8-bromo-6-chloro-2,3-dihydro-1H-quinolin-4-one | 263896-21-5

• 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: 8-bromo-6-chloro-2,3-dihydro-1H-quinolin-4-one
• CAS: 263896-21-5
• 化学式: C₉H₇BrClNO
• 分子量: 260.518
• InChiKey: DNNLKHPUJOFTBM-UHFFFAOYSA-N

物化性质

• 沸点：
  393.0±42.0 °C(Predicted)
• 密度：
  1.660±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-bromo-6-chloro-2,3-dihydro-1H-quinolin-4-one 在 sodium tetrahydroborate 、 正丁基锂 、 氯化亚砜 、 tetraphosphorus decasulfide 、 potassium tert-butylate 、 diethylzinc 、 potassium carbonate 、 三氟乙酸 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Discovery of potent α1L-adrenoceptor agonists: Design and synthesis of bicyclic derivatives

  摘要：

  We aimed to create a novel and potent alpha(1L)-adrenoceptor agonist because such agonists are possible drug candidates for stress urinary incontinence. We used ligand-based drug design and evaluated the alpha(1L)-adrenoceptor agonist activity of the designed compounds. Among them, tetrahydroquinoline derivative 50 showed the most potent activity (ratio of noradrenaline half maximal effective concentration, 0.0028) and effectively induced contraction of rat bladder neck. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.05.049
• 作为产物：
  描述：

  2-溴-4-氯苯胺 在 三氟甲磺酸 、 potassium carbonate 、 sodium t-butanolate 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 8-bromo-6-chloro-2,3-dihydro-1H-quinolin-4-one
  参考文献：
  名称：

  Discovery of potent α1L-adrenoceptor agonists: Design and synthesis of bicyclic derivatives

  摘要：

  We aimed to create a novel and potent alpha(1L)-adrenoceptor agonist because such agonists are possible drug candidates for stress urinary incontinence. We used ligand-based drug design and evaluated the alpha(1L)-adrenoceptor agonist activity of the designed compounds. Among them, tetrahydroquinoline derivative 50 showed the most potent activity (ratio of noradrenaline half maximal effective concentration, 0.0028) and effectively induced contraction of rat bladder neck. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.05.049

文献信息

• [EN] QUINOLONES AS T-RNA SYNTHETASE INHIBITORS AND ANTIBACTERIAL AGENTS<br/>[FR] QUINOLONES TENANT LIEU D'INHIBITEURS D'ARNT SYNTHETASE ET D'AGENTS ANTIBACTERIENS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO2000021949A1

  公开（公告）日：2000-04-20

  Compounds of formula (I), in which: R1 is aryl or heteroaryl; R2 is hydrogen, C¿(1-6)?alkyl, arylC(1-4)alkyl, arylC(2-4)alkenyl or C(1-6)alkylcarbonyl; R?3¿ is selected from halo, cyano, hydroxy, (C¿1-6)?alkyl (optionally substituted by halo, hydroxy, amino, carboxy or (C1-6)alkoxycarbonyl), (C3-7)cycloalkyl, C(1-6)alkoxy, amino, mono- or di-(C1-6)alkylamino, acylamino, carboxy, (C1-6)alkoxycarbonyl, carboxy(C1-6)alkyloxy, (C1-6)alkylthio, (C1-6)alkylsulphinyl, (C1-6)alkylsulphonyl, sulphamoyl, mono- and di-(C1-6)alkylsulphonyl, carbamoyl, mono- and di-(C1-6)alkylcarbamoyl, and heterocyclyl; m is 0 or an integer from 1 to 3; R?4¿ and a substituent on R1 are linked to form a saturated bridge comprising one or two carbon atoms and a heteroatom selected from O and NR5; R5 is hydrogen or C¿(1-6)?alkyl; Y is a linker group having from 2 to 6 methylene groups in a straight chain and in which one or more alkylene groups may have one or more C(1-6) alkyl substituents and which substituents may be linked to form a C2 or C3 alkylene bridge; Z is NH or O; and salts thereof, preferably pharmaceutically acceptable salts; are inhibitors of Saureus methionyl tRNA synthetase and thereof of use in therapy as antibacterial agents.

