2-[(Pyridin-4-yl)methoxy]benzonitrile | 911832-39-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[(Pyridin-4-yl)methoxy]benzonitrile
• 英文别名: 2-(pyridin-4-ylmethoxy)benzonitrile
• CAS: 911832-39-8
• 化学式: C₁₃H₁₀N₂O
• mdl: MFCD09945312
• 分子量: 210.235
• InChiKey: AYLLRHVCUUUHSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  45.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(Pyridin-4-yl)methoxy]benzonitrile 、 邻氨基三氟甲苯 在 三甲基铝 作用下， 以 甲苯 为溶剂， 以48%的产率得到2-(4-Pyridinylmethoxy)-N-[2-(trifluoromethyl)phenyl]benzenecarboximidamide
  参考文献：
  名称：

  Synthesis and biological evaluation of benzamides and benzamidines as selective inhibitors of VEGFR tyrosine kinases

  摘要：

  A series of benzamidines and benzamides was synthesized as selective inhibitors of vascular endothelial growth factor receptor (VEGFR) tyrosine kinases, and tested for inhibitory activity toward autophosphorylation by the enzyme assay. Selective inhibition of VEGFR-2 tyrosine kinase was observed in the salicylic amide 4e and the anthranilic amidine 5a, and their percent inhibitions of VEGFR-2 tyrosine kinase were 44-60% at a 10 mu M concentration of compounds. The salicylic amide 4a showed inhibition of both VEGFR-1 and VEGFR-2 tyrosine kinases at a 10 mu M concentration. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.075
• 作为产物：
  描述：

  4-氯甲基吡啶 、 邻羟基苯甲腈 在 氢氧化钾 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 以41%的产率得到2-[(Pyridin-4-yl)methoxy]benzonitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of benzamides and benzamidines as selective inhibitors of VEGFR tyrosine kinases

  摘要：

  A series of benzamidines and benzamides was synthesized as selective inhibitors of vascular endothelial growth factor receptor (VEGFR) tyrosine kinases, and tested for inhibitory activity toward autophosphorylation by the enzyme assay. Selective inhibition of VEGFR-2 tyrosine kinase was observed in the salicylic amide 4e and the anthranilic amidine 5a, and their percent inhibitions of VEGFR-2 tyrosine kinase were 44-60% at a 10 mu M concentration of compounds. The salicylic amide 4a showed inhibition of both VEGFR-1 and VEGFR-2 tyrosine kinases at a 10 mu M concentration. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.075

文献信息

• [EN] SUBSTITUTED PHENYL COMPOUNDS AS ENDOTHELIN ANTAGONISTS<br/>[FR] COMPOSES PHENYLES SUBSTITUES UTILISES COMME ANTAGONISTES DE L'ENDOTHELINE
  申请人：RHONE POULENC RORER LIMITED

  公开号：WO1996022978A1

  公开（公告）日：1996-08-01

  (EN) Compounds of formula (I) are described, wherein: R1 is CN, CH2CN, CH=CHCN, CHO, or CH=CHCO2H; R2 is aryl lower alkoxy, heteroaryl lower alkoxy, aryl lower alkylthio or heteroaryl lower alkylthio in which each of the aryl and heteroaryl moieties is optionally substituted; R3 is halogen; R4 is optionally substituted aryl or optionally substituted heteroaryl; R5 is carboxy or an acid isostere; X is oxygen or sulphur; and n is zero or 1; and their N-oxides and prodrugs, and pharmaceutically acceptable salts thereof. The compounds have endothelin antagonist activity and are useful as pharmaceuticals.(FR) L'invention porte sur des composés de la formule (I), leurs oxydes d'azote, leurs précurseurs de médicament ainsi que les sels acceptables du point de vue pharmaceutique qui en sont issus. Dans cette formule, R1 est CN, CH2CN, CH=CHCN, CHO, ou CH=CHCO2H; R2 est aryle alcoxy inférieur, hétéroaryle alcoxy inférieur, aryle alkylthio inférieur ou hétéroaryle alkylthio inférieur, dans lequel chacun des fragments aryle ou hétéroaryle peut, éventuellement, être substitué; R3 est halogène; R4 est éventuellement aryle substitué ou hétéroaryle substitué; R5 est carboxy ou un isostère acide; X est oxygène ou soufre et n vaut zéro ou 1. Ces composés, qui ont une activité antagoniste de celle de l'endothéline, ont montré leur efficacité en tant que préparations pharmaceutiques

  化合物的公式（I）被描述，其中：R1为CN，CH2CN，CH=CHCN，CHO或CH=CHCO2H; R2为芳基低烷氧基，杂芳基低烷氧基，芳基低烷硫基或杂芳基低烷硫基，其中每个芳基和杂芳基可以选择性地被取代; R3为卤素; R4为可选择性取代的芳基或可选择性取代的杂芳基; R5为羧基或酸异构体; X为氧或硫; n为零或1; 以及它们的N-氧化物和前药，以及药学上可接受的盐。这些化合物具有内皮素拮抗剂活性，可用作制药用途。
• SUBSTITUTED PHENYL COMPOUNDS AS ENDOTHELIN ANTAGONISTS
  申请人：RHONE-POULENC RORER LIMITED

  公开号：EP0805802A1

  公开（公告）日：1997-11-12
• Synthesis and biological evaluation of benzamides and benzamidines as selective inhibitors of VEGFR tyrosine kinases
  作者：Hiroyuki Nakamura、Yusuke Sasaki、Masaharu Uno、Tomohiro Yoshikawa、Toru Asano、Hyun Seung Ban、Hidesuke Fukazawa、Masabumi Shibuya、Yoshimasa Uehara

  DOI：10.1016/j.bmcl.2006.07.075

  日期：2006.10

  A series of benzamidines and benzamides was synthesized as selective inhibitors of vascular endothelial growth factor receptor (VEGFR) tyrosine kinases, and tested for inhibitory activity toward autophosphorylation by the enzyme assay. Selective inhibition of VEGFR-2 tyrosine kinase was observed in the salicylic amide 4e and the anthranilic amidine 5a, and their percent inhibitions of VEGFR-2 tyrosine kinase were 44-60% at a 10 mu M concentration of compounds. The salicylic amide 4a showed inhibition of both VEGFR-1 and VEGFR-2 tyrosine kinases at a 10 mu M concentration. (c) 2006 Elsevier Ltd. All rights reserved.