3-allyl-2-(2-(dimethylamino)ethylthio)-3H-spiro[benzo[h]quinazoline-5,1'-cyclohexan]-4(6H)-one | 1239648-04-4

• 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: 3-allyl-2-(2-(dimethylamino)ethylthio)-3H-spiro[benzo[h]quinazoline-5,1'-cyclohexan]-4(6H)-one
• 英文别名: 2-[2-(dimethylamino)ethylsulfanyl]-3-prop-2-enylspiro[6H-benzo[h]quinazoline-5,1'-cyclohexane]-4-one
• CAS: 1239648-04-4
• 化学式: C₂₄H₃₁N₃OS
• 分子量: 409.596
• InChiKey: DAQKGKVWKVXNJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氰基环己亚基乙酸乙酯 在 potassium hydroxide 作用下， 以 乙醚 、 乙醇 、 丁酮 为溶剂， 反应 101.0h， 生成 3-allyl-2-(2-(dimethylamino)ethylthio)-3H-spiro[benzo[h]quinazoline-5,1'-cyclohexan]-4(6H)-one
  参考文献：
  名称：

  Novel inhibitors of bacterial virulence: Development of 5,6-dihydrobenzo[h]quinazolin-4(3H)-ones for the inhibition of group A streptococcal streptokinase expression

  摘要：

  Resistance to antibiotics is an increasingly dire threat to human health that warrants the development of new modes of treating infection. We recently identified 1 (CCG-2979) as an inhibitor of the expression of streptokinase, a critical virulence factor in Group A Streptococcus that endows blood-borne bacteria with fibrinolytic capabilities. In this report, we describe the synthesis and biological evaluation of a series of novel 5,6-dihydrobenzo[h]quinazolin-4(3H)-one analogs of 1 undertaken with the goal of improving the modest potency of the lead. In addition to achieving an over 35-fold increase in potency, we identified structural modifications that improve the solubility and metabolic stability of the scaffold. The efficacy of two new compounds 12c (CCG-203592) and 12k (CCG-205363) against biofilm formation in Staphylococcus aureus represents a promising additional mode of action for this novel class of compounds. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.046

文献信息

• METHODS AND COMPOSITIONS FOR TREATING BACTERIAL INFECTION
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US20150132352A1

  公开（公告）日：2015-05-14

  The present invention relates to chemical compounds, methods for their discovery, and their therapeutic and research use. In particular, the present invention provides compounds as therapeutic agents against bacterial infections (e.g., biofilms).

  本发明涉及化学化合物，它们的发现方法，以及它们的治疗和研究用途。具体而言，本发明提供了作为治疗剂抗击细菌感染（例如生物膜）的化合物。
• Methods and compositions for treating bacterial infection
  申请人：Ginsburg David

  公开号：US08501722B2

  公开（公告）日：2013-08-06

  The present invention relates to chemical compounds, methods for their discovery, and their therapeutic and research use. In particular, the present invention provides compounds as therapeutic agents against bacterial infections.

  本发明涉及化合物、其发现方法以及它们的治疗和研究用途。特别地，本发明提供了化合物作为治疗细菌感染的治疗剂。
• US8501722B2
  申请人：——

  公开号：US8501722B2

  公开（公告）日：2013-08-06
• US9504688B2
  申请人：——

  公开号：US9504688B2

  公开（公告）日：2016-11-29
• US9814719B2
  申请人：——

  公开号：US9814719B2

  公开（公告）日：2017-11-14