3,4-二氢-2-(2-羟乙基)-3-氧代-2H-1,4-苯并恶嗪 | 161176-99-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 中文名称: 3,4-二氢-2-(2-羟乙基)-3-氧代-2H-1,4-苯并恶嗪
• 英文名称: 3,4-Dihydro-2-(2-hydroxyethyl)-3-oxo-2H-1,4-benzoxazine
• 英文别名: 2-(2-hydroxyethyl)-1,4-benzoxazin-3-one；2-(2-hydroxyethyl)-2H-1,4-benzoxazin-3(4H)-one；2-(2-hydroxyethyl)-4H-1,4-benzoxazin-3-one
• CAS: 161176-99-4
• 化学式: C₁₀H₁₁NO₃
• mdl: MFCD03617589
• 分子量: 193.202
• InChiKey: SELSMKTXYUHOMK-UHFFFAOYSA-N

物化性质

• 熔点：
  72-75 °C(Solv: methanol (67-56-1))
• 沸点：
  415.4±38.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-二氢-2-(2-羟乙基)-3-氧代-2H-1,4-苯并恶嗪 在 咪唑 、 sodium hydroxide 、 三丁基膦 、 sodium hydride 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 15.0h， 生成 Benzeneacetic acid, 2-[2-[3,4-dihydro-3-oxo-4-(5-oxohexyl)-2H-1,4-benzoxazin-2-yl]ethoxy]-
  参考文献：
  名称：

  Benzoxazinones as PPARγ Agonists. 2. SAR of the Amide Substituent and In Vivo Results in a Type 2 Diabetes Model

  摘要：

  A series of benzoxazinones has been synthesized and tested for PPARgamma agonist activity. Synthetic approaches were developed to provide either racemic or chiral compounds. In vitro functional potency could be measured through induction of the aP2 gene, a target of PPARgamma. These studies revealed that compounds with large aliphatic chains at the nitrogen of the benzoxazinone were the most potent. Substitution of the chain was tolerated and in many cases enhanced the in vitro potency of the compound. Select compounds were further tested for metabolic stability, oral bioavailability in rats, and efficacy in db/db mice after 11 days of dosing. In vivo analysis with 13 and 57 demonstrated that the series has potential for the treatment of type 2 diabetes.

  DOI：

  10.1021/jm0301888
• 作为产物：
  描述：

  硝苯酚 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 31.0h， 生成 3,4-二氢-2-(2-羟乙基)-3-氧代-2H-1,4-苯并恶嗪
  参考文献：
  名称：

  The Preparation of 2-Hydroxyethyl-2,3-dihydro-2h-1,4-benzoxazin-3(4h)-one Derivatives

  摘要：

  An efficient synthesis of 2-hydroxyethyl-2,3-dihydro-2H-1,4-benzoxazin-3(4H)one derivatives is described using alpha-bromo-gamma-butyrolactone as a bis-electrophile containing a latent hydroxyethyl functional group.

  DOI：

  10.1080/00397919808004455

文献信息

• [EN] BENZOXAZINE ANTIMICROBIAL AGENTS<br/>[FR] AGENTS ANTIMICROBIENS A BASE DE BENZOXAZINE
  申请人：ORTHO PHARMACEUTICAL CORPORATION

  公开号：WO1997017333A1

  公开（公告）日：1997-05-15

  (EN) The invention relates to benzoxazine and pyrido-oxazine antibacterial compounds of general formula (1), 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.(FR) L'invention porte sur des composés antimicrobiens de benzoxazine et de pyrido-oxazyne de formule générale (1), dans laquelle la fraction Q est une fraction phényle condensée ou pyridyle condensée telle que spécifiée dans la description, des compositions pharmaceutiques contenant ces composés, leurs procédés de fabrication et leur utilisation dans le traitement des infections bactériennes.

  该发明涉及通式（1）的苯并噁唑和吡啶并噁唑抗菌化合物，其中基团Q是如本说明中所述的融合苯基或融合吡啶基团，以及含有这些化合物的制药组合物、其制备方法和在治疗细菌感染中的使用。
• Substituted heterocycles and their use in medicaments
  申请人：Schering Aktiengesellschaft

  公开号：US06191127B1

  公开（公告）日：2001-02-20

  Compounds of Formula I wherein X and R1-6, are as defined herein, tautomeric forms thereof, and isomeric forms thereof, and salts thereof, are suitable for treating diseases that are induced by the action of nitrogen monooxide at pathological concentration. Such diseases include neurodegenerative diseases, inflammatory diseases, auto-immune diseases, and cardiovascular diseases.

  式I的化合物，其中X和R1-6如本文所定义，其互变异构体和同分异构体，以及其盐，适用于治疗由于病理性浓度的一氧化氮作用引起的疾病。这些疾病包括神经退行性疾病、炎症性疾病、自身免疫性疾病和心血管疾病。
• [EN] MPRO TARGETING ANTIVIRAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIVIRAUX CIBLANT LES MPRO
  申请人：EXSCIENTIA AI LTD

  公开号：WO2023180189A1

  公开（公告）日：2023-09-28

  Disclosed are novel viral Mpro inhibitors according to Formula (I), their pharmaceutically acceptable salts, and pharmaceutical compositions thereof. Also disclosed are methods of using such compounds and compositions to inhibit Mpro and/or to treat various viral infections; particularly related to coronavirus. The compounds and compositions of the disclosure may be particularly useful in treating a broad spectrum of coronavirus.

  公开了根据式（I）的新型病毒 Mpro 抑制剂、它们的药学上可接受的盐及其药物组合物。还公开了使用此类化合物和组合物抑制 Mpro 和/或治疗各种病毒感染的方法；特别是与冠状病毒有关的病毒感染。本公开的化合物和组合物在治疗广谱冠状病毒方面可能特别有用。
• [DE] SUBSTITUIERTE HETEROCYCLEN UND DEREN VERWENDUNG IN ARZNEIMITTELN<br/>[EN] SUBSTITUTED HETEROCYCLES AND THEIR USE IN MEDICAMENTS<br/>[FR] HETEROCYCLIQUES SUBSTITUES ET LEUR UTILISATION DANS DES MEDICAMENTS
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：WO1998050372A1

  公开（公告）日：1998-11-12

  (DE) Es werden Verbindungen der Formel (I) beschrieben, deren Herstellung und Verwendung in Arzneimitteln.(EN) The invention relates to compounds of formula (I), to the production of said compounds and their use in medicaments.(FR) L'invention concerne des composés de la formule (I), leur production et leur utilisation dans des médicaments.

  （德）描述了式 (I) 的化合物，及这些化合物的制备和药用用途。（英）本发明涉及式 (I) 化合物，及其制备及其用于医药品。（法）涉及式 (I) 化合物的发明，这些化合物的制备和药用用途。
• Benzoxazinones as PPARγ agonists. part 1: SAR of three aromatic regions
  作者：Philip J. Rybczynski、Roxanne E. Zeck、Donald W. Combs、Ignatius Turchi、Thomas P. Burris、Jun Z. Xu、Maria Yang、Keith T. Demarest

  DOI：10.1016/s0960-894x(03)00401-3

  日期：2003.7

  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.