6-metil-8-idrazino-1,3-diossol<4,5-g>chinolina | 91918-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-metil-8-idrazino-1,3-diossol<4,5-g>chinolina
• 英文别名: 8-Hydrazinyl-6-methyl-2H-[1,3]dioxolo[4,5-g]quinoline；(6-methyl-[1,3]dioxolo[4,5-g]quinolin-8-yl)hydrazine
• CAS: 91918-90-0
• 化学式: C₁₁H₁₁N₃O₂
• 分子量: 217.227
• InChiKey: SGSHZGYZRDZABO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  69.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-metil-8-idrazino-1,3-diossol<4,5-g>chinolina 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以95%的产率得到6-methyl[1,3]dioxolo[4,5-g]quinolin-8-amine
  参考文献：
  名称：

  微波辅助合成4-喹啉基肼，然后还原硼化镍：一种方便的制备4-氨基喹啉及其衍生物的方法

  摘要：

  氯化镍（II）/硼氢化钠组合用于将4-肼基喹啉衍生物还原为相应的苯胺。该还原方案被有效地应用于单取代肼的还原裂解。我们在本文中描述了4-肼基喹啉的微波辅助合成，其提供了高产率和快速的两步法，用于在温和条件下合成4-氨基喹啉作为抗疟原体。

  DOI：

  10.1016/j.tetlet.2008.01.128
• 作为产物：
  描述：

  6-metil-8-cloro-1,3-diossol<4,5-g>chinolina 在 一水合肼 作用下， 反应 0.08h， 以86%的产率得到6-metil-8-idrazino-1,3-diossol<4,5-g>chinolina
  参考文献：
  名称：

  微波辅助合成4-喹啉基肼，然后还原硼化镍：一种方便的制备4-氨基喹啉及其衍生物的方法

  摘要：

  氯化镍（II）/硼氢化钠组合用于将4-肼基喹啉衍生物还原为相应的苯胺。该还原方案被有效地应用于单取代肼的还原裂解。我们在本文中描述了4-肼基喹啉的微波辅助合成，其提供了高产率和快速的两步法，用于在温和条件下合成4-氨基喹啉作为抗疟原体。

  DOI：

  10.1016/j.tetlet.2008.01.128

文献信息

• Design, Synthesis, and Structure–Activity Relationship Studies of 4-Quinolinyl- and 9-Acrydinylhydrazones as Potent Antimalarial Agents
  作者：Caterina Fattorusso、Giuseppe Campiani、Gagan Kukreja、Marco Persico、Stefania Butini、Maria Pia Romano、Maria Altarelli、Sindu Ros、Margherita Brindisi、Luisa Savini、Ettore Novellino、Vito Nacci、Ernesto Fattorusso、Silvia Parapini、Nicoletta Basilico、Donatella Taramelli、Vanessa Yardley、Simon Croft、Marianna Borriello、Sandra Gemma

  DOI：10.1021/jm7012375

  日期：2008.3.13

  synthesis, and biological investigation of novel antimalarial agents with low potential to develop resistance and structurally based on a highly conjugated scaffold. Starting from a new hit, the designed modifications were performed hypothesizing a specific interaction with free heme and generation of radical intermediates. This approach provided antimalarials with improved potency against chloroquine-resistant

  疟疾是贫困地区的主要健康问题，在这些地区，人们迫切需要以负担得起的价格购买新的抗寄生虫药。我们在此报告了新型抗疟疾药物的设计，合成和生物学研究，这些药物具有发展抗药性的低潜力，并且在结构上基于高度偶联的支架。从新的命中开始，进行设计的修饰，假设与游离血红素发生特定的相互作用并产生自由基中间体。与已知药物相比，该方法为抗疟药提供了增强的抗氯喹抗疟原虫能力。确定了许多结构-活性关系（SAR）趋势，在合成的类似物中，吡咯烷基甲基亚芳基和咪唑衍生物5r，5t，发现8b和8b是新系列中最有效的抗疟药。研究了新化合物的作用机理，并评估了它们的体内活性。
• Quinolylhydrazones as novel inhibitors of Plasmodium falciparum serine protease PfSUB1
  作者：Sandra Gemma、Simone Giovani、Margherita Brindisi、Pierangela Tripaldi、Simone Brogi、Luisa Savini、Isabella Fiorini、Ettore Novellino、Stefania Butini、Giuseppe Campiani、Maria Penzo、Michael J. Blackman

  DOI：10.1016/j.bmcl.2012.06.023

  日期：2012.8

  Plasmodium falciparum subtilisin-like protease 1 (PfSUB1) is a serine protease that plays key roles in the egress of the parasite from red blood cells and in preparing the released merozoites for the subsequent invasion of new erythrocytes. The development of potent and selective PfSUB1 inhibitors could pave the way to the discovery of potential antimalarial drugs endowed with an innovative mode of action and consequently able to overcome the current problems of resistance to established chemotherapies. Through the screening of a proprietary library of compounds against PfSUB1, we identified hydrazone 2 as a hit compound. Here we report a preliminary investigation of the structure-activity relationships for a class of PfSUB1 inhibitors related to our identified hit. (C) 2012 Elsevier Ltd. All rights reserved.
• Targeting clinically-relevant metallo-<b>β</b>-lactamases: from high-throughput docking to broad-spectrum inhibitors
  作者：Margherita Brindisi、Simone Brogi、Simone Giovani、Sandra Gemma、Stefania Lamponi、Filomena De Luca、Ettore Novellino、Giuseppe Campiani、Jean-Denis Docquier、Stefania Butini

  DOI：10.3109/14756366.2016.1172575

  日期：2016.11.1

  Metallo-beta-lactamases (MBLs) represent one of the most important and widespread mechanisms of resistance to beta-lactam antibiotics (including the life-saving carbapenems), against which no clinically useful inhibitors are currently available. We report herein a structure-based high-throughput docking (HTD) campaign on three clinically-relevant acquired MBLs (IMP-1, NDM-1 and VIM-2). The initial hit NF1810 (1) was optimized providing the broad-spectrum inhibitor 3i, which is able to potentiate the in vitro activity of cefoxitin on a VIM-2-producing E. coli strain.
• Development of antitubercular compounds based on a 4-quinolylhydrazone scaffold. Further structure–activity relationship studies
  作者：Sandra Gemma、Luisa Savini、Maria Altarelli、Pierangela Tripaldi、Luisa Chiasserini、Salvatore Sanna Coccone、Vinod Kumar、Caterina Camodeca、Giuseppe Campiani、Ettore Novellino、Sandra Clarizio、Giovanni Delogu、Stefania Butini

  DOI：10.1016/j.bmc.2009.06.051

  日期：2009.8

  A series of 4-quinolylhydrazones was synthesized and tested in vitro against Mycobacterium tuberculosis. At a concentration of 6.25 mu g/mL, most of the newly synthesized compounds displayed 100% inhibitory activity against M. tuberculosis in cellular assays. Further screening allowed the identification of very potent antitubercular agents. Compound 4c was also tested in a time-course experiment and against mtb clinical isolates, displaying interesting results. (C) 2009 Elsevier Ltd. All rights reserved.
• Pellerano; Savini; Brizzi, Farmaco, Edizione Scientifica, 1985, vol. 40, # 7, p. 486 - 492
  作者：Pellerano、Savini、Brizzi

  DOI：——

  日期：——