7-(3-溴丙氧基)色满-2-酮 | 69150-28-3

• 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
• 中文名称: 7-(3-溴丙氧基)色满-2-酮
• 英文名称: 7-(3-bromopropyloxy)coumarin
• 英文别名: 7-(3-Bromopropoxy)-chromen-2-one；7-(3-bromopropoxy)chromen-2-one
• CAS: 69150-28-3
• 化学式: C₁₂H₁₁BrO₃
• 分子量: 283.122
• InChiKey: ASDNDKTVOWYXTH-UHFFFAOYSA-N

物化性质

• 沸点：
  431.7±45.0 °C(Predicted)
• 密度：
  1.511±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-(3-溴丙氧基)色满-2-酮 在 sodium azide 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 4-(benzyloxy)-6,6-dimethyl-1-(3-((2-oxo-2H-chromen-7-yl)oxy)propyl)-1,6-dihydro-1,2,3,4-tetrazin-5(4H)-one
  参考文献：
  名称：

  [3 + 3] Cycloaddition of Azides with in Situ Formed Azaoxyallyl Cations To Synthesize 1,2,3,4-Tetrazines

  摘要：

  A formal [3 + 3] cycloaddition reaction between azides and in situ formed azaoxyallyl cations has been realized. This reaction provided an efficient and practical pathway to synthesize 1,2,3,4-tetrazines in good yields under mild conditions. Biologically active molecules could also be well compatible, highlighting the potential value of this reaction.

  DOI：

  10.1021/acs.orglett.8b00280
• 作为产物：
  描述：

  间苯二酚 在 硫酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 7.0h， 生成 7-(3-溴丙氧基)色满-2-酮
  参考文献：
  名称：

  Design, synthesis and evaluation of novel tacrine–coumarin hybrids as multifunctional cholinesterase inhibitors against Alzheimer's disease

  摘要：

  A series of tacrine-coumarin hybrids (8a-t) were designed, synthesized and evaluated as multifunctional cholinesterase (ChE) inhibitors against Alzheimer's disease (AD). The screening results showed that most of them exhibited a significant ability to inhibit ChE and self-induced,beta-amyloid (A beta) aggregation, and to act as metal chelators. Especially, 8f displayed the greatest ability to inhibit acetylcholinesterase (AChE, IC50 = 0.092 mu M) and A beta aggregation (67.8%, 20 mu M). It was also a good butyrylcholinesterase inhibitor (BuChE, IC50 = 0.234 mu M) and metal chelator. Besides, kinetic and molecular modeling studies indicated that 8f was a mixed-type inhibitor, binding simultaneously to active, peripheral and mid-gorge sites of AChE. These results suggested that 8f might be an excellent multifunctional agent for AD treatment. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.051

文献信息

• A highly selective colorimetric and fluorescent chemosensor for Cr2+ in aqueous solutions
  作者：J. Rull-Barrull、M. d'Halluin、E. Le Grognec、F.-X. Felpin

  DOI：10.1016/j.tetlet.2016.12.038

  日期：2017.2

  sensing properties toward various metal cations in aqueous solutions were investigated by colorimetric changes, UV–vis and fluorescence spectroscopies. The sensor exhibited a high selectivity for Cr2+ over Cr3+ and other divalent cations such as Cu2+, Mg2+, Zn2+, Ca2+, Cd2+, Co2+, Hg2+ and Ni2+. The linear range of detection by fluorescence spectroscopy is 0.07–3.5 mM, with a detection limit of ca. 64 μM

  一种新的基于罗丹明的化学传感器是通过经过修饰的铜催化阿奇多香豆素与炔基罗丹明的[3 + 2]-环加成反应而合成的。通过比色变化，紫外可见光谱和荧光光谱研究了其对水溶液中各种金属阳离子的传感特性。该传感器对Cr 2+的选择性高于Cr 3+和其他二价阳离子，如Cu 2 +，Mg 2 +，Zn 2 +，Ca 2 +，Cd 2 +，Co 2 +，Hg 2+和Ni 2的选择性高。+。荧光光谱检测的线性范围为0.07–3.5 mM，检出限为ca。64微米 Cr 2+与传感器的结合模式通过实验证据得以合理化。
• Harnessing the Dual Properties of Thiol-Grafted Cellulose Paper for Click Reactions: A Powerful Reducing Agent and Adsorbent for Cu
  作者：Jordi Rull-Barrull、Martin d'Halluin、Erwan Le Grognec、François-Xavier Felpin

  DOI：10.1002/anie.201606760

  日期：2016.10.17

  new approach exploiting the dual properties of thiol‐grafted cellulose paper for promoting copper‐catalyzed [3+2]‐cycloadditions of organic azides with alkynes and adsorbing residual copper species in solution was developed. The thiol‐grafted cellulose paper, used as a paper strip, effects the reduction of CuII to catalytically active CuI and acts as a powerful adsorbent for copper, thereby facilitating

  开发了一种新方法，该方法利用硫醇接枝纤维素纸的双重特性来促进炔烃与有机叠氮化物的铜催化[3 + 2]-环加成反应，并吸附溶液中的残留铜物种。用作纸带的硫醇接枝纤维素纸可将Cu II还原为催化活性Cu I，并作为强力的铜吸附剂，从而简化了后处理过程，并使粗混合物几乎不含铜残留物一次过滤后。
• Synthesis of N-substituted indole derivatives as potential antimicrobial and antileishmanial agents
  作者：Shweta Tiwari、Seema Kirar、Uttam Chand Banerjee、Kishore Babu Neerupudi、Sushma Singh、Aabid Abdullah Wani、Prasad V. Bharatam、Inder Pal Singh

