7-((2',2'-dimethyl)-n-propoxy)coumarin | 1416562-97-4

• 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-((2',2'-dimethyl)-n-propoxy)coumarin
• 英文别名: 7-(2',2′-dimethyl)n-propoxycoumarin；7-(2,2-Dimethylpropoxy)chromen-2-one；7-(2,2-dimethylpropoxy)chromen-2-one
• CAS: 1416562-97-4
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: RQMLUJJGVYFTQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  新戊醇 在 吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 7-((2',2'-dimethyl)-n-propoxy)coumarin
  参考文献：
  名称：

  Novel Insect-Repellent Coumarin Derivatives, Syntheses, and Methods of Use

  摘要：

  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。

  公开号：

  US20120329832A1

文献信息

• Combined molecular modeling and cholinesterase inhibition studies on some natural and semisynthetic O-alkylcoumarin derivatives
  作者：Ilkay Erdogan Orhan、F. Sezer Senol Deniz、Ramin Ekhteiari Salmas、Serdar Durdagi、Francesco Epifano、Salvatore Genovese、Serena Fiorito

  DOI：10.1016/j.bioorg.2018.11.044

  日期：2019.3

  reference (galanthamine, IC50 = 46.58 ± 0.91 µM). In fact, 10 of the active coumarins showed higher inhibition (IC50 = 7.01 ± 0.28 µM - 43.31 ± 3.63 µM) than that of galanthamine. The most active ones were revealed to be 7-styryloxycoumarin (IC50 = 7.01 ± 0.28 µM) and 7-isopentenyloxy-4-methylcoumarin (IC50 = 8.18 ± 0.74 µM). In addition to the in vitro tests, MetaCore/MetaDrug binary QSAR models and docking

  合成或天然来源的香豆素是发挥多种药理活性的重要化学类别。在本研究中，合成了26种新颖的O-烷基香豆素衍生物，并已在100 µM的条件下测试了它们对乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）靶标的体外抑制潜力，而乙酰胆碱酯酶（BChE）靶标是在阿尔茨海默氏病发病机理中发挥关键作用。在测试的香豆素中，没有一种能够抑制AChE，而与参考文献（加兰他敏，IC50 = 46.58±0.91 µM）相比，它们中的12种对BChE表现出显着的选择性抑制作用。实际上，有10种活性香豆素具有比加兰他敏更高的抑制作用（IC50 = 7.01±0.28 µM-43.31±3.63 µM）。发现最活跃的是7-苯乙烯基香豆素（IC50 = 7.01±0。28 µM）和7-异戊烯氧基-4-甲基香豆素（IC50 = 8.18±0.74 µM）。除体外测试外，MetaCore / MetaDrug二元QSAR模型
• Interaction of 7-Alkoxycoumarins with the Aryl Hydrocarbon Receptor
  作者：Marco Gargaro、Francesco Epifano、Serena Fiorito、Vito Alessandro Taddeo、Salvatore Genovese、Matteo Pirro、Antonella Turco、Paolo Puccetti、Carsten B. Schmidt-Weber、Francesca Fallarino

  DOI：10.1021/acs.jnatprod.7b00173

  日期：2017.6.23

  plays a pivotal role in numerous physiological and pathological responses, such as cell proliferation and differentiation, induction of xenobiotic metabolizing enzymes, response to environmental toxins, and several others. In this study, we investigated the ability of some natural compounds (oxyprenylated ferulic acid and umbelliferone derivatives) and their semisynthetic analogues (e.g., differently

  芳基烃受体（AhR）是被大量天然和合成配体激活的转录因子。它在许多生理和病理反应中起着关键作用，例如细胞增殖和分化，异种生物代谢酶的诱导，对环境毒素的反应等。在这项研究中，我们使用报告荧光素酶测定法研究了某些天然化合物（氧炔丙基阿魏酸和伞形酮衍生物）及其半合成类似物（例如，不同取代的7-烷氧基香豆素）激活AhR的能力。其中，我们发现7-异戊烯氧基香豆素是最好的AhR活化剂。七氢硼酸，7-but-2'-烯氧基香豆素，7-（2'，2'-二甲基-n-丙氧基）香豆素，7-苄氧基香豆素和7-（3'-羟甲基-3'-甲基烯丙氧基）香豆素也有活性，尽管程度较小。还使用参考配体6-甲酰基吲哚并[3,2- b ]咔唑分析了所有化合物抑制AhR活化的能力。在本研究中记录的数据指出，连接到香豆素环核上的3,3-二甲基烯丙氧基侧链作为AhR激活的关键部分的重要性。
• Indirect modeling of new repellent molecules active against insects, acarids, and other arthropods
  申请人：Delaveau Jean

  公开号：US20130079394A1

  公开（公告）日：2013-03-28

  This invention relates to novel coumarin derivatives, 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. This invention also relates to novel methods for modeling and/or predicting the repellency of unknown compounds.
• [EN] NOVEL INSECT-REPELLENT COUMARIN DERIVATIVES, SYNTHESES, AND METHODS OF USE<br/>[FR] DÉRIVÉS INSECTIFUGES INÉDITS DE COUMARINE, LEUR SYNTHÈSE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：MERIAL LTD

  公开号：WO2013003168A1

  公开（公告）日：2013-01-03

  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.
• [EN] INDIRECT MODELING OF NEW REPELLENT MOLECULES ACTIVE AGAINST INSECTS, ACARIDS, AND OTHER ARTHROPODS<br/>[FR] MODÉLISATION INDIRECTE DE MOLÉCULES RÉPULSIVES INÉDITES ACTIVES CONTRE LES INSECTES, LES ACARIENS ET AUTRES ARTHROPODES
  申请人：MERIAL LTD

  公开号：WO2013044118A2

  公开（公告）日：2013-03-28

  This invention relates to novel coumarin derivatives, 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. This invention also relates to novel methods for modeling and/or predicting the repeilency of unknown compounds.