2-thioxo-2,3-dihydro-4H-naphtho[2,3-e][1,3]oxazin-4-one | 69894-93-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-thioxo-2,3-dihydro-4H-naphtho[2,3-e][1,3]oxazin-4-one
• 英文别名: 2-thioxo-2,3-dihydro-naphtho[2,3-e][1,3]oxazin-4-one；2-Sulfanylidene-2,3-dihydro-4H-naphtho[2,3-e][1,3]oxazin-4-one；2-sulfanylidenebenzo[g][1,3]benzoxazin-4-one
• CAS: 69894-93-5
• 化学式: C₁₂H₇NO₂S
• 分子量: 229.259
• InChiKey: YHJCLEPNQGXTLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  吗啉 、 2-thioxo-2,3-dihydro-4H-naphtho[2,3-e][1,3]oxazin-4-one 以 1,4-二氧六环 为溶剂， 以72%的产率得到2-Morpholino-2H-naphth<2,1-c><1,3>oxazin-4-on
  参考文献：
  名称：

  Synthesis, structural elucidation, DNA-PK inhibition, homology modelling and anti-platelet activity of morpholino-substituted-1,3-naphth-oxazines

  摘要：

  A number of new angular 2-morpholino-(substituted)-naphth-1,3-oxazines (compound 10b), linear 2-morpholino-(substituted)-naphth-1,3-oxazines (compounds 13b-c), linear 6, 7 and 9-0-substituted-2-morpholino-(substituted)-naphth-1,3-oxazines (compounds 17-22, 24, and 25) and angular compounds 14-16 and 23 were synthesised. The O-substituent was pyridin-2yl-methyl (15, 18, and 21) pyridin-3yl-methyl (16, 19, and 22) and 4-methylpipreazin-1-yl-ethoxy (23-25). Twelve compounds were tested for their inhibitory effect on collagen induced platelet aggregation and it was found that the most active compounds were compounds 19 and 22 with IC(50) = 55 +/- 4 and 85 +/- 4 mu M, respectively. Furthermore, the compounds were also assayed for their ability to inhibit DNA-dependent protein kinase (DNA-PK) activity. The most active compounds were 18 IC(50) = 0.091 mu M, 24 IC(50) = 0.191 mu M, and 22 IC(50) = 0.331 mu M.Homology modelling was used to build a 3D model of DNA-PK based on the X-ray structure of phosphatidylinositol 3-kinases (PI3Ks). Docking of synthesised compounds within the binding pocket and structure-activity relationships (SAR) analyses of the poses were performed and results agreed well with observed activity. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.032
• 作为产物：
  描述：

  2-羟基-3-萘甲酸 以51%的产率得到
  参考文献：
  名称：

  TAMURA Y.; KAWASAKI T.; TANIO M.; KITA Y., CHEM. AND IND., 1978, NO 20, 806-807

  摘要：

  DOI：

文献信息

• Generalized Method for the Production of 1,3‐Benzoxazine, 1,3‐Benzothiazine, and Quinazoline Derivatives from 2‐(Hydroxy, Thio, or Amino) Aromatic Acids Using Triphenylphosphine Thiocyanogen
  作者：Kaylene M. Pritchard、Jasim M. Al‐Rawi、Andrew B. Hughes

  DOI：10.1081/scc-200061564

  日期：2005.6.1

  derivatives has been achieved, respectively. It was also found that 3‐hydroxypyridine‐2‐carboxylic acid and 2‐hydroxynicotinic acid using a modified method gave 2‐thioxo‐2,3‐dihydro‐4H‐pyrido[2,3‐e][1,3]oxazin‐4‐one and 2‐thioxo‐2,3‐dihydro‐4H‐pyrido[3,2‐e][1,3]oxazin‐4‐one, respectively. The structures of the new compounds were confirmed by the analysis of their IR, 1H, and 13C NMR spectra.

  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。
• Synthesis, structural elucidation, DNA-PK inhibition, homology modelling and anti-platelet activity of morpholino-substituted-1,3-naphth-oxazines
  作者：Saleh Ihmaid、Jasim Al-Rawi、Christopher Bradley、Michael J. Angove、Murray N. Robertson、Rachel L. Clark

  DOI：10.1016/j.bmc.2011.05.032

  日期：2011.7

  A number of new angular 2-morpholino-(substituted)-naphth-1,3-oxazines (compound 10b), linear 2-morpholino-(substituted)-naphth-1,3-oxazines (compounds 13b-c), linear 6, 7 and 9-0-substituted-2-morpholino-(substituted)-naphth-1,3-oxazines (compounds 17-22, 24, and 25) and angular compounds 14-16 and 23 were synthesised. The O-substituent was pyridin-2yl-methyl (15, 18, and 21) pyridin-3yl-methyl (16, 19, and 22) and 4-methylpipreazin-1-yl-ethoxy (23-25). Twelve compounds were tested for their inhibitory effect on collagen induced platelet aggregation and it was found that the most active compounds were compounds 19 and 22 with IC(50) = 55 +/- 4 and 85 +/- 4 mu M, respectively. Furthermore, the compounds were also assayed for their ability to inhibit DNA-dependent protein kinase (DNA-PK) activity. The most active compounds were 18 IC(50) = 0.091 mu M, 24 IC(50) = 0.191 mu M, and 22 IC(50) = 0.331 mu M.Homology modelling was used to build a 3D model of DNA-PK based on the X-ray structure of phosphatidylinositol 3-kinases (PI3Ks). Docking of synthesised compounds within the binding pocket and structure-activity relationships (SAR) analyses of the poses were performed and results agreed well with observed activity. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.
• TAMURA Y.; KAWASAKI T.; TANIO M.; KITA Y., CHEM. AND IND., 1978, NO 20, 806-807
  作者：TAMURA Y.、 KAWASAKI T.、 TANIO M.、 KITA Y.

  DOI：——

  日期：——