1-苄基-4-羟基-6-甲基喹啉-2-酮 | 141750-04-1

• 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
• 中文名称: 1-苄基-4-羟基-6-甲基喹啉-2-酮
• 英文名称: 1-benzyl-4-hydroxy-6-methyl-2(1H)-quinolinone
• 英文别名: 1-Benzyl-4-hydroxy-6-methylquinolin-2(1H)-one；1-benzyl-4-hydroxy-6-methylquinolin-2-one
• CAS: 141750-04-1
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: IPZQPAQWOIIUGN-UHFFFAOYSA-N

物化性质

• 沸点：
  443.5±45.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-苄基-4-羟基-6-甲基喹啉-2-酮 生成 1-benzyl-3-formyl-4-hydroxy-6-methyl-2(1H)-quinolinone
  参考文献：
  名称：

  Acyl and alkoxy substituted quinolines

  摘要：

  抗DNA病毒药物化合物，如单纯疱疹病毒等DNA含量病毒的抗病毒剂被披露。这些化合物由Formula 1.0表示。其中包括Formula 1.0代表的化合物及其药用可接受的盐和溶剂。披露了含有Formula 1.0代表的化合物的药物组合物以及使用Formula 1.0代表的化合物治疗病毒感染的方法。还披露了作为降压药物的化合物以及使用这些化合物治疗高血压的方法。降压药物是由Formula 1.0代表的化合物，其中R.sup.4从由烷基和氨基烷基组成的群体中选择。最好R.sup.1是H。

  公开号：

  US05378694A1
• 作为产物：
  描述：

  苄基对甲苯胺 在 甲烷磺酸 、 四磷十氧化物 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 生成 1-苄基-4-羟基-6-甲基喹啉-2-酮
  参考文献：
  名称：

  Asymmetric synthesis of tetrahydropyran[3,2-c]quinolinones via an organocatalyzed formal [3 + 3] annulation of quinolinones and MBH 2-naphthoates of nitroolefin

  摘要：

  An efficient asymmetric and enantio-swithchable organocatalytic [3 + 3] annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed. Densely substituted tetrahydropyrano[3,2-c]quinolinones scaffolds with two adjacent stereogenic centers are obtained with high yield (up to 95% yield) and good stereoselectivities (up to >20:1 dr and 96% ee) in an enantio-switchable manner. Furthermore, gram scale synthesis was achieved and the nitro group could easily transform into an amino group without any appreciable loss in the diastereo- and enantioselectivity. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2019.08.040

文献信息

• Asymmetric Total Synthesis and Biological Evaluation of the Natural PDE4 Inhibitor Toddacoumalone
  作者：Ke-Qiang Hou、Xue-Ping Chen、Yiyou Huang、Albert S. C. Chan、Hai-Bin Luo、Xiao-Feng Xiong

  DOI：10.1021/acs.orglett.9b04355

  日期：2020.1.17

  We describe herein the first asymmetric total synthesis and biological evaluation of the natural PDE4 inhibitor toddacoumalone and its stereoisomers. The key step of the total synthesis is a formal asymmetric [4 + 2] cycloaddition reaction catalyzed by chiral secondary amine catalysts. A variety of pyranoquinolinones and 3-methylcrotonaldehyde are well tolerated under the optimized reaction conditions

  我们在本文中描述了天然PDE4抑制剂toddacoumalone及其立体异构体的首次不对称总合成和生物学评估。全合成的关键步骤是由手性仲胺催化剂催化的形式不对称[4 + 2]环加成反应。在优化的反应条件下，多种吡喃喹啉酮和3-甲基巴豆醛具有良好的耐受性，为进一步的SAR研究铺平了道路。进一步的生物学评估显示1a'具有最佳的PDE4抑制活性（IC50 = 0.18μM）。
• Quinoline-diones
  申请人：Schering Corporation

  公开号：US05179093A1

  公开（公告）日：1993-01-12

  Compounds of the formula ##STR1## or a pharmaceutically acceptable salt thereof wherein, R is H, halogen, (C.sub.1 -C.sub.6) alkyl, N(C.sub.1 -C.sub.6 alkyl/aryl).sub.2, OH, O--(C.sub.1 -C.sub.6) alkyl/aryl, CH.sub.2 OH, COOH, COO-alkyl/aryl, SO.sub.2 NH.sub.2, or SO.sub.2 NH (C.sub.1 -C.sub.6 alkyl/aryl); R.sub.1 is C.sub.1 -C.sub.6 alkyl, cycloalkyl, C.sub.2 -C.sub.6 alkenyl, heteroaryl, substituted heteroaryl, heterocycloalkyl, --CH.sub.2 -aryl, --CH.sub.2 -substituted aryl, --CH.sub.2 -heteroaryl, or --CH.sub.2 -substituted heteroaryl; R.sub.2 is H, C.sub.1 -C.sub.6 alkyl or aryl; ##STR2## is an aromatic ring or a heteroaromatic ring; and X is O or N-(alkyl/aryl/alkyl-aryl/alkoxylalkoxyaryl) are described. These compounds are useful as agents for treating viruses.

