7-Chloro-4-bromomethylcoumarin | 79344-39-1

• 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: 7-Chloro-4-bromomethylcoumarin
• 英文别名: 4-(bromomethyl)-7-chloro-2H-chromen-2-one；7-Chloro-4-bromometh-ylcoumarin；4-(bromomethyl)-7-chlorochromen-2-one
• CAS: 79344-39-1
• 化学式: C₁₀H₆BrClO₂
• 分子量: 273.513
• InChiKey: OXYFDMYIQWBAMG-UHFFFAOYSA-N

物化性质

• 熔点：
  217-218 °C(Solv: benzene (71-43-2))
• 沸点：
  372.4±42.0 °C(Predicted)
• 密度：
  1.695±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-Chloro-4-bromomethylcoumarin 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 10.25h， 生成 7-[[1-[(7-Chloro-2-oxo-chromen-4-yl)methyl]triazol-4-yl]methoxy]-4-methyl-chromen-2-one
  参考文献：
  名称：

  Click Chemistry Approach for Bis-Chromenyl Triazole Hybrids and Their Antitubercular Activity

  摘要：

  1,4‐Disubstituted bis‐chromenyl triazole hybrids 5a–m have been synthesized in a three‐step reaction sequence from 4‐(bromomethyl)‐2H‐chromen‐2‐ones 3a–m. The intermediate azides 4a–m underwent a regioselective 1,3‐dipolar cycloaddition with a 2H‐chromen‐2‐one linked acetylenic dipolarophile in the presence of Cu (II)/ascorbate/water/n‐butanol reaction medium. Three compounds 5h–j exhibited 6.25 μg/mL MIC against M. tuberculosis. Among the compounds screened for antifungal activity, lowest MIC of 6.25 μg/mL was observed for 5c against A. niger that also exhibited DNA cleavage observed by agarose gel electrophoresis. All the compounds were moderately active against both Gram‐positive and Gram‐negative bacterial strains. The cytotoxic effect of potent compounds on normal cells (V79 and HBL100) was assessed by MTT assay.

  DOI：

  10.1111/j.1747-0285.2012.01441.x
• 作为产物：
  描述：

  3-氯苯酚 在 三氯化铝 盐酸 作用下， 以 乙醇 、 硝基苯 为溶剂， 反应 48.0h， 生成 7-Chloro-4-bromomethylcoumarin
  参考文献：
  名称：

  Kimura, Hitoshi; Sato, Hirotoshi; Tsuchiya, Chizuko, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 2, p. 552 - 558

  摘要：

  DOI：

文献信息

• Synthesis of Coumarin-benzotriazole Hybrids and Evaluation of their Anti-tubercular Activity
  作者：Sachin P. Ambekar、Chakrabhavi Dhananjaya Mohan、Arunkumar Shirahatti、Mahesh K. Kumar、Shobith Rangappa、Surender Mohan、Basappa、Obelannavar Kotresh、Kanchugarakoppal S. Rangappa

  DOI：10.2174/1570178614666170710125501

  日期：2017.12.11

  Background: Tuberculosis is one of the top ranked airborne infectious diseases caused by the bacillus Mycobacterium tuberculosis with high mortality rate from a single infectious agent. In the present article, we aimed to synthesize oxadiazole-coumarin-triazole based small molecules and evaluate for their possible anti-mycobacterial activity. Method: Herein, we describe the facile synthesis of 5-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)-1,3,4- oxadiazole-2-thiol-tethered substituted 4-(bromomethyl)-7-methyl-2H-chromen-2-one derivatives and evaluated for their anti-mycobacterial activity against H37Rv strain of M. tuberculosis. We also evaluated the cytotoxic effect of new compounds on normal cells. Results: Among the 14 novel oxadiazole-coumarin-triazole derivatives, 4-((5-((1H-benzo[d][1,2,3]triazol-1- yl)methyl)-1,3,4-oxadiazol-2-ylthio)methyl)-6-methoxy-2H-chromen-2-one (5f) displayed good antimycobacterial activity towards M. tuberculosis with an MIC value of 15.5 µM. Pyrazinamide was used as reference drug. Our investigation also revealed that, 5f is not cytotoxic to normal cells. Conclusion: In summary, the findings suggested that novel 1,3,4-oxadiazole coumarin-triazole hybrids are promising antimycobacterial agents against M. tuberculosis.

  背景：结核病是由结核分枝杆菌引起的高度致死性空气传播传染病之一。在本文中，我们的目标是合成基于噁二唑-香豆素-三唑的小分子并评估它们可能的抗结核活性。 方法：在此，我们描述了5-((1H-苯并[d][1,2,3]三唑-1-基)甲基)-1,3,4-噁二唑-2-硫醇缀合的取代4-(溴甲基)-7-甲基-2H-色烯-2-酮衍生物的简易合成，并评估了它们对M. tuberculosis H37Rv菌株的抗结核活性。我们还评估了新化合物对正常细胞的细胞毒性效应。 结果：在14种新型噁二唑-香豆素-三唑衍生物中，4-((5-((1H-苯并[d][1,2,3]三唑-1-基)甲基)-1,3,4-噁二唑-2-基硫)甲基)-6-甲氧基-2H-色烯-2-酮(5f)显示出对M. tuberculosis的良好抗菌活性，MIC值为15.5 µM。利福平被用作参考药物。我们的研究还揭示，5f对正常细胞没有细胞毒性。 结论：总之，研究结果表明，新型1,3,4-噁二唑香豆素-三唑杂化物是针对M. tuberculosis有前景的抗结核药物。
• Click chemistry approach for the regioselective synthesis of iso-indoline-1,3-dione-linked 1,4 and 1,5 coumarinyl 1,2,3-triazoles and their photophysical properties
  作者：Ashish Anand、Manohar V. Kulkarni

