7-羟基-2H-苯并[b][1,4]噁嗪-3(4H)-酮 | 67193-97-9

• 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: 7-羟基-2H-苯并[b][1,4]噁嗪-3(4H)-酮
• 中文别名: 7-羟基-4H-苯并[1,4]恶嗪-3-酮；7-羟基-2H-苯并[b][1,4]恶嗪-3(4H)-酮
• 英文名称: 7-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one
• 英文别名: 7-hydroxy-4H-1,4-benzoxazin-3-one
• CAS: 67193-97-9
• 化学式: C₈H₇NO₃
• mdl: MFCD11878414
• 分子量: 165.148
• InChiKey: GAHMCUIGTHMIFD-UHFFFAOYSA-N

物化性质

• 熔点：
  208-209℃
• 密度：
  1.396

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  7-羟基-2H-苯并[b][1,4]噁嗪-3(4H)-酮 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3,4-二氢-2H-苯并[1,4]恶嗪-7-醇
  参考文献：
  名称：

  Novel 2,3-Dihydro-1,4-Benzoxazines as Potent and Orally Bioavailable Inhibitors of Tumor-Driven Angiogenesis

  摘要：

  Angiogenesis is vital for solid tumor growth, and its prevention is a proven strategy for the treatment of disease states such as cancer. The vascular endothelial growth factor (VEGF) pathway provides several opportunities by which small molecules can act as inhibitors of endothelial proliferation and migration. Critical to these processes is signaling through VEGFR-2 or the kinase insert domain receptor (KDR) upon stimulation by its ligand VEGF. Herein, we report the discovery of 2,3-dihydro-1,4-benzoxazines as inhibitors of intrinsic KDR activity (IC 50 < 0.1 microM) and human umbilical vein endothelial cell (HUVEC) proliferation with IC 50 < 0.1 microM. More specifically, compound 16 was identified as a potent (KDR: < 1 nM and HUVEC: 4 nM) and selective inhibitor that exhibited efficacy in angiogenic in vivo models. In addition, this series of molecules is typically well-absorbed orally, further demonstrating the 2,3-dihydro-1,4-benzoxazine moiety as a promising platform for generating kinase-based antiangiogenic therapeutic agents.

  DOI：

  10.1021/jm701129j
• 作为产物：
  描述：

  2-硝基-5-溴苯酚 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 水 、 双氧水 、 potassium acetate 、 氯化铵 、 caesium carbonate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 乙醇 、 乙腈 为溶剂， 反应 6.5h， 生成 7-羟基-2H-苯并[b][1,4]噁嗪-3(4H)-酮
  参考文献：
  名称：

  Discovery of anilinopyrimidine-based naphthamide derivatives as potent VEGFR-2 inhibitors

  摘要：

  血管内皮生长因子受体-2（VEGFR-2）在肿瘤血管生成中发挥重要作用，抑制VEGFR-2信号通路已成为治疗癌症的一种吸引人的策略。

  DOI：

  10.1039/c5md00191a

文献信息

• Phenyl and heterocyclic tetrahydropyridyl alkoxy-benzheterocyclic
  申请人：Warner-Lambert Company

  公开号：US04704390A1

  公开（公告）日：1987-11-03

  Novel phenyl and heterocyclic tetrahydropyridyl and piperazinyl alkoxy benzheterocyclic compounds are described which have valuable neuroleptic properties by virtue of their dopamine autoreceptor agonist activity. Methods of preparation, pharmaceutical compositions, and methods for treating psychoses, such as schizophrenia, are also described.

  描述了具有有价值的神经阻滞特性的新型苯基和杂环四氢吡啶基和哌嗪基烷氧基苯杂环化合物，这是由于它们的多巴胺自受体激动剂活性。还描述了制备方法、药物组合物以及治疗精神病，如精神分裂症的方法。
• [EN] ANTI-NEOPLASTIC COMPOUNDS, COMPOSITIONS AND METHODS<br/>[FR] COMPOSÉS ANTINÉOPLASIQUES, COMPOSITIONS ET PROCÉDÉS
  申请人：PROGENRA INC

  公开号：WO2010114881A1

  公开（公告）日：2010-10-07

  Disclosed are novel compounds which are useful as therapeutics, especially in anti-neoplastic therapy and in other therapeutic regimes where cysteine protease inhibition is implicated.

