4-oxo-4H-chromene-3-carbothioic acid N-phenylamide | 1170086-89-1

• 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: 4-oxo-4H-chromene-3-carbothioic acid N-phenylamide
• 英文别名: 4-oxo-N-phenylchromene-3-carbothioamide
• CAS: 1170086-89-1
• 化学式: C₁₆H₁₁NO₂S
• 分子量: 281.335
• InChiKey: RKVBVNLAEDZRHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 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：

  1-氨基-4-甲基哌嗪 、 4-oxo-4H-chromene-3-carbothioic acid N-phenylamide 以 乙醇 为溶剂， 反应 2.0h， 以53%的产率得到3-[(4-methylpiperazin-1-yl)imino]methyl-2-phenylamino-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：

  4-oxo-2-(N-phenyl)amino-4H-chromene-3-carbaldehyde 在 硫代苯甲酰胺 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 5.0h， 以70%的产率得到4-oxo-4H-chromene-3-carbothioic acid N-phenylamide
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2009.11.001

文献信息

• Unusual transformations of 3-thiocarbamoylchromones
  作者：Dmitrii Y. Demin、Artem N. Fakhrutdinov、Igor R. Ilyasov、Tatyana K. Baryshnikova、Mikhail M. Krayushkin、Vladimir N. Yarovenko

  DOI：10.1016/j.tetlet.2020.152202

  日期：2020.8

  The reaction of malononitrile with 3-thiocarbamoylchromones was accompanied by rearrangement, resulting in the formation of 2,5-dihydro-1H-chromeno[2,3-b]pyridine-3-carbonitriles or 2-imino-5-oxo-1-phenyl-2,5-dihydro-1H-chromeno[2,3-b]pyridine-3-carbothioamides, depending on the nature of the substituents in the thiocarbamoyl moiety. This reaction sharply differs from the reaction of malononitrile

  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。
• 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
  作者：Tilak Raj、Richa Kaur Bhatia、Rakesh Kumar Sharma、Vivek Gupta、Deepak Sharma、Mohan Paul Singh Ishar

  DOI：10.1016/j.ejmech.2009.03.030

  日期：2009.8

  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.
• 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.
• Synthesis of 2-aminochromone-3-carbaldehyde hydrazones from 3-thiocarbamoylchromones and hydrazines
  作者：D. Yu. Demin、G. М. Rodionova、V. N. Yarovenko、М. М. Krayushkin

  DOI：10.1007/s11172-018-2328-8

  日期：2018.11

  Reaction of 3-thiocarbamoylchromones with hydrazines is accompanied by recyclization affording 2-aminochromone-3-carbaldehyde hydrazones.

  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。