(2S)-2-[(tert-butoxy)carbonylamino]-3-(2-naphthyl)-N-benzylpropanamide | 138449-28-2

• 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: (2S)-2-[(tert-butoxy)carbonylamino]-3-(2-naphthyl)-N-benzylpropanamide
• 英文别名: Boc-D-β-(2-Naphthyl)alanine Benzylamide；N-(Boc-3-(2-naphthyl)-L-alanyl)benzylamine；tert-butyl N-[(2S)-1-(benzylamino)-3-naphthalen-2-yl-1-oxopropan-2-yl]carbamate
• CAS: 138449-28-2
• 化学式: C₂₅H₂₈N₂O₃
• 分子量: 404.509
• InChiKey: ZGIRDKXPYNEHSK-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(tert-butoxy)carbonylamino]-3-(2-naphthyl)-N-benzylpropanamide 在 盐酸 、 氢氧化钾 、 盐酸羟胺 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 6.0h， 生成 (2R)-N-[(2S)-1-(benzylamino)-3-naphthalen-2-yl-1-oxopropan-2-yl]-N'-hydroxy-2-(2-methylpropyl)butanediamide
  参考文献：
  名称：

  Matrix Metalloproteinase Inhibitors:  A Structure−Activity Study

  摘要：

  Modifications around the dipeptide-mimetic core of a hydroxamic acid based matrix metalloproteinase inhibitor were studied. These variations incorporated a variety of natural, unnatural, and synthetic amino acids in addition to modifications of the P1' and P3' substituents. The results of this study indicate the following structural requirements: (1) Two key hydrogen bonds must be present between the enzyme and potent substrates. (2) Potent inhibitors must possess strong zinc-binding functionalities. (3) The potential importance of the hydrophobic group at position R3 as illustrated by its ability to impart greater relative potency against stromelysin when larger hydrophobic groups are used. (4) Requirements surrounding the nature of the amino acid appear to be more restrictive for stromelysin than for neutrophil collagenase, 72 kDa gelatinase, and 92 kDa gelatinase. These requirements may involve planar fused-ring aryl systems and possibly hydrogen-bonding capabilities.

  DOI：

  10.1021/jm970494j
• 作为产物：
  描述：

  Boc-3-(2-萘基)-L-丙氨酸 、 苄胺 以to give N-(Boc-3-(2-naphthyl)-L-alanyl)benzylamine (3.0 g) as white crystals (yield 94%)的产率得到(2S)-2-[(tert-butoxy)carbonylamino]-3-(2-naphthyl)-N-benzylpropanamide
  参考文献：
  名称：

  Aziridine derivatives, their production and use

  摘要：

  本发明涉及一种化合物，其化学式为：##STR1## 其中R.sub.1和Q分别为可选的酯化或酰胺化的羧基；R.sub.2为氢、酰基或可选的取代的碳氢残基；X为可选的取代的二价碳氢残基；或其盐。该化合物可用作预防和治疗骨疾病的药物和抑制巯基蛋白酶的药物。

  公开号：

  US05668128A1

文献信息

• Aziridine derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05668128A1

  公开（公告）日：1997-09-16

  The present invention relates to a compound of the formula: ##STR1## wherein R.sub.1 and Q are independently an optionally esterified or amidated carboxyl group; R.sub.2 is hydrogen, an acyl group or an optionally substituted hydrocarbon residue; X is a divalent hydrocarbon residue which may be substituted; or a salt thereof, which is useful as prophylactic and therapeutic agents of bone diseases and as agents for inhibiting thiol protease.

  本发明涉及一种化合物，其化学式为：##STR1## 其中R.sub.1和Q分别是可选择酯化或酰胺化的羧基；R.sub.2是氢、酰基或可选择取代的碳氢残基；X是可能被取代的二价碳氢残基；或其盐，可用作预防和治疗骨疾病的药剂以及抑制硫醇蛋白酶的药剂。
• [EN] EFFLUX PUMP INHIBITORS<br/>[FR] INHIBITEURS DE POMPE D'ECOULEMENT
  申请人：MICROCIDE PHARMACEUTICALS, INC.

  公开号：WO1999037667A1

  公开（公告）日：1999-07-29

  (EN) 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.(FR) L'invention concerne des composés présentant une activité d'inhibiteur de pompe d'écoulement. L'invention concerne également des méthodes d'utilisation de ces composés inhibiteurs et des compositions pharmaceutiques renfermant de tels composés.

  （中文翻译）描述了具有外排泵抑制剂活性的化合物。还描述了使用这种外排泵抑制剂化合物的方法和包括这种化合物的药物组合物。
• Inhibitors of anthrax lethal factor
  申请人：Rideout Darryl

  公开号：US20070197577A1

  公开（公告）日：2007-08-23

  Methods, compounds and compositions for preventing and treating anthrax infections by inhibiting Anthrax Lethal Factor (LF) activity.

  通过抑制炭疽病致命因子（LF）活性，预防和治疗炭疽感染的方法，化合物和组合物。
• An Efficient and Practical N-Methylation of Amino Acid Derivatives
  作者：Mahavir Prashad、Denis Har、Bin Hu、Hong-Yong Kim、Oljan Repic、Thomas J. Blacklock

  DOI：10.1021/ol0268440

  日期：2003.1.1

  An efficient and practical N-methylation of amino acid derivatives with dimethyl sulfate in the presence of sodium hydride and a catalytic amount of water is described. Reaction of water with sodium hydride generated highly reactive dry sodium hydroxide, which led to much faster reaction rates than powdered sodium hydroxide itself.
• AZIRIDINE DERIVATIVES, THEIR PRODUCTION AND USE
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0753003A1

  公开（公告）日：1997-01-15