6-methoxy-4-azidomethylcoumarin | 1217436-21-9

• 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-methoxy-4-azidomethylcoumarin
• 英文别名: 4-azidomethyl-6-methoxy-chromen-2-one；6-Methoxy-4-azidomethyl coumarin；4-(azidomethyl)-6-methoxychromen-2-one
• CAS: 1217436-21-9
• 化学式: C₁₁H₉N₃O₃
• 分子量: 231.211
• InChiKey: ZKTVAJYFDXIQSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-溴苯基炔丙基醚 、 6-methoxy-4-azidomethylcoumarin 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 以89%的产率得到4-((4-((4-bromophenoxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-6-methoxy-2H-chromen-2-one
  参考文献：
  名称：

  A click chemistry approach for the synthesis of mono and bis aryloxy linked coumarinyl triazoles as anti-tubercular agents

  摘要：

  A series of mono and bis-triazole coumarin hybrids 6a-u and 9a-f respectively have been synthesized using 4-(azidomethyl)-2H-chromen-2-ones 5a-i and aryl propargyl ethers 2a-c/8 employing Click chemistry modified protocol for Azide-Alkyne cycloadditions(CuAAC). Anti-tubercular screening showed moderate activity for mono aryloxy compounds 6a-u with MIC 50-100 mu g/mL, whereas the bis compounds 9a-f were more effective with MICs between 0.2 and 12.5 mu g/mL. Molecular modeling and 3D-QSAR measurements using CoMFA and Topomer CoMFA further supported the observed results. The his compound 9b showed excellent activity with MIC value as low as 0.2 mu g/mL. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.019
• 作为产物：
  描述：

  4-甲氧基苯酚 在 sodium azide 、 硫酸 作用下， 以 水 、 丙酮 为溶剂， 反应 10.0h， 生成 6-methoxy-4-azidomethylcoumarin
  参考文献：
  名称：

  单击化学方法区域选择性合成iso-indoline-1,3-dione-linked 1,4 and 1,5 coumarinyl 1,2,3-triazoles 及其光物理性质

  摘要：

  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

  DOI：

  10.1080/00397911.2017.1283524

文献信息

• Click chemistry based regioselective one‐pot synthesis of coumarin‐3‐yl‐methyl‐1,2,3‐triazolyl‐1,2,4‐triazol‐3(4 <i>H</i> )‐ones as newer potent antitubercular agents
  作者：Shilpa M. Somagond、Ravindra R. Kamble、Praveen K. Bayannavar、Saba Kauser J. Shaikh、Shrinivas D. Joshi、Vijay M. Kumbar、Aravind R. Nesaragi、Mahadevappa Y. Kariduraganavar

  DOI：10.1002/ardp.201900013

  日期：2019.10

  Coumarin‐3‐yl‐methyl‐1,2,3‐triazolyl‐1,2,4‐triazol‐3(4H)‐ones (8k‐z) were synthesized via copper(I)‐catalyzed azide‐alkyne cycloaddition click chemistry. The synthesized hybrid molecules were characterized by spectral studies. Compounds 8k‐z were screened for their in vitro anti‐TB activity by using the Microplate Alamar Blue assay and for cytotoxicity using the MTT assay. Some of the compounds were

  香豆素-3-基-甲基-1,2,3-三唑基-1,2,4-三唑-3（4H）-酮（8k-z）是通过铜（I）催化的叠氮化物-炔环加成点击化学合成的. 合成的杂化分子通过光谱研究表征。使用 Microplate Alamar Blue 测定法筛选化合物 8k-z 的体外抗结核活性，并使用 MTT 测定法筛选其细胞毒性。发现其中一些化合物对测试的结核分枝杆菌 H37Rv 菌株最有效，MIC 为 1.60 µg/ml。此外，将化合物对接到 InhA 结合口袋中显示出强烈的结合相互作用，并记录了有效的总体对接分数。分别使用 Molinspiration 和 Protox 计算药物相似性和毒性研究。
• Unusual anisotropic effects from 1,3-dipolar cycloadducts of 4-azidomethyl coumarins
  作者：Raviraj A. Kusanur、Manohar V. Kulkarni、Geetha M. Kulkarni、Susanta K. Nayak、Tayur N. Guru Row、Kilivelu Ganesan、Chung-Ming Sun

  DOI：10.1002/jhet.273

  日期：——

  acetone to give 4-azidomethylcoumarins (), which underwent 1,3-dipolar cycloaddition with acetylenic dipolarophiles to give triazoles (). These triazoles () have been found to exhibit interesting variations in the chemical shifts of C3H and C4-methylene protons. Protonation studies indicate that the shielding effect of the C3H of coumarin is due to π-electrons of the triazole ring, further supported

