7-Morpholin-4-yl-methyl-quinolin-8-ol | 77910-06-6

• 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: 7-Morpholin-4-yl-methyl-quinolin-8-ol
• 英文别名: 7-(morpholinomethyl)quinolin-8-ol；7-((N-morpholino)methyl)-8-hydroxy-quinoline；7-(Morpholin-4-ylmethyl)quinolin-8-ol
• CAS: 77910-06-6
• 化学式: C₁₄H₁₆N₂O₂
• 分子量: 244.293
• InChiKey: MNLWSYVFKKLRKO-UHFFFAOYSA-N

物化性质

• 沸点：
  416.9±40.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  45.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-Morpholin-4-yl-methyl-quinolin-8-ol 在 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 [7-(bromomethyl)quinolin-8-yl] acetate
  参考文献：
  名称：

  Synthesis of Ethylene-Bridged Bis(8-hydroxyquinoline) Derivatives: New Building Blocks for Metallo-Supramolecular Chemistry

  摘要：

  报道了线性乙烯桥接双（8-羟基喹啉）配体1-H和2-H的合成，这些配体是金属引导自组装的螺旋型配合物的构建模块。反应步骤涉及尼克尔(0)催化的苄基溴化物6或9的同偶联反应作为关键步骤。

  DOI：

  10.1055/s-1997-1163
• 作为产物：
  描述：

  吗啉 、 8-羟基喹啉 在 聚合甲醛 作用下， 以 乙醇 为溶剂， 以5%的产率得到7-Morpholin-4-yl-methyl-quinolin-8-ol
  参考文献：
  名称：

  Novel Quinoline-Hepcidine Antagonists

  摘要：

  本发明涉及一种新型的肝铁蛋白拮抗剂，其一般式为(I)，包括它们的药物组合物以及将其用作药物的用途，特别是用于治疗铁代谢紊乱的疾病，如特别是铁缺乏病和贫血，特别是与慢性炎症性疾病相关的贫血（ACD：慢性疾病贫血和AI：炎症性贫血）。

  公开号：

  US20120196853A1

文献信息

• New tertiary 8-hydroxyquinoline-7-carboxamide derivatives and uses thereof
  申请人：POLICHEM S.A.

  公开号：EP2345643A1

  公开（公告）日：2011-07-20

  New tertiary 8-hydroxyquinoline-7-carboxamide derivatives of general formula (I) and pharmaceutically acceptable salts thereof are disclosed. These compounds are useful as antifungal agents. Specifically, these compounds were tested against Tricophyton Rubrum, Tricophyton Mentagrophytes, Aspergillus Niger and Scopulariopsis Brevicaulis. These compounds are also active against Candida species such as Candida Albicans and Candida Glabrata.

  新的三级8-羟基喹啉-7-甲酰胺衍生物的一般化学式（I）及其药用盐已被披露。 这些化合物可用作抗真菌剂。具体来说，这些化合物已对白色念珠菌、白色念珠菌、黑曲霉和短柄曲霉进行了测试。这些化合物也对白色念珠菌属的物种如白色念珠菌和光滑白色念珠菌具有活性。
• Substituted oxines inhibit endothelial cell proliferation and angiogenesis
  作者：Shridhar Bhat、Joong Sup Shim、Feiran Zhang、Curtis Robert Chong、Jun O. Liu

  DOI：10.1039/c2ob06978d

  日期：——

  Two substituted oxines, nitroxoline (5) and 5-chloroquinolin-8-yl phenylcarbamate (22), were identified as hits in a high-throughput screen aimed at finding new anti-angiogenic agents. In a previous study, we have elucidated the molecular mechanism of antiproliferative activity of nitroxoline in endothelial cells, which comprises of a dual inhibition of type 2 human methionine aminopeptidase (MetAP2)

  两个取代的oxines， 硝基氧( 5 ) 和5-氯喹啉-8-基苯基氨基甲酸酯( 22 )，在旨在寻找新的抗血管生成剂的高通量筛选中被鉴定为命中。在先前的研究中，我们阐明了抗增殖活性的分子机制硝基氧 在内皮细胞中，包括对 2 型人的双重抑制 蛋氨酸氨肽酶 (MetAP2) 和 Sirtuin 1 (SIRT1)。构效关系研究 (SAR)硝基氧提供了许多惊喜，其中微小的修改产生了对人脐静脉内皮细胞 (HUVEC) 效力增加的 oxine 衍生物，但具有完全不同的未知机制。例如，5-nitrosoquinolin-8-ol( 33 ) 以亚微摩尔 IC 50抑制 HUVEC 生长，但不影响 MetAP2 或 MetAP1，仅对 SIRT1 显示出微弱的抑制作用。其他亚微摩尔抑制剂是5-aminoquinolin-8-ol( 34 ) 和8-磺胺喹啉( 32 )。氨基磺酸盐衍生物硝基氧( 48 )
• Synthesis of Phosphonodithioate, Oxathiaphosphinin, Oxathiaphosphole, and Dithiaphosphole Derivatives from the Reaction of Lawesson's Reagent with Phenolic Mannich Bases and Oxime Derivatives
  作者：Soher S. Maigali、Fouad M. Soliman、Rashad Shabana、Marwa El-Hussieny

