9-allyl-2-phenylimidazo[1,2-a]benzimidazole | 342385-23-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 9-allyl-2-phenylimidazo[1,2-a]benzimidazole
• 英文别名: 8-allyl-2-phenyl-8H-1,3a,8-triaza-cyclopenta[a]-indene；8-Allyl-2-phenyl-8H-1,3a,8-triaza-cyclopenta[a]indene；2-phenyl-4-prop-2-enylimidazo[1,2-a]benzimidazole
• CAS: 342385-23-3
• 化学式: C₁₈H₁₅N₃
• mdl: MFCD01412926
• 分子量: 273.337
• InChiKey: SSXFTSIOKPEQLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-allyl-2-phenylimidazo[1,2-a]benzimidazole 在 盐酸 作用下， 以 丙酮 为溶剂， 以95%的产率得到9-allyl-2-phenylimidazo[1,2-a]benzimidazole hydrochloride
  参考文献：
  名称：

  Imidazo[1,2-a]benzimidazole derivatives: XXIX. 1-allyl-2-amino-3-acylmethylbenzimidazolium halides and syntheses on their base

  摘要：

  Cyclization of 1-allyl-2-amino-3-acylmethylbenzimidazolium halides under alkaline conditions gave 9-allyl-substituted imidazo[1,2-a]benzimidazoles. Cyclization of the same compounds on heating in concentrated hydrobromic acid was accompanied by addition of hydrogen bromide at the exocyclic double bond. Competing cyclizations with participation of the 1-(2-bromopropyl) and 3-acylmethyl substituents in 2-imino-2,3-dihydro-1H-benzimidazole were studied. Functionalization of the imidazo[1,2-a]benzimidazole system was performed via introduction of substituents into the 3-position and replacement of bromine in the 2-bromopropyl group in the 9-position.

  DOI：

  10.1134/s1070428011090168
• 作为产物：
  描述：

  1-allyl-1H-benzimidazol-2-amine 在 氨 作用下， 以 水 、 丙酮 为溶剂， 反应 3.25h， 生成 9-allyl-2-phenylimidazo[1,2-a]benzimidazole
  参考文献：
  名称：

  Imidazo[1,2-a]benzimidazole derivatives: XXIX. 1-allyl-2-amino-3-acylmethylbenzimidazolium halides and syntheses on their base

  摘要：

  Cyclization of 1-allyl-2-amino-3-acylmethylbenzimidazolium halides under alkaline conditions gave 9-allyl-substituted imidazo[1,2-a]benzimidazoles. Cyclization of the same compounds on heating in concentrated hydrobromic acid was accompanied by addition of hydrogen bromide at the exocyclic double bond. Competing cyclizations with participation of the 1-(2-bromopropyl) and 3-acylmethyl substituents in 2-imino-2,3-dihydro-1H-benzimidazole were studied. Functionalization of the imidazo[1,2-a]benzimidazole system was performed via introduction of substituents into the 3-position and replacement of bromine in the 2-bromopropyl group in the 9-position.

  DOI：

  10.1134/s1070428011090168

文献信息

• Compounds capable of modulating the activity of multidrug transporters and therapeutic use of the same
  申请人：——

  公开号：US20030073611A1

  公开（公告）日：2003-04-17

  Methods of modulating the activity of multidrug transporters are disclosed. The methods of modulating the activity of multidrug transporters use compounds that selectively increase or decrease the efflux capabilities of the multidrug transporter. The methods can be used therapeutically to enhance performance of therapeutic drugs, like chemotherapeutic drugs and antibiotics; to promote detoxification of cells and tissues; and to increase or decrease the efficacy of the blood-brain barrier or placental barrier.

  揭示了调节多药转运蛋白活性的方法。调节多药转运蛋白活性的方法使用能够选择性增加或减少多药转运蛋白外流能力的化合物。这些方法可以用于治疗，以增强治疗药物（如化疗药物和抗生素）的表现；促进细胞和组织的解毒；以及增加或减少血脑屏障或胎盘屏障的效力。
• Methods and compositions for therapeutic treatment
  申请人：Robbins Wendye

  公开号：US20060111308A1

  公开（公告）日：2006-05-25

  Methods and compositions are described for the modulation of central nervous system and/or fetal effects of substances. Methods and compositions are described for the modulation of efflux transporter activity to increase the efflux of drugs and other compounds out of a physiological compartment and into an external environment. In particular, the methods and compositions disclosed herein provide for the increase of efflux transporter activity at blood-brain, blood-CSF and placental-maternal barriers to increase the efflux of drugs and other compounds from physiological compartments, including central nervous system and fetal compartments.

  所述方法和组合物用于调节物质对中枢神经系统和/或胎儿的影响。本文描述了调节外排转运体活性的方法和组合物，以增加药物和其他化合物从生理区室向外部环境的外排。特别是，本文公开的方法和组合物可以提高血脑屏障、血液-脑脊液屏障和胎盘-母体屏障的外排转运体活性，以增加药物和其他化合物从生理区室（包括中枢神经系统和胎儿区室）的外排。
• Methods and compositions for treating pain
  申请人：Robbins Wendye

  公开号：US20060111307A1

  公开（公告）日：2006-05-25

  Methods and compositions are described for the modulation of central nervous system and/or fetal effects of substances. Methods and compositions are described for the modulation of efflux transporter activity to increase the efflux of drugs and other compounds out of a physiological compartment and into an external environment. In particular, the methods and compositions disclosed herein provide for the increase of efflux transporter activity at blood-brain, blood-CSF and placental-maternal barriers to increase the efflux of drugs and other compounds from physiological compartments, including central nervous system and fetal compartments.

  所述方法和组合物用于调节物质对中枢神经系统和/或胎儿的影响。本文描述了调节外排转运体活性的方法和组合物，以增加药物和其他化合物从生理区室向外部环境的外排。特别是，本文公开的方法和组合物可以提高血脑屏障、血液-脑脊液屏障和胎盘-母体屏障的外排转运体活性，以增加药物和其他化合物从生理区室（包括中枢神经系统和胎儿区室）的外排。
• METHODS FOR TREATING PAIN WITH REDUCED NUASEA AND VOMITING
  申请人：Limerick BioPharma, Inc.

  公开号：EP2066331A2

  公开（公告）日：2009-06-10
• METHODS AND COMPOSITIONS FOR TREATING PAIN
  申请人：Robbins Wendye

  公开号：US20070087977A1

  公开（公告）日：2007-04-19

  Methods and compositions are described for the modulation of central nervous system and/or fetal effects of substances. Methods and compositions are described for the modulation of efflux transporter activity to increase the efflux of drugs and other compounds out of a physiological compartment and into an external environment. In particular, the methods and compositions disclosed herein provide for the increase of efflux transporter activity at blood-brain, blood-CSF and placental-maternal barriers to increase the efflux of drugs and other compounds from physiological compartments, including central nervous system and fetal compartments.