6-溴-4-氯-2-(甲基磺酰基)喹唑啉 | 1003043-76-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 6-溴-4-氯-2-(甲基磺酰基)喹唑啉
• 英文名称: 6-bromo-4-chloro-2-(methylsulfanyl)quinazoline
• 英文别名: 6-bromo-4-chloro-2-(methylthio)quinazoline；6-bromo-4-chloro-2-methylsulfanylquinazoline
• CAS: 1003043-76-2
• 化学式: C₉H₆BrClN₂S
• 分子量: 289.583
• InChiKey: JVOCVKFAENOWJO-UHFFFAOYSA-N

物化性质

• 熔点：
  124 °C
• 沸点：
  438.8±48.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-溴-4-氯-2-(甲基磺酰基)喹唑啉 、 2,2,2-三氟乙胺盐酸盐 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 ((6-bromo-2-methylthio)-quinazolin-4-yl)-(2,2,2-trifluoroethyl)-amine
  参考文献：
  名称：

  WO2008/9078

  摘要：

  公开号：
• 作为产物：
  描述：

  6-溴-2-(甲硫基)-4(3H)-喹唑啉酮 在 吡啶 、 三氯氧磷 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 18.0h， 以75%的产率得到6-溴-4-氯-2-(甲基磺酰基)喹唑啉
  参考文献：
  名称：

  [EN] GABAa RECEPTOR MODULATORS
  [FR] MODULATEURS DES RÉCEPTEURS GABAA

  摘要：

  这项最新的发明涉及具有广谱公式(I)的新化合物，具有镇静、抗惊厥、催眠-催眠和肌肉松弛条件，以及作为GABAA受体调节剂的哺乳动物，包括人类，具有焦虑、催眠和癫痫症状。

  公开号：

  WO2009123537A1

文献信息

• 4,6-DI- AND 2,4,6-TRISUBSTITUTED QUINAZOLINE DERIVATIVES USEFUL FOR TREATING VIRAL INFECTIONS
  申请人：Gao Ling-Jie

  公开号：US20090285782A1

  公开（公告）日：2009-11-19

  This invention provides quinazoline derivatives represented by the structural formula: (I); wherein: R 2 is hydrogen, NR′R″, C 1-7 alkyl, arylC 1-7 alkyl or C 3-10 cycloalkyl; R 4 is amino, C 1-7 alkyl, C 2-7 alkenyl, C 3-10 cycloalkyl, C 3-10 cycloalkenyl, aryl, heterocyclic, arylalkyl, heterocyclic-substituted C 1-7 alkyl or C 3-10 cycloalkyl-C 1-7 alkyl; R 5 is hydrogen or C 1-7 alkyl, or R 5 and R 4 together with the nitrogen atom to which they are attached form a heterocyclic ring; Y is a single bond, C 1-7 alkylene, C 2-7 alkenylene or C 2-7 alkynylene; R 6 is halogen, heteroaryl or aryl; R′ and R″ are each independently hydrogen, C 1-7 alkyl-carbonyl or C 1-7 alkyl; provided that R 4 is not phenyl substituted with morpholino when R 2 is H and R 5 is H, and provided that when NR 4 R 5 is piperazinyl, said NR 4 R 5 is either non-substituted or substituted with methyl or acetyl; a pharmaceutically acceptable addition salt, a stereoisomer, a mono- or a di-N-oxide, a solvate or a pro-drug thereof, for the treatment of viral infections.

  该发明提供了由结构式(I)表示的喹唑啉衍生物；其中：R2是氢、NR′R″、C1-7烷基、芳基C1-7烷基或C3-10环烷基；R4是氨基、C1-7烷基、C2-7烯基、C3-10环烷基、C3-10环烯基、芳基、杂环、芳基烷基、杂环取代的C1-7烷基或C3-10环烷基-C1-7烷基；R5是氢或C1-7烷基，或者R5和R4与它们所连接的氮原子一起形成杂环环；Y是单键、C1-7烷基、C2-7烯基或C2-7炔基；R6是卤素、杂环芳基或芳基；R′和R″各自独立地是氢、C1-7烷基-羰基或C1-7烷基；前提是当R2为H且R5为H时，R4不是取代有吗啡啶基的苯基；当NR4R5是哌嗪基时，所述的NR4R5要么未取代，要么被甲基或乙酰基取代；其药学上可接受的加合物、立体异构体、单烯氮或双烯氮、溶剂化合物或前药，用于治疗病毒感染。
• GABAA RECEPTOR MODULATORS
  申请人：Nielsen Mogens

  公开号：US20110092525A1

  公开（公告）日：2011-04-21

  The resent invention relates to novel compounds of the general formula (I) having anxiolytic, anticonvulsant, sedative-hypnotic and myorelaxant conditions as well as anxiogenic, somnolytic and convulsant conditions in mammals, including humans, as GABA A receptor modulator.

