6-chloro-1,2,3,4-tetrahydroquinoxalin-2-one | 89938-22-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-chloro-1,2,3,4-tetrahydroquinoxalin-2-one
• 英文别名: 6-Chloro-3,4-dihydroquinoxalin-2(1h)-one；6-chloro-3,4-dihydro-1H-quinoxalin-2-one
• CAS: 89938-22-7
• 化学式: C₈H₇ClN₂O
• 分子量: 182.609
• InChiKey: WXIXSRNTPHCSPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-chloro-1,2,3,4-tetrahydroquinoxalin-2-one 在 potassium tert-butylate 、 N,N-二异丙基乙胺 、 叔丁醇 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 7-chloro-5-<(1-(cis-3,5-dimethyl)-piperazino)carbonyl>-4,5-dihydroimidazo<1,5-a>quinoxaline-3-carboxylic acid 1,1-dimethylethyl ester
  参考文献：
  名称：

  Piperazine Imidazo[1,5-a]quinoxaline Ureas as High-Affinity GABA_A Ligands of Dual Functionality

  摘要：

  A series of imidazo[1,5-alpha]quinoxaline piperazine ureas appended with a tert-butyl ester side chain at the 3-position was developed. Analogues within this series have high affinity for the gamma-aminobutyric acid A (GABA(A))/benzodiazepine receptor complex with efficacies ranging from inverse agonists to full agonists. Many analogues were found to be partial agonists as indicated by [S-35]TBPS and Cl- current ratios. Uniquely, a number of these analogues were found to have a bell-shaped dose-response profile in the alpha(1)beta(2)gamma(2) subtype as determined by whole cell patch-clamp technique, where in vitro efficacy was found to decrease with increasing drug concentration. Many of the compounds from this series were effective in antagonizing metrazole-induced seizures, consistent with anticonvulsant and possibly anxiolytic activity. Additionally, several analogues were also effective in lowering cGMP levels (to control values) after applied stress, also consistent with anxiolytic-like properties. The most effective compounds in these screens were also active in animal models of anxiety such as the Vogel and Geller assays. The use of the piperazine substituent allowed for excellent drug levels and a long duration of action in the central nervous system for many of the quinoxalines, as determined by ex vivo assay. Pharmacokinetic analysis of several compounds indicated excellent oral bioavailability and a reasonable half-life in rats. From this series emerged two partial agonists (55, 91) which had good activity in anxiolytic models, acceptable pharmacokinetics, and minimal benzodiazepine-type side effects.

  DOI：

  10.1021/jm9801307
• 作为产物：
  描述：

  4-氯-1,2-苯二胺 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 26.5h， 生成 6-chloro-1,2,3,4-tetrahydroquinoxalin-2-one
  参考文献：
  名称：

  High-Affinity Partial Agonist Imidazo[1,5-a]quinoxaline Amides, Carbamates, and Ureas at the γ-Aminobutyric Acid A/Benzodiazepine Receptor Complex

  摘要：

  A series of imidazo[1,5-alpha]quinoxaline amides, carbamates, and ureas which have high affinity for the gamma-aminobutyric acid A/benzodiazepine receptor complex was developed. Compounds within this class have varying efficacies racing from antagonists to full agonists. However, most analogs were found to be partial agonists as indicated by [S-35]TBPS and Cl- current ratios. Many of these compounds were also effective in antagonizing metrazole-induced seizures in accordance with anticonvulsant and possible anxiolytic activity. Selected quinoxalines displayed limited benzodiazepine-type side effects such as ethanol potentiation and physical dependence in animal models. Dimethylamino urea 41 emerged as the most interesting analog, having a partial agonist profile in vitro while possessing useful activity in animal models of anxiety such as the Vogel and Geller assays. In accordance with its partial agonist profile, 41 was devoid of typical benzodiazepine side effects.

  DOI：

  10.1021/jm940765f

文献信息

• OXINDOLE DERIVATIVES
  申请人：Chen Li

  公开号：US20080081810A1

  公开（公告）日：2008-04-03

  There is provided compounds of the formula wherein R 6 , V, W, X, Y, Q and n are as described. The compounds exhibit activity as anticancer agents.

  提供的化合物具有以下结构式，其中R6、V、W、X、Y、Q和n如所述。这些化合物表现出抗癌药物的活性。
• Imidazo[1,5-A]quinoxalines
  申请人：The Upjohn Company

  公开号：US05541324A1

  公开（公告）日：1996-07-30

  An invention relating to Imidazo[1,5-a]quinoxalines (I) ##STR1## which do not contain an endocyclic carbonyl group and which are useful as anxiolytic and sedative/hypnotic agents.

  一种涉及咪唑并[1,5-a]喹喔啉(I)的发明，不含内环羰基，并且可用作抗焦虑和镇静/催眠剂。
• Palladium-catalyzed direct Hiyama arylation of quinoxalin-2(1H)-ones with aryl siloxanes in water
  作者：Xinya Liu、Zhenwei Liu、Yingying Xue、Jingya Li、Dapeng Zou、Yangjie Wu、Yusheng Wu

  DOI：10.1016/j.tetlet.2020.152612

  日期：2020.12

  An efficient method for palladium-catalyzed direct Hiyama coupling of various quinoxalin-2(1H)-ones with aryl siloxanes has been developed. The protocol provides a convenient access to a variety of useful C3-arylated 1-methylquinoxalin-2(1H)-one derivatives in reasonable yields by using low cost water as a solvent and oxygen as an oxidant.

  已开发出一种有效的方法，用于钯催化的各种喹喔啉-2（1H）-与芳基硅氧烷的直接Hiyama偶联。该协议通过使用低成本的水作为溶剂和氧气作为氧化剂，以合理的产率方便地获得了各种有用的C3芳基化的1-甲基喹喔啉-2（1H）-衍生物。
• Copper catalyzed aerobic oxidative amination of 3,4-dihydroquinoxalin-2(1H)-ones
  作者：Shuocheng Wan、Jie Wang、Congde Huo

  DOI：10.1016/j.tetlet.2021.153271

  日期：2021.8

  3,4-dihydroquinoxalin-2(1H)-ones is developed. This protocol provides a concise method to access 3-aminoquinoxalinone derivatives with good functional-group tolerances, utilizing primary and secondary aliphatic amines as nitrogen sources under mild and simple reaction conditions. It provides a practical approach to the synthesis of pharmaceutical active 3-aminoquinoxalinones.

  开发了铜催化的 3,4-dihydroquinoxalin-2(1H)-ones 的有氧 sp 3 C H 胺化。该协议提供了一种简洁的方法来获得具有良好官能团耐受性的 3-氨基喹喔啉酮衍生物，在温和和简单的反应条件下利用伯和仲脂肪胺作为氮源。它提供了一种合成药物活性 3-氨基喹喔啉酮的实用方法。
• 4,5-cyclicimidazo[1,5-A]quinoxalines
  申请人：Pharmacia & Upjohn Company

  公开号：US05668282A1

  公开（公告）日：1997-09-16

  The invention discloses imidazo[1,5-a]quinoxalines (I) ##STR1## which do not contain an endocyclic carbonyl group that are useful as anxiolytic and sedative/hypnotic agents.

  本发明揭示了不含内环羰基的咪唑[1,5-a]喹啉(I) ##STR1## 作为抗焦虑和镇静/催眠剂使用。