1-(2-Fluorobenzyl)-4-chloro-7-hydroxy-1,2,3-triazolo[4,5]pyridazine | 252007-88-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并哒嗪类
• 英文名称: 1-(2-Fluorobenzyl)-4-chloro-7-hydroxy-1,2,3-triazolo[4,5]pyridazine
• CAS: 252007-88-8
• 化学式: C₁₁H₇ClFN₅O
• 分子量: 279.661
• InChiKey: AXDKSJZTEKFJPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  76.72
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-甲基苯胺 、 1-(2-Fluorobenzyl)-4-chloro-7-hydroxy-1,2,3-triazolo[4,5]pyridazine 反应 12.0h， 以20%的产率得到1-(2-Fluorobenzyl)-4-(m-toluidino)-7-hydroxy-1,2,3-triazolo[4,5-d]pyridazine
  参考文献：
  名称：

  1,2,3-Triazolo[4,5-d]pyridazines

  摘要：

  Starting from the appropriate azides ( 4-chlorobenzyl-, 2-thiophenemethyl-, 2-fluorobenzyl-, and 4-fluorobenzylazides) agreeing with the substituent determining four series of derivatives (a-d), some 4-amino-substituted 1,2,3-triazolo[4,5-d]pyridazines (4a-d) corresponding to previously prepared derivatives were obtained by a well experimented synthetic route. Other new derivatives (6c,e) which were different from 4a-d because a chlorine atom had substituted the hydroxyl or the tautomeric oxamido group in the 7 position of the triazolopyridazine ring, were prepared from the suitable azides (2-fluorobenzyl and 2-chlorobenzyl), which similarly determine the series c and e, respectively, via the 4,7-dichloro derivatives 5. The radioligand binding assays at bovine brain adenosine A(1) and A(2A) receptors showed that some compounds 4 possessed high affinity and selectivity for the A(1) receptor subtype whilst binding affinity decreased in compounds 6 indicating the importance of a hydrogen bond donor in the 7 position of the triazolopyridazine ring. It is worth noting that compounds bearing the new lipophilic substituents 2-fluorobenzyl and 2-thiophenemethyl in the 1 position of the triazolopyridazine ring were the most active in the series. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00072-5
• 作为产物：
  描述：

  1-(o-fluorobenzyl)-1H-1,2,3-triazole-4,5-dicarboxylic acid dimethyl ester 在 盐酸 、 水 、 一水合肼 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 1-(2-Fluorobenzyl)-4-chloro-7-hydroxy-1,2,3-triazolo[4,5]pyridazine
  参考文献：
  名称：

  1,2,3-Triazolo[4,5-d]pyridazines

  摘要：

  Starting from the appropriate azides ( 4-chlorobenzyl-, 2-thiophenemethyl-, 2-fluorobenzyl-, and 4-fluorobenzylazides) agreeing with the substituent determining four series of derivatives (a-d), some 4-amino-substituted 1,2,3-triazolo[4,5-d]pyridazines (4a-d) corresponding to previously prepared derivatives were obtained by a well experimented synthetic route. Other new derivatives (6c,e) which were different from 4a-d because a chlorine atom had substituted the hydroxyl or the tautomeric oxamido group in the 7 position of the triazolopyridazine ring, were prepared from the suitable azides (2-fluorobenzyl and 2-chlorobenzyl), which similarly determine the series c and e, respectively, via the 4,7-dichloro derivatives 5. The radioligand binding assays at bovine brain adenosine A(1) and A(2A) receptors showed that some compounds 4 possessed high affinity and selectivity for the A(1) receptor subtype whilst binding affinity decreased in compounds 6 indicating the importance of a hydrogen bond donor in the 7 position of the triazolopyridazine ring. It is worth noting that compounds bearing the new lipophilic substituents 2-fluorobenzyl and 2-thiophenemethyl in the 1 position of the triazolopyridazine ring were the most active in the series. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00072-5