(R)-N-allyl-2-(3-morpholin-4-ylmethyl-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl)-acetamide | 1310683-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: (R)-N-allyl-2-(3-morpholin-4-ylmethyl-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl)-acetamide
• 英文别名: 2-[(3R)-3-(morpholin-4-ylmethyl)-2-oxo-5-phenyl-3H-1,4-benzodiazepin-1-yl]-N-prop-2-enylacetamide
• CAS: 1310683-90-9
• 化学式: C₂₅H₂₈N₄O₃
• 分子量: 432.522
• InChiKey: QERLNLWCBOXMPY-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-N-allyl-2-(3-morpholin-4-ylmethyl-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl)-acetamide 、 丁烯酮 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到(R)-2-(3-(morpholinomethyl)-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-1-yl)-N-(4-oxopent-2-en-1-yl)acetamide
  参考文献：
  名称：

  Peptidomimetics containing a vinyl ketone warhead as falcipain-2 inhibitors

  摘要：

  The design, chemical synthesis, and enzymatic activity evaluation of a set of falcipain-2 inhibitors are reported. These compounds contain a proven peptidomimetic recognition motif based on a benzo[1,4] diazepin-2-one (1,4-BDZ) framework built on a dipeptide sequence, and a Michael acceptor terminal moiety capable of deactivating the cysteine protease active site. Our goal is to modify the P-3 site of this motif in order to identify the structural requirements for the interaction with the target. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.058
• 作为产物：
  描述：

  (R)-(3-hydroxymethyl-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl)-acetic acid ethyl ester 在 三苯基膦 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 lithium hydroxide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (R)-N-allyl-2-(3-morpholin-4-ylmethyl-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl)-acetamide
  参考文献：
  名称：

  Peptidomimetics containing a vinyl ketone warhead as falcipain-2 inhibitors

  摘要：

  The design, chemical synthesis, and enzymatic activity evaluation of a set of falcipain-2 inhibitors are reported. These compounds contain a proven peptidomimetic recognition motif based on a benzo[1,4] diazepin-2-one (1,4-BDZ) framework built on a dipeptide sequence, and a Michael acceptor terminal moiety capable of deactivating the cysteine protease active site. Our goal is to modify the P-3 site of this motif in order to identify the structural requirements for the interaction with the target. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.058

文献信息

• Peptidomimetics containing a vinyl ketone warhead as falcipain-2 inhibitors
  作者：Roberta Ettari、Maria Zappalà、Nicola Micale、Giovanni Grazioso、Salvatore Giofrè、Tanja Schirmeister、Silvana Grasso

  DOI：10.1016/j.ejmech.2011.02.058

  日期：2011.6

  The design, chemical synthesis, and enzymatic activity evaluation of a set of falcipain-2 inhibitors are reported. These compounds contain a proven peptidomimetic recognition motif based on a benzo[1,4] diazepin-2-one (1,4-BDZ) framework built on a dipeptide sequence, and a Michael acceptor terminal moiety capable of deactivating the cysteine protease active site. Our goal is to modify the P-3 site of this motif in order to identify the structural requirements for the interaction with the target. (C) 2011 Elsevier Masson SAS. All rights reserved.