8-bromo-3-(2-bromoacetyl)-2H-chromen-2-one

• 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: 8-bromo-3-(2-bromoacetyl)-2H-chromen-2-one
• 英文别名: 8-Bromo-3-(2-bromoacetyl)chromen-2-one
• 化学式: C₁₁H₆Br₂O₃
• 分子量: 345.975
• InChiKey: PNUFTEGTGSJWQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-bromo-3-(2-bromoacetyl)-2H-chromen-2-one 在 吡啶 、 盐酸 、 氨 作用下， 以 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.17h， 生成 N-[4-(8-bromo-2-oxochromen-3-yl)-1,3-thiazol-2-yl]acetamide
  参考文献：
  名称：

  Ramanna, S.; Rao, V. Rajeswar; Kumari, T. Surya, Phosphorus, Sulfur and Silicon and the Related Elements, 1995, vol. 107, # 1-4, p. 197 - 204

  摘要：

  DOI：

文献信息

• One-pot synthesis of trisubstituted pyrazoles via multicomponent approach
  作者：P. Santhosh、V. S. R. Chunduru、V. Rajeswar Rao

  DOI：10.1007/s10593-011-0779-z

  日期：2011.7

  An efficient one-pot multicomponent reaction for the synthesis of 1-aryl- or 1-heteryl-substituted 3,5-dimethylpyrazoles with excellent yields has been described. Reaction of 3-(2-bromoacetyl)coumarins or phenacyl bromides with acetylacetone and hydrazine hydrate in ethanol afforded the corresponding 3,5-dimethylpyrazoles in good yields. All the synthesized compounds were characterized by their analytical

  已经描述了以优异的产率合成1-芳基-或1-杂基-取代的3，5-二甲基吡唑的有效的一锅多组分反应。3-（2-溴乙酰基）香豆素或苯甲酰溴与乙酰丙酮和肼水合物在乙醇中的反应以良好的产率得到了相应的3,5-二甲基吡唑。所有合成的化合物均以其分析和光谱数据为特征。
• 1,2,3-triazole-thiazole hybrids: Synthesis, in vitro antimicrobial activity and antibiofilm studies
  作者：Ramesh Gondru、Sirisha Kanugala、Sneha Raj、C Ganesh Kumar、Mukesh Pasupuleti、Janardhan Banothu、Rajitha Bavantula

  DOI：10.1016/j.bmcl.2020.127746

  日期：2021.2

  A new series of triazole-thiazole hybrids were designed, synthesized by the Multi-component reaction approach and evaluated in vitro antimicrobial activity. Most of the tested series of compounds exhibited promising inhibitory activity against the bacterial strains with values in the range of 2.8 to 15.7 µM. The compounds 8i-8l and 8r showed potential-Candida activity against various Candida strains

  设计了一系列新的三唑-噻唑杂化物，通过多组分反应方法合成并评估了其体外抗菌活性。测试的大多数化合物系列均显示出对细菌菌株有希望的抑制活性，其值在2.8至15.7 µM的范围内。化合物8i-8 l和8r对各种念珠菌菌株显示潜在的念珠菌活性，其光谱值在5.9-14.2 µM范围内。此外，还测试了有效化合物的抗生物膜和毒性，结果发现化合物8i，8 k和8 l发现抑制与IC生物膜形成50个分别针对6.6，16.6和15.9μM，的值枯草芽孢杆菌MTCC 121.此外，8 ķ和8升还显示有希望的生物膜形成的抑制活性向金黄色葡萄球菌MTCC 96与IC 50个的值分别为13.5和12.0 µM。总之，活性结果强调了化合物8 k和8 l是进一步开发抗菌，抗念珠菌和抗生物膜剂的潜在先导。
• Recyclization of 2,6-Diamino-4-aryl(cyclohexyl)-3,5-dicyano-4H-thio(seleno)pyrans
  作者：V. D. Dyachenko、A. N. Chernega、S. G. Garasevich

