5,6,7,8-四氢-1H-苯并[D][1,3]噁嗪-2,4-二酮 | 108472-08-8

• 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: 5,6,7,8-四氢-1H-苯并[D][1,3]噁嗪-2,4-二酮
• 英文名称: 5,6,7,8-tetrahydro-2H-3,1-benzoxazine-2,4(1H)-dione
• 英文别名: 5,6,7,8-Tetrahydro-1H-benzo[d][1,3]oxazine-2,4-dione；5,6,7,8-tetrahydro-1H-3,1-benzoxazine-2,4-dione
• CAS: 108472-08-8
• 化学式: C₈H₉NO₃
• 分子量: 167.164
• InChiKey: SEMIIYLLPWLNMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  靛红 、 5,6,7,8-四氢-1H-苯并[D][1,3]噁嗪-2,4-二酮 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以14%的产率得到1,2,3,4-Tetrahydroindolo[2,1-b]quinazoline-6,12-dione
  参考文献：
  名称：

  Design, Synthesis, and Structure–Activity Relationship Studies of Tryptanthrins As Antitubercular Agents

  摘要：

  The natural product tryptanthrin (la) represents a potential lead for new tuberculosis (TB) drugs since tryptanthrin and its synthetic analogues possess potent in vitro activity against Mycobacterium tuberculosis (Mtb). However, in spite of their in vitro activity, none of these agents have been shown to be efficacious in vivo against animal models of TB. Described herein are syntheses of new tryptanthrin analogues together with a systematic investigation of their in vitro antitubercular activity and ADME properties followed by pharmacokinetic characterization in rodents for the most promising compounds. Those with the best potency and oral bioavailability were progressed to evaluations of efficacy against acute murine TB. The work aimed to prove the concept that this compound class can limit growth of Mtb during infection as well as to establish the SAR for in vitro activity against Mtb and the range of in vitro ADME parameters for this class of natural products. Novel C-11-deoxy (5b) and A-ring-saturated (6) tryptanthrin analogues were discovered that maintained activity against Mtb and showed improved solubility compared to tryptanthrin as well as evidence of oral bioavailability in rodents. However, neither 5b nor 6 demonstrated efficacy against acute murine TB following administration at doses up to 400 mg/kg daily for 4 weeks. Although 5b and 6 failed to inhibit replication or kill Mtb in vivo, they illuminate a path to new structural variations of the tryptanthrin scaffold that may maximize the potential of this class of compounds against TB.

  DOI：

  10.1021/np3007167
• 作为产物：
  描述：

  4,5,6,7-tetrahydro-1H-benzo[c]isoxazol-3-one 在 硫酸 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 四氯化碳 为溶剂， 反应 3.3h， 生成 5,6,7,8-四氢-1H-苯并[D][1,3]噁嗪-2,4-二酮
  参考文献：
  名称：

  The Vilsmeier-Haack reaction of isoxazolin-5-ones. Synthesis and reactivity of 2-(dialkylamino)-1,3-oxazin-6-ones

  摘要：

  DOI：

  10.1021/jo00391a048

文献信息

• Anti-infective agents
  申请人：——

  公开号：US20040087577A1

  公开（公告）日：2004-05-06

  Compounds having the formula 1 are hepatitis C (HCV) polymerase inhibitors. Also disclosed are a composition and method for inhibiting hepatitis C (HCV) polymerase, processes for making the compounds, and synthetic intermediates employed in the processes.

  具有公式1的化合物是丙型肝炎（HCV）聚合酶抑制剂。还公开了一种用于抑制丙型肝炎（HCV）聚合酶的组成和方法，用于制造这些化合物的过程，以及在这些过程中使用的合成中间体。
• Pyridinone derivatives for treatment of atherosclerosis
  申请人：Hickey Mary Bernadette Deirdre

  公开号：US20050014793A1

  公开（公告）日：2005-01-20

  Compounds of formula (I): are inhibitors of the enzyme L p -PLA 2 and are of use in therapy, in particular for treating atherosclerosis. Compounds of formula (I): are inhibitors of the enzyme Lp-PLA 2 and are of use in therapy, in particular for treating atherosclerosis.

  化学式为（I）的化合物是Lp-PLA2酶的抑制剂，可用于治疗，特别是用于治疗动脉粥样硬化。
• BECCALLI, E. M.;MARCHESINI, A., J. ORG. CHEM., 52,(1987) N 15, 3426-3434
  作者：BECCALLI, E. M.、MARCHESINI, A.

  DOI：——

  日期：——
• ANTI-INFECTIVE AGENTS
  申请人：ABBOTT LABORATORIES

  公开号：EP1560827B1

  公开（公告）日：2010-12-29
• US7235566B2
  申请人：——

  公开号：US7235566B2

  公开（公告）日：2007-06-26