1-N-[(2,4-dimethoxyphenyl)methyl]isoquinoline-1,6-diamine | 681427-43-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-N-[(2,4-dimethoxyphenyl)methyl]isoquinoline-1,6-diamine
• CAS: 681427-43-0
• 化学式: C₁₈H₁₉N₃O₂
• 分子量: 309.368
• InChiKey: USLOOOLPXMLNBP-UHFFFAOYSA-N

物化性质

• 沸点：
  533.6±45.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  69.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-N-[(2,4-dimethoxyphenyl)methyl]isoquinoline-1,6-diamine 、 3-[4-(2,2-dimethylpropylcarbamoyl)-2-[(2-methylpropan-2-yl)oxycarbonyl]phenyl]-6-oxo-1H-pyridine-2-carboxylic acid 在 4-二甲氨基吡啶 、 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以69%的产率得到tert-butyl 2-[2-[[1-[(2,4-dimethoxyphenyl)methylamino]isoquinolin-6-yl]carbamoyl]-6-oxo-1H-pyridin-3-yl]-5-(2,2-dimethylpropylcarbamoyl)benzoate
  参考文献：
  名称：

  Discovery of nonbenzamidine factor VIIa inhibitors using a biaryl acid scaffold

  摘要：

  In this Letter, we describe the synthesis of several nonamidine analogs of biaryl acid factor VIla inhibitor 1 containing weakly basic or nonbasic P1 groups. 2-Aminoisoquinoline was found to be an excellent surrogate for the benzamidine group (compound 2) wherein potent inhibition of factor VIla is maintained relative to most other related serine proteases. In an unanticipated result, the m-benzamide P1 (compounds 21a and 21b) proved to be a viable benzamidine replacement, albeit with a 20-40 fold loss in potency against factor Vlla. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.06.028
• 作为产物：
  描述：

  6-硝基-1-异喹啉胺 生成 1-N-[(2,4-dimethoxyphenyl)methyl]isoquinoline-1,6-diamine
  参考文献：
  名称：

  Processes for the preparation of acid derivatives useful as serine protease inhibitors

  摘要：

  这项发明涉及一种新型的制备氨基异喹啉、苄基氨基异喹啉和酸衍生物的过程，这些化合物可用作丝氨酸蛋白酶抑制剂。

  公开号：

  US20040077865A1

文献信息

• Acid derivatives useful as serine protease inhibitors
  申请人：——

  公开号：US20030166685A1

  公开（公告）日：2003-09-04

  Compounds having the formula (I), 1 are useful as serine protease inhibitors, more particularly inhibitors of Factors VIIa, IXa, Xa, and/or XIa, wherein ring B is phenyl or pyridyl, W is preferably C(═O)NR 4 R 5 , L is a linker group, X 2 comprises nitrogen or carbon, Z is an optionally-substituted monocyclic or bicyclic ring system, and R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined in the specification.

  具有式(I)的化合物、 1 可用作丝氨酸蛋白酶抑制剂，尤其是 VIIa、IXa、Xa 和/或 XIa 因子的抑制剂，其中环 B 是苯基或吡啶基，W 最好是 C(═O)NR 4 R 5 L 是连接基团，X 2 包括氮或碳，Z 是任选取代的单环或双环环状系统，以及 R 1 , R 2 , R 3 , R 4 , R 5 和 R 6 的定义。
• US6642252B2
  申请人：——

  公开号：US6642252B2

  公开（公告）日：2003-11-04
• Processes for the preparation of acid derivatives useful as serine protease inhibitors
  申请人：——

  公开号：US20040077865A1

  公开（公告）日：2004-04-22

  This invention relates to novel processes for the preparation of amino isoquinolines, benzylamino isoquinolines, and acid derivatives useful as serine protease inhibtors.

  这项发明涉及一种新型的制备氨基异喹啉、苄基氨基异喹啉和酸衍生物的过程，这些化合物可用作丝氨酸蛋白酶抑制剂。
• Discovery of nonbenzamidine factor VIIa inhibitors using a biaryl acid scaffold
  作者：Scott A. Bolton、James C. Sutton、Rushith Anumula、Gregory S. Bisacchi、Bruce Jacobson、William A. Slusarchyk、Uwe D. Treuner、Shung C. Wu、Guohua Zhao、Zulan Pi、Steven Sheriff、Rebecca A. Smirk、Sharon Bisaha、Daniel L. Cheney、Anzhi Wei、William A. Schumacher、Karen S. Hartl、Eddie Liu、Robert Zahler、Steven M. Seiler

  DOI：10.1016/j.bmcl.2013.06.028

  日期：2013.9

  In this Letter, we describe the synthesis of several nonamidine analogs of biaryl acid factor VIla inhibitor 1 containing weakly basic or nonbasic P1 groups. 2-Aminoisoquinoline was found to be an excellent surrogate for the benzamidine group (compound 2) wherein potent inhibition of factor VIla is maintained relative to most other related serine proteases. In an unanticipated result, the m-benzamide P1 (compounds 21a and 21b) proved to be a viable benzamidine replacement, albeit with a 20-40 fold loss in potency against factor Vlla. (C) 2013 Published by Elsevier Ltd.