Z-Orn-OBn | 98512-07-3

• 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: Z-Orn-OBn
• 英文别名: benzyl (2S)-5-amino-2-(phenylmethoxycarbonylamino)pentanoate
• CAS: 98512-07-3
• 化学式: C₂₀H₂₄N₂O₄
• 分子量: 356.422
• InChiKey: QYHMYIXZAFCFPM-SFHVURJKSA-N

物化性质

• 沸点：
  536.6±50.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Z-Orn-OBn 在 sodium acetate 、 乙酸酐 作用下， 以 氯仿 为溶剂， 反应 48.0h， 生成 benzyl (2S)-5-(2,5-dioxopyrrol-1-yl)-2-(phenylmethoxycarbonylamino)pentanoate
  参考文献：
  名称：

  Synthesis and evaluation of peptidic maleimides as transglutaminase inhibitors

  摘要：

  A series of novel transglutaminase inhibitors was prepared, based on the scaffold of a commonly used peptide substrate and bearing an electrophilic maleimide group. These compounds were evaluated in vitro and shown to lead to irreversible inactivation of tissue transglutaminase. Comparison with inhibitors studied previously provides insight into the steric environment of the enzyme active site. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.061
• 作为产物：
  描述：

  N-苄氧羰基-N’-叔丁氧羰基-L-鸟氨酸 在 三乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 Z-Orn-OBn
  参考文献：
  名称：

  Synthesis and evaluation of peptidic maleimides as transglutaminase inhibitors

  摘要：

  A series of novel transglutaminase inhibitors was prepared, based on the scaffold of a commonly used peptide substrate and bearing an electrophilic maleimide group. These compounds were evaluated in vitro and shown to lead to irreversible inactivation of tissue transglutaminase. Comparison with inhibitors studied previously provides insight into the steric environment of the enzyme active site. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.061

文献信息

• Cycloalkylcarbonylamino Acid Ester Derivative and Process for Producing The Same
  申请人：Kobayashi Nobuo

  公开号：US20090137799A1

  公开（公告）日：2009-05-28

  Cycloalkylcarbonylamino acid ester derivatives, which are raw material intermediates for a novel cycloalkane carboxamide derivative having an action that selectively inhibits cathepsin K, and a production process thereof, are provided. A cycloalkylcarbonylamino acid ester derivative represented by formula (I), or a pharmaceutically acceptable salt thereof: (wherein, R 1 and R 2 represent alkyl groups, alkenyl groups, alkynyl groups, aromatic hydrocarbon groups, heterocyclic groups, etc., R 8 represents an alkyl group having 1 to 6 carbon atoms, and ring A represents a cyclic alkylidene group having 5, 6 or 7 carbon atoms).

  环烷基羰基氨基酸酯衍生物是一种新型环烷烃羧酰胺衍生物的原料中间体，具有选择性抑制卡特普辛K的作用，提供其生产工艺。 表示为式（I）的环烷基羰基氨基酸酯衍生物，或其药学上可接受的盐： （其中，R1和R2代表烷基、烯基、炔基、芳香烃基、杂环基等，R8代表具有1至6个碳原子的烷基，环A代表具有5、6或7个碳原子的环烷基亚基）。
• <i>N</i>^G-Aminoguanidines from Primary Amines and the Preparation of Nitric Oxide Synthase Inhibitors
  作者：Nathaniel I. Martin、William T. Beeson、Joshua J. Woodward、Michael A. Marletta

  DOI：10.1021/jm701119v

  日期：2008.2.1

  A concise, general, and high-yielding method for the preparation of N(G)-aminoguanidines from primary amines is reported. Using available and readily prepared materials, primary amines are converted to protected N(G)-aminoguanidines in a one-pot procedure. The method has been successfully applied to a number of examples including the syntheses of four nitric oxide synthase (NOS) inhibitors. The inhibitors

  报道了一种由伯胺制备N（G）-氨基胍的简洁，通用，高产的方法。使用可用且易于制备的材料，伯胺可通过一锅法将伯胺转化为受保护的N（G）-氨基胍。该方法已成功应用于许多实例，包括四种一氧化氮合酶（NOS）抑制剂的合成。研究了制备的抑制剂作为竞争性抑制剂和NOS诱导型亚型（iNOS）的机械失活剂。另外，所制备的四种抑制剂之一，N（G）-氨基-N（G）-2,2,2,2-三氟乙基-L-精氨酸19，显示出独特的抑制iNOS形成NO和防止NADPH消耗的能力。没有不可逆转的酶失活。
• Cycloalkane Carboxamide Derivatives and Production Process of Same
  申请人：Kobayashi Nobuo

