(S)-2-((methoxycarbonyl)methyl)-4-methylpentanoic acid | 181487-68-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-2-((methoxycarbonyl)methyl)-4-methylpentanoic acid
• 英文别名: (2S)-2-(2-methoxy-2-oxoethyl)-4-methylpentanoic acid
• CAS: 181487-68-3
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: REUDDXCWANRXHG-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-((methoxycarbonyl)methyl)-4-methylpentanoic acid 在 氢氧化钾 、 盐酸羟胺 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (2S)-N4-hydroxy-N1-[(1S)-1-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl]-2-isobutylsuccinamide
  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：

  dihydro-3-(RS)-(2-methylpropyl)-2,5-furandione 在 盐酸 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 216.0h， 生成 (S)-2-((methoxycarbonyl)methyl)-4-methylpentanoic acid
  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

文献信息

• 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。
• WO2008/104755
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] SUCCINATE DERIVATIVES AND THEIR THERAPEUTIC USE<br/>[FR] DÉRIVÉS SUCCINATE ET LEUR UTILISATION THÉRAPEUTIQUE
  申请人：SERENTIS LTD

  公开号：WO2008104755A1

  公开（公告）日：2008-09-04

  [EN] A compound of formula (I) wherein R¹ is C_1-4 alkyl, allyl or propargyl; R² is C_1-6 alkyl, -(CH₂)_m-aryl or -(CH₂)_m-heteroaryl; R³ is H or C_1-4 alkyl; R⁴ is C_1-4 alkyl, -(CH₂)_n-aryl or -(CH₂)_n-heteroaryl; R⁵ is H, OH or C_1-4 alkoxy; and m and n independently represent 0 or an integer of up to 3; or a pharmaceutically acceptable salt or solvate thereof, has utility in the treatment of conditions such as atopic dermatitis.
  [FR] La présente invention concerne un composé représenté par la formule (I) ou l'un de ses sels ou solvates pharmaceutiquement admis. Ce composé convient au traitement d'états tels que la dermatite atopique. Dans cette formule, R¹ est C_1-4 alkyle, allyle ou propargyle; R² est C_1-6 alkyle, -(CH₂)_m-aryle ou -(CH₂)m-hétéroaryl; R³ est H ou C_1-4 alkyle; R⁴ est C_1-4 alkyle, -(CH₂)_n-aryle ou -(CH₂)_n-hétéroaryle; R⁵ est H, OH ou C1-4 alcoxy; enfin, m et n représentent indépendamment 0 ou un entier valant 3 au maximum.
• 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.