7-Butoxycoumarin | 71783-00-1

• 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-Butoxycoumarin
• 英文别名: 2H-1-Benzopyran-2-one, 7-butoxy-；7-butoxychromen-2-one
• CAS: 71783-00-1
• 化学式: C₁₃H₁₄O₃
• mdl: MFCD00449865
• 分子量: 218.252
• InChiKey: BDOGTORASJEUBW-UHFFFAOYSA-N

物化性质

• 熔点：
  40 °C
• 沸点：
  367.5±37.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

ADMET

代谢

7-丁氧基-2H-色烯-2-酮已知的人类代谢物包括7-(4-羟基丁氧基)-3,4,4a,5,6,7,8,8a-八氢-2H-色烯-2-醇，7-(1-羟基丁氧基)-3,4,4a,5,6,7,8,8a-八氢-2H-色烯-2-醇和7-(3-羟基丁氧基)-3,4,4a,5,6,7,8,8a-八氢-2H-色烯-2-醇。

7-butoxy-2h-chromen-2-one has known human metabolites that include 7-(4-hydroxybutoxy)-3,4,4a,5,6,7,8,8a-octahydro-2H-chromen-2-ol, 7-(1-hydroxybutoxy)-3,4,4a,5,6,7,8,8a-octahydro-2H-chromen-2-ol, and 7-(3-hydroxybutoxy)-3,4,4a,5,6,7,8,8a-octahydro-2H-chromen-2-ol.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  7-Butoxycoumarin 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Synthesis and Biological Evaluation ofortho-ArylN-Hydroxycinnamides as Potent Histone Deacetylase (HDAC) 8 Isoform-Selective Inhibitors

  摘要：

  AbstractHistone deacetylases (HDACs) are a family of enzymes that play a crucial role in biological process and diseases. In contrast to other isozymes, HDAC8 is uniquely incapable of histone acetylation. In order to delineate its physiological function, we developed HDAC8‐selective inhibitors using knowledge‐based design combined with structural modeling techniques. Enzyme inhibitory analysis demonstrated that some of the resulting compounds (22 b, 22 d, 22 f, and 22 g) exhibited anti‐HDAC8 activity superior to PCI34051, a known HDAC8‐specific inhibitor, with IC50 values in the range of 5–50 nM. Among them, compound 22 d showed antiproliferative effects toward several human lung cancer cell lines (A549, H1299, and CL1‐5); it exhibited cytotoxicity against human lung CL1‐5 cells similar to that of SAHA yet without significant cytotoxicity for normal IMR‐90 cells. Expression profiling of HDAC isoforms in three cancer cell lines indicated that the HDAC8 level in CL1‐5 is higher than that in H1299 and CL1‐1 cells, a result consistent with the differential cytotoxicity of compound 22 d. These results suggest the effectiveness of our design concept, which may lead to a tool compound for studying the specific role of HDAC8 in cellular biological processes.

  DOI：

  10.1002/cmdc.201200300
• 作为产物：
  描述：

  7-羟基香豆素 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 7-Butoxycoumarin
  参考文献：
  名称：

  Inhibitory Effects of 6-Alkoxycoumarin and 7-Alkoxycoumarin Derivatives on Lipopolysaccharide/Interferon γ-Stimulated Nitric Oxide Production in RAW264 Cells

  摘要：

  众所周知，香豆素及其衍生物具有抗炎和抗氧化作用。在这项研究中，我们从市售的 6-羟基香豆素（6HC）和 7-羟基香豆素（7HC）中合成了 32 种香豆素衍生物，并考察了它们对鼠巨噬细胞 RAW264 在脂多糖/干扰素γ（LPS/IFNγ）刺激下产生一氧化氮（NO）的影响。在这些衍生物中，6HC-8（6-(3-苯基丙氧基)香豆素）、6HC-14（6-(2-辛炔氧基)香豆素）、7HC-14（7-(2-辛炔氧基)香豆素）和 7HC-16（7-(3,5-二甲氧基苄氧基)香豆素）在低浓度（25 µ<小>M<小>）下明显抑制了一氧化氮的产生。这些合成的香豆素衍生物也明显抑制了诱导型 NO 合酶（iNOS）蛋白和 mRNA 的表达，这可以通过 Western 印迹和定量实时聚合酶链反应（RT-PCR）进行评估。