  公开号：US20090156805A1

  公开（公告）日：2009-06-18

  Novel cycloalkane carboxamide derivatives having an action that selectively inhibits cathepsin K, and a production process thereof, are provided. A cycloalkane carboxamide derivative represented by the following general formula (I), or a pharmaceutically acceptable salt thereof: (wherein R 1 and R 2 represent (substituted) alkyl groups, (substituted) alkenyl groups, (substituted) alkynyl groups, (substituted) aromatic hydrocarbon groups or (substituted) heterocyclic groups, ring A represents an alkylidene group having 5 to 7 carbon atoms, and ring B represents a formyl group or a hydroxymethyl group).

  本发明提供了一种具有选择性抑制蛋白酶K的作用的新型环烷基羧酰胺衍生物及其生产工艺。其中，所述环烷基羧酰胺衍生物由下述通式（I）表示，或其药学上可接受的盐所表示（其中，R1和R2代表（取代）烷基、（取代）烯基、（取代）炔基、（取代）芳香族碳氢基或（取代）杂环基，环A表示具有5至7个碳原子的烷基亚基，环B表示甲酰基或羟甲基）。
• CYCLOALKANECARBOXAMIDE DERIVATIVE AND METHOD FOR PRODUCING SAME
  申请人：SEIKAGAKU CORPORATION

  公开号：EP1972615A1

  公开（公告）日：2008-09-24

  Novel cycloalkane carboxamide derivatives having an action that selectively inhibits cathepsin K, and a production process thereof, are provided. A cycloalkane carboxamide derivative represented by the following general formula (I), or a pharmaceutically acceptable salt thereof: (wherein R1 and R2 represent (substituted) alkyl groups, (substituted) alkenyl groups, (substituted) alkynyl groups, (substituted) aromatic hydrocarbon groups or (substituted) heterocyclic groups, ring A represents an alkylidene group having 5 to 7 carbon atoms, and ring B represents a formyl group or a hydroxymethyl group).

  本发明提供了具有选择性抑制 cathepsin K 作用的新型环烷烃羧酰胺衍生物及其生产工艺。 由以下通式(I)代表的环烷烃羧酰胺衍生物或其药学上可接受的盐： (其中R1和R2代表（取代的）烷基、（取代的）烯基、（取代的）炔基、（取代的）芳香烃基团或（取代的）杂环基团，环A代表具有5至7个碳原子的亚烷基，环B代表甲酰基或羟甲基）。
• CYCLOALKYLCARBONYLAMINO ACID ESTER DERIVATIVE AND PROCESS FOR PRODUCING THE SAME
  申请人：SEIKAGAKU CORPORATION

  公开号：EP2036920A1

  公开（公告）日：2009-03-18

  Cycloalkylcarbonylamino acid ester derivatives, which are raw material intermediates for a novel cycloalkane carboxamide derivative having an action that selectively inhibits cathepsin K, and a production process thereof, are provided. A cycloalkylcarbonylamino acid ester derivative represented by formula (I), or a pharmaceutically acceptable salt thereof: (wherein, R1 and R2 represent alkyl groups, alkenyl groups, alkynyl groups, aromatic hydrocarbon groups, heterocyclic groups, etc., R8 represents an alkyl group having 1 to 6 carbon atoms, and ring A represents a cyclic alkylidene group having 5, 6 or 7 carbon atoms).

  本发明提供了环烷基羰基氨基酸酯衍生物，它是一种新型环烷羧酰胺衍生物的原料中间体，该衍生物具有选择性抑制凝血酶 K 的作用，并提供了其生产工艺。 一种由式（I）代表的环烷基羰基氨基甲酸酯衍生物，或其药学上可接受的盐： (其中，R1 和 R2 代表烷基、烯基、炔基、芳香烃基、杂环基等，R8 代表具有 1 至 6 个碳原子的烷基，环 A 代表具有 5、6 或 7 个碳原子的环亚烷基）。