4-benzyl-3,4-dihydro-2-(2-hydroxyethyl)-3-oxo-2H-1,4-benzoxazine | 106201-23-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 4-benzyl-3,4-dihydro-2-(2-hydroxyethyl)-3-oxo-2H-1,4-benzoxazine
• 英文别名: 4-benzyl-2-(2-hydroxyethyl)-2H-1,4-benzoxazin-3(4H)-one；4-benzyl-2-(2-hydroxyethyl)-1,4-benzoxazin-3-one
• CAS: 106201-23-4
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: QZPGWMCOSDLRNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-benzyl-3,4-dihydro-2-(2-hydroxyethyl)-3-oxo-2H-1,4-benzoxazine 在 sodium hydroxide 、 三丁基膦 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 甲醇 、 苯 为溶剂， 生成 {2-[2-(4-Benzyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl)-ethoxy]-phenyl}-acetic acid
  参考文献：
  名称：

  Benzoxazinones as PPARγ agonists. part 1: SAR of three aromatic regions

  摘要：

  A series of benzoxazinones was synthesized as PPARgamma agonists. The compounds were obtained in seven steps, and SAR was developed by variations to the core shown below. The compounds were tested as functional agonists in the induction of the aP2 gene in preadipocytes, and the most potent compound in the series has an EC50=0.51 muM. The potency was further confirmed through a PPAR-Ga14 construct. Efficacy has been demonstrated in the db/db mouse model of hyperglycemia. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00401-3
• 作为产物：
  描述：

  3,4-二氢-2-(2-羟乙基)-3-氧代-2H-1,4-苯并恶嗪 在 咪唑 、 甲烷磺酸 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-benzyl-3,4-dihydro-2-(2-hydroxyethyl)-3-oxo-2H-1,4-benzoxazine
  参考文献：
  名称：

  Benzoxazinones as PPARγ agonists. part 1: SAR of three aromatic regions

  摘要：

  A series of benzoxazinones was synthesized as PPARgamma agonists. The compounds were obtained in seven steps, and SAR was developed by variations to the core shown below. The compounds were tested as functional agonists in the induction of the aP2 gene in preadipocytes, and the most potent compound in the series has an EC50=0.51 muM. The potency was further confirmed through a PPAR-Ga14 construct. Efficacy has been demonstrated in the db/db mouse model of hyperglycemia. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00401-3

文献信息

• Syntheses of 3,4-dihydro-2H-1,4-benzoxazine-2-acetates and related compounds.
  作者：YUTAKA MASUOKA、TSUNEHIKO(deceased) ASAKO、GIICHI GOTO、SHUNSAKU NOGUCHI

  DOI：10.1248/cpb.34.130

  日期：——

  The intramolecular Michael addition of 4-(2-hydroxyanilino)-2-butenoates (3), -2-buteno-nitrile, and their 3-phenyl analogs (8) gave 3, 4-dihydro-2H-1, 4-benzoxazine-2-acetates (4), -2-acetonitrile (6), and their 3-phenyl analogs (9), respectively, in good yields. In addition, 3, 4-dihydro-3-oxo-2H-1, 4-benzoxazine-2-acetates (13) and 3, 4-dihydro-2-(p-nitrobenzyl)-2H-1, 4-benzoxazine (16) were synthesized from 2-hydroxyanilines (1) by the addition reaction of fumaric acid chloride monoester (11) and p-nitrocinnamyl bromide (14), respectively. In order to examine the biological activities of the 2H-1, 4-benzoxazine analogs, 2-(2-dialkylaminoethyl)-(18) and 2-(2, 2-diphenylethyl)-2H-1, 4-benzoxazines (19, 20) were prepared.Among the compounds synthesized, 4b and 19a showed considerable anxiolytic activity in the conflict test in rats, while the oxalates of 18a-c showed potent anticonvulsant activity.

  4-(2-羟基苯氨基)-2-丁烯酸酯(3)、-2-丁烯腈及其3-苯基类似物(8)的分子内Michael加成反应，分别以良好的产率得到了3,4-二氢-2H-1,4-苯并噁嗪-2-乙酸酯(4)、-2-乙腈(6)及其3-苯基类似物(9)。此外，3,4-二氢-3-氧代-2H-1,4-苯并噁嗪-2-乙酸酯(13)和3,4-二氢-2-(对硝基苄基)-2H-1,4-苯并噁嗪(16)分别通过富马酸氯甲酸单酯(11)和对硝基肉桂基溴(14)的加成反应，从2-羟基苯胺(1)合成得到。为了考察2H-1,4-苯并噁嗪类似物的生物活性，合成了2-(2-二烷基氨基乙基)-(18)和2-(2,2-二苯基乙基)-2H-1,4-苯并噁嗪(19, 20)。在所合成的化合物中，4b和19a在小鼠冲突实验中表现出显著的抗焦虑活性，而18a-c的草酸盐则显示出强效的抗惊厥活性。
• Benzoxazine antimicrobial agents
  申请人：Ortho Pharmaceutical Corporation

  公开号：US05696117A1

  公开（公告）日：1997-12-09

  The invention relates to benzoxazine and pyrido-oxazine antibacterial compounds of the general formula: ##STR1## wherein the moiety Q is a fused phenyl or fused pyridyl moiety as herein described, pharmaceutical compositions containing the compounds, methods for their production and their use in treating bacterial infections.

  该发明涉及一般式为：##STR1##的苯并噁嗪和吡啶噁嗪抗菌化合物，其中基团Q是如本文所述的融合苯或融合吡啶基团，含有这些化合物的药物组合物，其生产方法以及在治疗细菌感染中的应用。
• BENZOXAZINE ANTIMICROBIAL AGENTS
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：EP0869949B1

  公开（公告）日：2002-12-18
• US5696117A
  申请人：——

  公开号：US5696117A

  公开（公告）日：1997-12-09
• US5854242A
  申请人：——

  公开号：US5854242A

  公开（公告）日：1998-12-29