5-(2-Chlor-phenyl)-1,3,4-oxathiazol-2-on | 23589-72-2

• 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: 5-(2-Chlor-phenyl)-1,3,4-oxathiazol-2-on
• 英文别名: 5-(2-Chlorophenyl)-1,3,4-oxathiazol-2-one
• CAS: 23589-72-2
• 化学式: C₈H₄ClNO₂S
• 分子量: 213.644
• InChiKey: JBXYULKSXBGDJI-UHFFFAOYSA-N

物化性质

• 熔点：
  54 °C(Solv: isopropyl ether (108-20-3))
• 沸点：
  308.2±44.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• 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

• 作为反应物：
  描述：

  5-(2-Chlor-phenyl)-1,3,4-oxathiazol-2-on 、 thioacetophenone 以25%的产率得到
  参考文献：
  名称：

  WAI, KWOK-FAI;SAMMES, MICHAEL P., J. CHEM. SOC. PERKIN TRANS. PT 1,(1991) N, C. 183-187

  摘要：

  DOI：
• 作为产物：
  描述：

  邻氯苯甲酰氯 在 ammonium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 5-(2-Chlor-phenyl)-1,3,4-oxathiazol-2-on
  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

• Dithiazoles and related compounds. Part 3. Preparation of 5H-1,4,2-dithiazoles via 1,3-dipolar cycloadditions between nitrile sulphides and thiocarbonyl compounds, and some conversions into 3,5-diaryl-1,4,2-dithiazolium salts
  作者：Kwok-Fai Wai、Michael P. Sammes

  DOI：10.1039/p19910000183

  日期：——

  Thermolysis of 1,3,4 -oxathiazol-2-ones 3 in the presence of thiocarbonyl compounds gives modest to good yields of the little-known 5H-1,4,2-dithiazoles 1, the reaction being successful with diaryl, aryl alkyl and dialkyl ketones, and thiono esters, but failing with dithio esters and tertiary thioamides. The influence of substituents is discussed. Solvolysis of 5-ethoxy-5H-1,4,2-dithiazoles, derived

  在硫代羰基化合物的存在下，对1,3,4-氧杂噻唑-2-酮3的热解反应可得到中等程度的中等收率的鲜为人知的5 H -1,4,2-二噻唑1，该反应可成功地与二芳基，芳基烷基和二烷基酮，以及硫代酸酯，但不能与二硫代酯和叔硫代酰胺结合使用。讨论了取代基的影响。5-乙氧基-5 H -1,4,2-二噻唑类化合物，由硫代酸酯衍生，与高氯酸在乙酸酐中溶剂化，可高产率生成3,5-二芳基-1,4,2-二噻唑鎓盐9。
• Senning,A.; Kelly,P., Acta Chemica Scandinavica (1947), 1967, vol. 21, p. 1871 - 1878
  作者：Senning,A.、Kelly,P.

  DOI：——

  日期：——
• US4261728A
  申请人：——

  公开号：US4261728A

  公开（公告）日：1981-04-14
• 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.
• WAI, KWOK-FAI;SAMMES, MICHAEL P., J. CHEM. SOC. PERKIN TRANS. PT 1,(1991) N, C. 183-187
  作者：WAI, KWOK-FAI、SAMMES, MICHAEL P.

  DOI：——

  日期：——