3,4,5-trimethoxy-N-(2-methylsulfanyl-[1,3]thiazolo[4,5-g][1,3]benzothiazol-7-yl)benzamide | 361173-10-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 3,4,5-trimethoxy-N-(2-methylsulfanyl-[1,3]thiazolo[4,5-g][1,3]benzothiazol-7-yl)benzamide
• CAS: 361173-10-6
• 化学式: C₁₉H₁₇N₃O₄S₃
• 分子量: 447.56
• InChiKey: PJXJZNALRVJTLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  164
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,4,5-trimethoxy-N-(2-methylsulfanyl-[1,3]thiazolo[4,5-g][1,3]benzothiazol-7-yl)benzamide 在 potassium permanganate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 N-[7-[2-(dimethylamino)ethylamino]-[1,3]thiazolo[4,5-g][1,3]benzothiazol-2-yl]-3,4,5-trimethoxybenzamide
  参考文献：
  名称：

  Optimization of a novel potent and selective bacterial DNA helicase inhibitor scaffold from a high throughput screening hit

  摘要：

  Benzobisthiazole derivatives were identified as novel helicase inhibitors through high throughput screening against purified Staphylococcus aureus (Sa) and Bacillus anthracis (Ba) replicative helicases. Chemical optimization has produced compound 59 with nanomolar potency against the DNA duplex strand unwinding activities of both B. anthracis and S. aureus helicases. Selectivity index (SI = CC50/IC50) values for 59 were greater than 500. Kinetic studies demonstrated that the benzobisthiazole-based bacterial helicase inhibitors act competitively with the DNA substrate. Therefore, benzobisthiazole helicase inhibitors represent a promising new scaffold for evaluation as antibacterial agents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.055
• 作为产物：
  描述：

  7-(甲基硫烷基)[1,3]噻唑并[4,5-G][1,3]苯并噻唑-2-胺 、 3,4,5-三甲氧基苯甲酰氯 在 吡啶 、 N,N-二异丙基乙胺 作用下， 反应 72.0h， 以96%的产率得到3,4,5-trimethoxy-N-(2-methylsulfanyl-[1,3]thiazolo[4,5-g][1,3]benzothiazol-7-yl)benzamide
  参考文献：
  名称：

  Optimization of a novel potent and selective bacterial DNA helicase inhibitor scaffold from a high throughput screening hit

  摘要：

  Benzobisthiazole derivatives were identified as novel helicase inhibitors through high throughput screening against purified Staphylococcus aureus (Sa) and Bacillus anthracis (Ba) replicative helicases. Chemical optimization has produced compound 59 with nanomolar potency against the DNA duplex strand unwinding activities of both B. anthracis and S. aureus helicases. Selectivity index (SI = CC50/IC50) values for 59 were greater than 500. Kinetic studies demonstrated that the benzobisthiazole-based bacterial helicase inhibitors act competitively with the DNA substrate. Therefore, benzobisthiazole helicase inhibitors represent a promising new scaffold for evaluation as antibacterial agents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.055

文献信息

• Optimization of a novel potent and selective bacterial DNA helicase inhibitor scaffold from a high throughput screening hit
  作者：Bing Li、Ramdas Pai、Daniel Aiello、Ming Di、Marjorie H. Barnes、Norton P. Peet、Terry L. Bowlin、Donald T. Moir

  DOI：10.1016/j.bmcl.2013.04.055

  日期：2013.6

  Benzobisthiazole derivatives were identified as novel helicase inhibitors through high throughput screening against purified Staphylococcus aureus (Sa) and Bacillus anthracis (Ba) replicative helicases. Chemical optimization has produced compound 59 with nanomolar potency against the DNA duplex strand unwinding activities of both B. anthracis and S. aureus helicases. Selectivity index (SI = CC50/IC50) values for 59 were greater than 500. Kinetic studies demonstrated that the benzobisthiazole-based bacterial helicase inhibitors act competitively with the DNA substrate. Therefore, benzobisthiazole helicase inhibitors represent a promising new scaffold for evaluation as antibacterial agents. (C) 2013 Elsevier Ltd. All rights reserved.