(R)-methyl 3-((S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-ylcarbamoyl)-5-methylhexanoate | 200866-11-1

• 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: (R)-methyl 3-((S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-ylcarbamoyl)-5-methylhexanoate
• 英文别名: methyl (3R)-3-[[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]carbamoyl]-5-methylhexanoate
• CAS: 200866-11-1
• 化学式: C₁₆H₃₀N₂O₄
• 分子量: 314.425
• InChiKey: HAUZVZDVNIVRFY-DGCLKSJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-methyl 3-((S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-ylcarbamoyl)-5-methylhexanoate 在 氢氧化钾 、 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以7%的产率得到(2R)-N1-[(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-N4-hydroxy-2-(2-methylpropyl)-butanediamide
  参考文献：
  名称：

  Novel method of treatment of inflammatory skin conditions

  摘要：

  提供了一种治疗或预防由金黄色葡萄球菌定植引起的炎症性皮肤病的方法，包括局部施用一种金黄色葡萄球菌溶素抑制剂。

  公开号：

  US20070049518A1
• 作为产物：
  描述：

  N-Boc-L-叔亮氨酸 在 盐酸 、 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 32.0h， 生成 (R)-methyl 3-((S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-ylcarbamoyl)-5-methylhexanoate
  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
• 作为试剂：
  描述：

  (R)-methyl 3-((S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-ylcarbamoyl)-5-methylhexanoate 、 、 盐酸羟胺 、 氢氧化钾 在 (R)-methyl 3-((S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-ylcarbamoyl)-5-methylhexanoate 、 甲醇 、 水 、 methanol-dichloromethane 、 ethyl acetate isopropanol 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以to give (R)—N1—((S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-N4-hydroxy-2-isobutylsuccinamide as a white solid (68 mg, 7%)的产率得到(2R)-N1-[(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-N4-hydroxy-2-(2-methylpropyl)-butanediamide
  参考文献：
  名称：

  Novel method of treatment of inflammatory skin conditions

  摘要：

  其中提供了一种用于治疗或预防由金黄色葡萄球菌定植引起的炎症性皮肤病的方法，包括局部使用金黄色葡萄球菌溶血酶抑制剂。

  公开号：

  US20070049518A1

文献信息

• WO2007/25999
  申请人：——

  公开号：——

  公开（公告）日：——
• USE OF AN AUREOLYSIN INHIBITOR FOR THE TREATMENT OF INFLAMMATORY SKIN CONDITIONS CHARACTERISED BY COLONISATION WITH STAPHYLOCOCCUS AUREUS
  申请人：Serentis Limited

  公开号：EP1931624A1

  公开（公告）日：2008-06-18
• [EN] USE OF AN AUREOLYSIN INHIBITOR FOR THE TREATMENT OF INFLAMMATORY SKIN CONDITIONS CHARACTERISED BY COLONISATION WITH STAPHYLOCOCCUS AUREUS<br/>[FR] UTILISATION D'UN INHIBITEUR DE L'AUREOLYSINE POUR LE TRAITEMENT DE MALADIES INFLAMMATOIRES DE LA PEAU CARACTERISEES PAR UNE COLONISATION PAR STAPHYLOCOCCUS AUREUS
  申请人：SURFACE THERAPEUTICS LTD

  公开号：WO2007025999A1

  公开（公告）日：2007-03-08

  [EN] There is provided, inter alia, a method for the treatment or prevention of an inflammatory skin condition which is characterised by colonisation with Staphylococcus aureus, comprising the topical administration of an aureolysin inhibitor.
  [FR] L'invention concerne notamment une méthode de traitement ou de prévention d'une maladie inflammatoire de la peau caractérisées par une colonisation par Staphylococcus aureus, cette méthode consistant en l'administration topique d'un de l'auréolysine.
• Matrix Metalloproteinase Inhibitors:  A Structure−Activity Study
  作者：Daniel E. Levy、France Lapierre、Weisheng Liang、Wenqing Ye、Christopher W. Lange、Xiaoyuan Li、Damian Grobelny、Marie Casabonne、David Tyrrell、Kevin Holme、Alex Nadzan、Richard E. Galardy

  DOI：10.1021/jm970494j

  日期：1998.1.1

  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.
• Novel method of treatment of inflammatory skin conditions
  申请人：Chandler Rupert Stephen

  公开号：US20070049518A1

  公开（公告）日：2007-03-01

  There is provided, inter alia, a method for the treatment or prevention of an inflammatory skin condition which is characterised by colonisation with Staphylococcus aureus , comprising the topical administration of an aureolysin inhibitor.

  提供了一种治疗或预防由金黄色葡萄球菌定植引起的炎症性皮肤病的方法，包括局部施用一种金黄色葡萄球菌溶素抑制剂。