N-[(3,4-dichlorophenyl)methyl]-N'-(6-fluoro-1,3-benzothiazol-2-yl)propane-1,3-diamine | 1374820-29-7

• 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: N-[(3,4-dichlorophenyl)methyl]-N'-(6-fluoro-1,3-benzothiazol-2-yl)propane-1,3-diamine
• CAS: 1374820-29-7
• 化学式: C₁₇H₁₆Cl₂FN₃S
• 分子量: 384.305
• InChiKey: PUCSCVJVHDGBAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  65.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氯-6-氟苯并噻唑 在 sodium methylate 、 sodium cyanoborohydride 、 potassium carbonate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.17h， 生成 N-[(3,4-dichlorophenyl)methyl]-N'-(6-fluoro-1,3-benzothiazol-2-yl)propane-1,3-diamine
  参考文献：
  名称：

  Preparation, antibacterial evaluation and preliminary structure–activity relationship (SAR) study of benzothiazol- and benzoxazol-2-amine derivatives

  摘要：

  In this study, a novel benzothiazol- and benzooxazol-2-amine scaffold with antibacterial activity was designed and synthesized. Preliminary structure-activity relationship analysis displayed that compound 8t with a 5,6-difluorosubstituted benzothiazole was found to be a potent inhibitor of Gram-positive pathogens, and exhibited some potential against drug-resistant bacteria and without cytotoxicity in therapeutic concentrations. In addition, molecular docking studies indicated that Staphylococcus aureus methionyl-tRNA synthetase might be the possible target of these compounds. Taken together, the present study provides an effective entry to the synthesis of a good lead for subsequent optimization and a new small molecule candidate drug for antibacterial therapeutics. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.079

文献信息

• Preparation, antibacterial evaluation and preliminary structure–activity relationship (SAR) study of benzothiazol- and benzoxazol-2-amine derivatives
  作者：Liang Ouyang、Yuhui Huang、Yuwei Zhao、Gu He、Yongmei Xie、Jie Liu、Jun He、Bo Liu、Yuquan Wei

  DOI：10.1016/j.bmcl.2012.03.079

  日期：2012.5

  In this study, a novel benzothiazol- and benzooxazol-2-amine scaffold with antibacterial activity was designed and synthesized. Preliminary structure-activity relationship analysis displayed that compound 8t with a 5,6-difluorosubstituted benzothiazole was found to be a potent inhibitor of Gram-positive pathogens, and exhibited some potential against drug-resistant bacteria and without cytotoxicity in therapeutic concentrations. In addition, molecular docking studies indicated that Staphylococcus aureus methionyl-tRNA synthetase might be the possible target of these compounds. Taken together, the present study provides an effective entry to the synthesis of a good lead for subsequent optimization and a new small molecule candidate drug for antibacterial therapeutics. (C) 2012 Elsevier Ltd. All rights reserved.