D-hPhe-3-aminoquinoline | 254882-55-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: D-hPhe-3-aminoquinoline
• 英文别名: (2R)-2-amino-4-phenyl-N-quinolin-3-ylbutanamide
• CAS: 254882-55-8
• 化学式: C₁₉H₁₉N₃O
• 分子量: 305.379
• InChiKey: JYOXFDYYLLQQNE-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  68
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  D-hPhe-3-aminoquinoline 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  含二胺外排泵抑制剂类似物的理化性质，体外活性与药代动力学特征之间的关系。

  摘要：

  在体外增强活性，体内稳定性和急性毒性方面优化含二胺的外排泵抑制剂后，我们解决了如何控制该系列药代动力学特性的问题。在大鼠中静脉内给药后，与血清中的组织水平相比，MC-04,124（先导化合物）的组织水平较高且持续时间较长。系统地改变了该化合物类似物的亲脂性和碱性，并探讨了其对药效和药代动力学的影响。在任何检查的活性类似物中，组织与血清中药物水平的比率均未显着降低。

  DOI：

  10.1016/j.bmcl.2003.07.030
• 作为产物：
  描述：

  3-氨基喹啉 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 D-hPhe-3-aminoquinoline
  参考文献：
  名称：

  构象受限的外排泵抑制剂类似物，可增强铜绿假单胞菌中左氧氟沙星的活性。

  摘要：

  构象限制了外排泵抑制剂D-鸟氨酸-D-高苯丙氨酸-3-氨基喹啉（MC-02,595，2）的鸟氨酸残基，提供了生物等位脯氨酸衍生物，其体内毒性较小，并具有增强铅活性的铅的活性。通过抑制铜绿假单胞菌的外排泵抑制氟喹诺酮左氧氟沙星。

  DOI：

  10.1016/s0960-894x(03)00556-0

文献信息

• POLYBASIC BACTERIAL EFFLUX PUMP INHIBITORS AND THERAPEUTIC USES THEREOF
  申请人：GLINKA TOMASZ

  公开号：US20080318957A1

  公开（公告）日：2008-12-25

  Disclosed are compounds having polybasic functionalities. The compounds inhibit bacterial efflux pump inhibitors and are used in combination with an anti-bacterial agent to treat or prevent bacterial infections. These combinations can be effective against bacterial infections that have developed resistance to anti-bacterial agents through an efflux pump mechanism.

  揭示了具有多元碱功能的化合物。这些化合物抑制细菌外流泵抑制剂，并与抗菌剂结合使用以治疗或预防细菌感染。这些组合物可以有效对抗通过外流泵机制对抗菌剂产生抗药性的细菌感染。
• Bacterial efflux pump inhibitors and methods of treating bacterial infections
  申请人：Glinka Tomasz

  公开号：US20060003944A1

  公开（公告）日：2006-01-05

  This invention relates to the field of antimicrobial agents and more specifically it relates to Efflux Pump Inhibitor (EPI) compounds to be co-administered with antimicrobial agents for the treatment of infections caused by drug resistant pathogens. The EPI compounds are soft drugs which exhibit a reduced propensity for tissue accumulation. The invention includes novel compounds useful as efflux pump inhibitors, compositions and devices comprising such efflux pump inhibitors, and therapeutic use of such compounds.

  本发明涉及抗微生物制剂领域，更具体地涉及与抗微生物制剂共同使用的外排泵抑制剂（EPI）化合物，用于治疗由耐药病原体引起的感染。EPI化合物是软药，具有较低的组织积累倾向。本发明包括用作外排泵抑制剂的新化合物，包含这种外排泵抑制剂的组合物和装置，以及这种化合物的治疗用途。
• ENHANCEMENT OF TIGECYCLINE POTENCY USING EFFLUX PUMP INHIBITORS
  申请人：Glinka Tomasz

  公开号：US20080076741A1

  公开（公告）日：2008-03-27

  Disclosed herein are Efflux Pump Inhibitor (EPI) compounds that can be co-administered with antimicrobial agents for the treatment of infections caused by drug resistant pathogens. The EPI compounds are soft drugs which exhibit a reduced propensity for tissue accumulation. It is demonstrated that the EPIs can be used to increase the potency, decrease bacterial resistance and development of bacterial resistance, and increase killing effectivness of tigecycline. Also disclosed are methods of treatment and pharmaceutical compositions for co-administering tigecylcine with an EPI.

  本文公开了外排泵抑制剂（EPI）化合物，可以与抗微生物药物联合使用，用于治疗由耐药病原体引起的感染。这些EPI化合物是软药物，具有降低组织积累的倾向。证明EPI可以用于增加替加环素的效力，降低细菌耐药性和细菌耐药性的发展，并增加杀菌效果。同时，还公开了联合使用替加环素和EPI的治疗方法和制药组合物。
• Addressing the stability of C-capped dipeptide efflux pump inhibitors that potentiate the activity of levofloxacin in Pseudomonas aeruginosa
  作者：Thomas E Renau、Roger Léger、Eric M Flamme、Miles W She、Carla L Gannon、Kristina M Mathias、Olga Lomovskaya、Suzanne Chamberland、Ving J Lee、Toshiharu Ohta、Kiyoshi Nakayama、Yohei Ishida

  DOI：10.1016/s0960-894x(01)00033-6

  日期：2001.3

  Synthetic optimization of a biologically labile class of dipeptides that function as efflux pump inhibitors to potentiate the antibacterial agent levofloxacin in Pseudomonas aeruginosa has led to the discovery of a related series of compounds that are completely stable in a variety of biological matrices. Other than the stability profile, the in vitro profile of the new series is essentially identical to that observed with the original one. A prototypical compound from the new series demonstrates potentiation in an in vivo model of infection. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Peptidomimetics of Efflux Pump Inhibitors Potentiate the Activity of Levofloxacin in Pseudomonas aeruginosa
  作者：Thomas E. Renau、Roger Léger、Rose Yen、Miles W. She、Eric M. Flamme、Joan Sangalang、Carla L. Gannon、Suzanne Chamberland、Olga Lomovskaya、Ving J. Lee

  DOI：10.1016/s0960-894x(02)00006-9

  日期：2002.3

  Several classes of peptidomimetics of the efflux pump inhibitor D-ornithine-D-homophenylalanine-3-aminoquinoline (MC-02,595) have been prepared and evaluated for their ability to potentiate the activity of the fluoroquinolone levofloxacin in Pseudomonas aeruginosa. A number of the new analogues were as active or more active than the lead. demonstrating that a peptide backbone is not essential for activity. (C) 2002 Elsevier Science Ltd. All rights reserved.