(R)-(3-morpholin-4-ylmethyl-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl)-acetic acid | 1310683-87-4

• 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)-(3-morpholin-4-ylmethyl-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl)-acetic acid
• 英文别名: 2-[(3R)-3-(morpholin-4-ylmethyl)-2-oxo-5-phenyl-3H-1,4-benzodiazepin-1-yl]acetic acid
• CAS: 1310683-87-4
• 化学式: C₂₂H₂₃N₃O₄
• 分子量: 393.442
• InChiKey: GECQPNPMDMPNTF-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-(3-morpholin-4-ylmethyl-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl)-acetic acid 在 Hoveyda-Grubbs catalyst second generation 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 (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 、 lithium hydroxide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 8.0h， 生成 (R)-(3-morpholin-4-ylmethyl-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl)-acetic acid
  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.