2-(tert-butoxycarbonylamino)-2-(ethoxycarbonyl)hex-5-enoic acid | 1345673-05-3

• 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: 2-(tert-butoxycarbonylamino)-2-(ethoxycarbonyl)hex-5-enoic acid
• 英文别名: 2-(Tert-butoxycarbonylamino)-2-(ethoxycarbonyl)hex-5-enoic acid；2-ethoxycarbonyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]hex-5-enoic acid
• CAS: 1345673-05-3
• 化学式: C₁₄H₂₃NO₆
• 分子量: 301.34
• InChiKey: QTSGSSLQNLUHFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(tert-butoxycarbonylamino)-2-(ethoxycarbonyl)hex-5-enoic acid 在 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 草酰氯 、 三乙酰氧基硼氢化钠 、 potassium carbonate 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 1,2-双(二苯基膦)乙烷 作用下， 以 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 47.5h， 生成 2-amino-2-((benzylamino)methyl)-6-boronohexanoic acid
  参考文献：
  名称：

  2-Substituted-2-amino-6-boronohexanoic acids as arginase inhibitors

  摘要：

  Substitution at the alpha center of the known human arginase inhibitor 2-amino-6-boronohexanoic acid (ABH) is acceptable in the active site pockets of both human arginase land arginase II. In particular, substituents with a tertiary amine linked via a two carbon chain show improved inhibitory potency for both enzyme isoforms. This potency improvement can be rationalized by X-ray crystallography, which shows a water-mediated contact between the basic nitrogen and the carboxylic acid side chain of Asp200, which is situated at the mouth of the active site pocket of arginase II (Asp181 in arginase I). We believe that this is the first literature report of compounds with improved arginase inhibitory activity, relative to ABH, and represents a promising starting point for further optimization of in vitro potency and the identification of better tool molecules for in vivo investigations of the potential pathophysiological roles of arginases. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.024
• 作为产物：
  描述：

  diethyl 2-but-3-enyl-2-(tert-butoxycarbonylamino)propanedioate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 19.5h， 以82%的产率得到2-(tert-butoxycarbonylamino)-2-(ethoxycarbonyl)hex-5-enoic acid
  参考文献：
  名称：

  [EN] INHIBITORS OF ARGINASE AND THEIR THERAPEUTIC APPLICATIONS
  [FR] INHIBITEURS D'ARGINASE ET LEURS APPLICATIONS THÉRAPEUTIQUES

  摘要：

  根据式I和式II，化合物是Arginase I和II活性的强效抑制剂：式(I)，(II)中的R1、R2、R3、R4、R5、R6、R7、R8、R9、D、M、X和Y的定义如规范所述。该发明还提供了这些化合物的药物组合物以及它们用于治疗或预防与Arginase活性相关的疾病或病况的方法。

  公开号：

  WO2011133653A1

文献信息

• [EN] INHIBITORS OF ARGINASE AND THEIR THERAPEUTIC APPLICATIONS<br/>[FR] INHIBITEURS D'ARGINASE ET LEURS APPLICATIONS THÉRAPEUTIQUES
  申请人：MARS INC

  公开号：WO2011133653A1

  公开（公告）日：2011-10-27

  Compounds according to Formula I and Formula II are potent inhibitors of Arginase I and II activity : Formule (I), (II) where R1, R2, R3, R4, R5, R6, R7, R8, R9, D, M, X, and Y are defined as set forth in the specification. The invention also provides pharmaceutical compositions of the compounds and methods of their use for treating or preventing a disease or a condition associated with arginase activity.

  根据式I和式II，化合物是Arginase I和II活性的强效抑制剂：式(I)，(II)中的R1、R2、R3、R4、R5、R6、R7、R8、R9、D、M、X和Y的定义如规范所述。该发明还提供了这些化合物的药物组合物以及它们用于治疗或预防与Arginase活性相关的疾病或病况的方法。
• INHIBITORS OF ARGINASE AND THEIR THERAPEUTIC APPLICATIONS
  申请人：Van Zandt Michael

  公开号：US20120083469A1

  公开（公告）日：2012-04-05

  Compounds according to Formula I and Formula II are potent inhibitors of Arginase I and II activity: where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , D, M, X, and Y are defined as set forth in the specification. The invention also provides pharmaceutical compositions of the compounds and methods of their use for treating or preventing a disease or a condition associated with arginase activity.

  根据公式I和公式II的化合物是Arginase I和II活性的有效抑制剂：其中R1，R2，R3，R4，R5，R6，R7，R8，R9，D，M，X和Y的定义如规范中所述。该发明还提供了这些化合物的制药组合物和使用它们治疗或预防与Arginase活性相关的疾病或病况的方法。
• Inhibitors of arginase and their therapeutic applications
  申请人：Van Zandt Michael

  公开号：US09040703B2

  公开（公告）日：2015-05-26

  Compounds according to Formula I and Formula II are potent inhibitors of Arginase I and II activity: where R1, R2, R3, R4, R5, R6, R7, R8, R9, D, M, X, and Y are defined as set forth in the specification. The invention also provides pharmaceutical compositions of the compounds and methods of their use for treating or preventing a disease or a condition associated with arginase activity.

  根据公式I和公式II，化合物是Arginase I和II活性的有效抑制剂：其中R1，R2，R3，R4，R5，R6，R7，R8，R9，D，M，X和Y的定义如规范所述。该发明还提供了这些化合物的药物组合物以及它们的用于治疗或预防与Arginase活性相关的疾病或病况的方法。
• US9040703B2
  申请人：——

  公开号：US9040703B2

  公开（公告）日：2015-05-26
• US9994594B2
  申请人：——

  公开号：US9994594B2

  公开（公告）日：2018-06-12