6-fluoro-4-oxo-4H-chromene-3-carbothioic acid N-phenylamide | 1170086-91-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-fluoro-4-oxo-4H-chromene-3-carbothioic acid N-phenylamide
• 英文别名: 6-fluoro-4-oxo-N-phenylchromene-3-carbothioamide
• CAS: 1170086-91-5
• 化学式: C₁₆H₁₀FNO₂S
• 分子量: 299.325
• InChiKey: IUPWSWUIAQAWIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  2
• 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：
  4

反应信息

• 作为反应物：
  描述：

  6-fluoro-4-oxo-4H-chromene-3-carbothioic acid N-phenylamide 、 苯肼 以 乙醇 为溶剂， 反应 3.0h， 以37%的产率得到6-fluoro-2-phenylamino-3-[(2-phenylhydrazono)methyl]-4H-chromen-4-one
  参考文献：
  名称：

  3-硫代氨基甲酰基色酮和肼合成 2-氨基色酮-3-甲醛腙

  摘要：

  3-硫代氨基甲酰基色酮与肼的反应伴随着再循环，得到 2-氨基色酮-3-甲醛腙。

  DOI：

  10.1007/s11172-018-2328-8
• 作为产物：
  描述：

  2-Anilino-6-fluoro-4-oxochromene-3-carbaldehyde 在 硫代苯甲酰胺 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 以76%的产率得到6-fluoro-4-oxo-4H-chromene-3-carbothioic acid N-phenylamide
  参考文献：
  名称：

  Mechanism of unusual formation of 3-(5-phenyl-3H-[1,2,4]dithiazol-3-yl)chromen-4-ones and 4-oxo-4H-chromene-3-carbothioic acid N-phenylamides and their antimicrobial evaluation

  摘要：

  6/6,7-Substituted 3-formylchromones (9a-e) react with 2 equivalents of 2-phenyl-4-dimethylamino-1-thia-3-azabuta-1,3-diene (10) or thiobenzamide (11) in refluxing toluene to furnish novel substituted 3-(5-phenyl-3H-[1,2,4]dithiazol-3-yl)chromen-4-ones (12a-e). However, reactions of substituted 2-anilino-3-formylchromones (15a-d) with thiobenzamide (11, 2 equivalents) in refluxing xylene furnish 4-oxo-4H-chromene-3-carbothioic acid N-phenylamide (17a-d) in high yields. A mechanistic rationalization of the conversion of 2-anilino-3-formylchromones (15a-d) to N-phenylamides (17a-d), and 3-formylchromones (9a-e) to the corresponding thioaldehydes, is proffered. All the compounds (12a-e, 17a-d) display very high antifungal and antibacterial activities against a number of strains. Dithiazole 12d exhibits a very high antifungal activity (MIC 5 mu g/ml) against Geotrichum candidum, better than fluconazole (MIC 09 mu g/ml) and also possesses good antibacterial activity (MIC 52 mu g/ml) against Shigella flexneri. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.03.030

文献信息

• Cytotoxic activity of 3-(5-phenyl-3 H -[1,2,4]dithiazol-3-yl)chromen-4-ones and 4-oxo-4 H -chromene-3-carbothioic acid N -phenylamides
  作者：Tilak Raj、Richa Kaur Bhatia、Ashish kapur、Madhunika Sharma、A.K. Saxena、M.P.S. Ishar

  DOI：10.1016/j.ejmech.2009.11.001

  日期：2010.2

  6/6,7-Substituted-3-formylchromones (8a-g) were reacted with 2 equivalents thiobenzamide (9) in refluxing toluene to furnish substituted -3-(5-phenyl-3H-[1,2,4]dithiazol-3-yl)chromen-4-ones (10a-g) in high yields. Similarly, when substituted-2-anilino-3-formylchromones (8a-d) were reacted with thiobenzamide (9, 2 equivalents) in refluxing xylene, 4-oxo-4H-chromene-3-carbothioic acid N-phenylamides (11a-d) were obtained in high yields. All the compounds (10a-g) and (11a-d) display significant cytotoxic activity against a number of human cancer cell lines. Among these compounds 10e (IC50 = 10 mu M), 10b (IC50 = 14.6 mu M) and 10a (IC50 = 10.5 mu M) showed maximum cytotoxic activity on neuroblastoma. Also, the compound 10c (IC50 = 10.5 mu M) showed maximum cytotoxic activity on ovarian cancer cell line. (C) 2009 Elsevier Masson SAS. All rights reserved.