7-fluoro-10H-benzo[b]pyrido[2,3-e][1,4]thiazine | 117326-42-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 7-fluoro-10H-benzo[b]pyrido[2,3-e][1,4]thiazine
• 英文别名: 10H-7-fluoropyrido[3,2-b][1,4]benzothiazine；7-fluoro-10H-pyrido[3,2-b][1,4]benzothiazine
• CAS: 117326-42-8
• 化学式: C₁₁H₇FN₂S
• 分子量: 218.254
• InChiKey: RUQPPYVMKJRGLK-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C(Solv: benzene (71-43-2))
• 沸点：
  392.7±42.0 °C(Predicted)
• 密度：
  1.372±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 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：
  50.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-fluoro-10H-benzo[b]pyrido[2,3-e][1,4]thiazine 、 N-(4-溴丁基)邻苯二甲酰亚胺 在 四丁基溴化铵 、 potassium carbonate 作用下， 反应 0.2h， 以54%的产率得到10-(4-phthalimidobutyl)-7-fluoropyrido[3,2-b][1,4]benzothiazine
  参考文献：
  名称：

  10-(邻苯二甲酰亚胺烷基)-卤代吡啶并[3,2-b][1,4]-苯并噻嗪在干燥介质中的微波辅助合成

  摘要：

  摘要 10H-9-氟吡啶并[3,2-b][1,4]-苯并噻嗪5a、10H-7-氟吡啶并[3,2-b][1,4]-苯并噻嗪5b和10H-的N-烷基化7-氯吡啶并[3,2-b][1,4]-苯并噻嗪5c与不同的N-(溴烷基)邻苯二甲酰亚胺使用无水K2CO3和四丁基溴化铵(TBAB)在干燥条件下微波辐射导致形成10-(邻苯二甲酰亚胺烷基) )-卤代吡啶并[3,2-b][1,4]-苯并噻嗪(6a-f)以及一些不明产物。化合物5a是一种新的氮杂吩噻嗪衍生物，是从迄今为止未知的2-乙酰氨基-3-氟苯基-3'-硝基-2'-吡啶基硫醚4a通过Smiles重排获得的。化合物 4a 是合成所必需的，它是从 2-氨基-3-氟苯硫醇 1a 开始分三步制备的。

  DOI：

  10.1080/00397910701575533
• 作为产物：
  描述：

  2-amino-5-fluorophenyl-3'-nitro-2'-pyridylsulfide 在 potassium hydroxide 作用下， 以 丙酮 为溶剂， 生成 7-fluoro-10H-benzo[b]pyrido[2,3-e][1,4]thiazine
  参考文献：
  名称：

  Synthesis and antimicrobial activity of novel bis-azaphenothiazines

  摘要：

  N-alkylation of azaphenothiazines using dibromoalkanes or dibromoalkenes did not result in the formation of bis-azaphenothiazines under known conditions such as refluxing, for more than 100 h, with NaNH2/xylene or NaH/toluene. However, when the same reaction was tried with NaH/DMF at -5 A degrees C to r.t., it yielded the desired product in 68-71 % yield. These novel bis-azaphenothiazines containing a suitable alkyl or alkenyl spacer were found to possess moderate to significant antimicrobial activities against three gram positive bacteria (Staphylococcus aureus, Bacillus subtilis, and Staphylococcus epidermis), four gram negative bacteria (Escherichia coli, Pseudomonas aeruginosa, Salmonella typhi, and Klebsiella pneumoniae) as well as four fungi (Aspergillus niger, Aspergillus fumigatus, Aspergillus flavus, and Candida albicans). Compounds 2b-d were found to exhibit strong antifungal activity, comparable to the standard drug miconazole against A. niger and A. fumigatus.

  DOI：

  10.1007/s00044-012-0454-7

文献信息

• Novel aminoalkylated azaphenothiazines as potential inhibitors of T98G, H460 and SNU80 cancer cell lines in vitro
  作者：Khushbu Kushwaha、Nagendra Kumar Kaushik、Neha Kaushik、Mahesh Chand、Reena Kaushik、Eun ha Choi、Subhash C. Jain

  DOI：10.1016/j.bmcl.2016.03.056

  日期：2016.5

  A set of twenty-one novel aminoalkylated azaphenothiazines is synthesized using a two-step methodology starting from azaphenothiazines. The key step was the selective monoalkylation at position 10 of azaphenothiazines. In all, twenty-five molecules, including intermediates, were investigated for their in vitro anticancer activity, of which fourteen azaphenothiazines (2b, 3a, 3c, 3d, 3e-h, 3j, 3n, 3o, 3p, 3s, and 3u) were found to decrease the metabolic viability and growth of the T98G, H460 and SNU80 cancer cells effectively in a dose-dependent manner. In silico, pharmacokinetic studies suggest that these molecules have good bioavailability, water solubility and other drug-like parameters. Compounds 3a, 3c and 3g were identified as the leading molecules for future investigation due to their (a) high activity against T98G brain, H460 lung and SNU80 thyroid cancer cells; (b) low cytotoxicity with regard to non-malignant HEK293 and MRC5 cells; (c) low toxic risk levels based on in vitro and in silico evaluations; (d) good theoretical oral bioavailability according to Lipinski 'rule of five' pharmacokinetic parameters; and (e) better drug-likeness and drug-score values. (C) 2016 Published by Elsevier Ltd.
• TANEJA, POONAM;KHATRI, VINCETA;PRAKASH, LALIT;MITAL, R. L., ACTA CIEN. INDICA. CHEM., 13,(1987) N, C. 118-122
  作者：TANEJA, POONAM、KHATRI, VINCETA、PRAKASH, LALIT、MITAL, R. L.

  DOI：——

  日期：——
• MITAL, R. L.;TANEJA, POONAM;KHATRI, VINEETA;PRAKASH, LALIT, REV. ROUM. CHIM., 33,(1988) N 5, C. 463-465
  作者：MITAL, R. L.、TANEJA, POONAM、KHATRI, VINEETA、PRAKASH, LALIT

  DOI：——

  日期：——