2,3-双(溴甲基)苯并[g]喹喔啉 | 95379-91-2

• 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: 2,3-双(溴甲基)苯并[g]喹喔啉
• 英文名称: 2,3-bis(bromomethyl)benzoquinoxaline
• 英文别名: 2,3-Bis(bromomethyl)benzo[g]quinoxaline
• CAS: 95379-91-2
• 化学式: C₁₄H₁₀Br₂N₂
• 分子量: 366.055
• InChiKey: DORCFNSTVCUNDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-双(溴甲基)苯并[g]喹喔啉 在 palladium on activated charcoal 三甲基溴硅烷 、 potassium tert-butylate 、 氢气 作用下， 以 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 24.08h， 生成 α-amino-3-(phosphonomethyl)benzoquinoxaline-2-propanoic acid
  参考文献：
  名称：

  Potent quinoxaline-spaced phosphono .alpha.-amino acids of the AP-6 type as competitive NMDA antagonists: synthesis and biological evaluation

  摘要：

  A series of alpha-amino-3-(phosphonoalkyl)-2-quinoxalinepropanoic acids was synthesized and evaluated for NMDA receptor affinity using a[H-3]CPP binding assay. Functional antagonism of the NMDA receptor complex was evaluated in vitro using a stimulated [H-3]TCP binding assay and in vivo by employing an NMDA-induced seizure model. Some analogues also were evaluated in the [H-3]-glycine binding assay. Several compounds of the AP-6 type show potent and selective NMDA antagonistic activity both in vitro and in vivo. In particular alpha-amino-7-chloro-3-(phosphonomethyl)-2-quinoxalinepropanoic acid (1) displayed an ED50 Of 1.1 mg/kg ip in the NMDA lethality model. Noteworthy is alpha-amino-6,7-dichloro-3-(phosphonomethyl)-2-quinoxalinepropanoic acid (3) with a unique dual activity, displaying in the NMDA receptor binding assay an IC50 of 3.4 nM and in the glycine binding assay an IC50 of 0.61 muM.

  DOI：

  10.1021/jm00055a004
• 作为产物：
  描述：

  2,3-二氨基萘 、 1,4-二溴-2,3-丁二酮 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 2,3-双(溴甲基)苯并[g]喹喔啉
  参考文献：
  名称：

  Naphtho- and Benzo[g]quinoxalino-Fused Oxazocinoquinolinones and Their Diaryl and Alkynyl Analogues from Quinolin-8-ols: A Library of Novel Polynuclear Heteroaromatics

  摘要：

  在一锅法序列中实现了6,6,8,6,6-五环并萘稠合草酰二喹啉酮和6,6,8,6,6,6-六环并苯并[g]喹啉并草酰二喹啉酮的高效合成。通过Suzuki-Miyaura和Sonogashira交叉偶联反应，分别生成了它们的二芳基和炔基取代类似物库。

  DOI：

  10.1055/s-0030-1257974

文献信息

• Quinoxaline phosphono-amino acids
  申请人：American Home Products Corporation

  公开号：US05118675A1

  公开（公告）日：1992-06-02

  The compounds of the formula: ##STR1## in which Q is the quinoxaline nucleus; m is one of the integers 0, 1 or 2; n is one of the integers 1,2 or 3; or a pharmaceutically acceptable salt, alkyl ester or ##STR2## where R.sup.3 and R.sup.4 are, independently, hydrogen, nitro, halo or methoxy, are NMDA antagonists useful in the treatment and prevention of central nervous system related pathological conditions resulting from overstimulation by excitatory amino acids.

  公式为：##STR1##的化合物，其中Q为喹诺酮核；m为0、1或2之一的整数；n为1、2或3之一的整数；或为药学上可接受的盐、烷基酯或##STR2##其中R.sup.3和R.sup.4分别为氢、硝基、卤素或甲氧基，是NMDA拮抗剂，可用于治疗和预防由兴奋性氨基酸过度刺激引起的中枢神经系统相关病理状况。
• Reaching strong absorption up to 700 nm with new benzo[<i>g</i>]quinoxaline-based heteroleptic copper(<scp>i</scp>) complexes for light-harvesting applications
  作者：Cecilia Bruschi、Xin Gui、Olaf Fuhr、Wim Klopper、Claudia Bizzarri

