2-Chloro-7-(4-chloro-phenyl)-4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid

• 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: 2-Chloro-7-(4-chloro-phenyl)-4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid
• 英文别名: 2-Chloro-7-(4-chlorophenyl)-4-oxothieno[2,3-b]pyridine-5-carboxylic acid
• 化学式: C₁₄H₇Cl₂NO₃S
• 分子量: 340.186
• InChiKey: IWWRCXILPDYZSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 2-chloro-7-(4-chlorophenyl)-4-oxo-1,4-dihydrothieno[2,3-b]pyridine-5-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以88%的产率得到2-Chloro-7-(4-chloro-phenyl)-4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid
  参考文献：
  名称：

  Thienopyridinone antibacterials: Synthesis and antibacterial activity of some 7-aryl-2-chloro-4,7-dihydro-4-oxothieno[2,3-b]pyridine-5-carboxylic acids

  摘要：

  A series of 7-aryl-4-oxothieno[2,3-D]pyridine-5-carboxylic acids 8 and their methyl esters 7 were synthesized by intramolecular cyclization of the respective 3-N-arylamino-2-(2,5-dichloro-3-thenoyl) acrylates 6. The latter are accessible from methyl 3-ethoxy-2-(2,5-dichloro-3-thenoyl) acrylate 5 which, in turn, is obtained via the parent beta-keto ester 4. Of the present series, the 7-(p-hydroxyphenyl) and 7-(2',4'-difluorophenyl) derivatives 8e,i possess the highest activity especially against Klebsiella pneumoniae,Escherichia coli and Staphylococcus aureus (MICs of 8e/8i approximate to 0.06:0.25, 0.5:1.0 and 1.0:2.0 mu g/mL, respectively). (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80073-7

文献信息

• Thienopyridinone antibacterials: Synthesis and antibacterial activity of some 7-aryl-2-chloro-4,7-dihydro-4-oxothieno[2,3-b]pyridine-5-carboxylic acids
  作者：Mustafa M. El-Abadelah、Musa Z. Nazer、Shadia F. Okasha、Michèle Calas、Jacques Bompart、Pierre Mion

  DOI：10.1016/s0223-5234(99)80073-7

  日期：1998.1

  A series of 7-aryl-4-oxothieno[2,3-D]pyridine-5-carboxylic acids 8 and their methyl esters 7 were synthesized by intramolecular cyclization of the respective 3-N-arylamino-2-(2,5-dichloro-3-thenoyl) acrylates 6. The latter are accessible from methyl 3-ethoxy-2-(2,5-dichloro-3-thenoyl) acrylate 5 which, in turn, is obtained via the parent beta-keto ester 4. Of the present series, the 7-(p-hydroxyphenyl) and 7-(2',4'-difluorophenyl) derivatives 8e,i possess the highest activity especially against Klebsiella pneumoniae,Escherichia coli and Staphylococcus aureus (MICs of 8e/8i approximate to 0.06:0.25, 0.5:1.0 and 1.0:2.0 mu g/mL, respectively). (C) Elsevier, Paris.