6-Chloro-9-o-tolyl-thieno[2,3-c][1,5]naphthyridine | 180057-12-9

• 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: 6-Chloro-9-o-tolyl-thieno[2,3-c][1,5]naphthyridine
• 英文别名: 6-Chloro-9-(2-methylphenyl)thieno[2,3-c][1,5]naphthyridine；6-chloro-9-(2-methylphenyl)thieno[2,3-c][1,5]naphthyridine
• CAS: 180057-12-9
• 化学式: C₁₇H₁₁ClN₂S
• 分子量: 310.807
• InChiKey: HTRLVPPAKCZXPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  4-氨基-1-丁醇 、 6-Chloro-9-o-tolyl-thieno[2,3-c][1,5]naphthyridine 反应 3.0h， 以85%的产率得到4-(9-o-Tolyl-thieno[2,3-c][1,5]naphthyridin-6-ylamino)-butan-1-ol
  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：

  1-methyl-2-(trimethylstannyl)benzene 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

文献信息

• 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.