ethyl 2-(1-oxoisoquinolin-2(1H)-yl)acetate | 59139-95-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(1-oxoisoquinolin-2(1H)-yl)acetate
• 英文别名: Ethyl 2-(1-oxoisoquinolin-2-yl)acetate
• CAS: 59139-95-6
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: HGUGEXAHZLWSLP-UHFFFAOYSA-N

物化性质

• 沸点：
  393.2±42.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-(1-oxoisoquinolin-2(1H)-yl)acetate 在 1-羟基苯并三唑 、 lithium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 9.33h， 生成 R-1-[(1-oxo-1H-isoquinolin-2-yl)acetamido]-3-methylbutylboronic acid pinandiol ester
  参考文献：
  名称：

  Optimization of peptidomimetic boronates bearing a P3 bicyclic scaffold as proteasome inhibitors

  摘要：

  A new series of pseudopeptide boronate proteasome inhibitors (2-3) was developed, through optimization of our previously described analogs of bortezomib, bearing a bicyclic 1,6-naphthyridin-5(6H)-one scaffold as P3 fragment (1). The biological evaluation on human 20S proteasome displayed a promising inhibition profile, especially for compounds bearing a P2 ethylene fragment, which exhibited Ki values in the nanomolar range for the ChT-L activity (e.g. 2a, Ki = 0.057 μM) and considerable selectivity for proteasome over bovine pancreatic α-chymotrypsin. Docking experiments into the yeast 20S proteasome revealed that the ligands are accommodated predominantly into the ChT-L site and that they covalently bind to the active site threonine residue via boron atom. Within the cellular assays performed against a 60 cancer cell line panel, compounds 3e and 3f demonstrated also good antiproliferative activity and compound 3f emerged as promising lead compound for the development of anticancer agents targeting melanoma and non-small cell lung cancer.

  DOI：

  10.1016/j.ejmech.2014.06.017
• 作为产物：
  描述：

  1-羟基异喹啉 、 溴乙酸乙酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 3.5h， 以95%的产率得到ethyl 2-(1-oxoisoquinolin-2(1H)-yl)acetate
  参考文献：
  名称：

  Discovery of a novel and potent inhibitor with differential species-specific effects against NLRP3 and AIM2 inflammasome-dependent pyroptosis

  摘要：

  DOI：

  10.1016/j.ejmech.2022.114194

文献信息

• I ₂ ‐Promoted Direct C−H Sulfenylation of Isoquinolin‐1(2 <i>H</i> )‐ones with Sulfonyl Chlorides
  作者：Cai‐Yun Yang、Xia Li、Bo Liu、Guo‐Li Huang

  DOI：10.1002/ejoc.202001371

  日期：2021.1.8

  conditions was described. These methods provide an alternative and facile synthetic route to access a series of 4‐arylthio‐substituted isoquinolin‐1(2H)‐one derivatives in moderate to good yields. This is a useful, time‐efficient, and scalable procedure for the construction of C(sp2)−S bonds.

  描述了在无金属和无溶剂条件下，使用市售的芳基磺酰氯作为硫源，碘促进的异喹啉-1（2 H）-酮的区域选择性C-4亚磺酰化。这些方法提供了另一种简便的合成途径，以中等到良好的产率获得了一系列4-芳硫基取代的异喹啉-1（2 H）-one衍生物。这是构造C（sp 2）-S键的有用，省时和可扩展的过程。
• Electrochemical regioselective synthesis of N-substituted/unsubstituted 4-selanylisoquinolin-1(2H)-ones
  作者：Zhi-Lin Wu、Jin-Yang Chen、Xian-Zhi Tian、Wen-Tao Ouyang、Zhuo-Tao Zhang、Wei-Min He

  DOI：10.1016/j.cclet.2021.08.071

  日期：2022.3

  A novel and efficient electro-chemical initiated radical strategy was developed for the preparation of both N-substituted and N-unsubstituted 4-selanylisoquinolin-1(2H)-ones through selenylation of isoquinolin-1(2H)-ones with organodiselenides under chemical oxidant-, additive-free and ambient conditions.

  开发了一种新颖高效的电化学引发自由基策略，用于通过异喹啉-1(2 H)-酮与有机二硒化物的硒化制备N-取代和N-未取代的 4-硒基异喹啉-1(2 H )-酮。化学氧化剂，无添加剂和环境条件。
• <i>p</i>-Toluenesulfonic acid-catalyzed regioselective C4–H iodination of isoquinolin-1(2<i>H</i>)-ones
  作者：Cai-Yun Yang、Lin-Ping Hu、De-Run Zhang、Xia Li、Ming-Yu Teng、Bo Liu、Guo-Li Huang

  DOI：10.1039/d2nj00159d

  日期：——

  A general and efficient procedure for p-toluenesulfonic acid-catalyzed iodination of isoquinolin-1(2H)-ones with N-iodosuccinimide at room temperature is described. This method provides an alternative way of constructing C–I bonds, affords various 4-iodoisoquinolin-1(2H)-ones in moderate to good yields, and shows a broad substrate scope and good functional group tolerance.

  描述了在室温下对甲苯磺酸催化异喹啉-1(2 H)-酮与 N-碘代琥珀酰亚胺碘化的一般有效程序。该方法提供了另一种构建 C-I 键的方法，以中等至良好的产率提供各种 4-iodoisoquinolin-1(2 H )-one，并显示出广泛的底物范围和良好的官能团耐受性。
• 一种制备4-碘异喹啉-1(2H)-酮类化合物的方法
  申请人：云南师范大学

  公开号：CN114805204B

  公开（公告）日：2023-09-15

  本方案属于有机合成化学领域，公开了一种制备4‑碘异喹啉‑1(2H)‑酮类化合物的方法，其以异喹啉‑1(2H)‑酮或其衍生物为底物，以酸为仅有的催化剂，与碘代丁二酰亚胺(NIS)在一定反应温度和溶剂中反应得到。本方案采用常见廉价易得的无机酸或有机酸作为反应的催化剂，不使用任何金属和有机催化剂，不需要任何氧化剂和添加剂，反应条件温和，产物收率高、操作简单、绿色环保；所用的试剂和催化剂工业来源丰富易得，生产成本低廉，产物纯度高，具有良好的工业应用前景。
• Optimization of peptidomimetic boronates bearing a P3 bicyclic scaffold as proteasome inhibitors
  作者：Valeria Troiano、Kety Scarbaci、Roberta Ettari、Nicola Micale、Carmen Cerchia、Andrea Pinto、Tanja Schirmeister、Ettore Novellino、Silvana Grasso、Antonio Lavecchia、Maria Zappalà

  DOI：10.1016/j.ejmech.2014.06.017

  日期：2014.8

  A new series of pseudopeptide boronate proteasome inhibitors (2-3) was developed, through optimization of our previously described analogs of bortezomib, bearing a bicyclic 1,6-naphthyridin-5(6H)-one scaffold as P3 fragment (1). The biological evaluation on human 20S proteasome displayed a promising inhibition profile, especially for compounds bearing a P2 ethylene fragment, which exhibited Ki values in the nanomolar range for the ChT-L activity (e.g. 2a, Ki = 0.057 μM) and considerable selectivity for proteasome over bovine pancreatic α-chymotrypsin. Docking experiments into the yeast 20S proteasome revealed that the ligands are accommodated predominantly into the ChT-L site and that they covalently bind to the active site threonine residue via boron atom. Within the cellular assays performed against a 60 cancer cell line panel, compounds 3e and 3f demonstrated also good antiproliferative activity and compound 3f emerged as promising lead compound for the development of anticancer agents targeting melanoma and non-small cell lung cancer.