7-acetamido-4-methylcoumarin | 66611-72-1

• 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-acetamido-4-methylcoumarin
• 英文别名: N-(4-methyl-2-oxo-2H-chromen-7-yl)acetamide；N-(4-methyl-2-oxochromen-7-yl)acetamide
• CAS: 66611-72-1
• 化学式: C₁₂H₁₁NO₃
• mdl: MFCD00453240
• 分子量: 217.224
• InChiKey: AOVJSWHKUGNIDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-acetamido-4-methylcoumarin 在 盐酸 、 乙醇 、 copper(l) chloride 作用下， 生成 7-chloro-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  Rao; Sundaramurthy, Proceedings - Indian Academy of Sciences, Section A, 1956, # 43, p. 149

  摘要：

  DOI：
• 作为产物：
  描述：

  (3-羟基-苯基)-氨基甲酸乙酯 在 4-二甲氨基吡啶 、 硫酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 28.0h， 生成 7-acetamido-4-methylcoumarin
  参考文献：
  名称：

  Substrate specificity of acetoxy derivatives of coumarins and quinolones towards Calreticulin mediated transacetylation: Investigations on antiplatelet function

  摘要：

  Calreticulin transacetylase (CRTAase) is known to catalyze the transfer of acetyl group from polyphenolic acetates (PA) to certain receptor proteins (RP), thus modulating their activity. Herein, we studied for the first time the substrate specificity of CRTAase towards N-acetylamino derivatives of coumarins and quinolones. This study is endowed with antiplatelet action by virtue of causing CRTAase catalyzed activation of platelet Nitric Oxide Synthase (NOS) by way of acetylation leading to the inhibition of ADP/Arachidonic acid (AA)-dependent platelet aggregation. Among all the N-acetylamino/acetoxy coumarins and quinolones screened, 7-N-acetylamino-4-methylcoumarin (7-AAMC, 17) was found to be the superior substrate to platelet CRTAase and emerged as the most promising antiplatelet agent both in vitro and in vivo. Further it caused the inhibition of cyclooxygenase-1 (Cox-1) resulting in the down regulation of thromboxane A2 (TxA2), modulation of tissue factor and the inhibition of platelet aggregation. It was also found effective in the inhibition of LPS induced pro-thrombotic conditions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.016

文献信息

• Synthesis of Water-Soluble Highly Charged and Methylene-Bridged ­Resorcin[4]arenes
  作者：Stefan Bossmann、Xiaoxuan Leaym、Stefan Kraft

  DOI：10.1055/s-2008-1032192

  日期：2008.3

  Methylene-bridged resorcin[4]arenes featuring electrochemically active and hydrophilic viologen units, chemically attached to their ‘rim’ regions, and a variety of pendent groups (‘feet’) have been synthesized. These compounds were designed to act as electrochemically active cavitands and especially as guests in mycobacteria­l channel proteins (channel blockers).

  具有电活性亲水性紫罗碱单元、化学结合于其“边缘”区域以及多种悬挂基团（“足部”）的亚甲基桥联间苯二酚[4]芳烃已合成。这些化合物被设计为发挥电活性腔体作用，并尤其作为分枝杆菌通道蛋白的客体（通道阻断剂）。
• [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。
• Structure activity studies with xenobiotic substrates using carboxylesterases isolated from Arabidopsis thaliana
  作者：Ian Cummins、Marie Landrum、Patrick G. Steel、Robert Edwards

  DOI：10.1016/j.phytochem.2006.12.014

  日期：2007.3

  cloned, expressed and the purified recombinant proteins assayed for esterase activity with xenobiotic substrates. Two members, AtCXE5 and AtCXE18 were found to be active carboxylesterases, though AtCXE5 proved to be highly unstable as a soluble protein. AtCXE18 and the previously characterised S-formylglutathione hydrolase from Arabidopsis (AtSFGH) were assayed against a series of esters based on methylumbelliferone

  羧酸酯酶 (CXE) 催化异生物质和天然产物的水解，从根本上改变它们的生物活性。虽然动物 CXE 的底物选择性，如猪肝酯酶 (PLE) 已得到充分研究，但植物中的相应酶尚未确定，其活性尚未确定。使用拟南芥 (At) 作为来源，已经克隆、表达了 α/β 水解酶 AtCXE 蛋白质家族的五个代表性成员，并用异生物质底物测定了纯化的重组蛋白的酯酶活性。两个成员 AtCXE5 和 AtCXE18 被发现是有活性的羧酸酯酶，尽管 AtCXE5 作为可溶性蛋白质被证明是高度不稳定的。AtCXE18 和先前表征的来自拟南芥 (AtSFGH) 的 S-甲酰谷胱甘肽水解酶针对一系列基于甲基伞形酮的酯进行了测定，其中酰基部分的大小和构象各不相同。使用同一系列测定拟南芥植物的粗酯酶制剂，并将结果与​​常用的 PLE 获得的结果进行比较。对于直链酯，AtCXE18 的行为类似于 PLE，但拟南芥水解酶证明对支链酰
• Monoterpene-Containing Substituted Coumarins as Inhibitors of Respiratory Syncytial Virus (RSV) Replication
  作者：Tatyana M. Khomenko、Anna A. Shtro、Anastasia V. Galochkina、Yulia V. Nikolaeva、Galina D. Petukhova、Sophia S. Borisevich、Dina V. Korchagina、Konstantin P. Volcho、Nariman F. Salakhutdinov

  DOI：10.3390/molecules26247493

  日期：——

  Respiratory syncytial virus (RSV) is a critical cause of infant mortality. However, there are no vaccines and adequate drugs for its treatment. We showed, for the first time, that O-linked coumarin–monoterpene conjugates are effective RSV inhibitors. The most potent compounds are active against both RSV serotypes, A and B. According to the results of the time-of-addition experiment, the conjugates act at the early stages of virus cycle. Based on molecular modelling data, RSV F protein may be considered as a possible target.

  呼吸道合胞病毒（RSV）是婴儿死亡的一个重要原因。然而，目前尚无疫苗和足够的药物用于治疗。我们首次展示，O-连接的香豆素-单萜共轭物是有效的RSV抑制剂。最有效的化合物对RSV的A型和B型两种血清型都具有活性。根据添加时间实验的结果，这些共轭物在病毒周期的早期阶段起作用。根据分子模拟数据，RSV F蛋白可能被视为一个可能的靶点。
• [EN] CHEMICAL PROBES OF LYSYL OXIDASE-LIKE 2 AND USES THEREOF<br/>[FR] SONDES CHIMIQUES DE LYSYL OXYDASE DE TYPE 2 ET LEURS UTILISATIONS
  申请人：PHARMAKEA INC

  公开号：WO2018048928A1

  公开（公告）日：2018-03-15

  Described herein are probe compounds that interact with the LOXL2 receptor, methods of making such probe compounds, and methods of using such probe compounds in vitro and in vivo.

  本文描述了与LOXL2受体相互作用的探针化合物，制备这种探针化合物的方法，以及在体外和体内使用这种探针化合物的方法。