(S)-2-cyano-N-(1-phenylbutyl)acetamide | 1240038-58-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-cyano-N-(1-phenylbutyl)acetamide
• 英文别名: 2-cyano-N-[(1S)-1-phenylbutyl]acetamide
• CAS: 1240038-58-7
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: XEOGUPMBOMULMI-LBPRGKRZSA-N

物化性质

• 沸点：
  428.7±38.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-cyano-N-(1-phenylbutyl)acetamide 在 哌啶 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 27.0h， 生成 3-(6-bromopyridin-2-yl)-2-cyano-N-((S)-1-phenylbutyl)propanamide
  参考文献：
  名称：

  Degrasyn exhibits antibiotic activity against multi-resistant Staphylococcus aureus by modifying several essential cysteines

  摘要：

  Degrasyn被发现对多重耐药的金黄色葡萄球菌表现出抗生素活性。化学蛋白质组学揭示了其作用机制。

  DOI：

  10.1039/c9cc09204h
• 作为产物：
  描述：

  (S)-1-苯基丁胺 、 氰乙酸甲酯 生成 (S)-2-cyano-N-(1-phenylbutyl)acetamide
  参考文献：
  名称：

  Tyrphostin-like compounds with ubiquitin modulatory activity as possible therapeutic agents for multiple myeloma

  摘要：

  With the goal of developing small molecules as novel regulators of signal transduction and apoptosis, a series of tyrphostin-like compounds were synthesized and screened for their activity against MM-1 (multiple myeloma) cells and other cell lines representing this malignancy. Synthesis was completed in solution-phase initially and then adopted to solid-phase for generating a more diverse set of compounds. A positive correlation was noted between compounds capable of inducing apoptosis and their modulation of protein ubiquitination. Further analysis suggested that ubiquitin modulation occurs through inhibition of cellular deubiquitinase activity. Bulky groups on the sidechain near the alpha,beta-unsaturated ketone caused a complete loss of activity, whereas cyclization on the opposite side was tolerated. Theoretical calculations at the B3LYP/LACV3P** level were completed on each molecule, and the resulting molecular orbitals and Fukui reactivity values for C(beta) carbon were utilized in developing a model to explain the compound activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.057
• 作为试剂：
  描述：

  2-cyano-N-(1-(4-(2-(diethylamino)ethoxy)phenyl)butyl)acetamide 、 (S)-1-苯基丁胺 在 (S)-2-cyano-N-(1-phenylbutyl)acetamide 、 crude product 、 silica gel 、 hexanes ethyl acetate 作用下， 以to give 39 (375 mg, 58%) as a white solid的产率得到(S)-2-cyano-N-(1-phenylbutyl)acetamide
  参考文献：
  名称：

  Deubiquitinase inhibitors and methods for use of the same

  摘要：

  本文公开了抑制去泛素化酶（DUB）的方法，治疗病原体感染（例如病毒，细菌和/或寄生虫）的方法，抑制细胞增殖的方法，治疗神经退行性疾病的方法，治疗神经退行性疾病或遗传性疾病的一个或多个症状的方法，以及化合物，其中化合物可以具有公式（III）的结构：

  公开号：

  US08809377B2

文献信息

• Deubiquitinase Inhibitors and Methods for Use of the Same
  申请人：Donato Nicholas J.

  公开号：US20120077806A1

  公开（公告）日：2012-03-29

  Disclosed herein are methods of inhibiting a deubiquitinase (DUB), methods of treating pathogenic infections (e.g., viral, bacterial, and/or parasitic), methods of inhibiting cell proliferation, methods of treating a neurodegenerative disease, methods of treating one or more symptoms of a neurodegenerative disease or a genetic disorder, and compounds.

  本文揭示了抑制去泛素化酶（DUB）的方法，治疗病原体感染（例如病毒、细菌和/或寄生虫）的方法，抑制细胞增殖的方法，治疗神经退行性疾病的方法，治疗神经退行性疾病或遗传疾病症状的方法，以及化合物。
• [EN] COMPOSITIONS AND METHODS OF DELIVERY OF DEUBIQUITINASE INHIBITORS<br/>[FR] COMPOSITIONS ET MÉTHODES D'ADMINISTRATION D'INHIBITEURS DE DÉUBIQUITINASE
  申请人：PHARMAKEA INC

  公开号：WO2015183987A1

  公开（公告）日：2015-12-03

  Described herein are compositions comprising deubiquitinase inhibitors in combination with albumin, methods of making such compositions, and methods of using such compositions in the treatment of conditions, diseases, or disorders that would benefit from inhibition of deubiquitinase activity.

  本文描述了含有去泛素化酶抑制剂与白蛋白组合的组合物，制备这种组合物的方法，以及利用这种组合物治疗需要抑制去泛素化酶活性的病症、疾病或紊乱的方法。
• [EN] DEUBIQUITINASE INHIBITORS AND METHODS FOR USE OF THE SAME<br/>[FR] INHIBITEURS DE DÉUBIQUITINASE ET MÉTHODES D'UTILISATION DE CEUX-CI
  申请人：UNIV MICHIGAN

  公开号：WO2015054555A1

  公开（公告）日：2015-04-16

  Disclosed herein are methods of inhibiting a deubiquitinase (DUB) by contact with a compound of formula (I)

  本文披露了通过与式（I）化合物接触来抑制去泛素酶（DUB）的方法。
• DEUBIQUITINASE INHIBITORS AND METHODS FOR USE OF THE SAME
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US20160237082A1

  公开（公告）日：2016-08-18

  Disclosed herein are methods of inhibiting a deubiquitinase (DUB) by contact with a compound of formula (I)

  本文公开了一种通过接触式化合物（I）来抑制去泛素化酶（DUB）的方法。
• Tyrphostin-like compounds with ubiquitin modulatory activity as possible therapeutic agents for multiple myeloma
  作者：Zhenghong Peng、Ashutosh Pal、Dongmei Han、Shimei Wang、David Maxwell、Alexander Levitzki、Moshe Talpaz、Nicholas J. Donato、William Bornmann

  DOI：10.1016/j.bmc.2011.09.057

  日期：2011.12

  With the goal of developing small molecules as novel regulators of signal transduction and apoptosis, a series of tyrphostin-like compounds were synthesized and screened for their activity against MM-1 (multiple myeloma) cells and other cell lines representing this malignancy. Synthesis was completed in solution-phase initially and then adopted to solid-phase for generating a more diverse set of compounds. A positive correlation was noted between compounds capable of inducing apoptosis and their modulation of protein ubiquitination. Further analysis suggested that ubiquitin modulation occurs through inhibition of cellular deubiquitinase activity. Bulky groups on the sidechain near the alpha,beta-unsaturated ketone caused a complete loss of activity, whereas cyclization on the opposite side was tolerated. Theoretical calculations at the B3LYP/LACV3P** level were completed on each molecule, and the resulting molecular orbitals and Fukui reactivity values for C(beta) carbon were utilized in developing a model to explain the compound activity. (C) 2011 Elsevier Ltd. All rights reserved.