2,3-bis(bromomethyl)-6-chloroquinoxaline | 3298-97-3

• 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-chloroquinoxaline
• CAS: 3298-97-3
• 化学式: C₁₀H₇Br₂ClN₂
• 分子量: 350.44
• InChiKey: FFBZVHUMCXCGNW-UHFFFAOYSA-N

物化性质

• 熔点：
  150.5-152.0 °C
• 沸点：
  377.1±37.0 °C(Predicted)
• 密度：
  1.936±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 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-chloroquinoxaline 在 盐酸 、 sodium 作用下， 以 甲苯 为溶剂， 反应 9.0h， 生成 α-amino-6-chloro-3-(phosphonomethyl)-2-quinoxalinepropanoic acid hydrochloride
  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-氯-1,2-苯二胺 、 1,4-二溴-2,3-丁二酮 在 silica gel 作用下， 反应 0.33h， 以80%的产率得到2,3-bis(bromomethyl)-6-chloroquinoxaline
  参考文献：
  名称：

  在无溶剂条件下硅胶催化高效合成喹喔啉衍生物

  摘要：

  首次使用硅胶作为催化剂，在无溶剂条件下，以各种 1,2-二酮和 1,2-二胺为原料制备了喹喔啉衍生物，收率非常好。该方法的优点是反应时间短、反应简单、后处理程序方便、化合物可通过非色谱法纯化。

  DOI：

  10.1080/00397910903576685

文献信息

• Quinoxalines. Part 13: Synthesis and mass spectrometric study of aryloxymethylquinoxalines and benzo[b]furylquinoxalines
  作者：Ines Starke、Gerhard Sarodnick、Vladimir V. Ovcharenko、Kalevi Pihlaja、Erich Kleinpeter

  DOI：10.1016/j.tet.2004.05.064

  日期：2004.7

  aryloxymethylquinoxalines, benzo[b]- and naphtho[2,1-b]furylquinoxalines, possessing potential biological activity, was prepared, characterized by IR and NMR spectroscopy and their electron ionization (EI) mass spectra studied in detail. The aryloxymethylquinoxalines were obtained by reacting halogenomethylquinoxalines with bifunctional O-nucleophiles. The benzo[b]furylquinoxalines and naphtho[2,1-b]furylquinoxalines

  制备了一系列具有潜在生物活性的新型芳氧基甲基喹喔啉，苯并[ b ]-和萘并[ 2,1- b ]呋喃基喹喔啉，并通过红外光谱和核磁共振谱进行了表征，并对其电子电离（EI）质谱进行了详细研究。通过使卤代甲基喹喔啉与双官能O-亲核试剂反应获得芳氧基甲基喹喔啉。所述苯并[ b ] furylquinoxalines和萘并[2,1- b通过两个途径制备]呋喃基喹喔啉，这两个途径在合成中涉及的两个环化步骤的顺序上是不同的。通过精确的质谱测量确定了通过EI质谱法获得的离子的组成，并通过B / E链接扫描和碰撞诱导的离解阐明了裂解途径。研究的化合物的质谱行为与可能的OH损失有关 自由基被证明是非常有特色的。
• Luminescent bis(benzo[<i>d</i>]thiazolyl)quinoxaline: facile synthesis, nucleic acid and protein BSA interaction, live-cell imaging, biopharmaceutical research and cancer theranostic application
  作者：Lavanya Thilak Babu、Gajanan Raosaheb Jadhav、Priyankar Paira

  DOI：10.1039/c9ra01498e

  日期：——

  A series of luminescent bis(benzo[d]thiazolyl)quinoxalines have been synthesized and their fluorescence properties, anticancer potency, DNA and BSA interactions, cellular uptake, and metabolic stabilities are investigated.

  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。
• Silica-Gel–Catalyzed Efficient Synthesis of Quinoxaline Derivatives Under Solvent-Free Conditions
  作者：Ganesh Chandra Nandi、Subhasis Samai、Ram Kumar、M. S. Singh

  DOI：10.1080/00397910903576685

  日期：2011.1.25

  Quinoxaline derivatives have been prepared in good to excellent yields using silica gel as catalyst from various 1,2-diketones and 1,2-diamines under solvent-free conditions for the first time. The advantages of this method are short reaction time, reaction simplicity, convenient workup procedure, and purification of compounds by a nonchromatographic method.

  首次使用硅胶作为催化剂，在无溶剂条件下，以各种 1,2-二酮和 1,2-二胺为原料制备了喹喔啉衍生物，收率非常好。该方法的优点是反应时间短、反应简单、后处理程序方便、化合物可通过非色谱法纯化。
• Synthesis of 2,3-Bis(halomethyl)quinoxaline Derivatives and Evaluation of Their Antibacterial and Antifungal Activities
  作者：Hisato Ishikawa、Takayuki Sugiyama、Akihiro Yokoyama

  DOI：10.1248/cpb.c12-01061

  日期：——

  Quinoxaline derivatives having bis(fluoromethyl), bis(chloromethyl), or bis(iodomethyl) groups at the 2- and 3-positions, and various electron-donating/withdrawing substituents at the 6- and/or 7-positions, were synthesized. Their antibacterial and antifungal activities were evaluated by means of minimum inhibitory concentration assays. The relationships between the substituents and the antimicrobial activities of the quinoxaline derivatives indicate that the electrophilicity of the halomethyl units plays an important role in generating the antimicrobial activity.

  合成了在2位和3位具有双（氟甲基）、双（氯甲基）或双（碘甲基）基团，在6位和/或7位具有各种电子给体/电子受体取代基的喹喔啉衍生物。通过最小抑菌浓度测定法评估了它们的抗菌和抗真菌活性。喹喔啉衍生物的取代基与抗菌活性之间的关系表明，卤甲基单元的电负性在产生抗菌活性方面起着重要作用。
• 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。