N,5,5,8,8-pentamethyl-6,7-dihydronaphthalene-2-carboxamide | 146772-35-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,5,5,8,8-pentamethyl-6,7-dihydronaphthalene-2-carboxamide
• CAS: 146772-35-2
• 化学式: C₁₆H₂₃NO
• 分子量: 245.365
• InChiKey: XBLWURJSGAVUMC-UHFFFAOYSA-N

物化性质

• 沸点：
  345.6±31.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 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 、 甲胺 在 N-羟基丁二酰亚胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N,5,5,8,8-pentamethyl-6,7-dihydronaphthalene-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

• PHENYLPROPIONIC ACID DERIVATIVE AND USE THEREOF
  申请人：MORITA Kohei

  公开号：US20100093819A1

  公开（公告）日：2010-04-15

  A compound represented by the following general formula (1) or a salt thereof, which has superior inhibitory activity against type 4 PLA 2 , and thus has prostaglandin and/or leucotriene production suppressing action [X represents a halogen atom, an alkyl group which may be substituted, or the like, Y represents hydrogen atom or an alkyl group which may be substituted, and Z represents hydrogen atom or an alkyl group which may be substituted].

  由以下一般式（1）表示的化合物或其盐，具有优越的抑制对4型PLA2的活性，因此具有前列腺素和/或白三烯产生抑制作用【X代表卤素原子、可能被取代的烷基或类似物，Y代表氢原子或可能被取代的烷基，Z代表氢原子或可能被取代的烷基】。
• US8334314B2
  申请人：——

  公开号：US8334314B2

  公开（公告）日：2012-12-18
• US8772327B2
  申请人：——

  公开号：US8772327B2

  公开（公告）日：2014-07-08
• 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.