4-chloro-6-methyl-2-(methylthio)quinazoline | 1189797-90-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-chloro-6-methyl-2-(methylthio)quinazoline
• 英文别名: 4-chloro-6-methyl-2-(methylsulfanyl)quinazoline；4-Chloro-6-methyl-2-(methylthio)quinazoline；4-chloro-6-methyl-2-methylsulfanylquinazoline
• CAS: 1189797-90-7
• 化学式: C₁₀H₉ClN₂S
• 分子量: 224.714
• InChiKey: JOCNKAIBWLDHNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-6-methyl-2-(methylthio)quinazoline 、 乙基1-苯基肼羧酸酯 在 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 50.0h， 生成 9-methyl-5-(methylthio)-2-phenyl[1,2,4]triazolo[4,3-c]-quinazolin-3(2H)-one
  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
• 作为产物：
  描述：

  6-methyl-2-(methylsulfanyl)quinazolin-4(3H)-one 在 吡啶 、 三氯氧磷 作用下， 反应 18.0h， 以77%的产率得到4-chloro-6-methyl-2-(methylthio)quinazoline
  参考文献：
  名称：

  Triazoloquinazolinediones as novel high affinity ligands for the benzodiazepine site of GABAA receptors

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2010.11.050

文献信息

• [EN] PIPERIDINE SUBSTITUTED PYRAZOLO[1,5-A]PYRIMIDINE DERIVATIVES WITH INHIBITORY ACTIVITY ON THE REPLICATION OF THE RESPIRATORY SYNCYTIAL VIRUS (RSV)<br/>[FR] DÉRIVÉS DE PYRAZOLO[1,5-A]PYRIMIDINE SUBSTITUÉS PAR PIPÉRIDIN, AYANT UNE ACTIVITÉ INHIBITRICE SUR LA RÉPLICATION DU VIRUS RESPIRATOIRE SYNCYTIAL (RSV)
  申请人：JANSSEN SCIENCES IRELAND UC

  公开号：WO2016091774A1

  公开（公告）日：2016-06-16

  The invention concerns novel substituted bicyclic pyrazolo pyrimidine compounds of formula (I) having antiviral activity, in particular, having an inhibitory activity on the replication of the respiratory syncytial virus (RSV). The invention further concerns the preparation of such novel compounds, compositions comprising these compounds, and the compounds for use in the treatment of respiratory syncytial virus infection.

  这项发明涉及具有抗病毒活性的新型取代的双环吡唑嘧啶化合物，特别是对呼吸道合胞病毒（RSV）复制具有抑制活性的化合物。该发明还涉及制备这种新型化合物，包含这些化合物的组合物，以及用于治疗呼吸道合胞病毒感染的化合物。
• [EN] GABAa RECEPTOR MODULATORS<br/>[FR] MODULATEURS DES RÉCEPTEURS GABAA
  申请人：FORSKARPATENT I SYD AB

  公开号：WO2009123537A1

  公开（公告）日：2009-10-08

  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 GABAA receptor modulator.

  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。
• 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。
• PIPERIDINE SUBSTITUTED PYRAZOLO[1,5-A]PYRIMIDINE DERIVATIVES WITH INHIBITORY ACTIVITY ON THE REPLICATION OF THE RESPIRATORY SYNCYTIAL VIRUS (RSV)
  申请人：Janssen Sciences Ireland UC

  公开号：EP3230287A1

  公开（公告）日：2017-10-18