1-(3,6,7-trimethylquinoxalin-2-yl)ethanone | 119426-76-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-(3,6,7-trimethylquinoxalin-2-yl)ethanone
• 英文别名: 2-acetyl-3,6,7-trimethyl-quinoxaline；1-(3,6,7-Trimethylquinoxaline-2-yl)ethanone
• CAS: 119426-76-5
• 化学式: C₁₃H₁₄N₂O
• 分子量: 214.267
• InChiKey: MMTSLWXLRRBHLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3,6,7-trimethylquinoxalin-2-yl)ethanone 在 一水合肼 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 48.0h， 生成 2,6,7-trimethyl-3-[5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazol3-yl]quinoxaline
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New Quinoxaline Derivatives as Antioxidant and Anti-Inflammatory Agents

  摘要：

  We report the synthesis, anti‐inflammatory, and antioxidant activities of novel quinoxaline and quinoxaline 1,4‐di‐N‐oxide derivatives. Microwave‐assisted methods have been used to optimize reaction times and to improve yields. The tested compounds presented important scavenging activities and promising in vitro inhibition of soybean lipoxygenase (LOX). Two of the best LOX inhibitors (compounds 7b and 8f) were evaluated as in vivo anti‐inflammatory agents using the carrageenin‐induced edema model. One of them (compound 7b) showed important in vivo anti‐inflammatory effect (41%) similar to that of indomethacin (47%) used as the reference drug.

  DOI：

  10.1111/j.1747-0285.2011.01076.x
• 作为产物：
  描述：

  在 sodium dithionite 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 1-(3,6,7-trimethylquinoxalin-2-yl)ethanone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New Quinoxaline Derivatives as Antioxidant and Anti-Inflammatory Agents

  摘要：

  We report the synthesis, anti‐inflammatory, and antioxidant activities of novel quinoxaline and quinoxaline 1,4‐di‐N‐oxide derivatives. Microwave‐assisted methods have been used to optimize reaction times and to improve yields. The tested compounds presented important scavenging activities and promising in vitro inhibition of soybean lipoxygenase (LOX). Two of the best LOX inhibitors (compounds 7b and 8f) were evaluated as in vivo anti‐inflammatory agents using the carrageenin‐induced edema model. One of them (compound 7b) showed important in vivo anti‐inflammatory effect (41%) similar to that of indomethacin (47%) used as the reference drug.

  DOI：

  10.1111/j.1747-0285.2011.01076.x

文献信息

• Synthesis, Biological Evaluation and Structure-Activity Relationships of New Quinoxaline Derivatives as Anti-Plasmodium falciparum Agents
  作者：Ana Gil、Adriana Pabón、Silvia Galiano、Asunción Burguete、Silvia Pérez-Silanes、Eric Deharo、Antonio Monge、Ignacio Aldana

  DOI：10.3390/molecules19022166

  日期：——

  We report the synthesis and antimalarial activities of eighteen quinoxaline and quinoxaline 1,4-di-N-oxide derivatives, eight of which are completely novel. Compounds 1a and 2a were the most active against Plasmodium falciparum strains. Structure-activity relationships demonstrated the importance of an enone moiety linked to the quinoxaline ring.

  我们报道了十八种喹喔啉和喹喔啉1,4-双-N-氧化物衍生物的合成及其抗疟活性，其中八种是完全新颖的。化合物1a和2a对恶性�隆疟原虫株表现出最强的活性。结构-活性关系表明，与喹喔啉环相连的烯酮部分的重要性。
• Substituted quinoxalyl-imidazolidine-2,4-diones, processes for their
  申请人：Hoechst Aktiengesellschaft

  公开号：US04943576A1

  公开（公告）日：1990-07-24

  Substituted quinoxalyl-imidazolidine-2,4-diones, processes for their preparation, their use as medicaments and pharmaceutical preparations 5-Quinoxalyl-imidazolidine-2,4-diones of the formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the meanings given, and physiologically tolerated salts thereof and processes for their preparation are described. The compounds inhibit aldose reductase and can be used as medicaments.

