[(S)-4-Methylamino-4-(naphthalen-2-ylcarbamoyl)-butyl]-carbamic acid tert-butyl ester | 233689-61-7

• 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: [(S)-4-Methylamino-4-(naphthalen-2-ylcarbamoyl)-butyl]-carbamic acid tert-butyl ester
• 英文别名: Ndelta-Boc-Nalpha-methylornithine beta-naphthylamide；tert-butyl N-[(4S)-4-(methylamino)-5-(naphthalen-2-ylamino)-5-oxopentyl]carbamate
• CAS: 233689-61-7
• 化学式: C₂₁H₂₉N₃O₃
• 分子量: 371.48
• InChiKey: CAVLQLFBZULFTO-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  79.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(S)-4-Methylamino-4-(naphthalen-2-ylcarbamoyl)-butyl]-carbamic acid tert-butyl ester 在 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-5-Amino-2-[((S)-2-amino-3-phenyl-propionyl)-methyl-amino]-pentanoic acid naphthalen-2-ylamide; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Addressing the stability of C-capped dipeptide efflux pump inhibitors that potentiate the activity of levofloxacin in Pseudomonas aeruginosa

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(01)00033-6
• 作为产物：
  描述：

  [(S)-4-(Benzyl-methyl-amino)-4-(naphthalen-2-ylcarbamoyl)-butyl]-carbamic acid tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 [(S)-4-Methylamino-4-(naphthalen-2-ylcarbamoyl)-butyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Addressing the stability of C-capped dipeptide efflux pump inhibitors that potentiate the activity of levofloxacin in Pseudomonas aeruginosa

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(01)00033-6

文献信息

• Efflux pump inhibitors
  申请人：Microcide Pharmaceuticals, Inc.

  公开号：US06245746B1

  公开（公告）日：2001-06-12

  Compounds are described which have efflux pump inhibitor activity. Also described are methods of using such efflux pump inhibitor compounds and pharmaceutical compositions which include such compounds.

  描述了具有外流泵抑制剂活性的化合物。还描述了使用这种外流泵抑制剂化合物的方法和包括这种化合物的制药组合物。
• 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.