1-[5-(Hydroxymethyl)-8-(trifluoromethyl)-1,2,3,5-tetrahydropyrido[2,3-e][1,4]diazepin-4-yl]-2-(3-phenoxyphenyl)ethanone | 1552296-82-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[5-(Hydroxymethyl)-8-(trifluoromethyl)-1,2,3,5-tetrahydropyrido[2,3-e][1,4]diazepin-4-yl]-2-(3-phenoxyphenyl)ethanone
• 英文别名: 1-[5-(hydroxymethyl)-8-(trifluoromethyl)-1,2,3,5-tetrahydropyrido[2,3-e][1,4]diazepin-4-yl]-2-(3-phenoxyphenyl)ethanone
• CAS: 1552296-82-8
• 化学式: C₂₄H₂₂F₃N₃O₃
• 分子量: 457.452
• InChiKey: OYEVKWLJQNICPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.7
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-[5-(Hydroxymethyl)-8-(trifluoromethyl)-1,2,3,5-tetrahydropyrido[2,3-e][1,4]diazepin-4-yl]-2-(3-phenoxyphenyl)ethanone 在 Jones reagent 作用下， 以 二氯甲烷 为溶剂， 以17%的产率得到4-[2-(3-Phenoxyphenyl)acetyl]-8-(trifluoromethyl)-1,2,3,5-tetrahydropyrido[2,3-e][1,4]diazepine-5-carboxylic acid
  参考文献：
  名称：

  Discovery of novel chiral diazepines as bombesin receptor subtype-3 (BRS-3) agonists with low brain penetration

  摘要：

  The discovery and optimization of a novel series of BRS-3 agonists are described. We explored a potent BRS-3 agonist with low brain penetration to avoid an adverse effect derived from central nervous system exposure. Through the derivatization process, chiral diazepines 9f and 9g were identified as possessing low brain penetration as well as potent in vitro activity against human and mouse BRS-3s. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.106
• 作为产物：
  描述：

  2-氯-6-三氟甲基吡啶 在 盐酸 、 sodium tetrahydroborate 、 正丁基锂 、 titanium(IV)isopropoxide 、 三溴化硼 、 二异丙胺 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 生成 1-[5-(Hydroxymethyl)-8-(trifluoromethyl)-1,2,3,5-tetrahydropyrido[2,3-e][1,4]diazepin-4-yl]-2-(3-phenoxyphenyl)ethanone
  参考文献：
  名称：

  Discovery of novel chiral diazepines as bombesin receptor subtype-3 (BRS-3) agonists with low brain penetration

  摘要：

  The discovery and optimization of a novel series of BRS-3 agonists are described. We explored a potent BRS-3 agonist with low brain penetration to avoid an adverse effect derived from central nervous system exposure. Through the derivatization process, chiral diazepines 9f and 9g were identified as possessing low brain penetration as well as potent in vitro activity against human and mouse BRS-3s. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.106

文献信息

• Discovery of novel chiral diazepines as bombesin receptor subtype-3 (BRS-3) agonists with low brain penetration
  作者：Tetsuyoshi Matsufuji、Kousei Shimada、Shozo Kobayashi、Asuka Kawamura、Teppei Fujimoto、Tsuyoshi Arita、Takashi Hara、Masahiro Konishi、Rie Abe-Ohya、Masanori Izumi、Yoshitaka Sogawa、Youko Nagai、Kazuhiro Yoshida、Hisashi Takahashi

  DOI：10.1016/j.bmcl.2013.12.106

  日期：2014.2

  The discovery and optimization of a novel series of BRS-3 agonists are described. We explored a potent BRS-3 agonist with low brain penetration to avoid an adverse effect derived from central nervous system exposure. Through the derivatization process, chiral diazepines 9f and 9g were identified as possessing low brain penetration as well as potent in vitro activity against human and mouse BRS-3s. (C) 2014 Elsevier Ltd. All rights reserved.