  取代的喹喹啉基咪唑啉-2,4-二酮，其制备方法，作为药物和药物制剂使用的过程。公式I的5-喹啉基咪唑啉-2,4-二酮 其中R.sup.1、R.sup.2、R.sup.3、R.sup.4和R.sup.5具有给定的含义，以及其生理耐受盐和其制备方法。这些化合物抑制醛糖还原酶，可用作药物。
• Microwave-Assisted Domino Benzannulation of α-Oxo Ketenes: Preparation of 1,3-Dihydro-2H-1,5-benzodiazepin-2-ones
  作者：Juan-Carlos Castillo、Marc Presset、Rodrigo Abonia、Yoann Coquerel、Jean Rodriguez

  DOI：10.1002/ejoc.201200093

  日期：2012.4

  The microwave irradiation of a series of 2-diazo-1,3-diketones in the presence of an o-phenylenediamine derivative triggered a domino Wolff rearrangement/nucleophilic addition/intramolecular imination sequence to provide a new synthetic entry to 1,3-dihydr-2H-1,5-benzodiazepin-2-ones, a class of molecules with important biological properties.

  在邻苯二胺衍生物的存在下，一系列 2-重氮-1,3-二酮的微波辐射触发了多米诺沃尔夫重排/亲核加成/分子内亚胺化序列，为 1,3-二氢- 2H-1,5-benzodiazepin-2-ones，一类具有重要生物学特性的分子。
• 2,3-二取代喹喔啉衍生物的制备方法
  申请人：广西师范大学

  公开号：CN104086491B

  公开（公告）日：2016-04-06

  本发明公开了2,3-二取代喹喔啉衍生物的一种新型制备方法。以芳胺和1,3-二羰基-2-肟类化合物为原料进行缩合后，利用分子内氮正离子的亲电取代反应进行环化，巧妙地将“缩合-环化”反应联系起来，两步一釜法操作得到苯环上具有不同取代基的2,3-二取代喹喔啉衍生物。与传统合成方法相比，该方法原料廉价易得，过程中无需对中间产物进行处理，简化了合成步骤，特别是芳胺类化合物在苯环上存在多种取代方式，实现了产物结构的多样化，有利于对喹喔啉衍生物的深入研究。利用本发明的方法还获得了18个未见报道的新化合物。
• Green synthesis of enantiopure quinoxaline alcohols using <scp> <i>Daucus carota</i> </scp>
  作者：Sneha H. Meshram、Tungana Ramesh、Jagadeesh Babu Nanubolu、Ajay Kumar Srivastava、Bhaskar Rao Adari、Nivedita Sahu

  DOI：10.1002/chir.23057

  日期：2019.4

  enantioselectivity (up to 98%). The absolute configuration of the chiral product (R)‐1‐(3‐methyl 7‐nitroquinoxalin‐2‐yl) ethan‐1‐ol 2b was confirmed by X‐ray crystallography studies. The chiral R‐configuration of the products obtained was confirmed by absolute configuration studies and was assigned following anti‐Prelogs rule. Quinoxaline pharmacophores form a part of well‐known potent drug molecules;

  绿色化学是使用生物催化剂合成生物活性化合物的新方法，从而减少了对人类健康和环境污染的危害。不对称生物还原是化学酶法合成中生产对映体纯的手性醇的最广泛采用的策略之一。本研究着重介绍了使用生物催化剂Daucus carota将喹喔啉酮1a-6a选择性生物还原为相应的光学纯醇1b-6b的方法，产率高（高达84％）和良好的对映选择性（高达98％）。手性产物（R）-1-（3-甲基7-硝基喹喔啉-2-基）乙醇-1-醇2b的绝对构型X射线晶体学研究证实了这一点。绝对构型研究证实了所得产物的手性R构型，并根据anti- Prelogs规则进行了分配。喹喔啉药效团是众所周知的有效药物分子的一部分。因此，研究了手性产品以使用SwissADME特性分析仪测定其分子特性。所有手性产品均未显示违反Lipinski规则，并且有望具有良好的口服生物利用度。根据分子特性预测研究，化合物6b（R）-1-（6,7-二氯-3-