  化合物的公式（I），其中：R1是芳基或杂环芳基；R2是氢，C（1-6）烷基，芳基C（1-4）烷基，芳基C（2-4）烯基或C（1-6）烷基羰基；R3是选自卤素，氰基，羟基，（C1-6）烷基（可选地被卤素，羟基，氨基，羧基或（C1-6）烷氧羰基取代），（C3-7）环烷基，C（1-6）烷氧基，氨基，单或双（C1-6）烷基氨基，酰胺基，羧基，（C1-6）烷氧羰基，羧基（C1-6）烷氧基，（C1-6）烷基硫醇，（C1-6）烷基亚磺酰基，（C1-6）烷基磺酰基，磺酰胺基，单和双（C1-6）烷基磺酰基，氨基甲酰基，单和双（C1-6）烷基氨基甲酰基和杂环基；m为0或1至3的整数；R4和R1上的取代基连接形成饱和桥，包括一个或两个碳原子和一个选自O和NR5的杂原子；R5是氢或C（1-6）烷基；Y是具有2至6个亚甲基基团的连接基，在其中一个或多个亚甲基基团中可能有一个或多个C（1-6）烷基取代基，并且这些取代基可能连接形成C2或C3烷基桥；Z是NH或O；及其盐，优选为药物可接受盐；是Saureus甲硫氨酰-tRNA合成酶的抑制剂，因此在治疗中作为抗菌剂使用。
• Substituted Thienopyridone Compounds With Antibacterial Activity
  申请人：GUILES Joseph

  公开号：US20080146609A1

  公开（公告）日：2008-06-19

  Novel bicyclic heteroaromatic compounds are provided that are inhibitors of bacterial methionyl tRNA synthetase (MetRS). Compounds of the invention generally have a left hand side chroman group or left hand side tetrahydroquinoline group and a right hand side thienopyridone group. Also disclosed are methods for their preparation and their use in therapy as antibacterial agents, particularly as anti- Clostridium difficile agents.

  本发明提供了新型双环杂环芳香化合物，它们是细菌甲硫氨酰-tRNA合成酶（MetRS）的抑制剂。本发明的化合物通常具有左侧的色基基团或左侧的四氢喹啉基团和右侧的噻吩吡啶酮基团。本发明还揭示了它们的制备方法以及它们作为抗菌药物在治疗中的应用，特别是作为抗难辨梭菌药物。
• Substituted thienopyridone compounds with antibacterial activity
  申请人：Crestone, Inc.

  公开号：US07994192B2

  公开（公告）日：2011-08-09

  Novel bicyclic heteroaromatic compounds are provided that are inhibitors of bacterial methionyl tRNA synthetase (MetRS). Compounds of the invention generally have a left hand side chroman group or left hand side tetrahydroquinoline group and a right hand side thienopyridone group. Also disclosed are methods for their preparation and their use in therapy as antibacterial agents, particularly as anti-Clostridium difficile agents.

  本发明提供了新型的双环杂环芳香化合物，它们是细菌甲硫氨酰-tRNA合成酶（MetRS）的抑制剂。本发明的化合物通常具有左侧的色满基团或左侧的四氢喹啉基团，以及右侧的噻吩吡啶酮基团。本发明还揭示了它们的制备方法和在治疗中作为抗菌剂的用途，特别是作为抗难辞氏梭菌剂。
• Optimisation of aryl substitution leading to potent methionyl tRNA synthetase inhibitors with excellent gram-Positive antibacterial activity
  作者：Richard L Jarvest、John M Berge、Murray J Brown、Pamela Brown、John S Elder、Andrew K Forrest、C.S.V Houge-Frydrych、Peter J O'Hanlon、David J McNair、Stephen Rittenhouse、Robert J Sheppard

  DOI：10.1016/s0960-894x(02)01027-2

  日期：2003.2

  Optimisation of the left-hand-side aryl moiety of a file compound screening hit against Staphylococcus aureus methionyl tRNA synthetase led to the identification of a series of potent nanomolar inhibitors. The best compounds showed excellent antibacterial activity against staphylococcal and enterococcal pathogens. including strains resistant to clinical antibiotics. (C) 2003 Elsevier Science Ltd. All rights reserved.
• WO2008/39639
  申请人：——

  公开号：——

  公开（公告）日：——