1-(3-carbonyl-2H-2-oxobenzo[b]pyran-3-yl)-4-phenyl thiosemicarbazide | 223763-44-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 1-(3-carbonyl-2H-2-oxobenzo[b]pyran-3-yl)-4-phenyl thiosemicarbazide
• 英文别名: 1-coumarin-3-oyl-4-phenyl-3-thiosemicarbazide；1-[(2-Oxochromene-3-carbonyl)amino]-3-phenylthiourea
• CAS: 223763-44-8
• 化学式: C₁₇H₁₃N₃O₃S
• 分子量: 339.375
• InChiKey: SDDOYQSIIUVELT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 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：
  112
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-carbonyl-2H-2-oxobenzo[b]pyran-3-yl)-4-phenyl thiosemicarbazide 在 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 N-methyl-N-[5-(2H-2-oxobenzo[b]pyran-3-yl)-1,3,4-thiadiazol-2-yl]aniline
  参考文献：
  名称：

  含桥头氮原子的杂环合成：合成 3-[(2H)-2-oxobenzo[b]pyran-3-yl]-s-triazolo[3,4-b]-1,3,4-thiadiaazine 和 thiazole 衍生物

  摘要：

  2H-2-氧代苯并[b]吡喃-3-酰肼(2)与二硫化碳在碱性DMF中反应生成硫代氨基甲酸钾3，其与肼和/或苯甲酰溴反应后容易发生杂环化生成1,2，分别为 4-噻唑 (4) 和噻唑 7 衍生物。4 与取代的苯甲酰溴和/或氯苯醌缩合得到 1,2,4-三唑 [3,4-b] 噻二嗪 (5a,b) 和 3,10-双-[2H-2-氧代苯并[b]吡喃- 3-基]-6,13-​​二氯-双-1,2,4-三唑并[3,4-b]-1,3,4-噻二嗪并[5',6'-b:5',6'- e]环己-1,4-二烯(6)，分别。通过在氢氧化钠和/或磷酰氯中回流使氨基硫脲 10 环化，分别得到三唑 13 和噻二唑 15 衍生物。此外，10在无水乙酸钠存在下与苯甲酰溴反应得到氧噻唑烷衍生物17。合成化合物的结构通过元素分析、IR、1H NMR和质谱证实。© 2003 Wiley Periodicals, Inc. 杂原子化学 14:114–120

  DOI：

  10.1002/hc.10109
• 作为产物：
  描述：

  香豆素-3-羧酸乙酯 在 一水合肼 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 3.0h， 生成 1-(3-carbonyl-2H-2-oxobenzo[b]pyran-3-yl)-4-phenyl thiosemicarbazide
  参考文献：
  名称：

  含桥头氮原子的杂环合成：合成 3-[(2H)-2-oxobenzo[b]pyran-3-yl]-s-triazolo[3,4-b]-1,3,4-thiadiaazine 和 thiazole 衍生物

  摘要：

  2H-2-氧代苯并[b]吡喃-3-酰肼(2)与二硫化碳在碱性DMF中反应生成硫代氨基甲酸钾3，其与肼和/或苯甲酰溴反应后容易发生杂环化生成1,2，分别为 4-噻唑 (4) 和噻唑 7 衍生物。4 与取代的苯甲酰溴和/或氯苯醌缩合得到 1,2,4-三唑 [3,4-b] 噻二嗪 (5a,b) 和 3,10-双-[2H-2-氧代苯并[b]吡喃- 3-基]-6,13-​​二氯-双-1,2,4-三唑并[3,4-b]-1,3,4-噻二嗪并[5',6'-b:5',6'- e]环己-1,4-二烯(6)，分别。通过在氢氧化钠和/或磷酰氯中回流使氨基硫脲 10 环化，分别得到三唑 13 和噻二唑 15 衍生物。此外，10在无水乙酸钠存在下与苯甲酰溴反应得到氧噻唑烷衍生物17。合成化合物的结构通过元素分析、IR、1H NMR和质谱证实。© 2003 Wiley Periodicals, Inc. 杂原子化学 14:114–120

  DOI：

  10.1002/hc.10109

文献信息

• Uses of 1-Cyanoacetyl-4-phenyl-3-thiosemicarbazide in Heterocyclic Synthesis: Synthesis of Thiazole, Coumarin, and Pyridine Derivatives with Antimicrobial and Antifungal Activities
  作者：Rafat M. Mohareb、Jonathan Z. Ho、Abeer A. Mohamed

  DOI：10.1080/10426500701289914

  日期：2007.6.14

  The reaction of cyanoacetyl hydrazine with phenylisothiocyanate gave the thiosemicarbazide 3. The latter underwent a series of heterocyclization reactions when it reacts with either aromatic aldehydes or alpha-haloketones, follwed by further reaction of the products with cyanomethylene reagents or hydrazines to give either thiazole, coumarin, or pyridine derivatives. The newly synthesized product showed antimicrobial and antifungal activities.
• Synthesis and biological evaluation of 2,5-disubstituted 1,3,4-oxadiazole derivatives with both COX and LOX inhibitory activity
  作者：Mymoona Akhter、Nayeema Akhter、M. M. Alam、M. S. Zaman、Rikta Saha、A. Kumar

  DOI：10.3109/14756366.2010.550890

  日期：2011.12.1

  Dual cyclooxygenase/lipoxygenase (COX/LOX) inhibitors constitute a valuable alternative to classical nonsteroidal anti-inflammatory drugs (NSAIDs) and selective COX-2 inhibitors for the treatment of inflammatory diseases. A series of 3-(5-phenyl/phenylamino-[1,3,4]oxadiazol-2-yl)-chromen-2-one and N-[5-(2-oxo-2H-chromen-3-yl)-[1,3,4] oxadiazol-2-yl]-benzamide derivatives were synthesized and screened for anti-inflammatory, analgesic activity. All the derivatives prepared are active in inhibiting oedema induced by carrageenan. Compound 4e was found more potent with 89% of inhibition followed by compound 4b (86%). Compounds with >70% of anti-inflammatory activity were tested for analgesic, ulcerogenic, and lipid peroxidation profile. Selected compounds were also evaluated for inhibition of COXs (COX-1 and COX-2) and LOXs (LOX-5, LOX-12, and LOX-15). Compound 4e was comparatively selective for COX-2, LOX-5, and LOX-15. Study revealed that these derivatives were more effective than ibuprofen with reduced side effects. It can be suggested that these derivatives could be used to develop more potent and safer NSAIDs.
• Bhalla; Shukla; Gujrati, Bollettino Chimico Farmaceutico, 1998, vol. 137, # 10, p. 403 - 411
  作者：Bhalla、Shukla、Gujrati、Saxena、Sanger、Shanker

  DOI：——

  日期：——