2-氯硫代烟碱酰胺 | 1240596-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-氯硫代烟碱酰胺
• 英文名称: 2-Chloropyridine-3-carbothioamide
• CAS: 1240596-59-1
• 化学式: C₆H₅ClN₂S
• mdl: MFCD16659867
• 分子量: 172.638
• InChiKey: UIBDAMGTUPCTOT-UHFFFAOYSA-N

物化性质

• 沸点：
  319.8±52.0 °C(Predicted)
• 密度：
  1.424±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  2-氯硫代烟碱酰胺 、 chlorocarbonylsulfinyl chloride 以 四氢呋喃 为溶剂， 反应 16.0h， 以83%的产率得到5-(2-Chloro-3-pyridyl)-1,2,4-dithiazol-3-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
• 作为产物：
  描述：

  2-氯烟酰胺 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 生成 2-氯硫代烟碱酰胺
  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

• Multicomponent synthesis of diphenyl-1,3-thiazole-barbituric acid hybrids and their fluorescence property studies
  作者：Alok Mahata、Prabhas Bhaumick、Anoop Kumar Panday、Rahul Yadav、Tasneem Parvin、Lokman H. Choudhury

  DOI：10.1039/d0nj00406e

  日期：——

  arylglyoxal and barbituric acid in water medium was developed. In this second method, in situ thioamides were prepared at room temperature from the reaction of alkyl/aryl nitriles and ammonium sulphide in aqueous medium. Arylglyoxal and barbituric acid were added to the in situ thioamides after neutralizing the reaction medium to provide trisubstituted thiazoles linked with barbituric acid derivatives. Some

  通过两种无催化剂的方法，从容易获得的起始原料中制备了一系列新型的二苯基-1,3-噻唑连接的巴比妥酸杂化物（4）。芳基乙二醛，巴比妥酸和芳基硫酰胺在3-4滴水和液体辅助研磨（LAG）存在下的反应在30分钟内提供了与巴比妥酸部分束缚的相应三取代噻唑。或者，开发了在水介质中涉及芳基腈，硫化铵，芳基乙二醛和巴比妥酸的连续两步一锅法。在第二种方法中，室温下由烷基/芳基腈和硫化铵在水性介质中的反应制备原位硫酰胺。将芳基乙二醛和巴比妥酸添加到中和反应介质后，将其原位加入硫代酰胺中，得到与巴比妥酸衍生物连接的三取代噻唑。我们的一些合成分子在DMSO介质中显示出非常好的量子产率的荧光性质。我们还观察到这些噻唑衍生物的荧光量子产率取决于R 1和R 3的电子给电子/吸电子特征的类型。R 2对调节荧光特性的影响很小。这项工作的主要特点是无催化剂反应，广泛的底物范围，绿色反应条件（在水介质中的液体辅助研磨和室温反应
• New promising methods of synthesis of pyridinecarbothioamides
  作者：N. Yu. Khromova、S. I. Malekin、A. V. Kutkin、V. B. Kondrat’ev

  DOI：10.1134/s1070363215100138

  日期：2015.10

  use of phosphorus pentasulfide as a thiontion agent were developed. The first method was based on the reaction of cyanopyridine with phosphorus pentasulfide in alcoholic ammonium solution followed by hydrolysis. The method provided the corresponding thioamides in 60–90% yield. The second procedure included the reaction of phosphorus pentasulfide with 4-cyanopyridine in aqueous ammonia solution, which

  开发了使用五硫化二磷作为硫磺化剂从相应的氰基吡啶合成吡啶碳硫基酰胺的新方法。第一种方法是基于氰基吡啶与五硫化二磷在乙醇铵溶液中的反应，然后进行水解。该方法以60–90％的产率提供了相应的硫代酰胺。第二个步骤包括五硫化二磷与4-氰基吡啶在氨水溶液中的反应，这导致定量产率地形成吡啶-4-碳硫代酰胺。
• KLIMESOVA, V.;VINSOVA, J.;CELADNIK, M.;ODLEROVA, Z., CS. FARM., 39,(1990) N, C. 104-108
  作者：KLIMESOVA, V.、VINSOVA, J.、CELADNIK, M.、ODLEROVA, Z.

  DOI：——

  日期：——
• 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.