  本发明涉及具有广泛公式（I）的新化合物，作为GABAA受体调节剂在哺乳动物，包括人类中具有抗焦虑，抗惊厥，镇静催眠和肌肉松弛条件，以及焦虑，催眠和惊厥条件。
• GABAA receptor modulators
  申请人：Nielsen Mogens Peter Cherly

  公开号：US08809355B2

  公开（公告）日：2014-08-19

  The present invention relates to novel compounds of the general formula (I) having anxiolytic, anticonvulsant, sedative-hypnotic and myorelaxant conditions as well as anxiogenic, somnolytic and convulsant conditions in mammals, including humans, as GABAA receptor modulator.

  本发明涉及一种新的化合物，其通式为(I)，在哺乳动物，包括人类中作为GABAA受体调节剂具有抗焦虑、抗癫痫、镇静催眠和肌肉松弛作用，同时具有焦虑、催眠和惊厥等作用。
• 4,6-di- and 2,4,6-trisubstituted quinazoline derivatives useful for treating viral infections
  申请人：Gao Ling-Jie

  公开号：US09259426B2

  公开（公告）日：2016-02-16

  This invention provides quinazoline derivatives represented by the structural formula: (I); wherein: R2 is hydrogen, NR′R″, C1-7 alkyl, arylC1-7 alkyl or C3-10 cycloalkyl; R4 is amino, C1-7 alkyl, C2-7 alkenyl, C3-10 cycloalkyl, C3-10 cycloalkenyl, aryl, heterocyclic, arylalkyl, heterocyclic-substituted C1-7 alkyl or C3-10 cycloalkyl-C1-7 alkyl; R5 is hydrogen or C1-7 alkyl, or R5 and R4 together with the nitrogen atom to which they are attached form a heterocyclic ring; Y is a single bond, C1-7 alkylene, C2-7 alkenylene or C2-7 alkynylene; R6 is halogen, heteroaryl or aryl; R′ and R″ are each independently hydrogen, C1-7 alkyl-carbonyl or C1-7 alkyl; provided that R4 is not phenyl substituted with morpholino when R2 is H and R5 is H, and provided that when NR4R5 is piperazinyl, said NR4R5 is either non-substituted or substituted with methyl or acetyl; a pharmaceutically acceptable addition salt, a stereoisomer, a mono- or a di-N-oxide, a solvate or a pro-drug thereof, for the treatment of viral infections.

  本发明提供了由结构式（I）表示的喹唑啉衍生物；其中：R2为氢、NR′R″、C1-7烷基、芳基C1-7烷基或C3-10环烷基；R4为氨基、C1-7烷基、C2-7烯基、C3-10环烷基、C3-10环烯基、芳基、杂环、芳基烷基、杂环取代的C1-7烷基或C3-10环烷基-C1-7烷基；R5为氢或C1-7烷基，或R5与R4一起与它们所连接的氮原子形成杂环环；Y为单键、C1-7亚烷基、C2-7烯基或C2-7炔基；R6为卤素、杂环芳基或芳基；R′和R″各自独立地为氢、C1-7烷基-羰基或C1-7烷基；前提是当R2为H且R5为H时，R4不是取代了吗啡啉的苯基，且当NR4R5为哌嗪基时，所述的NR4R5要么是非取代的，要么是取代了甲基或乙酰基的；其中所述的衍生物是药学上可接受的加合盐、立体异构体、单一或二重N-氧化物、溶剂合物或前药，用于治疗病毒感染。
• Triazoloquinazolinediones as novel high affinity ligands for the benzodiazepine site of GABAA receptors
  作者：Jakob Nilsson、Ritha Gidlöf、Elsebet Østergaard Nielsen、Tommy Liljefors、Mogens Nielsen、Olov Sterner

  DOI：10.1016/j.bmc.2010.11.050

  日期：2011.1

  Based on a pharmacophore model of the benzodiazepine-binding site of GABA(A) receptors, a series of 2-aryl-2,6-dihydro[1,2,4]triazolo[4,3-c]quinazoline-3,5-diones (structure type I) were designed, synthesized, and identified as high-affinity ligands of the binding site. For several compounds, K-i values of around 0.20 nM were determined. They show a structural resemblance with the previously described 2-phenyl-2H-pyrazolo[4,3-c]quinolin-3(5H)-ones (II) and 2-phenyl-[1,2,4]triazolo[1,5-a]quinoxalin-4(5H)-one (III). The 9-bromo substituted compounds 8a-d were prepared in an 8-step synthesis in an overall yield of approximately 40%, and a library of 9-substituted analogues was prepared by cross-coupling reactions. Compound 8e, 21, 22, and 24 were tested on recombinant rat alpha(1)beta(3)gamma(2), alpha(2)beta(3)gamma(2), alpha(3)beta(3)gamma(2), and alpha(5)beta(3)gamma(2) subtypes, and displayed selectivity for the alpha(1)beta(3)gamma(2) isoform. (C) 2010 Elsevier Ltd. All rights reserved.