5-(2-Naphthyl)-1,3,4-oxathiazol-2-one | 33743-82-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(2-Naphthyl)-1,3,4-oxathiazol-2-one
• 英文别名: 5-naphthalen-2-yl-1,3,4-oxathiazol-2-one
• CAS: 33743-82-7
• 化学式: C₁₂H₇NO₂S
• 分子量: 229.259
• InChiKey: WZELKOIZKSDATD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-萘甲酰氯 在 ammonium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 5-(2-Naphthyl)-1,3,4-oxathiazol-2-one
  参考文献：
  名称：

  3H-1,2,4-Dithiazol-3-one compounds as novel potential affordable antitubercular agents

  摘要：

  Small molecules with oxathiazol-2-one moiety were recently reported as potent inhibitors of Mycobacterium bovis var. bacilli Calmette-Guerin (BCG), among which HT1171 was the most potent and selective proteasome inhibitor. Herein we synthesized a series of novel compounds by bioisosteric replacement of the oxathiazol-2-one ring with 3H-1,2,4-dithiazol-3-one, and also fifteen 1,3,4-oxathiazol-2-one molecules in order for potency comparison and structure-activity relationship elucidation since their antibacterial effects on the virulent strains were not evaluated before. All the compounds were assessed for antitubercular activities on the virulent H37Rv strain by a serial dilution method. Among the tested compounds, 3H-1,2,4-dithiazol-3-one compound 4n was found to be the most active with a lowest MIC90 value of 1 mu g/mL. Furthermore, the cytotoxicities of all the compounds against normal human liver cell line L02 were determined by an MTT method. Compound 4n displayed a lower inhibitory ratio than HT1171 at the concentration of 100 mu M, indicating its better safety profile. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.065

文献信息

• [EN] AMINE COMPOUND AND SALT THEREOF<br/>[FR] COMPOSÉ D'AMINE ET SON SEL
  申请人：TOYAMA CHEMICAL CO LTD

  公开号：WO2013031694A1

  公开（公告）日：2013-03-07

  一般式 「式中、Ｒ１およびＲ２は、同一または異なって、ハロゲン原子、シアノ基、ニトロ基、置換されていてもよいＣ１－６アルキル基などを；Ｒ３は、置換されていてもよいピリジル基、置換されていてもよい単環の含酸素複素環式基などを；Ｒ４およびＲ５は、同一または異なって、水素原子、置換されていてもよいＣ１－６アルキル基などを；Ｘ１は、置換されていてもよい１，２－エチレン基、置換されていてもよい１，３－プロピレン基などを；Ｘ２は、酸素原子、硫黄原子、メチレン基などを；Ｚ１およびＺ２は、同一または異なって、窒素原子または式ＣＨで表される基を意味する。」で表される化合物またはその塩は、抗真菌剤として有用である。
• 3H-1,2,4-Dithiazol-3-one compounds as novel potential affordable antitubercular agents
  作者：Jianzhong Yang、Weiyi Pi、Li Xiong、Wei Ang、Tao Yang、Jun He、Yuanyuan Liu、Ying Chang、Weiwei Ye、Zhenling Wang、Youfu Luo、Yuquan Wei

  DOI：10.1016/j.bmcl.2012.12.065

  日期：2013.3

  Small molecules with oxathiazol-2-one moiety were recently reported as potent inhibitors of Mycobacterium bovis var. bacilli Calmette-Guerin (BCG), among which HT1171 was the most potent and selective proteasome inhibitor. Herein we synthesized a series of novel compounds by bioisosteric replacement of the oxathiazol-2-one ring with 3H-1,2,4-dithiazol-3-one, and also fifteen 1,3,4-oxathiazol-2-one molecules in order for potency comparison and structure-activity relationship elucidation since their antibacterial effects on the virulent strains were not evaluated before. All the compounds were assessed for antitubercular activities on the virulent H37Rv strain by a serial dilution method. Among the tested compounds, 3H-1,2,4-dithiazol-3-one compound 4n was found to be the most active with a lowest MIC90 value of 1 mu g/mL. Furthermore, the cytotoxicities of all the compounds against normal human liver cell line L02 were determined by an MTT method. Compound 4n displayed a lower inhibitory ratio than HT1171 at the concentration of 100 mu M, indicating its better safety profile. (C) 2012 Elsevier Ltd. All rights reserved.