0 °C(Predicted)
• 密度：
  0.948±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5,5,8,8-四甲基-5,6,7,8-四氢-2-萘羧酸 、 叔丁胺 在 草酰氯 、 N,N-二甲基甲酰胺 、 吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以59%的产率得到N-tert-butyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxamide
  参考文献：
  名称：

  Development of novel silicon-containing inverse agonists of retinoic acid receptor-related orphan receptors

  摘要：

  Retinoic acid receptor (RAR)-related orphan receptors (RORs) regulate a variety of physiological processes, including hepatic gluconeogenesis, lipid metabolism, circadian rhythm and immune function. The RAR agonist: all-trans retinoic acid was reported to be an ROR beta inverse agonist, but no information is available regarding ROR activity of its synthetic analogue Am580. Therefore, we screened Am580 and some related tetramethyltetrahydronaphthalene derivatives and carried out structural development studies, including substitution of carbon atoms with silicon, with the aim of creating a potent ROR transcriptional inhibitor. The phenyl amide disila compound 22 showed the most potent ROR-inhibitory activity among the compounds examined. Its activity towards ROR alpha, ROR beta and ROR gamma was increased compared to that of Am580. The IC50 values for ROR alpha, ROR beta and ROR gamma are 1.3, > 10 and 4.5 mu M, respectively. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.023

文献信息

• Development of novel silicon-containing inverse agonists of retinoic acid receptor-related orphan receptors
  作者：Hirozumi Toyama、Masaharu Nakamura、Masahiko Nakamura、Yotaro Matsumoto、Madoka Nakagomi、Yuichi Hashimoto

  DOI：10.1016/j.bmc.2014.01.023

  日期：2014.3

  Retinoic acid receptor (RAR)-related orphan receptors (RORs) regulate a variety of physiological processes, including hepatic gluconeogenesis, lipid metabolism, circadian rhythm and immune function. The RAR agonist: all-trans retinoic acid was reported to be an ROR beta inverse agonist, but no information is available regarding ROR activity of its synthetic analogue Am580. Therefore, we screened Am580 and some related tetramethyltetrahydronaphthalene derivatives and carried out structural development studies, including substitution of carbon atoms with silicon, with the aim of creating a potent ROR transcriptional inhibitor. The phenyl amide disila compound 22 showed the most potent ROR-inhibitory activity among the compounds examined. Its activity towards ROR alpha, ROR beta and ROR gamma was increased compared to that of Am580. The IC50 values for ROR alpha, ROR beta and ROR gamma are 1.3, > 10 and 4.5 mu M, respectively. (C) 2014 Elsevier Ltd. All rights reserved.