6-bromo-3-(2-bromoacetyl)-8-methoxy-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: 6-bromo-3-(2-bromoacetyl)-8-methoxy-2H-chromen-2-one
• 英文别名: 6-bromo-3-(bromoacetyl)-8-methoxy-2H-chromen-2-one；6-bromo-3-(2-bromoacetyl)-8-methoxychromen-2-one
• 化学式: C₁₂H₈Br₂O₄
• 分子量: 376.001
• InChiKey: MVWSQZMWLDSTSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-bromo-3-(2-bromoacetyl)-8-methoxy-2H-chromen-2-one 在 吡啶 作用下， 反应 24.1h， 生成 N-Allyl-N-[4-(6-bromo-8-methoxy-2-oxo-2H-chromen-3-yl)-thiazol-2-yl]-acetamide
  参考文献：
  名称：

  Kumar, P. Vijay; Reddy, R. Vinod; Rao, V. Rajeswar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 7, p. 1738 - 1741

  摘要：

  DOI：

文献信息

• Novel one-pot expeditious synthesis of 2,4-disubstituted thiazoles through a three-component reaction under solvent free conditions
  作者：Kodam Sujatha、Rajeswar Rao Vedula

  DOI：10.1080/00397911.2017.1399422

  日期：2018.2.1

  expeditious one pot method has been developed for the synthesis of 2,4-disubstituted thiazoles under solvent free conditions via a multicomponent approach. Substituted thiazoles were synthesized with high yields by the reaction of cyclic ketones, thiosemicarbazide, and phenacyl bromides or 3-(2-bromoacetyl)-2H-chromen-2-ones in a shorter reaction time with high purity via simple purification technique

  摘要开发了一种快速的一锅法，用于在无溶剂条件下通过多组分方法合成 2,4-二取代噻唑。通过环酮、氨基硫脲和苯甲酰溴或3-(2-溴乙酰)-2H-色烯-2-酮在较短的反应时间内反应，通过简单的纯化技术以高产率合成取代的噻唑。图形概要
• 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。
• Synthesis of Novel 3-(3-(5-Methylisoxazol-3-yl)-7<i>H</i>-[1,2,4]Triazolo [3,4-<i>b</i>][1,3,4]Thiadiazin-6-yl)-2<i>H</i>-Chromen-2-Ones
  作者：Krishnaiah Vaarla、Rajeswar Rao Vedula

  DOI：10.1002/jhet.2301

  日期：2016.1

  4‐amino‐5‐(5‐methylisoxazol‐3‐yl)‐4H‐1,2,4‐triazole‐3‐thiol (3). This intermediate on further reaction with substituted 3‐(2‐bromo acetyl) coumarins under simple reaction conditions formed the title products 3‐(3‐(5‐methylisoxazol‐3‐yl)‐7H‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazin‐6‐yl‐2H‐chromen‐2‐ones (5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i, 5j) in good to excellent yields. All the synthesized compounds were well

  通过使用5-甲基异恶唑-3-羧酸（1），硫代碳酰肼（2）和各种取代的3-（2-溴乙酰基）香豆素（4a，4b）设计和合成了一系列香豆素取代的三唑并噻二嗪衍生物。，4c，4e，4d，4f，4g，4h，4i，4j）。5-甲基异恶唑-3-羧酸与硫代氨基甲酰肼的熔融导致形成中间体4-氨基-5-（5-甲基异恶唑-3-基）-4 - H -1,2,4-三唑-3-硫醇（3）。该中间体与取代的3-（2-溴乙酰基）进一步反应而形成简单的反应条件的标题产物3-（3-（5-甲基异恶唑-3-基）-7下香豆素ħ - [1,2,4]三唑并[3,4-b] [1,3,4]噻二嗪-6-yl-2 H -chromen-2-ones（5a，5b，5c，5d，5e，5f，5g，5h，5i，5j）在所有合成的化合物均通过物理，分析和光谱技术进行了很好的表征。
• An efficient one-pot expeditious synthesis of 3-phenyl-1-(6-phenyl-7H-[1,2,4] triazolo[3,4-b] [1,3,4] thiadiazin-3-yl)-1H-pyrazol-5-amines via multicomponent approach
  作者：Kodam Sujatha、Ravindra Pramod Deshpande、Rajesh Kumar Kesharwani、Phanithi Prakash Babu、Rajeswar Rao Vedula

  DOI：10.1080/00397911.2018.1537398

  日期：2019.1.2

  accomplished by a simple, atom-economical, and multicomponent approach. Reaction of 4-amino-5-hydrazinyl-4H-1,2,4-triazole-3-thiol with various phenacyl bromides and benzoylacetonitriles in ethanol and catalytic amount of acetic acid afforded the titled compounds. The structures of newly synthesized compounds were confirmed by their analytical and spectral (IR, 1H-NMR, 13C-NMR, and Mass) data. Graphical Abstract

  摘要 3-苯基-1-(6-苯基-7H-[1,2,4]三唑并[3,4-b][1,3,4]噻二嗪-3-基)-1H-吡唑的高效合成-5-胺是通过一种简单的、原子经济的、多组分的方法完成的。4-氨基-5-肼基-4H-1,2,4-三唑-3-硫醇与各种苯甲酰溴和苯甲酰乙腈在乙醇和催化量的乙酸中反应，得到标题化合物。新合成化合物的结构通过其分析和光谱（IR、1H-NMR、13C-NMR 和质谱）数据得到证实。图形概要
• Synthesis and Cytotoxicity Activity of Novel Benzotrizolyl Methyl[1,2,4-triazolo][3,4-b]thiadiazinyl Substituted Chromene 2-ones
  作者：S. Yakaiah、K. Durgaprasad、A.K.S. Bhujanga Rao、P. Baby Rani、S. Awantika、G. Buchappa、P. Aparna

  DOI：10.14233/ajchem.2016.19714

  日期：——

  The biological importance of the coumarins and triazolothiadiazines, prompted as to synthesize a series of novel benzotrizolyl methyl[1,2,4-triazolo][3,4-b]thiadiazinyl substituted chromene 2-ones applying simple experimental conditions with good yields. All the synthesized molecules were well characterized by physical, analytical and spectroscopic techniques. The novel synthesized molecules 5(a-k) were screened for the anticancer activity and some of the molecules exhibited moderate to good activity in vitro.

  香豆素和三唑并噻二嗪的生物学重要性促使我们采用简单的实验条件合成了一系列新型苯并三唑基甲基[1,2,4-三唑][3,4-b]噻二嗪基取代的色烯2-酮，并具有良好的产率。所有合成的分子都通过物理、分析和光谱技术得到了很好的表征。对新合成的分子5(a-k)进行了抗癌活性筛选，部分分子在体外表现出中等至良好的活性。