7-bromomethylthieno[2, 3-c]pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: 7-bromomethylthieno[2, 3-c]pyridine
• 英文别名: 7-(Bromomethyl)thieno[2,3-c]pyridine
• 化学式: C₈H₆BrNS
• 分子量: 228.112
• InChiKey: OJOCNDWCRGYQNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-bromomethylthieno[2, 3-c]pyridine 在 silver(I) acetate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 12.67h， 生成
  参考文献：
  名称：

  6-Arylmethylidene Penicillin-Based Sulfone Inhibitors for Repurposing Antibiotic Efficiency in Priority Pathogens

  摘要：

  The ability of 6-(aryl)methylidene penicillin-based sulfones 1-7 to repurpose beta-lactam antibiotics activity with bacterial species that carry carbapenem-hydrolyzing class D beta-lactamases (OXA-23, OXA-24/40 and OXA-48), as well as with class A (TEM-1, CTX-M-2) and class C (CMY-2, DHA-1) enzymes, is reported. The combinations imipenem/3 and imipenem/4 restored almost completely the antibiotic efficacy in OXA-23 and OXA-24/40 carbapenemase-producing A. baumannii strains (1 mu g mL(-1)) and also provided good results for OXA-48 carbapenemase-producing K. pneumoniae strains (4 mu g mL(-1)). Compounds 2-6 in combinations with ceftazidime and ampicillin were also efficient in restoring antibiotic efficacy in E. coli strains carrying class C (CMY-2 and DHA-1) and class A (TEM-1 and CTX-M-2) beta-lactamase enzymes, respectively. Kinetic and inhibition studies with the OXA-24/40 enzyme, protein mass spectrometry analysis and docking studies allowed us to gain an insight into the inhibition mechanism and the experimentally observed differences between the ligands.

  DOI：

  10.1021/acs.jmedchem.0c00127
• 作为产物：
  描述：

  7-Methyl-thieno<2,3-c>pyridin 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 生成 7-bromomethylthieno[2, 3-c]pyridine
  参考文献：
  名称：

  Thienopyridine derivatives useful in treating gastric ulcers

  摘要：

  提供的化合物的结构式为：##STR1##（其中R.sup.1为氢，C.sub.1 -C.sub.5烷基，C.sub.1 -C.sub.5烷氧基，C.sub.1 -C.sub.5烷氧羰基，或三氟甲基；R.sup.2为氢，C.sub.1 -C.sub.5烷氧羰基，C.sub.6 -C.sub.12芳基氧羰基，C.sub.1 -C.sub.5烷酰氧-C.sub.1 -C.sub.5烷基，C.sub.1 -C.sub.5烷氧羰氧-C.sub.1 -C.sub.5烷基，C.sub.1 -C.sub.5酰胺基-C.sub.1 -C.sub.5烷基，2-羟基-1-C.sub.2 -C.sub.5烯基，邻苯二甲酰胺基-C.sub.1 -C.sub.5烷基，卤代-C.sub.1 -C.sub.5烷氧羰基-C.sub.1 -C.sub.5烷基，羟基-C.sub.1 -C.sub.5烷基，C.sub.1 -C.sub.5烷硫基-C.sub.1 -C.sub.5烷基，或C.sub.1 -C.sub.5烷基亚砜基-C.sub.1 -C.sub.5烷基；##STR2##m为0或1的整数；R.sup.3和R.sup.4各自为氢，卤素，氰基，C.sub.1 -C.sub.5烷基，氨基，C.sub.1 -C.sub.5烷氧基，C.sub.6 -C.sub.12芳基-C.sub.1 -C.sub.5烷氧基，C.sub.1 -C.sub.5烷氧羰基，氟代-C.sub.1 -C.sub.5烷氧基，C.sub.1 -C.sub.5烷酰胺基，或羰胺基）或其盐，可用作抗溃疡药物。

  公开号：

  US04839365A1

文献信息

• Thienopyridine derivatives
  申请人：SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD.

  公开号：EP0292051A2

  公开（公告）日：1988-11-23

  A compound of the formula: (wherein R¹ is hydrogen, C₁-C₅ alkyl, C₁-C₅ alkoxy, C₁-C₅ alkoxy­carbonyl, or trifluoromethyl; R² is hydrogen, C₁-C₅ alkoxycarbo­nyl, C₆-C₁₂ aryloxycarbonyl, C₁-C₅ alkanoyloxy-C₁-C₅ alkyl, C₁-C₅ alkoxycarbonyloxy-C₁-C₅ alkyl, C₁-C₅ acylamino-C₁-C₅ alkyl, 2-­hydroxy-1-C₂-C₅ alkenyl, phthalimido-C₁-C₅ alkyl, halogeno-C₁-C₅ alkoxycarbonyl-C₁-C₅ alkyl, hydroxy-C₁-C₅ alkyl, C₁-C₅ alkylthio-­C₁-C₅ alkyl, or C₁-C₅ alkylsulfinyl-C₁-C₅ alkyl; m is an integer of 0 or 1; R³ and R⁴ each is hydrogen, halogen, cyano, C₁-C₅ alkyl, amino, C₁-C₅ alkoxy, C₆-C₁₂ aryl-C₁-C₅ alkoxy, C₁-C₅ alkoxycarbonyl, fluoro-C₁-C₅ alkoxy, C₁-C₅ alkanoylamino, or carbamoyl) or its salt, being useful as antiulcer agents, is provided.

