7-甲氧基-3-香豆素醋酸 | 765276-64-0

• 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-甲氧基-3-香豆素醋酸
• 英文名称: 2-(7-methoxy-2-oxo-2H-chromen-3-yl)acetic acid
• 英文别名: 3-acetic acid-7-methoxycoumarin；7-methoxycoumarin-3-acetic acid；2-(7-methoxy-2-oxochromen-3-yl)acetic acid
• CAS: 765276-64-0
• 化学式: C₁₂H₁₀O₅
• 分子量: 234.208
• InChiKey: UNHYHSXKOVCSSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-甲氧基-3-香豆素醋酸 在 对硝基苯酚 作用下， 以 丙酮 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Synthesis and antimicrobial activity of coumarin and benzodioxazepine-, diazazepine- and benzoxazepine-substituted penicillins

  摘要：

  Some semisynthetic penicillins 6-substituted with benzo-condensed heterocyclic derivatives were prepared using the reaction of carbon suboxide with Schiff bases and disubstituted benzoic acids. The microbiological assay performed with the penicillins and their intermediates showed a good activity for one Schiff base and a weak activity for the other compounds.

  DOI：

  10.1016/0223-5234(94)90075-2
• 作为产物：
  描述：

  3-甲氧基苯酚 在 三乙胺 、 magnesium chloride 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 7-甲氧基-3-香豆素醋酸
  参考文献：
  名称：

  Synthesis of Novel Coumarin Derivatives and in vitro Biological Evaluation as Potential PTP 1B Inhibitors

  摘要：

  The aim of protein tyrosine phosphatase 1B (PTP 1B) inhibitors is to develop effective drug for diabetes and obesity. Coumarin becomes as a good skeleton, and is often applied in drug design and synthesis. In this paper, we have synthesized a series of novel coumarin derivatives to be as potential PTP 1B inhibitors. The inhibition rate of compound 9 was more than 80%, and the IC50 value was 49.2 mu M, which would be considered for further study.

  DOI：

  10.3987/com-13-12730

文献信息

• Synthesis, reactions and antineoplastic activity of 3-(2-oxo-2H-chromen-3-yl)-2-oxo-2H,5H-pyrano[3,2-c]chromene derivatives
  作者：Renata Gašparová、Pavol Koiš、Margita Lácová、Silvia Kováčová、Andrej Boháč

  DOI：10.2478/s11532-012-0184-1

  日期：2013.4.1

  5-alkoxy-, 5-hydroxy- or 5-acylamino-2H,5H-pyrano[3,2-c]chromen-2-ones 4-6via nucleophilic substitution of acetyloxy group at C-5. Acetates and hydroxyl derivatives 3 and 5 undergo facile rearrangement in an acid medium yielding 5-hydroxypyrano[2,3-b]chromen-2(10aH)-ones 7. Twelve prepared compounds were evaluated on their antineoplastic activities on 60 human tumour cell line panels in NCI USA. The

  摘要 通过 4 环缩合反应，高收率合成了关键的 3-(2-oxo-2H-chromen-3-yl)-2-oxo-2H,5H-pyrano[3,2-c]chromen-5-yl 醋酸酯 3 -oxo-4H-chromen-3-carbaldehydes 1 与香豆素-3-乙酸 2 在温和条件下。反应途径包括羟醛缩合和随后的分子内内酯化，得到 2-氧代-2H,5H-吡喃并[3,2-c]色烯骨架 3。用醇、水或含氮化合物进一步处理乙酸酯 3 生成 5-烷氧基-, 5-羟基-或5-酰氨基-2H,5H-吡喃并[3,2-c]色烯-2-酮4-6通过乙酰氧基在C-5处的亲核取代。乙酸盐和羟基衍生物 3 和 5 在酸性介质中容易重排，产生 5-羟基吡喃并[2,3-b]色烯-2(10aH)-酮 7。在美国 NCI 的 60 个人类肿瘤细胞系面板上评估了 12 种制备的化合物的抗肿瘤活性。所获得的生物学结果证实
• Microwave assisted one pot synthesis of 7-substituted 2-(2-oxo-2H-chromen-3-yl)acetic acids as precursors of new anti-tumour compounds
  作者：Silvia Kováčová、Lucia Kováčiková、Margita Lácová、Andrej Boháč、Marta Sališová

  DOI：10.2478/s11696-010-0059-x

  日期：2010.1.1

  lactonisation as one pot syntheses of 2-(2-oxo-2H-chromen-3-yl)acetic acids VIIa-Xa has been studied. The required acids VIIa-Xa were prepared as precursors of recently discovered compounds possessing antineoplastic activities. Syntheses of VIIa-Xa were carried out using para substituted 2-hydroxybenzaldehydes II-VI, succinic acid anhydride, sodium succinate under thermal or microwave conditions. Significant