  公式##STR1##的化合物或其药用可接受的盐，其中，R为H，卤素，(C.sub.1 -C.sub.6)烷基，N(C.sub.1 -C.sub.6烷基/芳基).sub.2，OH，O-(C.sub.1 -C.sub.6)烷基/芳基，CH.sub.2 OH，COOH，COO-烷基/芳基，SO.sub.2 NH.sub.2，或SO.sub.2 NH (C.sub.1 -C.sub.6烷基/芳基)；R.sub.1为C.sub.1 -C.sub.6烷基，环烷基，C.sub.2 -C.sub.6烯基，杂环芳基，取代的杂环芳基，杂环烷基，--CH.sub.2 -芳基，--CH.sub.2 -取代的芳基，--CH.sub.2 -杂环芳基，或--CH.sub.2 -取代的杂环芳基；R.sub.2为H，C.sub.1 -C.sub.6烷基或芳基；##STR2##为芳香环或杂芳环；X为O或N-(烷基/芳基/烷基-芳基/烷氧基烷氧基芳基)。这些化合物可用作治疗病毒的药剂。
• Alkyl and acyl substituted quinolines
  申请人：Schering Corporation

  公开号：US05382572A1

  公开（公告）日：1995-01-17

  Compounds useful as antiviral agents against DNA-containing viruses, such as herpes group viruses, are disclosed. The compounds are represented by Formula 1.0: ##STR1## and their pharmaceutically acceptable salts and solvates; wherein: (A) X is selected from the group consisting of N--R.sup.3, O, S, and C(R.sup.3).sub.2 ; (B) R.sup.3 is selected from H and a range of substituents; (C) R.sup.1 is an etherifying or esterifying group; (D) R.sup.2 is selected from a range of substituents; (E) m is 0 or an integer from 1 to 4; and (F) R.sup.4 and R.sup.5 are the same and are selected from alkyl and acyl groups; together with the pharmaceutically acceptable salts of the compounds of Formula 1.0 that are acidic or basic. Pharmaceutical compositions containing compounds represented by Formula 1.0 are disclosed. Also disclosed are methods of treating a viral infection using compounds represented by Formula 1.0.

  抗DNA病毒药物化合物，如疱疹病毒群，被揭示。这些化合物由Formula 1.0表示：##STR1##及其药学上可接受的盐和溶剂；其中：（A）X选自N-R.sup.3，O，S和C(R.sup.3).sub.2组；（B）R.sup.3选自H和一系列取代基；（C）R.sup.1是醚化或酯化基团；（D）R.sup.2选自一系列取代基；（E）m为0或1至4之间的整数；（F）R.sup.4和R.sup.5相同，选自烷基和酰基；以及Formula 1.0化合物的酸性或碱性药学上可接受的盐。揭示了含有Formula 1.0化合物的药物组合物。还揭示了使用Formula 1.0化合物治疗病毒感染的方法。
• Antiviral compounds and antihypertensive compounds
  申请人：Schering Corporation

  公开号：US05175151A1

  公开（公告）日：1992-12-29

  Compounds useful as antihypertensive agents, or antiviral agents against DNA containing viruses, such as herpes group viruses, are disclosed. The compounds are represented by Formula 1.0: ##STR1## and their pharmaceutically acceptable salts and solvates. Pharmaceutical compositions containing compounds represented by Formula 1.0 are disclosed. Also disclosed are methods of treating hypertension or a viral infection using compounds represented by Formulas 1.0. Also disclosed is a compound of Structure B ##STR2## useful as an intermediate in producing compounds of Formula 1.0. A process for preparing the compounds of Formula 1.0 is also disclosed. In the process a compound of Structure B ##STR3## is reacted with an alkoxide R.sub.1 O.sup.- M.sup.+ in a solvent comprising the corresponding alcohol R.sub.1 OH of the alkoxide. Optionally, an organic cosolvent may be used with the solvent.

  本文披露了一种对高血压药物或抗DNA病毒药物，如疱疹病毒组，具有用途的化合物。这些化合物由公式1.0表示：##STR1##及其药学上可接受的盐和溶剂。本文还披露了含有公式1.0所表示的化合物的制药组合物。本文还披露了使用公式1.0所表示的化合物治疗高血压或病毒感染的方法。本文还披露了一种结构B的化合物，##STR2##可用作制备公式1.0所表示的化合物的中间体。本文还披露了制备公式1.0所表示的化合物的方法。在该过程中，将结构B的化合物##STR3##与碱金属醇盐R.sub.1 O.sup.- M.sup.+在溶剂中反应，所述溶剂包括碱金属醇盐的相应醇R.sub.1 OH。可选地，有机共溶剂可与溶剂一起使用。
• Ester and alkoxy substituted benzopyrans
  申请人：Schering Corporation

  公开号：US05412104A1

  公开（公告）日：1995-05-02

  Compounds useful as antihypertensive agents and useful as antiviral agents against DNA-containing viruses, such as herpes group viruses, are disclosed. The compounds are represented by Formula 1.0: ##STR1## and their pharmaceutically acceptable salts and solvates. Pharmaceutical compositions containing compounds represented by Formula 1.0 are disclosed. Methods of treating a viral infection using compounds represented by Formula 1.0 are disclosed. Also disclosed are methods of treating hypertension using compounds of Formula 1.0 wherein R is selected from the group consisting of H, halogen and --C(O)OR.sup.6 ; and R.sup.1 is selected from the group consisting of --OR.sup.14, --O(CH.sub.2).sub.a C(H).sub.3-i Z.sub.i and --O(CH.sub.2).sub.h N(R.sup.15).sub.2.

  本发明揭示了一种化合物，可用作降压剂和抗DNA病毒剂，例如疱疹病毒组，该化合物由公式1.0表示：##STR1##以及它们的药学上可接受的盐和溶剂。本发明还揭示了含有由公式1.0表示的化合物的制药组合物。本发明揭示了使用由公式1.0表示的化合物治疗病毒感染的方法。还揭示了使用公式1.0中R选自H、卤素和--C（O）OR.sup.6；R.sup.1选自--OR.sup.14、--O（CH.sub.2）.sub.a C（H）.sub.3-i Z.sub.i和--O（CH.sub.2）.sub.h N（R.sup.15）.sub.2的化合物治疗高血压的方法。