2-cyano-N-[(1S)-1-(4-methoxyphenyl)ethyl]acetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-cyano-N-[(1S)-1-(4-methoxyphenyl)ethyl]acetamide
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: ULLRLUHVSBEXDY-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-溴吡啶-2-甲醛 、 2-cyano-N-[(1S)-1-(4-methoxyphenyl)ethyl]acetamide 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 (S,E)-3-(6-溴吡啶-2-基)-2-氰基-N-(1-(4-甲氧基苯基)乙基)丙烯酰胺
  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
• 作为产物：
  描述：

  (S)-(-)-1-(4-甲氧基苯)乙胺 、 氰乙酸甲酯 生成 2-cyano-N-[(1S)-1-(4-methoxyphenyl)ethyl]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

文献信息

• Degrasyn-like symmetrical compounds: Possible therapeutic agents for multiple myeloma (MM-I)
  作者：Zhenghong Peng、David S. Maxwell、Duoli Sun、Basvoju A. Bhanu Prasad、Paul T. Schuber、Ashutosh Pal、Yunming Ying、Dongmei Han、Liwei Gao、Shimei Wang、Alexander Levitzki、Vaibhav Kapuria、Moshe Talpaz、Matthew Young、Hollis D. Showalter、Nicholas J. Donato、William G. Bornmann

  DOI：10.1016/j.bmc.2013.12.048

  日期：2014.2

  A series of degrasyn-like symmetrical compounds have been designed, synthesized, and screened against B cell malignancy (multiple myeloma, mantle cell lymphoma) cell lines. The lead compounds T5165804 and CP2005 showed higher nanomolar potency against these tumor cells in comparison to degrasyn and inhibited Usp9x activity in vitro and in intact cells. These observations suggest that this new class of compounds holds promise as cancer therapeutic agents. (C) 2014 Published by Elsevier Ltd.
• 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.