ethyl 3-bromo-7-N-(carbethoxy)aminocoumarin-4-acetate | 1135458-72-8

• 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: ethyl 3-bromo-7-N-(carbethoxy)aminocoumarin-4-acetate
• CAS: 1135458-72-8
• 化学式: C₁₆H₁₆BrNO₆
• 分子量: 398.21
• InChiKey: GUQGDGFPRCFLQE-UHFFFAOYSA-N

物化性质

• 熔点：
  200-201 °C
• 沸点：
  474.1±45.0 °C(predicted)
• 密度：
  1.546±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  苯并呋喃-2-硼酸 、 ethyl 3-bromo-7-N-(carbethoxy)aminocoumarin-4-acetate 在 palladium diacetate 、 sodium carbonate 、 三苯基膦 作用下， 以 丙醇 为溶剂， 反应 2.08h， 以71%的产率得到KAWE-142
  参考文献：
  名称：

  Protease responsive nanoprobes with tethered fluorogenic peptidyl 3-arylcoumarin substrates

  摘要：

  通过将独特的绿色荧光双功能3-芳基香豆素衍生荧光基质连接到聚（丙烯酰胺-共-N-（3-氨丙基）甲基丙烯酰胺）纳米颗粒上，得到了蛋白酶响应的纳米传感器，其中蛋白酶解作用导致信号大幅放大。

  DOI：

  10.1039/b816637d
• 作为产物：
  描述：

  ethyl 7-ethoxycarbonylaminocoumarin-4-acetate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以77%的产率得到ethyl 3-bromo-7-N-(carbethoxy)aminocoumarin-4-acetate
  参考文献：
  名称：

  Protease responsive nanoprobes with tethered fluorogenic peptidyl 3-arylcoumarin substrates

  摘要：

  通过将独特的绿色荧光双功能3-芳基香豆素衍生荧光基质连接到聚（丙烯酰胺-共-N-（3-氨丙基）甲基丙烯酰胺）纳米颗粒上，得到了蛋白酶响应的纳米传感器，其中蛋白酶解作用导致信号大幅放大。

  DOI：

  10.1039/b816637d

文献信息

• Synthesis of Piperazinones, Piperazines, Tetrahydropyrazines, and Dihydropyrazinones from Polymer-Supported Acyclic Intermediates via N-Alkyl- and N-Acyl­iminiums
  作者：Barbora Vaňková、Lucie Brulíková、Boyuan Wu、Viktor Krchňák

  DOI：10.1002/ejoc.201200591

  日期：2012.9

  procedure from easily accessible polymer-supported acyclic precursors containing either a masked aldehyde or ketone group. Acid-mediated unmasking of the aldehyde triggered cyclic iminium formation followed by reduction with triethylsilane present in the cleavage cocktail. The effect of the substituent at the iminium-forming nitrogen was evaluated: whereas complete conversion to the target compounds was

  三取代的哌嗪酮、哌嗪、四氢吡嗪和二氢吡嗪酮通过一步法从含有掩蔽醛或酮基团的聚合物支撑的无环前体中制备。酸介导的醛的暴露引发了环状亚胺的形成，然后用裂解混合物中存在的三乙基硅烷进行还原。评估了亚胺形成氮上取代基的影响：虽然观察到 N-烷基、芳基和苯磺酰胺衍生物完全转化为目标化合物，但 N-酰基化合物的醛部分还原为醇. 类似地，酮容易为环状亚胺提供 N-烷基化合物，而它们与 N-酰基前体的环化则不情愿地进行。有趣的是，在三乙基硅烷的存在下，在 60 °C 下树脂结合的无环前体的裂解导致酰胺键分解并形成内酯。类似的合成路线也成功地用于制备哌嗪，并作为合成二氮杂卓的替代路线进行了测试。
• [EN] POLYAMINE COMPOUNDS THAT BIND TAR RNA OF HIV AND METHODS OF TREATING VIRAL DISORDERS<br/>[FR] COMPOSÉS POLYAMINES QUI SE LIENT À DE L'ARN TAR DU VIH ET PROCÉDÉS DE TRAITEMENT DE TROUBLES VIRAUX
  申请人：US GOV HEALTH & HUMAN SERV

  公开号：WO2009145839A1

  公开（公告）日：2009-12-03

  The invention provides for novel polyamine compounds, substituted at the side chains, which can treat various disease states including viral infection, e.g. HIV infection, at low cytotoxicity values.