  DOI：10.1007/s11176-005-0475-8

  日期：2005.10

  Recyclization of 2,6-diamino-4-aryl(cyclohexyl)-3,5-dicyano-4H-thio(seleno)pyrans in the presence of an equimolar amount of an α-bromo carbonyl compound, ethyl iodide, 1,2-dibromoethane, or 3-chlorophenyl isocyanate yields, respectively, 3-aryl(cyclohexyl)-2-[thiazol(selenazol)-2-yl]acrylonitriles, 6-amino-4-phenyl-2-ethylsulfanyl-1,4-dihydropyridine-3,5-dicarbonitrile, 5-amino-7-phenyl-2,3,4,7-tetrahydrothiazolo[3,2-a]pyridine-6,8-dicarbonitrile, or N,N′-bis(3-chlorophenyl)urea.

  2,6-二氨基-4-芳基(环己基)-3,5-二氰基-4H-硫(硒)吡喃的再环化在等摩尔的α-溴羰基化合物、乙基碘、1,2-二溴乙烷或3-氯苯异氰酸酯存在下，分别生成3-芳基(环己基)-2-[噻唑(硒唑)-2-基]丙烯腈、6-氨基-4-苯基-2-乙基硫醇-1,4-二氢吡啶-3,5-二氰基、5-氨基-7-苯基-2,3,4,7-四氢噻唑[3,2-a]吡啶-6,8-二氰基或N,N′-双(3-氯苯)尿素。
• Anthracene and 1,8-napthalimide aminothiazole hybrids: Synthesis, Antimicrobial activity and Molecular Docking Studies
  作者：Rambabu Palabindela Rambabu Palabindela、Prabhakar Myadaravenia、Rajashekar Korra Rajashekar Korra、Himabindu Mekala Himabindu Mekala、Mamatha Kasula Mamatha Kasula、DEVENDAR BANOTHU DEVENDAR BANOTHU

  DOI：10.13005/ojc/380117

  日期：2022.2.28

  With our efforts to develop potent antimicrobial agents, a series of anthracene and 1,8-napthalimide aminothiazole analogues were synthesized and characterized by using fundamental spectral analysis. All of the synthesized hybrids were screened for their anti-microbial activities against the bacterial strains E. coli, B. subtillis, and S. aureus, and the fungal strains A. niger and C. albicans. Among the compounds investigated, compounds 4c, 4d, and 6c exhibited the most potent antimicrobial activity. Fluconazole and Norfloxacin were used as standard drugs for antifungal and antibacterial activity. The molecular docking investigation revealed that the compounds 4c, 4d and 6c displayed the lowest binding energy values within the promoter regions of the PDB ID (1JIJ, 4WMZ). The in vitro antimicrobial activity results are well corroborated with the molecular docking results.

  通过我们努力开发强效抗微生物药剂，一系列蒽和1,8-萘酰亚胺氨基噻唑类似物已经合成，并通过基础光谱分析进行了表征。所有合成的混合物均对细菌株大肠杆菌、枯草芽孢杆菌和金黄色葡萄球菌，以及真菌株黑曲霉和白念珠菌的抗微生物活性进行了筛选。在研究的化合物中，化合物4c、4d和6c表现出最强的抗微生物活性。氟康唑和诺氟沙星作为抗真菌和抗细菌活性的标准药物。分子对接研究表明，化合物4c、4d和6c在PDB ID（1JIJ、4WMZ）的启动子区域内显示出最低的结合能量值。体外抗微生物活性结果与分子对接结果相互印证。
• Solid-State Synthesis of 1,3-Selenazoles Employing CuPy₂Cl₂as a Lewis Acid Catalyst
  作者：J. Venu Madhav、B. Suresh Kuarm、B. Rajitha

  DOI：10.1080/00397910802162975

  日期：2008.9.29

  1,3-Selenazoles were Synthesized from 3-bromo acetyl coumarin and selenourea in the presence of CuPy2Cl2 under solvent-free conditions at ambient temperature. The pure products were identified by spectral data.