methyl 2-hydroxy-7-methoxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-5-carboxylate | 105897-24-3

• 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: methyl 2-hydroxy-7-methoxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-5-carboxylate
• 英文别名: methyl 2-hydroxy-7-methoxy-2-methyl-3-oxo-4H-1,4-benzoxazine-5-carboxylate
• CAS: 105897-24-3
• 化学式: C₁₂H₁₃NO₆
• 分子量: 267.238
• InChiKey: IIKTWLUFEDMXFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-hydroxy-7-methoxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-5-carboxylate 在 甲基磺酰氯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以82%的产率得到巨毛霉素
  参考文献：
  名称：

  Development of benzo[1,4]oxazines as biofilm inhibitors and dispersal agents against Vibrio cholerae

  摘要：

  合成了一系列天然产物启发的生物膜抑制剂库，发现了一种对霍乱弧菌具有选择性和强效抗生物膜活性的化合物。

  DOI：

  10.1039/c4cc07003h
• 作为产物：
  描述：

  methyl 3,5-dimethoxy-2-nitrobenzoate 在 palladium on activated charcoal 盐酸 、 氢气 、 三氯化硼 、 sodium hydride 、 三乙胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 methyl 2-hydroxy-7-methoxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-5-carboxylate
  参考文献：
  名称：

  金霉素生色团降解产物的合成及其衍生物的DNA裂解活性

  摘要：

  描述了抗肿瘤抗生素金霉素及其衍生物的降解产物的合成和金属离子诱导的DNA切割活性。

  DOI：

  10.1016/s0040-4039(00)84256-2

文献信息

• Synthesis of the degradation product of auromomycin chromophore and DNA-cleaving activities of its derivatives
  作者：Masayuki Shibuya、Hiromu Sakurai、Toshio Maeda、Eiji Nishiwaki、Masako Saito

  DOI：10.1016/s0040-4039(00)84256-2

  日期：1986.1

  The syntheses and metallic ion induced DNA-cleaving activities of the degradation product of antitumor antibiotic auromomycin and its derivatives are described.

  描述了抗肿瘤抗生素金霉素及其衍生物的降解产物的合成和金属离子诱导的DNA切割活性。
• Novel small molecule inhibitors of biofilm formation and the novel use of previously identified compounds for inhibition of biofilm formation and applications for drug therapy and medical device coating
  申请人：LININGTON Roger

  公开号：US20160000079A1

  公开（公告）日：2016-01-07

  Novel compounds and the novel use a class of previously identified small molecules for the inhibition of biofilm formation. Inhibition of biofilm formation can play a very important role in contributing to pathogenicity. Bacteria in the biofilm state have been shown to be 10-10,000-fold less susceptible to antibiotic treatment. Estimations made by the Centers for Disease Control (CDC) and the National Institutes of Health (NIH) attribute 65% to 80% of human infections as biofilm mediated. Consequently, biofilm formation is often responsible for chronic infections due to bacterial persistence despite antibiotic treatment.
• US9596855B2
  申请人：——

  公开号：US9596855B2

  公开（公告）日：2017-03-21
• [EN] NOVEL SMALL MOLECULE INHIBITORS OF BIOFILM FORMATION AND THE NOVEL USE OF PREVIOUSLY IDENTIFIED COMPOUNDS FOR INHIBITION OF BIOFILM FORMATION AND APPLICATIONS FOR DRUG THERAPY AND MEDICAL DEVICE COATING<br/>[FR] NOUVEAUX INHIBITEURS À PETITES MOLÉCULES DE LA FORMATION DE BIOFILMS ET NOUVELLE UTILISATION DES COMPOSÉS PRÉCÉDEMMENT IDENTIFIÉS POUR INHIBER LA FORMATION DE BIOFILMS ET APPLICATIONS DE THÉRAPIE MÉDICAMENTEUSE ET DE REVÊTEMENT DE DISPOSITIFS MÉDICAUX
  申请人：LININGTON ROGER

  公开号：WO2014130587A1

  公开（公告）日：2014-08-28

  Novel compounds and the novel use a class of previously identified small molecules for the inhibition of biofilm formation. Inhibition of biofilm formation can play a very important role in contributing to pathogenicity. Bacteria in the biofilm state have been shown to be 10-10,000-fold less susceptible to antibiotic treatment. Estimations made by the Centers for Disease Control (CDC) and the National Institutes of Health (NIH) attribute 65% to 80% of human infections as biofilm mediated. Consequently, biofilm formation is often responsible for chronic infections due to bacterial persistence despite antibiotic treatment.
• Development of benzo[1,4]oxazines as biofilm inhibitors and dispersal agents against Vibrio cholerae
  作者：Christopher J. A. Warner、Andrew T. Cheng、Fitnat H. Yildiz、Roger G. Linington

  DOI：10.1039/c4cc07003h

  日期：——

  Synthesis of a library of natural product-inspired biofilm inhibitors has revealed a compound with selective and potent anti-biofilm activity against V. cholerae.

  合成了一系列天然产物启发的生物膜抑制剂库，发现了一种对霍乱弧菌具有选择性和强效抗生物膜活性的化合物。