  DOI：10.1039/d3dt00902e

  日期：——

  heteroleptic Cu(I) complexes, we designed a novel diimine based on 4-(benzo[g]quinoxal-2′-yl)-1,2,3-triazole derivatives. The large π-conjugation of the benzoquinoxaline moiety shifted bathochromically the absorption with regard to other diimine-based Cu(I) complexes. Adding another Cu(I) core broadened the absorption and extended it to considerably longer wavelengths. Moreover, by fine-tuning the structure

  杂配铜 ( I ) 配合物，以二亚胺作为发色单元，大体积二膦作为辅助配体，与相应的均配双（二亚胺）配合物相比，具有在激发态下伪 Jahn-Teller 效应降低的优势。然而，它们的最低吸收通常位于 350 至 500 nm 之间。针对稳定杂配 Cu( I ) 配合物在可见光中的强吸收，我们设计了一种基于 4-(benzo[ g ]quinoxal-2'-yl)-1,2,3-triazole 衍生物的新型二亚胺。苯并喹喔啉部分的大 π 共轭使其他基于二亚胺的 Cu( I ) 配合物的吸收向红移方向移动。添加另一个铜（我) 核心扩大了吸收并将其扩展到相当长的波长。此外，通过微调二螯合配体的结构，我们实现了高达 700 nm 的全色吸收，最大摩尔消光系数为 8000 M −1 cm −1 ( λ = 570 nm )，使该化合物具有吸引力光捕获天线。
• Thermal and Microwave-Assisted Synthesis of Diels−Alder Adducts of [60]Fullerene with 2,3-Pyrazinoquinodimethanes:  Characterization and Electrochemical Properties
  作者：Ursula M. Fernández-Paniagua、Beatriz Illescas、Nazario Martín、Carlos Seoane、Pilar de la Cruz、Antonio de la Hoz、Fernando Langa

  DOI：10.1021/jo9701344

  日期：1997.5.1

  [4+2] Cycloaddition reactions of six-membered heterocyclic o-quinodimethanes, generated ''in situ'' from pyrazine derivatives, to [60]fullerene, either under thermal or microwave irradiation are described. Other microwave assisted cycloadditions involving o-quinodimethanes derived from thiophene were also performed. A comparative study of the activation energy for the boat-to-boat conformational inversion has been carried out by dynamic NMR experiments, the Delta G(double dagger) values being highly dependent on the nature of the covalently attached heterocyclic systems. Theoretical calculations predict a more planar cyclohexene ring for the five member containing cycloadducts. The cycloaddition process is controlled by the HOMO of the heterocyclic o-quinodimethanes showing a LUMO(C-60)-HOMO(diene) energy differences typical for favoured cycloadditions. The redox properties of the novel organofullerenes have been determined by cyclic voltammetry in solution, showing a cathodically shifted first reduction potential values, related to [60]fullerene. Compound 15c bearing two cyano groups exhibited an opposite trend which was accounted for by the lower LUMO energy determined by semiempirical calculations.
• US5118675A
  申请人：——

  公开号：US5118675A

  公开（公告）日：1992-06-02
• [EN] BENZO[G]QUINOXALINE DERIVATIVES AS EFFECTIVE COMPOUNDS AGAINST INFECTIOUS DISEASES<br/>[FR] DERIVES DE LA BENZO[G]QUINOXALINE COMPOSES EFFICACES CONTRE LES MALADIES INFECTIEUSES
  申请人：AXXIMA PHARMACEUTICALS AG

  公开号：WO2002094796A2

  公开（公告）日：2002-11-28

  The present invention relates to benzo[g]quinoxaline derivatives of the general formula (I), processes for manufacturing said benzo[g]quinoxaline derivatives, the use of the benzo[g]quinoxaline derivatives as pharmaceutically active agents, especially for the prophylaxis and/or treatment of infectious diseases and opportunistic infections, diabetes, cancer, inflammation, as well as compositions containing at least one benzo[g]quinoxaline derivative and/or pharmaceutically acceptable salt thereof. Further, the present invention is directed to methods for preventing and/or treating of infectious diseases, diabetes, cancer, and inflammation using the inventive benzo[g]quinoxaline derivatives.