6-ethyl-3-sulfanylidene-2H-1,2,4-triazin-5-one | 452-12-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 6-ethyl-3-sulfanylidene-2H-1,2,4-triazin-5-one
• 英文别名: 6-ethyl-3-mercapto-1,2,4-triazin-5-ol；6-ethyl-3-thioxo-3,4-dihydro-2H-[1,2,4]triazin-5-one；5-Hydroxy-3-mercapto-6-ethyl-1,2,4-triazin
• CAS: 452-12-0
• 化学式: C₅H₇N₃OS
• 分子量: 157.2
• InChiKey: NBZOSCCFHLYVDE-UHFFFAOYSA-N

物化性质

• 熔点：
  168 °C(Solv: water (7732-18-5))
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  85.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933699090

反应信息

• 作为反应物：
  描述：

  6-ethyl-3-sulfanylidene-2H-1,2,4-triazin-5-one 在 sodium hydroxide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 8.0h， 生成 3-(4-(2,6-difluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)-6-ethyl-1,2,4-triazin-5-ol
  参考文献：
  名称：

  Original 2-(3-Alkoxy-1H-pyrazol-1-yl)azines Inhibitors of Human Dihydroorotate Dehydrogenase (DHODH)

  摘要：

  Following our discovery of human dihydroorotate dehydrogenase (DHODH) inhibition by 2-(3-alkoxy-1H-pyrazol-1-yl)pyrimidine derivatives as well as 2-(4-benzyl-3-ethoxy-5-methyl-1H-pyrazol-1-yl)-5-methylpyridine, we describe here the syntheses and evaluation of an array of azine-bearing analogues. As in out previous report, the structure activity study of this series of human DHODH inhibitors was based on a phenotypic assay measuring measles virus replication. Among other inhibitors, this round of syntheses and biological evaluation iteration led to the highly active 5-cyclopropyl-2-(4-(2,6-difluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)-3-fluoropyridine. Inhibition of DHODH by this compound was confirmed in an array of in vitro assays, including enzymatic tests and cell-based assays for viral replication and cellular growth. This molecule was found to be more active than the known inhibitors of DHODH, brequinar and teriflunomide, thus opening perspectives for its Use as a tool or for the design of an original series of immunosuppressive agent. Moreover, because other Series of inhibitors of human DHODH have been found to also affect Plasmodium falciparum DHODH, all the compounds were assayed for their effect on P. falciparum growth. However, the modest in vitro inhibition solely observed for two compounds did not correlate with their inhibition of P. falciparum DHODH.

  DOI：

  10.1021/acs.jmedchem.5b00606
• 作为产物：
  描述：

  2-(2-carbamothioylhydrazono)butanoic acid 在 sodium carbonate 作用下， 以 水 为溶剂， 反应 3.0h， 以86%的产率得到6-ethyl-3-sulfanylidene-2H-1,2,4-triazin-5-one
  参考文献：
  名称：

  Original 2-(3-Alkoxy-1H-pyrazol-1-yl)azines Inhibitors of Human Dihydroorotate Dehydrogenase (DHODH)

  摘要：

  Following our discovery of human dihydroorotate dehydrogenase (DHODH) inhibition by 2-(3-alkoxy-1H-pyrazol-1-yl)pyrimidine derivatives as well as 2-(4-benzyl-3-ethoxy-5-methyl-1H-pyrazol-1-yl)-5-methylpyridine, we describe here the syntheses and evaluation of an array of azine-bearing analogues. As in out previous report, the structure activity study of this series of human DHODH inhibitors was based on a phenotypic assay measuring measles virus replication. Among other inhibitors, this round of syntheses and biological evaluation iteration led to the highly active 5-cyclopropyl-2-(4-(2,6-difluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)-3-fluoropyridine. Inhibition of DHODH by this compound was confirmed in an array of in vitro assays, including enzymatic tests and cell-based assays for viral replication and cellular growth. This molecule was found to be more active than the known inhibitors of DHODH, brequinar and teriflunomide, thus opening perspectives for its Use as a tool or for the design of an original series of immunosuppressive agent. Moreover, because other Series of inhibitors of human DHODH have been found to also affect Plasmodium falciparum DHODH, all the compounds were assayed for their effect on P. falciparum growth. However, the modest in vitro inhibition solely observed for two compounds did not correlate with their inhibition of P. falciparum DHODH.

