D-phenylalanine isopentylamide | 148528-72-7

• 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: D-phenylalanine isopentylamide
• 英文别名: (R)-2-Amino-N-(3-methyl-butyl)-3-phenyl-propionamide；(2R)-2-amino-N-(3-methylbutyl)-3-phenylpropanamide
• CAS: 148528-72-7
• 化学式: C₁₄H₂₂N₂O
• mdl: MFCD17023917
• 分子量: 234.341
• InChiKey: XFYCBJHUCMXATG-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  溴乙酸 、 D-phenylalanine isopentylamide 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-bromoacetyl-D-phenylalanine isopentylamide
  参考文献：
  名称：

  N-Haloacetyl-amino-acid amides as active-site-directed inhibitors of papain and cathepsin B

  摘要：

  A series of N-haloacetyl-amino-acid amides were synthesized and tested as models of cysteine-protease inhibitors. They irreversibly inactivated papain and cathepsin B via a reversible enzyme--inhibitor intermediate. Apparent second-order rate constants of inactivation ranging from 65 to 16 700 M-1 s-1 were observed. Reactivity against papain, as compared to glutathione, was increased 16 400-fold for N-bromoacetyl-leucine isopentylamide and 25 700-fold for the corresponding iodoacetyl derivative; these increases are probably due to proximity effects. No inhibition of trypsin, chymotrypsin and porcine pancreatic elastase was observed. Haloacetamides represent an interesting class of easily synthesized, efficient. irreversible inhibitors of cysteine proteases, which have low non-specific alkylating properties.

  DOI：

  10.1016/0223-5234(92)90018-v
• 作为产物：
  描述：

  N-苄氧羰基-D-苯丙氨酸 在 palladium on activated charcoal N-甲基吗啉 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.5h， 生成 D-phenylalanine isopentylamide
  参考文献：
  名称：

  N-Haloacetyl-amino-acid amides as active-site-directed inhibitors of papain and cathepsin B

  摘要：

  A series of N-haloacetyl-amino-acid amides were synthesized and tested as models of cysteine-protease inhibitors. They irreversibly inactivated papain and cathepsin B via a reversible enzyme--inhibitor intermediate. Apparent second-order rate constants of inactivation ranging from 65 to 16 700 M-1 s-1 were observed. Reactivity against papain, as compared to glutathione, was increased 16 400-fold for N-bromoacetyl-leucine isopentylamide and 25 700-fold for the corresponding iodoacetyl derivative; these increases are probably due to proximity effects. No inhibition of trypsin, chymotrypsin and porcine pancreatic elastase was observed. Haloacetamides represent an interesting class of easily synthesized, efficient. irreversible inhibitors of cysteine proteases, which have low non-specific alkylating properties.

  DOI：

  10.1016/0223-5234(92)90018-v

文献信息

• UREA AND SULFAMIDE DERIVATIVES AS INHIBITORS OF TAFIa
  申请人：KALLUS Christopher

  公开号：US20100035930A1

  公开（公告）日：2010-02-11

  The invention relates to compounds of the formula I as defined herein, which are inhibitors of activated thrombin-activatable fibrinolysis inhibitor. The compounds of the formula I are suitable for manufacturing medicaments for the prophylaxis, secondary prevention and therapy of one or more disorders which are associated with thromboses, embolisms, hypercoagulability or fibrotic changes.

  这项发明涉及到本处定义的公式I的化合物，这些化合物是活化的凝血酶可激活纤溶抑制剂的抑制剂。公式I的化合物适用于制造用于预防、次级预防和治疗与血栓形成、栓塞、高凝状态或纤维变化相关的一个或多个疾病的药物。
• HARNSTOFF- UND SULFAMIDDERIVATE ALS INHIBITOREN VON TAFIA
  申请人：Sanofi-Aventis

  公开号：EP2104497A2

  公开（公告）日：2009-09-30
• SULFAMIDDERIVATE ALS INHIBITOREN VON TAFIA
  申请人：SANOFI

  公开号：EP2104497B1

  公开（公告）日：2015-02-25
• US8389764B2
  申请人：——

  公开号：US8389764B2

  公开（公告）日：2013-03-05
• [DE] HARNSTOFF- UND SULFAMIDDERIVATE ALS INHIBITOREN VON TAFIA<br/>[EN] UREA AND SULFAMIDE DERIVATIVES AS TAFIA INHIBITORS<br/>[FR] DÉRIVÉS D'URÉE ET DE SULFAMIDES UTILISÉS COMME INHIBITEURS DE TAFI-A
  申请人：SANOFI AVENTIS

  公开号：WO2008067909A2

  公开（公告）日：2008-06-12

  [EN] The invention relates to compounds of formula (I) which are inhibitors of activated thrombin-activatable fibrinolysis inhibitor. Said compounds of formula (I) are suitable for producing medicaments used for the prevention, secondary prevention, and treatment of one or several diseases associated with thromboses, embolisms, hypercoagulability, or fibrotic changes.
  [FR] L'invention concerne des composés de formule (I) qui sont des inhibiteurs de fibrinolyse activable par thrombine, activée. Les composés de formule (I) sont appropriés pour la production de médicaments destinés à la prophylaxie, à la prévention secondaire et à la thérapie d'une ou de plusieurs maladies associées à des thromboses, à des embolies, à l'hypercoagulabilité ou à des modifications fibrotiques.
  [DE] Die Erfindung betrifft Verbindungen der Formel (I) die Inhibitoren von aktivierter Thrombin-aktivierbarer Fibrinolyse Inhibitor sind. Die Verbindungen der Formel (I) eignen sich zur Herstellung von Arzneimitteln zur Prophylaxe, Sekundärprevention und Therapie von einer oder mehrerer Erkrankungen, die mit Thrombosen, Embolien, Hyperkoagulabilität oder fibrotischen Veränderungen einhergehen.