  式中的化合物： (其中 R¹ 是氢、C₁-C₅ 烷基、C₁-C₅ 烷氧基、C₁-C₅ 烷氧羰基或三氟甲基；R² 是氢、C₁-C₅ 烷氧基羰基、C₆-C₁₂ 芳氧基羰基、C₁-C₅ 烷酰氧基-C₁-C₅ 烷基、C₁-C₅ 烷氧基羰氧基-C₁-C₅ 烷基、C₁-C₅ 氨基酰基-C₁-C₅ 烷基、2-羟基-1-C₂-C₅ 烯基、邻苯二甲酰亚胺基-C₁-C₅ 烷基、卤素基-C₁-C₅ 烷氧基羰基-C₁-C₅ 烷基、羟基-C₁-C₅ 烷基、C₁-C₅ 烷硫基-C₁-C₅ 烷基或 C₁-C₅ 烷基亚磺酰基-C₁-C₅ 烷基； m 是 0 或 1 的整数； R³ 和 R⁴ 各为氢、卤素、氰基、C₁-C₅ 烷基、氨基、C₁-C₅ 烷氧基、C₆-C₁₂ 芳基-C₁-C₅ 烷氧基、C₁-C₅ 烷氧基羰基、氟-C₁-C₅ 烷氧基、C₁-C₅ 烷酰氨基或氨基甲酰基）或其盐，可用作抗溃疡剂。
• XIRAI, KEHNTARO;MIDZUSIMA, TAKAO;TSUTSUMIUTI, MASAMI
  作者：XIRAI, KEHNTARO、MIDZUSIMA, TAKAO、TSUTSUMIUTI, MASAMI

  DOI：——

  日期：——
• HIRAI, KENTARO;MIZUSHIMA, YUKIO;DOTEUCHI, MASAMI
  作者：HIRAI, KENTARO、MIZUSHIMA, YUKIO、DOTEUCHI, MASAMI

  DOI：——

  日期：——
• US4839365A
  申请人：——

  公开号：US4839365A

  公开（公告）日：1989-06-13
• Thienopyridine derivatives useful in treating gastric ulcers
  申请人：Shinogi & Co., Ltd.

  公开号：US04839365A1

  公开（公告）日：1989-06-13

  A compound of the formula: ##STR1## (wherein R.sup.1 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.5 alkoxycarbonyl, or trifluoromethyl; R.sup.2 is hydrogen, C.sub.1 -C.sub.5 alkoxycarbonyl, C.sub.6 -C.sub.12 aryloxycarbonyl, C.sub.1 -C.sub.5 alkanoyloxy-C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxycarbonyloxy-C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 acylamino-C.sub.1 -C.sub.5 alkyl, 2-hydroxy-1-C.sub.2 -C.sub.5 alkenyl, phthalimido-C.sub.1 -C.sub.5 alkyl, halogeno-C.sub.1 -C.sub.5 alkoxycarbonyl-C.sub.1 -C.sub.5 alkyl, hydroxy-C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkylthio-C.sub.1 -C.sub.5 alkyl, or C.sub.1 -C.sub.5 alkylsulfinyl-C.sub.1 -C.sub.5 alkyl; ##STR2## m is an integer of 0 or 1; R.sup.3 and R.sup.4 each is hydrogen, halogen, cyano, C.sub.1 -C.sub.5 alkyl, amino, C.sub.1 -C.sub.5 alkoxy, C.sub.6 -C.sub.12 aryl-C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.5 alkoxycarbonyl, fluoro-C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.5 alkanoylamino, or carbamoyl) or its salt, being useful as antiulcer agents, is provided.

  提供的化合物的结构式为：##STR1##（其中R.sup.1为氢，C.sub.1 -C.sub.5烷基，C.sub.1 -C.sub.5烷氧基，C.sub.1 -C.sub.5烷氧羰基，或三氟甲基；R.sup.2为氢，C.sub.1 -C.sub.5烷氧羰基，C.sub.6 -C.sub.12芳基氧羰基，C.sub.1 -C.sub.5烷酰氧-C.sub.1 -C.sub.5烷基，C.sub.1 -C.sub.5烷氧羰氧-C.sub.1 -C.sub.5烷基，C.sub.1 -C.sub.5酰胺基-C.sub.1 -C.sub.5烷基，2-羟基-1-C.sub.2 -C.sub.5烯基，邻苯二甲酰胺基-C.sub.1 -C.sub.5烷基，卤代-C.sub.1 -C.sub.5烷氧羰基-C.sub.1 -C.sub.5烷基，羟基-C.sub.1 -C.sub.5烷基，C.sub.1 -C.sub.5烷硫基-C.sub.1 -C.sub.5烷基，或C.sub.1 -C.sub.5烷基亚砜基-C.sub.1 -C.sub.5烷基；##STR2##m为0或1的整数；R.sup.3和R.sup.4各自为氢，卤素，氰基，C.sub.1 -C.sub.5烷基，氨基，C.sub.1 -C.sub.5烷氧基，C.sub.6 -C.sub.12芳基-C.sub.1 -C.sub.5烷氧基，C.sub.1 -C.sub.5烷氧羰基，氟代-C.sub.1 -C.sub.5烷氧基，C.sub.1 -C.sub.5烷酰胺基，或羰胺基）或其盐，可用作抗溃疡药物。