6,7-dichloro-4-oxo-4H-chromene-3-carbothioic acid N-phenylamide | 1170086-95-9

• 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: 6,7-dichloro-4-oxo-4H-chromene-3-carbothioic acid N-phenylamide
• 英文别名: 6,7-dichloro-4-oxo-N-phenylchromene-3-carbothioamide
• CAS: 1170086-95-9
• 化学式: C₁₆H₉Cl₂NO₂S
• 分子量: 350.225
• InChiKey: YKKAHLRTLRKDFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 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：
  3

反应信息

• 作为反应物：
  描述：

  6,7-dichloro-4-oxo-4H-chromene-3-carbothioic acid N-phenylamide 、 丙二腈 在 哌啶 作用下， 以 乙醇 为溶剂， 以80%的产率得到7,8-dichloro-2-imino-5-oxo-1-phenyl-1,5-dihydro-2H-chromeno[2,3-b]pyridine-3-carbonitrile
  参考文献：
  名称：

  3-硫代氨基甲酰基色酮的异常转化

  摘要：

  丙二腈与3-硫代氨基甲酰基色酮的反应伴有重排，导致形成2,5-二氢-1 H-色胺[2,3 - b ]吡啶-3-甲腈或2-亚氨基-5-氧代-1 -苯基-2,5-二氢-1 H-铬[2,3 - b ]吡啶-3-碳硫酰胺，具体取决于硫代氨基甲酰基部分中取代基的性质。该反应与丙二腈与3-氨基甲酰基色酮的反应截然不同，后者产生香豆素-吡啶。

  DOI：

  10.1016/j.tetlet.2020.152202
• 作为产物：
  描述：

  在 硫代苯甲酰胺 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 以72%的产率得到6,7-dichloro-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.