  4-溴甲基香豆素（）与 丙酮水溶液中的叠氮化钠制得4-叠氮甲基香豆素（），然后与炔属双极性亲和剂进行1,3-偶极环加成反应，得到三唑（）。这些三唑业已发现）在C 3 H和C 4-亚甲基质子的化学位移方面表现出有趣的变化。质子化研究表明，香豆素C 3 H的屏蔽作用归因于三唑环的π电子，这进一步受到衍射和计算研究的支持。J.杂环化​​学.2010。
• Click approach for synthesis of 3,4-dihydro-2(1H) quinolinone, coumarin moored 1,2,3-triazoles as inhibitor of mycobacteria tuberculosis H37RV, their antioxidant, cytotoxicity and in-silico studies
  作者：Nagashree U. Hebbar、Anilkumar R. Patil、Parashuram Gudimani、Samundeeswari L. Shastri、Lokesh A. Shastri、Shrinivas D. Joshi、Shyam Kumar. Vootla、Sheela Khanapure、Arun K. Shettar、Vinay A. Sungar

  DOI：10.1016/j.molstruc.2022.133795

  日期：2022.12

  assay and the compounds have shown moderate to low activity compared to standard ascorbic acid. The cytotoxicity of the synthesised compounds against lung cancer cell lines exhibited good to moderate activity and do not induce significant toxicity. In Superoxide dismutase(SOD) enzyme activity studies some of the compounds exhibited promising activity. The interactions of the molecules were studied against

  为了寻找抗结核病的新有效分子，通过点击化学有效地合成了基于 3,4-二氢-2(1H)-喹啉酮的 1,2,3-三唑，并通过光谱数据确认了它们的结构。在合成的十二个新分子中，七个是 3,4-二氢-2(1H)-喹啉酮、1,2,3-1H-三唑核与不同香豆素衍生物的杂化物，其余分子中香豆素被烷基、芳基、和吡喃糖衍生物。在合成的化合物中，筛选了八种化合物对H37Rv菌株的抗结核活性，发现它们具有良好的抑制活性，MIC 值较低（2.7-10.6 µM）。复合6 小时(6-(乙酰氧基甲基)四氢-2H-吡喃-2,4,5-三乙酸三酯)取代对MTB最有效。此外，使用 DPPH 测定法评估了它们的抗氧化活性，与标准抗坏血酸相比，这些化合物显示出中等至低的活性。合成的化合物对肺癌细胞系的细胞毒性表现出良好至中等的活性，并且不会引起显着的毒性。在超氧化物歧化酶 (SOD) 酶活性研究中，一些化合物表现出有希望的活性。
• Coumarin‐modified ruthenium complexes: Synthesis, characterization, and antiproliferative activity against human cancer cells
  作者：Silvio Jakopec、Lejla F. Hamzic、Luka Bočkor、Iris Car、Berislav Perić、Srećko I. Kirin、Mirela Sedić、Silvana Raić‐Malić

  DOI：10.1002/ardp.202400271

  日期：2024.9

  Ru(II) resulted in the enhancement of cytostatic activity in HepG2 hepatocellular carcinoma cells and PANC-1 pancreatic cancer cells. Coumarin derivative 2a positively regulated the expression and activity of c-Myc and NPM1 in RKO colon carcinoma cells, while the Ru(II) half-sandwich complex 2cRu induced downregulation of AKT and ERK signaling in PANC-1 cells concomitant with reduced intracellular levels

  在作为抗癌金属药物研究的钌配合物中，NKP-1339、NAMI-A、RM175和RAPTA-C由于临床前研究证明其具有强大的抗肿瘤活性，并且与铂类药物相比毒性较低，因此已进入临床试验。考虑到钌基抗癌药物的优势以及三唑和香豆素衍生配体的有机金属配合物的细胞抑制活性，我们着手合成香豆素-1,2,3,-三唑杂化物的Ru(II)配合物( L )具有通式[Ru( L )( p-伞花烃)(Cl)]ClO 4 。通过单晶X射线衍射确定了配合物[Ru( 2a )( p -伞花烯)(Cl)]ClO 4 ( 2a Ru )的分子结构，证实了配体与中心钌(II)的配位。 ) 阳离子通过双齿配位模式。与 Ru(II) 配合可增强 HepG2 肝细胞癌细胞和 PANC-1 胰腺癌细胞的细胞抑制活性。香豆素衍生物2a正向调节 RKO 结肠癌细胞中 c-Myc 和 NPM1 的表达和活性，而 Ru(II) 半夹心复合物2c
• Click Chemistry Approach for Bis-Chromenyl Triazole Hybrids and Their Antitubercular Activity
  作者：Reshma J. Naik、Manohar V. Kulkarni、K. Sreedhara Ranganath Pai、Pawan G. Nayak

  DOI：10.1111/j.1747-0285.2012.01441.x

  日期：2012.10

  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.