5-(pyrazin-2-yl)-1,3,4-oxathiazol-2-one | 345631-84-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-(pyrazin-2-yl)-1,3,4-oxathiazol-2-one
• 英文别名: 1,3,4-Oxathiazol-2-one, 5-pyrazinyl-；5-pyrazin-2-yl-1,3,4-oxathiazol-2-one
• CAS: 345631-84-7
• 化学式: C₆H₃N₃O₂S
• 分子量: 181.175
• InChiKey: MRKHBZRXPVADHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 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：
  89.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  吡嗪-2-甲酰氯 在 ammonium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 5-(pyrazin-2-yl)-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

• Antimycobacterial Activity of Substituted Isosteres of Pyridine- and Pyrazinecarboxylic Acids. 2.
  作者：Mikail H. Gezginci、Arnold R. Martin、Scott G. Franzblau

  DOI：10.1021/jm000350w

  日期：2001.5.1

  included in this study due to their interesting activity. Pivaloyloxymethyl derivatives of the isosteres were also prepared in order to increase their lipophilicity and therefore improve their cellular permeability. The derivatized isosteres were expected to be biotransformed by esterases to the active species after penetration of the mycobacterial cell wall. Biological properties of the compounds were compared

  合成被1,2,4-恶二唑-5-酮，1,2,4-恶二唑-5-硫酮和1,3,4-恶二唑啉-2-酮取代的吡啶和吡嗪，并测试其对结核分枝杆菌的抵抗力。文献中记录了前两个环系统起羧酸等位异构体的作用。后一系列作为1,2,4-噻二唑-3-酮的可能合成中间体被合成，由于其有趣的活性而被纳入本研究。还制备了等排烷的新戊酰氧基甲基衍生物，以增加其亲脂性，并因此改善其细胞渗透性。在分枝杆菌细胞壁穿透后，衍生的等排体有望被酯酶生物转化为活性物种。将化合物的生物学特性与吡嗪酸和烟酸的未修饰极性等排体进行了比较。大多数化合物表现出的活性为吡嗪酰胺效力的0.5至16倍。
• Optimization and Evaluation of 5-Styryl-Oxathiazol-2-one<i>Mycobacterium tuberculosis</i>Proteasome Inhibitors as Potential Antitubercular Agents
  作者：Francesco Russo、Johan Gising、Linda Åkerbladh、Annette K. Roos、Agata Naworyta、Sherry L. Mowbray、Anders Sokolowski、Ian Henderson、Torey Alling、Mai A. Bailey、Megan Files、Tanya Parish、Anders Karlén、Mats Larhed

  DOI：10.1002/open.201500001

  日期：2015.6

  5‐styryl‐oxathiazol‐2‐ones as inhibitors of the Mycobacterium tuberculosis (Mtb) proteasome. As part of the study, the structure–activity relationship of oxathiazolones as Mtb proteasome inhibitors has been investigated. Furthermore, the prepared compounds displayed a good selectivity profile for Mtb compared to the human proteasome. The 5‐styryl‐oxathiazol‐2‐one inhibitors identified showed little activity

  这是5-苯乙烯基草并恶唑-2-酮类药物作为结核分枝杆菌（Mtb）蛋白酶体抑制剂的首次报道。作为研究的一部分，已研究了草硫唑酮作为Mtb蛋白酶体抑制剂的构效关系。此外，与人蛋白酶体相比，制备的化合物对Mtb表现出良好的选择性。鉴定出的5-styryl-oxathiazol-2-one抑制剂对复制Mtb几乎没有活性，但对非复制细菌具有快速杀菌作用。（E）‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐ 4 ‐‐‐‐‐‐‐‐yré‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐‐ was ‐‐‐‐‐‐‐‐‐‐一was- ‐‐‐‐‐‐‐‐‐‐‐‐ 4？-‐‐‐‐‐‐‐‐‐‐‐‐‐‐5å？-‐‐‐‐‐‐‐‐‐‐‐‐ was？-‐‐‐‐‐‐‐‐‐‐‐‐waså？-‐‐‐ 5-（4-Chlorostyryl）‐1,3,4-Oxathiazol−2-1？的效果最佳，在所有测试浓度下的集落形成单位（CFU）/ mL仅在小于
• PROTEASOME INHIBITORS AND THEIR USE IN TREATING PATHOGEN INFECTION AND CANCER
  申请人：Nathan Carl

  公开号：US20110118274A1

  公开（公告）日：2011-05-19

  The present invention relates to proteasome inhibitors and their use in methods of treating a subject for a pathogen infection or cancer. The methods involve administering to the subject a compound of Formula (I). (I) where: Q is Formula or Formula, where the crossing dashed line illustrates the bond formed joining Q to the rest of the compound of Formula (I). The remainder of substituents of the compound of Formula (I) are defined in the present application.
• [EN] PROTEASOME INHIBITORS AND THEIR USE IN TREATING PATHOGEN INFECTION AND CANCER<br/>[FR] INHIBITEURS DE PROTÉASOME ET LEUR UTILISATION DANS LE TRAITEMENT D'UNE AFFECTION PATHOGÈNE ET DU CANCER
  申请人：CORNELL RES FOUNDATION INC

  公开号：WO2009026579A1

  公开（公告）日：2009-02-26

  The present invention relates to proteasome inhibitors and their use in methods of treating a subject for a pathogen infection or cancer. The methods involve administering to the subject a compound of Formula (I). (I) where: Q is Formula or Formula, where the crossing dashed line illustrates the bond formed joining Q to the rest of the compound of Formula (I). The remainder of substituents of the compound of Formula (I) are defined in the present application.
• [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。