N-(t-butoxycarbonyl)-L-4-fluorophenylalanine N-methoxy-N-methylamide | 135545-01-6

• 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: N-(t-butoxycarbonyl)-L-4-fluorophenylalanine N-methoxy-N-methylamide
• 英文别名: tert-butyl N-[(1S)-1-[(4-fluorophenyl)methyl]-2-[methoxy(methyl)amino]-2-oxo-ethyl]carbamate；tert-butyl (S)-(3-(4-fluorophenyl)-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate；[(1S)-2-(4-Fluoro-phenyl)-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic Acid Tert-Butyl Ester；tert-butyl N-[(2S)-3-(4-fluorophenyl)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl]carbamate
• CAS: 135545-01-6
• 化学式: C₁₆H₂₃FN₂O₄
• 分子量: 326.368
• InChiKey: XRKLGYFMVVWPMR-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(t-butoxycarbonyl)-L-4-fluorophenylalanine N-methoxy-N-methylamide 在 lithium aluminium tetrahydride 、 三乙胺 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (S)-2-Amino-N-[(S)-2-ethylcarbamoyl-1-(4-fluoro-benzyl)-2-hydroxy-ethyl]-3-methyl-butyramide
  参考文献：
  名称：

  Novel cell-penetrating α-keto-amide calpain inhibitors as potential treatment for muscular dystrophy

  摘要：

  Dipeptide-derived alpha-keto-amide compounds with potent calpain inhibitory activity have been identified. These reversible covalent inhibitors have IC50 values down to 25 nM and exhibit greatly improved activity in muscle cells compared to the reference compound MDL28170. Several novel calpain inhibitors have shown positive effects on histological parameters in an animal model of Duchenne muscular dystrophy demonstrating their potential as a treatment option for this fatal disease. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.064
• 作为产物：
  描述：

  BOC-L-4-氟苯丙氨酸 、 N-甲基-N-甲氧基胺盐酸盐 在 N-甲基吗啉 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到N-(t-butoxycarbonyl)-L-4-fluorophenylalanine N-methoxy-N-methylamide
  参考文献：
  名称：

  Novel cell-penetrating α-keto-amide calpain inhibitors as potential treatment for muscular dystrophy

  摘要：

  Dipeptide-derived alpha-keto-amide compounds with potent calpain inhibitory activity have been identified. These reversible covalent inhibitors have IC50 values down to 25 nM and exhibit greatly improved activity in muscle cells compared to the reference compound MDL28170. Several novel calpain inhibitors have shown positive effects on histological parameters in an animal model of Duchenne muscular dystrophy demonstrating their potential as a treatment option for this fatal disease. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.064

文献信息

• Piperizinones as modulators of chemokine receptor activity
  申请人：——

  公开号：US20030144277A1

  公开（公告）日：2003-07-31

  The present application describes modulators of CCR3 of formula (I): 1 or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.

  本申请描述了公式（I）的CCR3调节剂或其药用盐形式，用于预防哮喘和其他过敏性疾病。
• Structure-Based Lead Optimization of Enterovirus D68 2A Protease Inhibitors
  作者：Bin Tan、Chang Liu、Kan Li、Prakash Jadhav、George Lambrinidis、Lan Zhu、Linda Olson、Haozhou Tan、Yu Wen、Antonios Kolocouris、Wei Liu、Jun Wang

  DOI：10.1021/acs.jmedchem.3c00995

  日期：2023.11.9

  Enterovirus D68 (EV-D68) virus is a nonpolio enterovirus that typically causes respiratory illness and, in severe cases, can lead to paralysis and death in children. There is currently no vaccine or antiviral for EV-D68. We previously discovered the viral 2A protease (2Apro) as a viable antiviral drug target and identified telaprevir as a 2Apro inhibitor. 2Apro is a viral cysteine protease that cleaves

  肠道病毒 D68 （EV-D68） 病毒是一种非脊髓灰质炎肠道病毒，通常会导致呼吸道疾病，严重时可导致儿童瘫痪和死亡。目前尚无针对 EV-D68 的疫苗或抗病毒药物。我们之前发现病毒 2A 蛋白酶 （2Apro） 是一种可行的抗病毒药物靶点，并确定 telaprevir 是一种 2Apro 抑制剂。2Apro 是一种病毒半胱氨酸蛋白酶，可裂解病毒 VP1-2A 多蛋白连接。在这项研究中，我们报道了野生型 EV-D68 2Apro 和 C107A 突变体的 X 射线晶体结构以及特拉匹韦基于结构的先导化合物优化。在 X 射线晶体结构的引导下，我们使用分子动力学模拟预测了 telaprevir 在 2Apro 中的结合姿势。然后，我们利用该模型为特拉匹韦的反应性弹头和 P1-P4 替换的基于结构的优化提供信息。这些努力导致发现了 2Apro 抑制剂，其抗病毒活性优于 telaprevir。这些化合物代表了作为
• Calpain modulators and therapeutic uses thereof
  申请人：Blade Therapeutics, Inc.

  公开号：US10934261B2

  公开（公告）日：2021-03-02

  Disclosed herein are small molecule calpain modulator compositions, pharmaceutical compositions, the use and preparation thereof.

  本文公开了小分子钙蛋白酶调节剂组合物、药物组合物及其用途和制备方法。
• [EN] CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF<br/>[FR] MODULATEURS DE CALPAIN ET LEURS UTILISATIONS THÉRAPEUTIQUES
  申请人：BLADE THERAPEUTICS INC

  公开号：WO2018064119A8

  公开（公告）日：2019-04-25
• Design and synthesis of fused tetrahydroisoquinoline-iminoimidazolines
  作者：Valeria Moas-Héloire、Nicolas Renault、Vania Batalha、Angela Rincon Arias、Mathieu Marchivie、Said Yous、Noémie Deguine、Luc Buée、Philippe Chavatte、David Blum、Luisa Lopes、Patricia Melnyk、Laurence Agouridas

  DOI：10.1016/j.ejmech.2015.10.030

  日期：2015.12

  In the aim of identifying new privileged structures, we describe the 5-steps synthesis of cyclic guanidine compounds "tetrahydroisoquinoline-iminoimidazolines" derived from tetrahydroisoquinoline-hydantoin core. In order to evaluate this new minimal structure and the impact of replacing a carbonyle by a guanidine moiety, their affinity towards adenosine receptor A(2A) was evaluated and compared to those of tetrahydroisoquinoline-hydantoin compounds. (C) 2015 Elsevier Masson SAS. All rights reserved.