4-氯-1-(2-苯基乙基)咪唑并[1,2-a]喹喔啉 | 681284-73-1

• 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: 4-氯-1-(2-苯基乙基)咪唑并[1,2-a]喹喔啉
• 英文名称: 4-Chloro-1-(2-phenylethyl)imidazo[1,2-a]quinoxaline
• CAS: 681284-73-1
• 化学式: C₁₈H₁₄ClN₃
• 分子量: 307.782
• InChiKey: ZXLNHTNHMZEZNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-氯-1-(2-苯基乙基)咪唑并[1,2-a]喹喔啉 在 ammonium hydroxide 作用下， 反应 4.0h， 以62%的产率得到1-(2-phenethyl)imidazo[1,2-a]quinoxalin-4-amine
  参考文献：
  名称：

  Design and synthesis of novel imidazo[1,2- a ]quinoxalines as PDE4 inhibitors

  摘要：

  New imidazo[1,2-a]quinoxaline derivatives have been synthesised by condensation of an appropriate alpha-aminoalcohol with a quinoxaline followed by intramolecular cyclisation and nucleophilic substitutions. Their phosphodiesterase inhibitory activities have been assessed on a preparation of the PDE4 isoform purified from a human alveolar epithelial cell line (A549). These studies showed potent inhibitory properties that emphasize the importance of a methyl amino group at position 4 and a weakly hindered group at position 1. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.034
• 作为产物：
  描述：

  (RS)-3-苯基丙醛氰醇 在 lithium aluminium tetrahydride 、 三甲基铵三氧化硫共聚物 、 三乙胺 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 1,4-二氧六环 、 乙醚 、 二甲基亚砜 为溶剂， 反应 31.5h， 生成 4-氯-1-(2-苯基乙基)咪唑并[1,2-a]喹喔啉
  参考文献：
  名称：

  Design and synthesis of novel imidazo[1,2- a ]quinoxalines as PDE4 inhibitors

  摘要：

  New imidazo[1,2-a]quinoxaline derivatives have been synthesised by condensation of an appropriate alpha-aminoalcohol with a quinoxaline followed by intramolecular cyclisation and nucleophilic substitutions. Their phosphodiesterase inhibitory activities have been assessed on a preparation of the PDE4 isoform purified from a human alveolar epithelial cell line (A549). These studies showed potent inhibitory properties that emphasize the importance of a methyl amino group at position 4 and a weakly hindered group at position 1. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.034

文献信息

• IMIDAZOL[1,2-alpha]QUINOXALINES AND DERIVATIVES FOR THE TREATMENT OF CANCERS
  申请人：Deleuze-Masquefa Carine

  公开号：US20100249142A1

  公开（公告）日：2010-09-30

  Imidazo[1,2-a]quinoxaline compounds for the treatment of cancers as well as pharmaceutical compositions that include these compounds and their uses in therapy. The compound of general formula (I):

  咪唑并[1,2-a]喹噁啉化合物用于治疗癌症，以及包括这些化合物的药物组合物和它们在疗法中的用途。通式(I)的化合物：
• In vitro and in vivo anti-tumoral activities of imidazo[1,2-a]quinoxaline, imidazo[1,5-a]quinoxaline, and pyrazolo[1,5-a]quinoxaline derivatives
  作者：Georges Moarbess、Carine Deleuze-Masquefa、Vanessa Bonnard、Stéphanie Gayraud-Paniagua、Jean-Rémi Vidal、Françoise Bressolle、Frédéric Pinguet、Pierre-Antoine Bonnet

  DOI：10.1016/j.bmc.2008.05.022

  日期：2008.7.1

  Imidazoquinoxaline and pyrazoloquinoxaline derivatives, analogues of imiquimod, were synthesized, and their in vitro cytotoxic and pharmacodynamic activities were evaluated. In vitro cytotoxicity studies were assessed against melanoma (A375, M4Be, RPMI-7591), colon (LS174T), breast (MCF7), and lymphoma (Raji) human cancer cell lines. In vivo studies were carried out in M4Be xenografted athymic mice. EAPB0103, EAPB0201, EAPB0202, and EAPB0203 showed significant in vitro activities against A375 compared to fotemustine and imiquimod used as references. These compounds were 6-110 and 2-45 times more active than fotemustine and imiquimod, respectively. EAPB0203 bearing phenethyl as substituent at position 1 and methylamine at position 4 showed the highest activity. EAPB0203 has also a more potent cytotoxic activity than imiquimod and fotemustine in M4Be and RPMI-7591 and interesting cytotoxic activity in other tumor cell lines tested. In vivo, EAPB0203 treatment schedules caused a significant decrease in tumor size compared to vehicle control and fotemustine treatments. (c) 2008 Elsevier Ltd. All rights reserved.
• IMIDAZO[1,2-A]QUINOXALINES ET DÉRIVÉS POUR LE TRAITEMENT DES CANCERS
  申请人：Université de Montpellier

  公开号：EP2205602B1

  公开（公告）日：2018-09-26
• US8378098B2
  申请人：——

  公开号：US8378098B2

  公开（公告）日：2013-02-19