methyl 6-(bromomethyl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidine-2-carboxylate | 1596360-16-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: methyl 6-(bromomethyl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidine-2-carboxylate
• 英文别名: methyl 6-(bromomethyl)-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carboxylate；methyl 6-(bromomethyl)-7-methylpyrrolo[2,3-d]pyrimidine-2-carboxylate
• CAS: 1596360-16-5
• 化学式: C₁₀H₁₀BrN₃O₂
• 分子量: 284.112
• InChiKey: YCMIBIHRBIPYIU-UHFFFAOYSA-N

物化性质

• 沸点：
  442.9±53.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 6-(bromomethyl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidine-2-carboxylate 在 N-羟基-7-氮杂苯并三氮唑 、 lithium hydroxide monohydrate 、 水 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 9H-fluoren-9-ylmethyl N-[(5S)-5-[[6-[[3-[4-(2-carbamoylphenoxy)phenyl]-2,5-dioxo-imidazolidin-1-yl]methyl]-7-methyl-pyrrolo[2,3-d]pyrimidine-2-carbonyl]amino]-5-cyano-pentyl]carbamate
  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
• 作为产物：
  描述：

  methyl 4-methylamino-5-(3-tetrahydropyran-2-yloxyprop-1-ynyl)pyrimidine-2-carboxylate 在 盐酸 、 四溴化碳 、 碳酸氢钠 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 methyl 6-(bromomethyl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidine-2-carboxylate
  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

• Novel type of plasmin inhibitors: Providing insight into P4 moiety and alternative scaffold to pyrrolopyrimidine
  作者：Naoki Teno、Keigo Gohda、Keiko Wanaka、Yuko Tsuda、Maiko Akagawa、Eriko Akiduki、Mitsuhito Araki、Arisa Masuda、Tadamune Otsubo、Yukiko Yamashita

  DOI：10.1016/j.bmc.2015.04.013

  日期：2015.7

  Here we report a series of plasmin inhibitors which were originally derived from the parent structure of 1 and 2. Our efforts focused on the optimization of the P4 moiety of 2 and on the quest of alternative scaffold to pyrrolopyrimidine in the parent compounds. The results of the former gave us pivotal information on the further optimization of the P4 moiety in plasmin inhibitors and those of the latter revealed that appropriate moieties extending from the benzimidazole scaffold engaged with S4 pocket in the active site of plasmin. (C) 2015 Elsevier Ltd. All rights reserved.