1-bromothieno<2,3-c>-1,5-naphthyridine | 154418-91-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-bromothieno<2,3-c>-1,5-naphthyridine
• 英文别名: 9-Bromothieno[2,3-c][1,5]naphthyridine
• CAS: 154418-91-4
• 化学式: C₁₀H₅BrN₂S
• 分子量: 265.133
• InChiKey: AXARZWCHUCXWIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-bromothieno<2,3-c>-1,5-naphthyridine 在 氯化亚砜 、 1,4-双(二苯基膦丁烷)二氯化钯 、 间氯过氧苯甲酸 、 copper(II) oxide 作用下， 以 氯仿 为溶剂， 反应 20.08h， 生成 6-Chloro-9-o-tolyl-thieno[2,3-c][1,5]naphthyridine
  参考文献：
  名称：

  4-Substituted 1-(2-methylphenyl)thieno[2,3-c]-1,5-naphthyridines as possible reversible inhibitors of gastric H+,K+-ATPase

  摘要：

  Seven 1-(2-methylphenyl)thieno[2,3-c]-1,5-naphthyridines substituted in the 4-position with different amino-containing groups have been prepared. The reaction route to these compounds consisted of a palladium(0)-catalyzed cross-coupling between 1-bromothieno[2,3-c]-1,5-naphthyridine and 2-methyl-1-trimethylstannylbenzene, then oxidation of the 5-nitrogen, followed by treatment with thionyl chloride to give the 4-chloro derivative. The compounds obtained after nucleophilic substitution were tested with regard to their effects on H+,K+-ATPase activity and on acid formation in gastric glands. However, the inhibitory potency in vitro of the substituted naphthyridines was not high enough to be of interest from a pharmacological point of view.

  DOI：

  10.1016/0223-5234(96)89168-9
• 作为产物：
  描述：

  thieno<2,3-c><1,5>naphthyridine 在 硫酸 、 1,3-二溴-1,3,5-三嗪-2,4,6-三酮 作用下， 反应 24.0h， 以62%的产率得到1-bromothieno<2,3-c>-1,5-naphthyridine
  参考文献：
  名称：

  Malm, Johan; Hoernfeldt, Anna-Britta; Gronowitz, Salo, Journal of Heterocyclic Chemistry, 1994, vol. 31, # 2, p. 521 - 526

  摘要：

  DOI：

文献信息

• Malm, Johan; Hoernfeldt, Anna-Britta; Gronowitz, Salo, Heterocycles, 1994, vol. 37, # 1, p. 331 - 346
  作者：Malm, Johan、Hoernfeldt, Anna-Britta、Gronowitz, Salo

  DOI：——

  日期：——
• Malm Johan, Hoernfeldt Anna-Britta, Gronowitz Salo, Heterocycles, 37 (1994) N 1, S 331-345
  作者：Malm Johan, Hoernfeldt Anna-Britta, Gronowitz Salo

  DOI：——

  日期：——
• 4-Substituted 1-(2-methylphenyl)thieno[2,3-c]-1,5-naphthyridines as possible reversible inhibitors of gastric H+,K+-ATPase
  作者：P Björk、A.B. Hörnfeldt、S Gronowitz、U Edvardsson

  DOI：10.1016/0223-5234(96)89168-9

  日期：1996.1

  Seven 1-(2-methylphenyl)thieno[2,3-c]-1,5-naphthyridines substituted in the 4-position with different amino-containing groups have been prepared. The reaction route to these compounds consisted of a palladium(0)-catalyzed cross-coupling between 1-bromothieno[2,3-c]-1,5-naphthyridine and 2-methyl-1-trimethylstannylbenzene, then oxidation of the 5-nitrogen, followed by treatment with thionyl chloride to give the 4-chloro derivative. The compounds obtained after nucleophilic substitution were tested with regard to their effects on H+,K+-ATPase activity and on acid formation in gastric glands. However, the inhibitory potency in vitro of the substituted naphthyridines was not high enough to be of interest from a pharmacological point of view.
• Malm, Johan; Hoernfeldt, Anna-Britta; Gronowitz, Salo, Journal of Heterocyclic Chemistry, 1994, vol. 31, # 2, p. 521 - 526
  作者：Malm, Johan、Hoernfeldt, Anna-Britta、Gronowitz, Salo

  DOI：——

  日期：——