N-[(1S)-5-amino-1-cyano-pentyl]-6-[[2,5-dioxo-3-(4-phenoxyphenyl)imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carboxamide | 1596360-33-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: N-[(1S)-5-amino-1-cyano-pentyl]-6-[[2,5-dioxo-3-(4-phenoxyphenyl)imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carboxamide
• 英文别名: N-[(1S)-5-amino-1-cyanopentyl]-6-[[2,5-dioxo-3-(4-phenoxyphenyl)imidazolidin-1-yl]methyl]-7-methylpyrrolo[2,3-d]pyrimidine-2-carboxamide
• CAS: 1596360-33-6
• 化学式: C₃₀H₃₀N₈O₄
• 分子量: 566.619
• InChiKey: XNRITNLETHMDDQ-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  160
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 5-bromo-4-methylamino-pyrimidine-2-carboxylate 在 哌啶 、 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 N-羟基-7-氮杂苯并三氮唑 、 lithium hydroxide monohydrate 、 四溴化碳 、 水 、 碳酸氢钠 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.17h， 生成 N-[(1S)-5-amino-1-cyano-pentyl]-6-[[2,5-dioxo-3-(4-phenoxyphenyl)imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carboxamide
  参考文献：
  名称：

  Pyrrolopyrimidine-inhibitors with hydantoin moiety as spacer can explore P4/S4 interaction on plasmin

  摘要：

  In the development of plasmin inhibitors, a novel chemotype, pyrrolopyrimidine scaffold possessing two motifs, a hydantoin-containing P4 moiety and a warhead-containing P1 moiety, is uncovered. A unique feature of the new line of the plasmin inhibitors is that the interaction between the plasmin inhibitors and key subsites in plasmin can be controlled by a spacer like hydantoin. The application of the novel chemotype is demonstrated by 1n and provides further evidence on the importance of hydantoin as the spacer. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.002

文献信息

• Pyrrolopyrimidine-inhibitors with hydantoin moiety as spacer can explore P4/S4 interaction on plasmin
  作者：Naoki Teno、Keigo Gohda、Keiko Wanaka、Yuko Tsuda、Takuya Sueda、Yukiko Yamashita、Tadamune Otsubo

  DOI：10.1016/j.bmc.2014.02.002

  日期：2014.4

  In the development of plasmin inhibitors, a novel chemotype, pyrrolopyrimidine scaffold possessing two motifs, a hydantoin-containing P4 moiety and a warhead-containing P1 moiety, is uncovered. A unique feature of the new line of the plasmin inhibitors is that the interaction between the plasmin inhibitors and key subsites in plasmin can be controlled by a spacer like hydantoin. The application of the novel chemotype is demonstrated by 1n and provides further evidence on the importance of hydantoin as the spacer. (c) 2014 Elsevier Ltd. All rights reserved.