  已经研究了珀金（Perkin）缩合和随后的分子内内酯化，作为2-（2-氧代-2 H-铬-3-基）乙酸VIIa-Xa的一锅合成。所需的酸VIIa-Xa被制备为最近发现的具有抗肿瘤活性的化合物的前体。使用对位取代的2-羟基苯甲醛II-VI，琥珀酸酐，琥珀酸钠在热或微波条件下进行VIIa-Xa的合成。观察到微波辐照的反应时间显着缩短（18-50分钟，而不是加热1.5-5小时）。微波辅助反应进行得更加顺利，从而可以提高所需产物VIIa-Xa的产率（31–61％），相比之下，在经典的热条件下，例如IXa为21.8％（Hurenkamp等，2007）。副产物七个反应分离和确定为2 ħ，2' ħ -3,3'- bichromene -2,2'-二酮的VIIb-XB和（ë）-3-（2-羟基苯乙烯基）-2 ħ -色烯-2-ones VIIc-IXc。
• Tuning energy transfer in switchable donor–acceptor systems
  作者：Johannes H. Hurenkamp、Jaap J. D. de Jong、Wesley R. Browne、Jan H. van Esch、Ben L. Feringa

  DOI：10.1039/b719095f

  日期：——

  The synthesis and characterisation of a coumarin–dithienylcyclopentene–coumarin symmetric triad (CSC) and a perylene bisimide–dithienylcyclopentene–coumarin asymmetric triad (PSC) are reported. In both triads the switching function of the photochromic dithienylcyclopentene unit is retained. For CSC an overall 50% quenching of the coumarin fluorescence is observed upon ring-closure of the dithienylcyclopentene component, which, taken together with the low PSS (<70%), indicates that energy transfer quenching of the coumarin component by the dithienylcyclopentene in the closed state is efficient. Upon ring opening of the dithienylcyclopentene unit the coumarin emission is restored fully. The PSC triad shows efficient energy transfer from the coumarin to the perylene bisimide unit when the dithienylcyclopentene unit is in the open state. When the dithienylcyclopentene is in the closed (PSS) state a 60% decrease in sensitized perylene bisimide emission intensity is observed due to competitive quenching of the coumarin excited state and partial quenching of the perylene excited state by the closed dithienylcyclopentene unit. This modulation of energy transfer is reversible over several cycles for both the symmetric and asymmetric tri-component systems.

  报道了香豆素-二噻吩基环戊烯-香豆素对称三联体（CSC）和苝双酰亚胺-二噻吩基环戊烯-香豆素不对称三联体（PSC）的合成和表征。在这两个三元组中，光致变色二噻吩基环戊烯单元的开关功能被保留。对于 CSC，在二噻吩基环戊烯组分闭环时观察到香豆素荧光总体 50% 猝灭，这与低 PSS (<70%) 一起表明香豆素组分通过二噻吩基环戊烯在关闭状态是有效的。当二噻吩基环戊烯单元开环时，香豆素发射完全恢复。当二噻吩基环戊烯单元处于开放状态时，PSC 三元组显示出从香豆素到苝双酰亚胺单元的有效能量转移。当二噻吩基环戊烯处于闭合 (PSS) 状态时，由于闭合二噻吩基环戊烯单元对香豆素激发态的竞争性猝灭和苝激发态的部分猝灭，观察到敏化苝双酰亚胺发射强度降低了 60%。对于对称和不对称三组分系统，这种能量转移的调制在几个周期内是可逆的。
• Intramolecular energy transfer in a tetra-coumarin perylene system: influence of solvent and bridging unit on electronic properties
  作者：Johannes H. Hurenkamp、Wesley R. Browne、Ramūnas Augulis、Audrius Pugžlys、Paul H. M. van Loosdrecht、Jan H. van Esch、Ben L. Feringa

  DOI：10.1039/b711681k

  日期：——

  is reported, in which an energy-transfer efficiency of >99% is achieved. Comparison of the excited-state properties of the donor-acceptor system with model compounds revealed that although the photophysical properties of the perylene bisimide acceptor unit are affected considerably by the nature of the substituent at the imide positions and the solvent employed, through-bond interaction between the

  报道了一种新型香豆素供体-per联亚酰亚胺受体光收集系统的合成和表征，其中能量转移效率> 99％。将供体-受体体系与模型化合物的激发态性质进行比较表明，尽管the亚双酰亚胺受体单元的光物理性质受到酰亚胺位置上取代基的性质和所用溶剂的影响很大，但通过键间相互作用供体和受体单元之间的距离可以忽略不计。可以将本系统中的能量转移描述为经由空间能量转移机制发生。仔细考虑供体相对于受体单元的氧化还原性质可以避免潜在有害的激发态电子转移过程。
• [EN] ANTIMICROBIAL PEPTIDES AND USE THEREOF<br/>[FR] PEPTIDES ANTIMICROBIENS ET UTILISATIONS DE CES DERNIERS
  申请人：UNIV TEXAS

  公开号：WO2019136139A2

  公开（公告）日：2019-07-11