7-methoxy-2-thioxo-2,3-dihydro-4H-1,3-benzoxazin-4-one

• 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: 7-methoxy-2-thioxo-2,3-dihydro-4H-1,3-benzoxazin-4-one
• 英文别名: 7-Methoxy-2-sulfanylidene-1,3-benzoxazin-4-one
• 化学式: C₉H₇NO₃S
• 分子量: 209.225
• InChiKey: USSDHSOOEKLCEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  79.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-methoxy-2-thioxo-2,3-dihydro-4H-1,3-benzoxazin-4-one 在 碳酸氢钠 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 4.0h， 生成 L-methyl 2-((7-methoxy-4-oxo-4H-benz[e][1,3]oxazin-2-yl)amino)propanoate
  参考文献：
  名称：

  Synthesis, toxicity and chemo-sensitization of HeLa cells to etoposide, of some 2-methyl amino acid ester-substituted-1,3-benzoxazines

  摘要：

  A number of new L- or LD-2-amino acid ester-(substituted)-benz[1,3]oxazines 12-17 were synthesized from the reaction of free L- or LD-amino acid ester 9a-d with 2-methylthio-1,3-benzoxazines 11a-g. The structures of the new products 12-17 were confirmed from their H-1, (CNMR)-C-13 and IR spectra and CHN microanalysis. Some of these compounds weakly inhibited DNA-PK and platelet aggregation. Studies of the toxicity for some of the new compounds showed mostly no inhibitory effects on HeLa cell growth at 1 and 10 A mu M and some up to 40 A mu M. The chemo-sensitization to etoposide by some of the compounds revealed that the most effective chemo-sensitizers at 10 A mu M were 14c (1.83 fold), 12e (1.42 fold), 15a (0.8 fold), 16d (0.76 fold) and 1c (0.74). However, at 1 A mu M in the presence of etoposide, some compounds were shown to be more effective. No direct link was observed between the type of the L-amino acid methyl ester as well as the 7-, 8-, or 7, 8-substitution on the aromatic ring on the effectiveness of the chemo-sensitizers; however, the 7-hydroxy group did lower the effective chemo-sensitizers values.

  DOI：

  10.1007/s00044-015-1338-4
• 作为产物：
  描述：

  diisothiocyanato(triphenyl)-λ5-phosphane 、 4-甲氧基水杨酸 以 二氯甲烷 为溶剂， 以97%的产率得到7-methoxy-2-thioxo-2,3-dihydro-4H-1,3-benzoxazin-4-one
  参考文献：
  名称：

  使用三苯基膦硫氰从 2-（羟基、硫代或氨基）芳香酸生产 1,3-苯并恶嗪、1,3-苯并噻嗪和喹唑啉衍生物的通用方法

  摘要：

  摘要 开发了一种改进的一锅法合成 1,3-苯并恶嗪，其中省略了不稳定硫氰的制备。发现该方法适用于取代（甲基、甲氧基、卤素和羟基）2-羟基苯甲酸和 2-羟基萘甲酸。该方法扩展到 2-硫代、2-氨基和 N-甲基氨基苯甲酸，分别实现了 1,3-苯并噻嗪和喹唑啉衍生物的合成。还发现使用改进方法的 3-羟基吡啶-2-羧酸和 2-羟基烟酸得到 2-硫代-2,3-二氢-4H-吡啶并[2,3-e][1,3]恶嗪-分别为 4-one 和 2-thioxo-2,3-dihydro-4H-pyrido[3,2-e][1,3]oxazin-4-one。新化合物的结构通过其 IR、1H 和 13C NMR 光谱的分析得到证实。

  DOI：

  10.1081/scc-200061564

文献信息

• Synthesis, identification and antiplatelet evaluation of 2-morpholino substituted benzoxazines
  作者：Kaylene M. Pritchard、Jasim Al-Rawi、Christopher Bradley

  DOI：10.1016/j.ejmech.2007.01.021

  日期：2007.9

  A number of 2-morpholino substituted benzoxazines have been prepared in order to test their effectiveness against ADP and collagen induced platelet aggregation. The reaction of 2-thio-1,3-benzoxazines with morpholine has been generalised to enable the use of substituted benzoxazines. Two separate methods were used to prepare 7-O-2-morpholino substituted benzoxazines from 7-hydroxy-2-morpholino benzoxazines. Antiplatelet testing was carried out on 15 of the title compounds. 7-(2-Chloroethoxy)-8-methyl-2-morpholin-4-yl-4H-1,3-benzoxazin-4-one 15d and 7-[2-(4-methylpiperazin-1-yl)ethoxy]-8-methyl-2-morpholin-4-yl-4H-1,3-benzoxazin-4-one 16d showed potent activity against ADP and collagen induced platelet aggregation. The structures of the newly prepared compounds were confirmed by microanalysis as well as the analysis of IR, H-1 and C-13 NMR. (c) 2007 Elsevier Masson SAS. All rights reserved.