Fmoc-2-amino-2-(tetrahydro-2H-pyran-4-yl)acetic acid | 553643-51-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-2-amino-2-(tetrahydro-2H-pyran-4-yl)acetic acid
• 英文别名: 2-([(9H-Fluoren-9-ylmethoxy)carbonyl]amino)-2-(oxan-4-YL)acetic acid；2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-(oxan-4-yl)acetic acid
• CAS: 553643-51-9
• 化学式: C₂₂H₂₃NO₅
• 分子量: 381.428
• InChiKey: WNRMJMFKNFPDFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Fmoc-2-amino-2-(tetrahydro-2H-pyran-4-yl)acetic acid 在 lithium aluminium tetrahydride 、 三乙酰氧基硼氢化钠 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Discovery of a Novel Class of Potent HCV NS4B Inhibitors: SAR Studies on Piperazinone Derivatives

  摘要：

  HTS screening identified compound 2a (piper-azinone derivative) as a low micromolar HCV genotype 1 (GT-1) inhibitor. Resistance mapping studies suggested that this piperazinone chemotype targets the HCV nonstructural protein NS4B. Extensive SAR studies were performed around 2a and the amide function and the C-3/C-6 cis stereochemistry of the piperazinone core were essential for HCV activity. A 10-fold increase in GT-1 potency was observed when the chiral phenylcyclopropyl amide side chain of 2a was replaced with p-fluorophenylisoxazole-carbonyl moiety (67). Replacing the C-6 nonpolar hydrophobic moiety of 67 with a phenyl moiety (95) did not diminish the GT-1 potency. A heterocyclic thiophene moiety (103) and an isoxazole moiety (108) were incorporated as isosteric replacements for the C-6 phenyl moiety (95), resulting in significant improvement in GT-1b and la potency. However, the piperazonone class of compounds lacks GT-2 activity and, consequently, were not pursued further into development.

  DOI：

  10.1021/jm4012643

文献信息

• [EN] PYRAZINE AND IMIDAZOLIDINE DERIVATIVES AND THEIR USES TO TREAT HEPATITIS C<br/>[FR] DÉRIVÉS DE PYRAZINE ET D'IMIDAZOLIDINE ET LEURS UTILISATIONS EN VUE DU TRAITEMENT DE L'HÉPATITE C
  申请人：GILEAD PHARMASSET LLC

  公开号：WO2012103113A1

  公开（公告）日：2012-08-02

  Disclosed herein are compounds useful for treating a viral infection, such HCV.

  本文披露了一些用于治疗病毒感染，如HCV的化合物。
• [EN] MASP INHIBITORY COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS INHIBITEURS DE MASP ET LEURS UTILISATIONS
  申请人：BAYER AG

  公开号：WO2020225095A1

  公开（公告）日：2020-11-12

  The present invention relates to novel Mannose-binding lectin (MBL)-associated serine protease (MASP) inhibitory compounds, as well as analogues and derivatives thereof, to processes for the preparation thereof, to the use thereof alone or in combinations for treatment and/or prevention of diseases and to the use thereof for production of medicaments for treatment and/or prevention of diseases, especially for treatment and/or prevention of renal and cardiovascular disorders and of ischemia reperfusion injuries.

  本发明涉及新型甘霖结合凝集素（MBL）相关丝氨酸蛋白酶（MASP）抑制化合物，以及其类似物和衍生物，以及其制备方法，单独或组合用于治疗和/或预防疾病，以及用于生产药物治疗和/或预防疾病，特别是用于治疗和/或预防肾脏和心血管疾病以及缺血再灌注损伤。
• Probes, systems, and methods for drug discovery
  申请人：——

  公开号：US20030125315A1

  公开（公告）日：2003-07-03

  Aspects of the present invention include probes, methods, systems that have stand alone utility and may comprise features of a drug discovery system or method. The present invention also includes pharmaceutical compositions. In more detail, the present invention provides molecular probes and methods for producing molecular probes. The present invention provides also provides systems and methods for new drug discovery. An embodiment of the present invention utilizes sets of probes of the present invention and a new approach to computational chemistry in a drug discovery method having increased focus in comparison to heretofore utilized combinatorial chemistry. The present invention also provides computer software and hardware tools useful in drug discovery systems. In an embodiment of a drug discovery method of the present invention in silico methods and in biologico screening methods are both utilized to maximize the probability of success while minimizing the time and number of wet laboratory steps necessary to achieve the success.

  本发明的方面包括探针、方法、系统，具有独立实用性并可能包括药物发现系统或方法的特征。本发明还包括制药组合物。更详细地说，本发明提供了分子探针和制备分子探针的方法。本发明还提供了新药物发现的系统和方法。本发明的实施例利用本发明的探针集和一种新的计算化学方法在药物发现方法中具有更高的聚焦度，相比之前使用的组合化学方法。本发明还提供了在药物发现系统中有用的计算机软件和硬件工具。在本发明的药物发现方法的实施例中，同时利用了基于计算机的方法和生物筛选方法，以最大化成功的可能性，同时最小化必要的湿实验步骤的时间和数量。
• COMPOUNDS
  申请人：SOFIA MICHAEL JOSEPH

  公开号：US20120202794A1

  公开（公告）日：2012-08-09

  Disclosed herein are compounds useful for treating a viral infection, such as HCV.

  本文公开了用于治疗病毒感染，如HCV的化合物。
• Probes, Systems, and Methods for Drug Discovery
  申请人：Mjalli Adnan M. M.

  公开号：US20110039714A1

  公开（公告）日：2011-02-17

  Aspects of the present invention include probes, methods, systems that have stand alone utility and may comprise features of a drug discovery system or method. The present invention also includes pharmaceutical compositions. In more detail, the present invention provides molecular probes and methods for producing molecular probes. The present invention provides also provides systems and methods for new drug discovery. An embodiment of the present invention utilizes sets of probes of the present invention and a new approach to computational chemistry in a drug discovery method having increased focus in comparison to heretofore utilized combinatorial chemistry. The present invention also provides computer software and hardware tools useful in drug discovery systems. In an embodiment of a drug discovery method of the present invention in silico methods and in biologico screening methods are both utilized to maximize the probability of success while minimizing the time and number of wet laboratory steps necessary to achieve the success.

  本发明的方面包括探针、方法、系统，具有独立实用性，并可能包括药物发现系统或方法的特征。本发明还包括制药组合物。更详细地说，本发明提供了分子探针和制备分子探针的方法。本发明还提供了用于新药物发现的系统和方法。本发明的一种实施利用本发明的探针集和一种新的计算化学方法，在药物发现方法中具有比迄今所使用的组合化学更高的聚焦度。本发明还提供了在药物发现系统中有用的计算机软件和硬件工具。在本发明的药物发现方法的实施中，利用无机方法和生物筛选方法最大化成功的可能性，同时最小化实现成功所需的时间和实验室步骤数量。