  DOI：10.1016/j.bioorg.2020.103787

  日期：2020.6

  effects are major priority for researchers. Two series of N-substituted indole derivatives i.e. N-substituted indole based chalcones (12a-g) and N-substituted indole based hydrazide-hydrazones (18a-g, 19a-f, 21 a-g) were synthesized. The synthesized compounds were characterized by 1H NMR, 13C NMR, Mass and FT-IR spectral data. Further these derivatives were evaluated for their antimicrobial potential against

  利什曼病和微生物感染是导致全球死亡率和发病率的两个主要因素。因此，开发具有减少的副作用的新颖，有效和安全的抗真菌药和抗微生物剂是研究人员的首要任务。合成了两个系列的N-取代的吲哚衍生物，即N-取代的基于吲哚的查耳酮（12a-g）和N-取代的基于吲哚的酰肼-azo（18a-g，19a-f，21ag）。合成的化合物通过1 H NMR，13 C NMR，质量和FT-IR光谱数据表征。进一步评估了这些衍生物的抗大肠杆菌，枯草芽孢杆菌，恶臭假单胞菌和粘链假丝酵母的抗微生物潜力，以及抗利什曼原虫的前鞭毛体的抗疟药潜力。化合物18b，18d和19d表现出显着的活性，对枯草芽孢杆菌的IC50为0.19±0.03 µM，0.14±0.02 µM和0.16±0.06 µM，与氯霉素相当（IC50为0.25±0.03 µM）。化合物12b和12c在抗盲肠测定中表现出24.2±3.5 µM和21.5±2.1 µM
• Synthesis and biological evaluation of novel coumarin derivatives in rhabdoviral clearance
  作者：Yang Hu、Lipeng Shan、Tianxiu Qiu、Lei Liu、Jiong Chen

  DOI：10.1016/j.ejmech.2021.113739

  日期：2021.11

  industry. Therefore, in this study, IHNV was studied as a model to evaluate the antiviral activity of 35 novel coumarin derivatives. Coumarin A9 was specifically selected for further validation studies upon comparing the half maximum inhibitory concentration (IC50) of four screened candidate derivatives in epithelioma papulosum cyprinid (EPC) cells, as it exhibited an IC50 value of 2.96 μM against IHNV. The

  由弹状病毒引起的疾病对整个人类的生产生活产生了巨大影响。主要问题是缺乏治疗该病毒家族的药物。IHN的病原体传染性造血坏死病毒（IHNV）是一种典型的弹状病毒，给鲑鱼产业造成了巨大损失。因此，在本研究中，研究了 IHNV 作为评估 35 种新型香豆素衍生物抗病毒活性的模型。香豆素A9是专门于半最大抑制浓度（IC比较选择用于进一步的验证研究50在上皮瘤papulosum鲤科（EPC）的细胞筛选4种候选的衍生物），因为它表现出的IC 50对 IHNV 的值为 2.96 μM。数据显示，A9 处理显着抑制了 EPC 细胞中病毒诱导的细胞病变效应 (CPE)。另外，A9显示IC 50其他两种弹状病毒的值分别为 1.68 和 2.12 μM，即鲤鱼春季病毒血症和鲑鱼弹状病毒。此外，我们的结果表明 A9 发挥抗病毒活性，但不是通过破坏病毒颗粒和干扰 IHNV 的吸附。此外，我们发现 A9 对 IHNV 诱导的
• Synthesis, biological activity and multiscale molecular modeling studies of bis-coumarins as selective carbonic anhydrase IX and XII inhibitors with effective cytotoxicity against hepatocellular carcinoma
  作者：Belma Zengin Kurt、Aydan Dag、Berna Doğan、Serdar Durdagi、Andrea Angeli、Alessio Nocentini、Claudiu T. Supuran、Fatih Sonmez

  DOI：10.1016/j.bioorg.2019.03.003

  日期：2019.6

  and their inhibitory activity against the human carbonic anhydrase (hCA) isoforms I, II, IX and XII were evaluated. In addition, cytotoxic effects of the synthesized compounds on renal adenocarcinoma (769P), hepatocellular carcinoma (HepG2) and breast adeno carcinoma (MDA-MB-231) cell lines were examined. While the hCA I and II isoforms were inhibited in the micromolar range, the tumor-associated isoform

  合成了一系列新的含有三唑部分作为烷基链之间连接基的双香豆素衍生物，并评估了它们对人碳酸酐酶（hCA）同工型I，II，IX和XII的抑制活性。另外，检查了合成化合物对肾腺癌（769P），肝细胞癌（HepG2）和乳腺腺癌（MDA-MB-231）细胞系的细胞毒性作用。虽然hCA I和II亚型在微摩尔范围内受到抑制，但与肿瘤相关的同种型hCA IX和XII在高纳摩尔范围内受到抑制。4-甲基-7-（（1-（12-（（（2-oxo-2H-chromen-7-yl）oxy）十二烷基）-1H-1,1,2,3-三唑-4-基）甲氧基）-2H -chromen-2-one（5p）对hCA IX的抑制作用最强，Ki为144.6 nM，4-甲基-7-（（1-（10-（（2-oxo-2H-chromen-7-yl ）氧）癸基）-1H-1,2，3-三唑-4-基）甲氧基）-2H-铬-2--2-（5n）表现出最高的hCA XII抑制作用，Ki为71