N-[(2-s)-(methoxy-carbonylmethyl)-4-methylpentanoyl]-l-tryptophan-methylamide | 142880-35-1

• 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: N-[(2-s)-(methoxy-carbonylmethyl)-4-methylpentanoyl]-l-tryptophan-methylamide
• 英文别名: methyl (3S)-3-[[(2S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxopropan-2-yl]carbamoyl]-5-methylhexanoate
• CAS: 142880-35-1
• 化学式: C₂₁H₂₉N₃O₄
• 分子量: 387.479
• InChiKey: WWPKETMMBZXNGJ-KSSFIOAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  100
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(2-s)-(methoxy-carbonylmethyl)-4-methylpentanoyl]-l-tryptophan-methylamide 在 氢氧化钾 、 盐酸羟胺 作用下， 以 甲醇 为溶剂， 以35%的产率得到(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：

  N-叔丁氧羰基-L-色氨酸 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 N-[(2-s)-(methoxy-carbonylmethyl)-4-methylpentanoyl]-l-tryptophan-methylamide
  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

• PEPTIDES MARQUES ET LEUR UTILISATION POUR LE DOSAGE D'IRAP CIRCULANT
  申请人：Université Joseph Fourier

  公开号：EP2432800A2

  公开（公告）日：2012-03-28
• Compositions and methods for use of a protease inhibitor and adenosine for preventing organ ischemia and reperfusion injury
  申请人：Vinten-Johansen Jakob

  公开号：US20060205671A1

  公开（公告）日：2006-09-14

  Methods and compositions including combined use of a serine protease inhibitor and adenosine when administered as a single pharmaceutical composition, concomitantly or sequentially in any order to a living subject for preventing organ ischemia or reperfusion injury. The methods and compositions disclosed herein can be used in such procedures as cardiac surgery, non-surgical cardiac revascularization, organ transplantation, perfusion, ischemia, reperfusion, ischemia-reperfusion injury, oxidant injury, cytokine induced injury, shock induced injury, resuscitations injury or apoptosis.
• METHOD OF TREATING FATTY LIVER DISEASE
  申请人：Puder Mark

  公开号：US20090221533A1

  公开（公告）日：2009-09-03

  The present invention relates to a method for treating a fatty liver disease or disorder in a patient in need thereof. The method comprises administering at least one matrix metalloproteinase (“MMP”) inhibitor to the patient. Fatty liver disease or disorders include, for example, NAFLD, NASH, ALD, fatty liver associated with chronic hepatitis infection, TPN, steroid treatment, tamoxifen treatment, gastrointestional operations, diabetes and Reye's Syndrome. The method is particularly useful when the fatty liver disease is associated with TPN and the patient is an infant or when the patient is obese. MMP inhibitors useful in the present invention include, for example, Marimastat, tetracyclines, Prinomastat, Batimastat, BAY 12-9566, AG3340, BMS-275291, Neovastat, BB-3644, KB-R7785, TIMP1, TIMP2, doxycycline, minocycline, RS-130,830; CGS 27023A, Solimastat, Ro 32-3555, BMS-272591, and D2163. Marimastat is a preferred MMP inhibitor.
• MARKED PEPTIDES AND USE THEREOF FOR ASSAYING CIRCULATING IRAP
  申请人：Bottari Serge

  公开号：US20120115163A1

  公开（公告）日：2012-05-10

  A method for the assay of the circulating extracellular portion of the IRAP protein (“insulin responsive aminopeptidase”) includes at least one stage of quantitative assay of the purified, secreted, extracellular portion of IRAP, via at least one labelled peptide, the labelled peptide interacting specifically with the extracellular portion of IRAP.
• US7897591B2
  申请人：——

  公开号：US7897591B2

  公开（公告）日：2011-03-01