  DOI：10.1080/00397911.2017.1283524

  日期：2017.4.3

  ABSTRACT Copper-catalyzed reaction of N-propargyl isoindoline-1,3-dione and 4-azidomethyl coumarins / 4-azidomethyl-1-aza coumarins under click chemistry conditions afforded 1,4-disubstituted 1,2,3-triazoles, whereas ruthenium catalysis yielded isomeric 1,5-disubstituted 1,2,3-triazoles. The two regioisomers have been distinguished by NOE studies. UV absorption for a given pair of isomers exhibited

  摘要 在点击化学条件下，N-炔丙基异吲哚啉-1,3-二酮和 4-叠氮甲基香豆素/4-叠氮甲基-1-氮杂香豆素在铜催化下反应得到 1,4-二取代 1,2,3-三唑，而钌催化产生异构的 1,5-二取代的 1,2,3-三唑。两种区域异构体已通过 NOE 研究区分开来。一对给定异构体的紫外吸收显示出相似的趋势，而荧光测量显示出相当大的差异。还对叠氮化物与铜和钌的相互作用进行了光物理研究。图形概要
• Cyclopropanes in water: a diastereoselective synthesis of substituted 2H-chromen-2-one and quinolin-2(1H)-one linked cyclopropanes
  作者：Ashish Anand、Jayashree Yenagi、J. Tonannavar、Manohar V. Kulkarni

  DOI：10.1039/c5gc02443a

  日期：——

  A one-pot three component reaction has been developed for the synthesis of substituted cyclopropanes employing 4-bromomethyl-2H-chromen-2-one/quinolin-2(1H)-ones, aromatic aldehydes and activated nitriles.

  已开发出一种一锅法三组分反应，用于合成取代环丙烷，使用4-溴甲基-2H-香豆素/喹啉-2(1H)-酮、芳香醛和活化腈。
• Studies on Coumarins, I
  作者：Manohar V. Kulkarni、Vemanna D. Patil

  DOI：10.1002/ardp.19813140810

  日期：——

  4‐Bromomethylcoumarins, prepared by the reaction of phenols and 4‐bromoethyl acetoacetate, were reacted with primary aromatic amines to yield 4‐anilinomethylcoumarins. The spectral properties and antimicrobial activities against five micro‐organisms are reported.

  4-溴甲基香豆素是由苯酚和4-溴乙酰乙酸乙酯反应制备的，与芳香伯胺反应得到4-苯胺基甲基香豆素。报告了对五种微生物的光谱特性和抗菌活性。
• Biscoumarin–pyrimidine conjugates as potent anticancer agents and binding mechanism of hit candidate with human serum albumin
  作者：Dinesh S. Reddy、Manasa Kongot、Vishal Singh、Md. Abrar Siddiquee、Rajan Patel、Nitin K. Singhal、Fernando Avecilla、Amit Kumar

  DOI：10.1002/ardp.202000181

  日期：2021.1

  magnetic resonance). In addition, the structure of compound 1d (1,3‐bis[(7‐chloro‐2‐oxo‐2H‐chromen‐4‐yl)methyl]‐5‐methylpyrimidine‐2,4(1H,3H)‐dione) was established through X‐ray crystallography. Compounds 1a–l were screened for in vitro anticancer activity against C6 rat glioma cells. Among the screened compounds, 1,3‐bis[(6‐chloro‐2‐oxo‐2H‐chromen‐4‐yl)methyl]‐5‐methylpyrimidine‐2,4(1H,3H)‐dione (1c)

  在我们不断努力开发具有治疗活性的香豆素类化合物的过程中，通过取代的 4-溴甲基香豆素与胸腺嘧啶的 SN2 反应合成了一系列新的 C4-C4' 双香豆素-嘧啶缀合物（1a-l）。所有化合物均使用光谱技术进行表征，即衰减全反射红外 (ATR-IR)、CHN 元素分析以及 1H 和 13C NMR（核磁共振）。此外，化合物1d的结构（1,3-双[（7-氯-2-氧代-2H-色烯-4-基）甲基]-5-甲基嘧啶-2,4（1H,3H）-二酮）是通过 X 射线晶体学建立的。筛选化合物 1a-l 对 C6 大鼠神经胶质瘤细胞的体外抗癌活性。在筛选的化合物中，1,3-双[(6-chloro-2-oxo-2H-chromen-4-yl)methyl]-5-methylpyrimidine-2,4(1H, 3H)-二酮 (1c) 被确定为最佳的抗增殖候选药物，其 IC50 值为 4.85 μM。发现所有化合物 (1a-l)