2,3-bis(bromomethyl)-6,7-dichloroquinoxaline | 3298-96-2

• 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: 2,3-bis(bromomethyl)-6,7-dichloroquinoxaline
• 英文别名: 2,3-bis-bromomethyl-6,7-dichloro-quinoxaline；2,3-bis(bromomethyl)-6,7-dichloro-quinoxaline；6,7-Dichlor-2,3-bis-brommethyl-chinoxalin
• CAS: 3298-96-2
• 化学式: C₁₀H₆Br₂Cl₂N₂
• 分子量: 384.885
• InChiKey: LWXGVLAUAJHSID-UHFFFAOYSA-N

物化性质

• 熔点：
  171.0-172.5 °C
• 沸点：
  408.4±40.0 °C(Predicted)
• 密度：
  1.995±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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-bis(bromomethyl)-6,7-dichloroquinoxaline 在 sodium 作用下， 以 甲苯 为溶剂， 反应 6.0h， 生成 (acetylamino)<<6,7-dichloro-3-<(dimethoxyphosphinyl)methyl>-2-quinoxalinyl>methyl>propanedioic acid diethyl ester
  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：

  4,5-二氯邻苯二胺 、 1,4-二溴-2,3-丁二酮 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2,3-bis(bromomethyl)-6,7-dichloroquinoxaline
  参考文献：
  名称：

  Luminescent bis(benzo[d]thiazolyl)quinoxaline: facile synthesis, nucleic acid and protein BSA interaction, live-cell imaging, biopharmaceutical research and cancer theranostic application

  摘要：

  已合成一系列发光的双(苯并[d]噻唑基)喹喔啉化合物，并研究了它们的荧光特性、抗癌效力、与DNA和BSA的相互作用、细胞摄取以及代谢稳定性。

  DOI：

  10.1039/c9ra01498e

文献信息

• A new facile, efficient synthesis and structure peculiarity of quinoxaline derivatives with two benzimidazole fragments
  作者：Vakhid A. Mamedov、Nataliya A. Zhukova、Victor V. Syakaev、Aidar T. Gubaidullin、Tat'yana N. Beschastnova、Dil'bar I. Adgamova、Aida I. Samigullina、Shamil K. Latypov

  DOI：10.1016/j.tet.2012.10.045

  日期：2013.1

  A highly efficient and versatile method for the synthesis of quinoxaline derivatives with two benzimidazole fragments have been developed on the basis of the ring contraction of 3-(benzimidazo-2-yl)quinoxalin-2(1H)-one with 1,2-diaminobenzene and its various types of substituted and condensed derivatives. Owing to the inter- and intramolecular processes, involving self association, proton exchange

  基于3-（苯并咪唑-2-基）喹喔啉-2（1 H）-与1,2-的环收缩，已开发出一种高效且通用的具有两个苯并咪唑片段的喹喔啉衍生物的合成方法。二氨基苯及其各种类型的取代和稠合衍生物。由于分子间和分子内过程，涉及桥联和相邻碳原子的大多数双-苯并咪唑基喹喔啉信号的几种形式之间的自缔合，质子交换，构象和/或互变异构交换，且NMR光谱中的苯并咪唑片段变宽。苯并咪唑片段与分子的喹喔啉核心之间的共轭作用比喹喔啉衍生物（10c）与其噻二唑[ f ]-（17）和吡咯并[ a ]-（19）环化了衍生物，导致整个分子的平面度更大。
• Quinoxalino-fused sultines and their application in Diels–Alder reactions
  作者：Wen-Sheng Chung、Jing-Horng Liu

  DOI：10.1039/a606764f

  日期：——

  The synthesis of 7,8-disubstituted quinoxalino[2,3-d][1,2λ 4 ]oxathiine 2-oxides 7a–c, precursors for quinoxalino-o-quinodimethanes 3a–c, and their application in the Diels–Alder reactions are reported.

  报道了7,8-二取代喹咯啉[2,3-d][1,2λ4]噁二烯2-氧化物7a–c的合成，它们是喹咯啉-对奎纳二烯3a–c的前体，并且讨论了它们在Diels–Alder反应中的应用。
• 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。
• Diversity-Oriented Approach to 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid (Tic) Derivatives Using Diethyl Acetamidomalonate as a Glycine Equivalent: Further Expansion by Suzuki–Miyaura Cross-Coupling Reaction
  作者：Sambasivarao Kotha、Shilpi Misra、Nimita Gopal Krishna、Nagaraju Devunuri、Henning Hopf、Abhilash Keecherikunnel

  DOI：10.3987/com-09-s(s)103

  日期：——

  Synthesis of diverse 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives and its higher analogues are reported using diethyl acetamidomalonate as a glycine equivalent. In addition, various substituted Tic derivatives are assembled by application of Suzuki-Miyaura cross-coupling reaction as a key step.
• Diversity-Oriented Approach to 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid (Tic) Derivatives
  作者：Sambasivarao Kotha、Shilpi Misra、Nimita Gopal Krishna、Vijayalakshmi Bandi、Mohammad Saifuddin、Nagaraju Devunuri

  DOI：10.3987/com-15-s(t)16

  日期：——

  A convenient method is reported for synthesizing various 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives and bis-armed acid derivatives by treating dibromo-o-xylylenes precursor with diethyl acetamidomalonate under basic conditions. Suzuki coupling reaction has been to expand this methodology. One of the structure revision of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid into bis-armed amino acid is also reported.