  这项发明提供了一种新型的聚胺化合物，其侧链被取代，可以治疗包括病毒感染（如HIV感染）在内的各种疾病状态，并且具有低细胞毒性数值。
• Dendrimeric peptides, pharmaceutical compositions and methods of using the same
  申请人：Totsingan Filbert

  公开号：US09102712B2

  公开（公告）日：2015-08-11

  Novel peptide compounds and pharmaceutical compositions thereof are disclosed that have a formula represented by the following formula (I) wherein L1, L2, L3, Z, R1, R2, R4 and R5 are as described herein. The compounds demonstrate antimicrobial activity and may be prepared as pharmaceutical compositions and used for the prevention and treatment of a variety of conditions in mammals including humans where microbial invasion is involved. The present peptides are particularly valuable as their effect is rapid, broad in spectrum and mostly indifferent to resistance provided by standard antibiotics.

  揭示了具有以下公式（I）所代表的公式的新型肽化合物和其制药组合物，其中L1、L2、L3、Z、R1、R2、R4和R5如本文所述。这些化合物表现出抗微生物活性，可制备为制药组合物，并用于在涉及微生物入侵的哺乳动物中，包括人类的预防和治疗多种疾病。目前的肽特别有价值，因为它们的效果快速，谱广，并且大多不受标准抗生素提供的抗性影响。
• Piperazine Amide Linker for Cyclative Cleavage from Solid Support: Traceless Synthesis of Dihydroquinoxalin-2-ones
  作者：Cleopatra Neagoie、Viktor Krchňák

  DOI：10.1021/co300023b

  日期：2012.7.9

  was reduced, and acyclic precursors, in contrast to traditional ester-type linkage, remained attached to the resin. Target dihydroquinoxalinones were obtained either by acid- or microwave-mediated cyclative cleavage. The synthesis provided crude compounds of high purity and enabled the preparation of stable immobilized linear intermediates. The linker is suitable for combinatorial synthesis of compound

  描述了用于从固相支持物上环状裂解的哌嗪酰胺接头及其在二氢喹喔啉酮的无痕固相合成中的用途。哌嗪通过氨基甲酸酯键连接到Wang树脂上，并用Fmoc-氨基酸酰化。在除去Fmoc基团之后，使树脂结合的胺与1-氟-2-硝基苯反应。所得的2-硝基苯胺的硝基被还原，并且与传统的酯型连接相反，无环前体保持附着在树脂上。通过酸或微波介导的循环裂解获得目标二氢喹喔啉酮。该合成提供了高纯度的粗化合物，并使得能够制备稳定的固定化线性中间体。该接头适用于化合物文库的组合合成。
• N-Acylpolyamine inhibitors of HDM2 and HDMX binding to p53
  作者：Ryo Hayashi、Deyun Wang、Toshiaki Hara、Jaclyn A. Iera、Stewart R. Durell、Daniel H. Appella

  DOI：10.1016/j.bmc.2009.10.032

  日期：2009.12

  Selective inhibition of protein-protein interactions important for cellular processes could lead to the development of new therapies against disease. In the area of cancer, overexpression of the proteins human double minute 2 (HDM2) and its homolog HDMX has been linked to tumor aggressiveness. Both HDM2 and HDMX bind to p53 and prevent cell cycle arrest or apoptosis in damaged cells. Developing a strategy to simultaneously prevent the binding of both HDM2 and HDMX to p53 is an essential feature of inhibitors to restore p53 activity in a number of different cancers. Inhibition of protein-protein interactions with synthetic molecules is an emerging area of research that requires new inhibitors tailored to mimic the types of interfaces between proteins. Our strategy to create inhibitors of protein-protein interactions is to develop a non-natural scaffold that may be used as a starting point to identify important molecular components necessary for inhibition. In this study, we report an N-acylpolyamine (NAPA) scaffold that supports numerous sidechains in a compact atomic arrangement. NAPAs were constructed by a series of reductive aminations between amino acid derivatives followed by acylation at the resulting secondary amine. An optimized NAPA was able to equally inhibit the association of both HDM2 and HDMX with p53. Our results demonstrate some of the challenges associated with targeting multiple protein-protein interactions involved in overlapping cellular processes. Published by Elsevier Ltd.