  DOI：

  10.1021/acs.jmedchem.5b00606

文献信息

• [DE] AMID-SUBSTITUIERTE 1,2,4-TRIAZIN-5 (2H)-ONE ZUR BEHANDLUNG VON CHRONISCH INFLAMMATORISCHEN KRANKHEITEN<br/>[EN] AMIDE-SUBSTITUTED 1,2,4-TRIAZIN-5(2H)-ONES FOR THE TREATMENT OF CHRONICALLY INFLAMMATORY DISEASES<br/>[FR] 1,2,4-TRIAZINO-5(2H)-ONES A SUBSTITUTION AMIDE DESTINEES AU TRAITEMENT DE MALADIES INFLAMMATOIRES CHRONIQUES
  申请人：BAYER HEALTHCARE AG

  公开号：WO2005003118A1

  公开（公告）日：2005-01-13

  Die Erfindung betrifft Amid-substituierte 1,2,4-Triazin-5(2H)-one und Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Herstellung von Arzneimitteln zur Behandlung und/oder Prophylaxe von Krankheiten, insbesondere von chronisch inflammatorischen Erkrankungen, wie z.B. Erkrankungen des rheumatoiden Formenkreises, und Herz-Kreislauf-Erkrankungen, wie z.B. Dyslipidämien, Arteriosklerose und koronare Herzerkrankungen Formel (I).

  这项发明涉及取代酰胺的1,2,4-三嗪-5(2H)-酮以及其制备方法，以及它们用于制备治疗和/或预防疾病的药物，特别是慢性炎症性疾病，如风湿性疾病等，以及心血管疾病，如血脂异常、动脉粥样硬化和冠心病的用途，如化学式(I)。
• Transformation of a Cu ^II Thiazolo‐1,2,4‐triazine Derivative from a Metastable Coordination Network to a Monomer in Solution and Vapor Conditions
  作者：Akiko Hori、Takahiro Kikuchi、Kumiko Miyamoto、Takashi Okano、Chihiro Kachi‐Terajima、Hiroshi Sakaguchi

  DOI：10.1002/ejic.201100119

  日期：2011.7

  through bis(μ-chloro) linkages in a 2-propanol solution. The crystals show dynamic and irreversible structural transformation into blue crystals of [CuCl2(3a)2] (6a; Cu/3a = 1:2) not only in solution but also in vapor conditions. As 5a and 6a are ferromagnetic and paramagnetic, respectively, the transformation of 5a was monitored by magnetic susceptibility measurements in the solid state, and χT of 5a decreased

  虽然单核配合物主要是从 Cu2+ 离子和苯基、乙基或苄基取代的噻唑基-1,2,4-三嗪衍生物中获得的，但独特的亚稳橙黄色晶体 [CuCl2(3a)]n (5a; Cu/3a = 1:1) 与苯基取代的衍生物 3a 在 2-丙醇溶液中通过双 (μ-氯) 键获得作为一维配位聚合物。晶体显示出动态且不可逆的结构转变为 [CuCl2(3a)2] (6a; Cu/3a = 1:2) 蓝色晶体，不仅在溶液中而且在蒸气条件下。由于 5a 和 6a 分别是铁磁性和顺磁性的，因此 5a 的转变是通过固态磁化率测量来监测的，并且 5a 的 χT 根据颜色变化而降低。5a 的 XRD 谱也转变为新的聚集态，归因于一维网络的歧化形成单核络合物和结晶状态的溶剂化金属离子。这种不寻常的一维网络通过苯基和三嗪部分之间的分子间 π-π 堆积来稳定，对乙基和苄基取代的复合物的比较研究显示没有聚合物结构。通过 X 射线晶体学研究和
• Gut; Prystas, Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 2986,2988
  作者：Gut、Prystas

  DOI：——

  日期：——
• WO2015/155680
  申请人：——

  公开号：——

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• Hakimi, Fatemeh; Tabatabaee, Masoumeh; Heravi, Majid M., E-Journal of Chemistry, 2011, vol. 8, # 2, p. 798 - 802
  作者：Hakimi, Fatemeh、Tabatabaee, Masoumeh、Heravi, Majid M.、Roshani, Mina、Bamoharam, Fatemeh F.

  DOI：——

  日期：——