Methyl 2(R)-amino-4-(p-toluenesulfonylamino)butyrate hydrochloride

• 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: Methyl 2(R)-amino-4-(p-toluenesulfonylamino)butyrate hydrochloride
• 英文别名: methyl (2R)-2-amino-4-[(4-methylphenyl)sulfonylamino]butanoate;hydrochloride
• 化学式: C₁₂H₁₈N₂O₄S*ClH
• 分子量: 322.813
• InChiKey: AMQYMBSVCARANK-RFVHGSKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 2(R)-amino-4-(p-toluenesulfonylamino)butyrate hydrochloride 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 生成 Methyl 2(R)-(1(S)-carboxy-3-phenylpropylamino)-4-(p-toluenesulfonylamino)butyrate
  参考文献：
  名称：

  Potent matrix metalloproteinase inhibitors: Amino-carboxylate compounds containing modifications of the P1 residue

  摘要：

  A series of amino-carboxylate inhibitors of matrix metalloproteinases containing different p1 modifications have been synthesized. It was discovered that a toluenesulfonamide-type substituent at the P1 position considerably enhances the binding affinity of inhibitors for stromelysin. Replacements of the P2'-P3' residues with nonpeptide components result in loss of inhibitory activity.

  DOI：

  10.1016/0960-894x(96)00028-5
• 作为产物：
  描述：

  (R)-Methyl 2-((tert-butoxycarbonyl)amino)-3-cyanopropanoate 在 palladium on activated charcoal 盐酸 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 生成 Methyl 2(R)-amino-4-(p-toluenesulfonylamino)butyrate hydrochloride
  参考文献：
  名称：

  Potent matrix metalloproteinase inhibitors: Amino-carboxylate compounds containing modifications of the P1 residue

  摘要：

  A series of amino-carboxylate inhibitors of matrix metalloproteinases containing different p1 modifications have been synthesized. It was discovered that a toluenesulfonamide-type substituent at the P1 position considerably enhances the binding affinity of inhibitors for stromelysin. Replacements of the P2'-P3' residues with nonpeptide components result in loss of inhibitory activity.

  DOI：

  10.1016/0960-894x(96)00028-5

文献信息

• Hydroxamic acid compounds as metalloprotease and TNF inhibitors
  申请人：The DuPont Merck Pharmaceutical Company

  公开号：US05703092A1

  公开（公告）日：1997-12-30

  The present invention provides novel hydroxamic acids and carbocyclic acids and derivatives thereof and to pharmaceutical compositions and methods of use of these novel compounds for the inhibition of matrixmetalloproteinases, such as stromelysin and other matrix metalloproteinases, and also inhibit the production of tumor necrosis factor (TNF), and are therefore useful for the treatment of arthritis and other related inflammatory diseases. These novel compounds are represented by Formula I below: ##STR1##

  本发明提供了新型的羟肟酸、碳环酸及其衍生物，以及这些新化合物的药物组合物和使用方法，用于抑制基质金属蛋白酶，如基质金属蛋白酶和其他基质金属蛋白酶的活性，并且还能抑制肿瘤坏死因子（TNF）的产生，因此对于治疗关节炎和其他相关炎症性疾病非常有用。这些新化合物由下式I所表示： ##STR1##
• US5703092A
  申请人：——

  公开号：US5703092A

  公开（公告）日：1997-12-30
• Potent matrix metalloproteinase inhibitors: Amino-carboxylate compounds containing modifications of the P1 residue
  作者：Chu-Biao Xue、Xiaohua He、John Roderick、William F. DeGrado、Carl Decicco、Robert A. Copeland

  DOI：10.1016/0960-894x(96)00028-5

  日期：1996.2

  A series of amino-carboxylate inhibitors of matrix metalloproteinases containing different p1 modifications have been synthesized. It was discovered that a toluenesulfonamide-type substituent at the P1 position considerably enhances the binding affinity of inhibitors for stromelysin. Replacements of the P2'-P3' residues with nonpeptide components result in loss of inhibitory activity.