4-(2-amino-6-(2-nitrophenyl)-6H-1,3-thiazin-4-yl)phenol | 1408314-20-4

• 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: 4-(2-amino-6-(2-nitrophenyl)-6H-1,3-thiazin-4-yl)phenol
• 英文别名: 4-[2-amino-6-(2-nitrophenyl)-6H-1,3-thiazin-4-yl]phenol
• CAS: 1408314-20-4
• 化学式: C₁₆H₁₃N₃O₃S
• 分子量: 327.364
• InChiKey: PCSAGDPARUTILQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-chloro-N2,N4-bis(3-nitrophenyl)-1,3,5-triazine-2,4-diamine 、 4-(2-amino-6-(2-nitrophenyl)-6H-1,3-thiazin-4-yl)phenol 在 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.5h， 以76%的产率得到4-(2-(4,6-bis(3-nitrophenylamino)-1,3,5-triazin-2-ylamino)-6-(2-nitrophenyl)-6H-1,3-thiazin-4-yl)phenol
  参考文献：
  名称：

  Design, Synthesis, Antibacterial Activity, and Molecular Docking Studies of Novel Hybrid 1,3-Thiazine-1,3,5-Triazine Derivatives as Potential Bacterial Translation Inhibitor

  摘要：

  Some novel hybrid 1,3‐thiazine‐1,3,5‐triazine derivatives were synthesized and tested for antibacterial activity. Compounds 8c and 8f were found active against Gram positive and Gram negative microorganisms. Molecular docking studies have been performed on eubacterial ribosomal decoding A site (Escherichia coli 16S rRNA A site) to rationalize the probable mode of action, binding affinity, and orientation of the molecules at the active site of receptor. The structures of all these newly synthesized compounds were confirmed by their elemental analyses and spectral data techniques viz. IR, 1H NMR, 13C NMR, and mass.

  DOI：

  10.1111/j.1747-0285.2012.01430.x
• 作为产物：
  描述：

  邻硝基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 32.5h， 生成 4-(2-amino-6-(2-nitrophenyl)-6H-1,3-thiazin-4-yl)phenol
  参考文献：
  名称：

  Design, Synthesis, Antibacterial Activity, and Molecular Docking Studies of Novel Hybrid 1,3-Thiazine-1,3,5-Triazine Derivatives as Potential Bacterial Translation Inhibitor

  摘要：

  Some novel hybrid 1,3‐thiazine‐1,3,5‐triazine derivatives were synthesized and tested for antibacterial activity. Compounds 8c and 8f were found active against Gram positive and Gram negative microorganisms. Molecular docking studies have been performed on eubacterial ribosomal decoding A site (Escherichia coli 16S rRNA A site) to rationalize the probable mode of action, binding affinity, and orientation of the molecules at the active site of receptor. The structures of all these newly synthesized compounds were confirmed by their elemental analyses and spectral data techniques viz. IR, 1H NMR, 13C NMR, and mass.

  DOI：

  10.1111/j.1747-0285.2012.01430.x

文献信息

• Ceric ammonium nitrate (CAN) catalysed expeditious one-pot synthesis of 1,3-thiazine as IspE kinase inhibitor of Gram-negative bacteria using polyethylene glycol (PEG-400) as an efficient recyclable reaction medium
  作者：Udaya Pratap Singh、Hans Raj Bhat、Ramendra Kumar Singh

  DOI：10.1016/j.crci.2012.11.019

  日期：2013.5

  Résumé A novel, simple, inexpensive and efficient ceric ammonium nitrate (CAN) catalysed one-pot, multi-component synthesis of 1,3-thiazine in PEG-400 has been developed. These derivatives were identified as potent inhibitor of Gram-negative bacteria and acted via inhibition of 4-diphosphocytidyl-2-Cmethyl-D-erythritol (IspE) kinase, a novel target.

  简述 在硝酸铈铵（CAN）催化下，开发出了一种新颖、简单、廉价且高效的单锅多组分合成 1,3-噻嗪的 PEG-400。这些衍生物被鉴定为革兰氏阴性菌的强效抑制剂，通过抑制新靶点 4-二磷酸胞嘧啶-2-甲基-D-赤藓醇（IspE）激酶发挥作用。
• Design, Synthesis, Antibacterial Activity, and Molecular Docking Studies of Novel Hybrid 1,3-Thiazine-1,3,5-Triazine Derivatives as Potential Bacterial Translation Inhibitor
  作者：Udaya P. Singh、Manish Pathak、Vaibhav Dubey、Hans R. Bhat、Prashant Gahtori、Ramendra K. Singh

  DOI：10.1111/j.1747-0285.2012.01430.x

  日期：2012.10

  Some novel hybrid 1,3‐thiazine‐1,3,5‐triazine derivatives were synthesized and tested for antibacterial activity. Compounds 8c and 8f were found active against Gram positive and Gram negative microorganisms. Molecular docking studies have been performed on eubacterial ribosomal decoding A site (Escherichia coli 16S rRNA A site) to rationalize the probable mode of action, binding affinity, and orientation of the molecules at the active site of receptor. The structures of all these newly synthesized compounds were confirmed by their elemental analyses and spectral data techniques viz. IR, 1H NMR, 13C NMR, and mass.