  DOI：10.1080/10426500802487607

  日期：2009.9.18

  The reaction of Lawesson's reagent 1a, with niclosamide 2 proceeded by thionation and formation of carbothioamide 3 and the zwitterionic oxathiaphosphinin 4a. LR reacted with 8-hydroxyquinoline (5), 2-methylquinoline-4-ol (7), and β-naphthol (9) to give the phosphonodithioates 6, 8, or 10. The reaction of LR with the Mannich bases 11 and 14 afforded the oxathiaphosphinins 13 and 15, whereas the phosphonodithioates

  Lawesson 试剂 1a 与氯硝柳胺 2 的反应通过硫代化并形成硫代酰胺 3 和两性离子氧硫杂膦 4a 进行。LR 与 8-羟基喹啉 (5)、2-甲基喹啉-4-醇 (7) 和 β-萘酚 (9) 反应生成二硫代膦酸 6、8 或 10。 LR 与曼尼希碱 11 和 14 的反应得到氧硫杂膦 13 和 15，而在曼尼希碱 16 和 18 的情况下分离出二硫代膦酰基酯 17 和 19。LR 与邻苯二甲酰亚胺曼尼希碱 20 反应得到二硫酮 21 和 N-甲基邻苯二甲酰亚胺 (22)。酮单肟 23 与 LR 的反应导致形成氧硫杂磷 24 和二硫杂磷 25，而单肟 26 得到硫代乙酮硫肟 27。酮二肟 28 和 34 分别得到二硫代膦酸 29 和 36
• QUINOLINE COMPOUNDS AS INHIBITORS OF ANGIOGENESIS, HUMAN METHIONINE AMINOPEPTIDASE, AND SIRT1, AND METHODS OF TREATING DISORDERS
  申请人：Liu Jun O.

  公开号：US20110301163A1

  公开（公告）日：2011-12-08

  Described herein are methods of inhibiting methionine aminopeptidase or SirT1, inhibiting angiogenesis, and treating disorders (or symptoms thereof) associated with methionine aminopeptidase, SirT1 and/or angiogenesis, wherein a compound of the invention is administered to a subject.

  本文描述了抑制甲硫氨酸氨肽酶或SirT1，抑制血管生成以及治疗与甲硫氨酸氨肽酶、SirT1和/或血管生成有关的疾病（或其症状）的方法，其中将本发明的化合物给予受试者。
• Biocidal activity of some Mannich base cationic derivatives
  作者：Nabel A. Negm、Salwa M.I. Morsy、Medhat M. Said

  DOI：10.1016/j.bmc.2005.07.031

  日期：2005.11

  A novel series of cationic surfactants was prepared based on Mannich base (produced from the condensation of piperidine and/or morpholine as secondary amine and paraformaldehyde in the presence of 8-hydroxyquinoline). The chemical structures of the synthesized cationic surfactants were confirmed using elemental analyses, FTIR spectroscopy and H-1 NMR. Surface activities of the prepared surfactants were measured including: surface tension (gamma), critical micelle concentration (CMC), effectiveness (pi(CMC)), efficiency (Pc-20), maximum surface excess (Gamma(max)), minimum surface area (A(min)), interfacial tension (gamma(IT)), emulsification power and foaming power at 25 degrees C. The structural influences on their surface activities and adsorption free energy were discussed. The synthesized cationic surfactants were evaluated for their biocidal activity towards Gram +ve bacteria (Staph. Cocu., Bacillus), Gram -ve bacteria (Salmonella, E. coli), fungi (A. terrus., A.flav.) and yeast (Candida) at 1.0, 2.5 and 5.0 mg/mL, respectively. The target compounds showed good inhibition towards Gram +ve bacteria, Gram -ve bacteria and yeast. Meanwhile, excellent fungicidal results were obtained against the various types of fungi under investigation. (c) 2005 Elsevier Ltd. All rights reserved.