2,4-dichloro-5-(thiomorpholin-4-ylsulfonyl)benzoic acid | 352673-29-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4-dichloro-5-(thiomorpholin-4-ylsulfonyl)benzoic acid
• 英文别名: 2,4-Dichloro-5-(thiomorpholinosulfonyl)benzoic acid；2,4-dichloro-5-thiomorpholin-4-ylsulfonylbenzoic acid
• CAS: 352673-29-1
• 化学式: C₁₁H₁₁Cl₂NO₄S₂
• 分子量: 356.251
• InChiKey: PWGLMGPBMAGOAR-UHFFFAOYSA-N

物化性质

• 沸点：
  560.7±60.0 °C(Predicted)
• 密度：
  1.614±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4-dichloro-5-(thiomorpholin-4-ylsulfonyl)benzoic acid 在 吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2,4-dichloro-N-(3-cyano-4,5,6,7-tetrahydro-1-benzothiophen-2-yl)-5-(thiomorpholin-4-ylsulfonyl)benzamide
  参考文献：
  名称：

  Structure–activity relationships of new cyanothiophene inhibitors of the essential peptidoglycan biosynthesis enzyme MurF

  摘要：

  Peptidoglycan is an essential component of the bacterial cell wall, and enzymes involved in its biosynthesis represent validated targets for antibacterial drug discovery. MurF catalyzes the final intracellular peptidoglycan biosynthesis step: the addition of D-Ala-D-Ala to the nucleotide precursor UDP-MurNAc-L-Ala-gamma-D-Glu-meso-DAP (or L-Lys). As MurF has no human counterpart, it represents an attractive target for the development of new antibacterial drugs. Using recently published cyanothiophene inhibitors of MurF from Streptococcus pneumoniae as a starting point, we designed and synthesized a series of structurally related derivatives and investigated their inhibition of MurF enzymes from different bacterial species. Systematic structural modifications of the parent compounds resulted in a series of nanomolar inhibitors of MurF from S. pneumoniae and micromolar inhibitors of MurF from Escherichia coli and Staphylococcus aureus. Some of the inhibitors also show antibacterial activity against S. pneumoniae R6. These findings, together with two new co-crystal structures, represent an excellent starting point for further optimization toward effective novel antibacterials. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.013
• 作为产物：
  描述：

  2,4-二氯苯甲酸 在 氯磺酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 2,4-dichloro-5-(thiomorpholin-4-ylsulfonyl)benzoic acid
  参考文献：
  名称：

  Structure–activity relationships of new cyanothiophene inhibitors of the essential peptidoglycan biosynthesis enzyme MurF

  摘要：

  Peptidoglycan is an essential component of the bacterial cell wall, and enzymes involved in its biosynthesis represent validated targets for antibacterial drug discovery. MurF catalyzes the final intracellular peptidoglycan biosynthesis step: the addition of D-Ala-D-Ala to the nucleotide precursor UDP-MurNAc-L-Ala-gamma-D-Glu-meso-DAP (or L-Lys). As MurF has no human counterpart, it represents an attractive target for the development of new antibacterial drugs. Using recently published cyanothiophene inhibitors of MurF from Streptococcus pneumoniae as a starting point, we designed and synthesized a series of structurally related derivatives and investigated their inhibition of MurF enzymes from different bacterial species. Systematic structural modifications of the parent compounds resulted in a series of nanomolar inhibitors of MurF from S. pneumoniae and micromolar inhibitors of MurF from Escherichia coli and Staphylococcus aureus. Some of the inhibitors also show antibacterial activity against S. pneumoniae R6. These findings, together with two new co-crystal structures, represent an excellent starting point for further optimization toward effective novel antibacterials. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.013

文献信息

• Therapeutic compounds
  申请人：Egle Ian

  公开号：US20070021606A1

  公开（公告）日：2007-01-25

  The present invention provides novel compounds that function as potentiators of glutamate receptors, methods for their preparation, pharmaceutical compositions containing them, and methods of their use in therapy.

  本发明提供了一种新型化合物，其作为谷氨酸受体增强剂发挥作用，其制备方法、含有它们的药物组合物以及它们在治疗中的使用方法。
• SUBSTITUTED BENZOSULPHONAMIDES AS POTENTIATORS OF GLUTAMATE RECEPTORS
  申请人：AstraZeneca AB

  公开号：EP1615904B1

  公开（公告）日：2008-02-27