  DOI：

  10.1248/bpb.35.963

文献信息

• [EN] CARBONIC ANHYDRASE INHIBITORS WITH ANTIMETASTATIC ACTIVITY<br/>[FR] INHIBITEURS D'ANHYDRASE CARBONIQUE PRÉSENTANT UNE ACTIVITÉ ANTIMÉTASTATIQUE
  申请人：METASIGNAL THERAPEUTICS INC

  公开号：WO2012070024A1

  公开（公告）日：2012-05-31

  Compositions for the treatment of cancer comprising coumarin and thiocoumarin derivatives of Formulas I- XII are disclosed. Said derivatives preferentially inhibit carbonic anhydrase IX and XII (which are associated with hypoxic and metastatic tumours) over inhibiting carbonic anhydrase I and II activity. The compositions therefore are suited for treatment of hypoxic or metastatic cancers due to this selective mechanism of action.

  本发明揭示了用于治疗癌症的组合物，包括公开的具有I-XII式的香豆素和硫代香豆素衍生物。所述衍生物优先抑制与低氧和转移性肿瘤相关的碳酸酐酶IX和XII，而不是抑制碳酸酐酶I和II的活性。因此，这些组合物由于这种选择性作用机制而适用于治疗低氧或转移性癌症。
• Novel Insect-Repellent Coumarin Derivatives, Syntheses, and Methods of Use
  申请人：Delaveau Jean

  公开号：US20120329832A1

  公开（公告）日：2012-12-27

  This invention relates to novel coumarin derivative, formulations comprising same, and to methods of making and using these compounds and formulations, which are useful as repellents against insects and/or pests. The compounds also prevent illness and disease caused by insect/pest-borne vectors, and provide safer, more effective alternatives to existing repellents.

  本发明涉及新型香豆素衍生物、包含该衍生物的配方，以及制备和使用这些化合物和配方的方法，这些化合物和配方可作为驱虫剂防止昆虫和/或害虫。这些化合物还可以预防因昆虫/害虫传播的疾病和疾病，并提供比现有驱虫剂更安全、更有效的替代品。
• 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
• Copper‐Catalyzed C−H Difluoroalkylation of Coumarins with Fluoroalkyl Bromides
  作者：Min Rao、Zhenwei Wei、Yaofeng Yuan、Jiajia Cheng

  DOI：10.1002/cctc.202001025

  日期：2020.10.20

  An efficient method for the copper‐catalyzed selective C−H difluoroalkylation of coumarins and with low cost and readily available ethyl bromodifluoroacetate and N‐phenyl bromodifluoroacetamide has been reported. This reaction exhibits good functional group tolerance with respect to coumarins and difluoroalkylation reagents, and several redox‐sensitive substrates have been successfully C−H difluoroalkylated

  据报道，一种有效的方法可用于铜催化香豆素的选择性CH H二氟烷基化反应，成本低廉，易于获得，溴二氟乙酸乙酯和N-苯基溴二氟乙酰胺。该反应对香豆素和二氟烷基化试剂表现出良好的官能团耐受性，并且几种氧化还原敏感的底物已成功地以良好或高收率被CHH二氟烷基化。这种设计可以进一步将其范围扩展到其他杂芳烃，包括呋喃，苯并呋喃，吡咯，吡啶酮，色酮，吲哚和喹啉酮。提出了一种涉及铜催化氟烷基自由基原位生成的机理。
• Metal‐free, Visible‐Light‐Mediated Direct Csp ² −H Radical Mono‐ and Bis‐trifluoromethylation of Coumarins and Bioactivity Evaluation
  作者：Xiang Yu、Peng Dai、Yu‐Chuan Zhu、Peng Teng、Wei‐Hua Zhang、Chao Deng

  DOI：10.1002/cctc.201801332

  日期：2018.11.22

  A clean, transition metal‐ and oxidant‐free photochemical protocol was described for the direct trifluoromethylation of coumarins with Togni reagent. The reaction proceeded smoothly under mild condition to afford regioselective 3‐trifluoromethyl coumarins, moreover novel bis‐trifluoromethylated coumarins were formed. Preliminary bioactivity evaluation on some products showed potential antifungal activities

  描述了使用Togni试剂对香豆素进行直接三氟甲基化的清洁，无过渡金属和氧化剂的光化学方案。反应在温和的条件下平稳进行，得到区域选择性的3-三氟甲基香豆素，而且形成了新型的双三氟甲基化香豆素。对某些产品的初步生物活性评估显示出潜在的抗真菌活性。