9-(2,4-dimethoxybenzyl)-6-oxo-1,2,(S)-2a,3,6,9-hexahydro-4-oxa-9,10,10b-triazacyclobuta[a]anthracene-7-carboxylic acid | 908340-12-5

• 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: 9-(2,4-dimethoxybenzyl)-6-oxo-1,2,(S)-2a,3,6,9-hexahydro-4-oxa-9,10,10b-triazacyclobuta[a]anthracene-7-carboxylic acid
• 英文别名: (2aS)-9-(2,4-dimethoxybenzyl)-6-oxo-1,2,2a,3,6,9-hexahydroazeto[1',2':4,5][1,4]oxazino[3,2-b][1,8]-naphthyridine-7-carboxylic acid；(14S)-7-[(2,4-dimethoxyphenyl)methyl]-4-oxo-16-oxa-7,9,11-triazatetracyclo[8.6.0.03,8.011,14]hexadeca-1(10),2,5,8-tetraene-5-carboxylic acid
• CAS: 908340-12-5
• 化学式: C₂₂H₂₁N₃O₆
• 分子量: 423.425
• InChiKey: VGROCQUIFXDIRQ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  9-(2,4-dimethoxybenzyl)-6-oxo-1,2,(S)-2a,3,6,9-hexahydro-4-oxa-9,10,10b-triazacyclobuta[a]anthracene-7-carboxylic acid 在 三氟乙酸 作用下， 反应 1.0h， 生成 (2aS)-6-oxo-1,2,2a,3,6,9-hexahydroazeto[1',2':4,5][1,4]-oxazino[3,2-b][1,8]naphthyridine-7-carboxylic acid
  参考文献：
  名称：

  Antibacterial compounds

  摘要：

  揭示了具有式(I)的细菌蛋白合成抑制化合物及其盐、前药、前药的盐，制备这些化合物的过程和过程中间体，含有这些化合物的组合物，以及使用这些化合物的方法。

  公开号：

  US20070088040A1
• 作为产物：
  描述：

  1-(2,4-dimethoxybenzyl)-6-fluoro-7-[2-(S)-hydroxymethylazetidin-1-yl]-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid ethyl ester 在 lithium hydroxide 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 9-(2,4-dimethoxybenzyl)-6-oxo-1,2,(S)-2a,3,6,9-hexahydro-4-oxa-9,10,10b-triazacyclobuta[a]anthracene-7-carboxylic acid
  参考文献：
  名称：

  Novel Antibacterial Class:  A Series of Tetracyclic Derivatives

  摘要：

  We describe the synthesis and antibacterial activity of a series of tetracyclic naphthyridones. The members of this series act primarily via inhibition of bacterial translation and belong to the class of novel ribosome inhibitors (NRIs). In this paper we explore the structure-activity relationships (SAR) of these compounds to measure their ability both to inhibit bacterial translation and also to inhibit the growth of bacterial cells in culture. The most active of these compounds inhibit Streptococcus pneumoniae translation at concentrations of < 5 mu M and have minimum inhibitory concentrations (MICs) of < 8 mu g/mL against clinically relevant strains of bacteria.

  DOI：

  10.1021/jm060010w

文献信息

• Antibacterial compounds
  申请人：Hinman M. Mira

  公开号：US20070088040A1

  公开（公告）日：2007-04-19

  Bacterial protein synthesis-inhibiting compounds having formula (I) and salts, prodrugs, and salts of prodrugs thereof, processes for making the compounds and intermediates in the processes, compositions containing the compounds, and methods of using the compounds are disclosed.

  揭示了具有式(I)的细菌蛋白合成抑制化合物及其盐、前药、前药的盐，制备这些化合物的过程和过程中间体，含有这些化合物的组合物，以及使用这些化合物的方法。
• US7632946B2
  申请人：——

  公开号：US7632946B2

  公开（公告）日：2009-12-15
• Novel Antibacterial Class:  A Series of Tetracyclic Derivatives
  作者：Mira M. Hinman、Teresa A. Rosenberg、Darlene Balli、Candace Black-Schaefer、Linda E. Chovan、Douglas Kalvin、Philip J. Merta、Angela M. Nilius、Steve D. Pratt、Niru B. Soni、Frank L. Wagenaar、Moshe Weitzberg、Rolf Wagner、Bruce A. Beutel

  DOI：10.1021/jm060010w

  日期：2006.8.1

  We describe the synthesis and antibacterial activity of a series of tetracyclic naphthyridones. The members of this series act primarily via inhibition of bacterial translation and belong to the class of novel ribosome inhibitors (NRIs). In this paper we explore the structure-activity relationships (SAR) of these compounds to measure their ability both to inhibit bacterial translation and also to inhibit the growth of bacterial cells in culture. The most active of these compounds inhibit Streptococcus pneumoniae translation at concentrations of < 5 mu M and have minimum inhibitory concentrations (MICs) of < 8 mu g/mL against clinically relevant strains of bacteria.