  公开的是新型化合物，这些化合物在治疗上具有用途，特别是在抗肿瘤治疗和其他涉及半胱氨酸蛋白酶抑制的治疗方案中。
• [EN] A COMPOUND AS A THYROID HORMONE BETA RECEPTOR AGONIST AND USE THEREOF<br/>[FR] COMPOSÉ UTILISÉ COMME AGONISTE DU RÉCEPTEUR BÊTA DES HORMONES THYROÏDIENNES ET SON UTILISATION
  申请人：SUNSHINE LAKE PHARMA CO LTD

  公开号：WO2021043185A1

  公开（公告）日：2021-03-11

  Provided herein is a compound as a thyroid hormone β receptor agonist and use thereof. It further relates to a pharmaceutical composition comprising the compound. The compound or the pharmaceutical composition can be used in the manufacture of a medicament for preventing, treating or alleviating diseases regulated by thyroid hormone β receptors, especially in the manufacture of a medicament for treating non-alcoholic fatty liver disease.

  本文提供了一种作为甲状腺激素β受体激动剂的化合物及其使用。它进一步涉及包含该化合物的药物组合物。该化合物或药物组合物可用于制造用于预防、治疗或缓解由甲状腺激素β受体调节的疾病的药物，特别是用于制造治疗非酒精性脂肪肝病的药物。
• Therapeutic diphenyl ether ligands
  申请人：Fliri J. Anton

  公开号：US20060058361A1

  公开（公告）日：2006-03-16

  This invention is directed to compounds of formula Ia, Ib or Ic and to pharmaceutical compositions thereof: or a prodrug thereof and a pharmaceutically acceptable carrier, wherein the R groups are defined in the specification; and, in which the dashed line represents an optional double bond. The invention is also directed to methods of treating, diagnosing, and preventing disorders of the central nervous system that are associated with 5HT receptors, including obesity, attention deficit disorder, migraine, depression, epilepsy, anxiety, Alzheimer's disease, withdrawal from drug abuse, pain, schizophrenia, stress-related disorders, panic disorder, sleep disorders, phobias, obsessive compulsive disorder, post-traumatic-stress syndrome, immune system depression, stress-induced gastrointestinal dysfunction, stress-induced cardiovascular dysfunction, and sexual dysfunction.

  该发明涉及式Ia、Ib或Ic的化合物，以及其药物组成物：或其前药和药用可接受载体，其中R基在规范中定义；以及虚线代表可选的双键。该发明还涉及治疗、诊断和预防与5HT受体相关的中枢神经系统疾病的方法，包括肥胖、注意缺陷障碍、偏头痛、抑郁症、癫痫、焦虑、阿尔茨海默病、戒毒、疼痛、精神分裂症、应激相关疾病、恐慌症、睡眠障碍、恐惧症、强迫症、创伤后应激综合征、免疫系统抑郁、应激引起的胃肠功能障碍、应激引起的心血管功能障碍和性功能障碍。
• Anti-inflammatory properties of a series of phenyl- and phenoxy-alkanoic acids
  作者：D J Drain、M J Daly、B Davy、M Horlington、J G B Howes、J M Scruton、R A Selway

  DOI：10.1111/j.2042-7158.1970.tb12754.x

  日期：2012.1.25

  Some o-benzamidophenoxyacetic, phenylalkanoic and phenoxyalkanoic acids have been synthesized. Anti-inflammatory activity was measured by the phenylbenzoquinone writhing test in mice and the rat foot oedema test. Meta- and para-substitutions in the benzamido-ring, promoting lipid solubility, enhanced the potency, whereas substitution with polar groups reduced it. Further phenylring substitution in the 2-(3,4-dichlorobenzamido)phenoxyacetic acids only slightly affected the potency. Side-chain modifications did not increase the activity on the three substituted phenoxyacetic acids chosen. Two phenylpropionic acids showed a good order of activity but the respective cinnamic acids were virtually inactive. From the investigations 2-(3,4-dichlorobenzamido)phenoxyacetic acid (SNR. 1804) was selected for further studies is now undergoing clinical evaluation.

  摘要：已合成一些o-苯甲酰基苯氧乙酸、苯基烷酸和苯氧烷酸。通过小鼠苯基苯醌扭曲实验和大鼠足部水肿实验测量了抗炎活性。苯甲酰环中的间位和对位取代，促进了脂溶性，增强了效力，而用极性基团取代则降低了效力。在2-(3,4-二氯苯甲酰胺)苯氧乙酸中进一步取代苯环仅稍微影响了效力。侧链修饰并未增加所选的三种取代苯氧乙酸的活性。两种苯丙酸显示出良好的活性顺序，但相应的肉桂酸几乎无活性。从研究中选择了2-(3,4-二氯苯甲酰胺)苯氧乙酸（SNR. 1804）进行进一步研究，目前正在进行临床评估。