6-(2-氨基苯基)-3-疏基-1,2,4-噻嗪-5(4H)-酮 | 27161-64-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 6-(2-氨基苯基)-3-疏基-1,2,4-噻嗪-5(4H)-酮
• 中文别名: 6-(2-氨基苯基)-3-硫基亚甲基-2H-1,2,4-三嗪-5-酮；1,2,4-三嗪-5(4H)-酮,2,3-二氢-6-(2-氨基苯基)-3-硫代-；6-(2-氨基苯基)-3-巯基-1,2,4-三嗪-5(4H)-酮；6-(2-氨基苯基)-3-硫代-2H-1,2,4-三嗪-5-酮；1,2,4-三嗪-5(2H)-酮,3,4-二氢-6-(2-氨基苯基)-3-硫代-；6-(2-氨基-苯基)-3-巯基-4H-[1,2,4]三嗪-5-酮
• 英文名称: 3-thioxo-6-(2-aminophenyl)-1,2,4-triazin-5(2H,4H)-one
• 英文别名: 6-(2-aminophenyl)-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one；6-(2-aminophenyl)-3-thio-1,2,4-triazine-3,5-(2H,4H)-dione；6-(2’-aminophenyl)-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one；3-Mercapto-5-hydroxy-6-(2-aminophenyl)-1,2,4-triazin；6-(2-amino-phenyl)-3-thioxo-3,4-dihydro-2H-[1,2,4]triazin-5-one；6-o-Aminophenyl-3-thio-as-triazin-3,5-<2H, 4H>dion；6-(2-aminophenyl)-3-sulfanylidene-2H-1,2,4-triazin-5-one
• CAS: 27161-64-4
• 化学式: C₉H₈N₄OS
• mdl: MFCD23145003
• 分子量: 220.255
• InChiKey: TZQIBJNEKJDVAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 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：
  112
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2933699090

反应信息

• 作为反应物：
  描述：

  6-(2-氨基苯基)-3-疏基-1,2,4-噻嗪-5(4H)-酮 在 哌啶 哌啶 、 sodium acetate 作用下， 以 甲醇 、 乙醇 、 溶剂黄146 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Abdel-Rahman, Il Farmaco, 1991, vol. 46, # 2, p. 379 - 389

  摘要：

  DOI：
• 作为产物：
  描述：

  靛红 在 K₁₀ clay 、 NaOH adsorbed on neutral alumina 作用下， 以 水 为溶剂， 反应 0.05h， 生成 6-(2-氨基苯基)-3-疏基-1,2,4-噻嗪-5(4H)-酮
  参考文献：
  名称：

  AQUA MEDIATED ONE POT FACILE SYNTHESIS OF NOVEL THIOXO-1,2,4-TRIAZIN-5(2H)-ONE AND [1,2,4] TRIAZINO[5,6-A]INDOLE DERIVATIVES AND THEIR BIOLOGICAL ACTIVITIES

  摘要：

  Rapid and highly efficient one pot green chemical synthesis of substituted 6-(2-aminophenyl)-4-(4-substitutedphenyl)-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one and 8-substituted-3,5-dihydro-2H-[1,2,4]triazino[5,6-b]indole is carried out in aqueous medium under microwave irradiation. Improved synthesis of potent bioactive Schiff and N-Mannich bases of hexahydro-1H-indole-2,3-dione is also reported. The title compounds are easily accessible by various approaches; even waste free approaches have been developed. The operational simplicity, environmentally benign conditions and high yield achieved in a very short reaction time are major benefits that meet the requirements of green production, including saving energy and high efficiency. The results obtained under microwaves are compared with that of conventional heating. Structural assignments are based on spectroscopic data. Compounds have also been screened for antibacterial and antifungal activities.

  DOI：

  10.4067/s0717-97072012000400004

文献信息

• Discovery, Synthesis, and in vitro Evaluation of West Nile Virus Protease Inhibitors Based on the 9,10-Dihydro-3H,4aH-1,3,9,10a-tetraazaphenanthren-4-one Scaffold
  作者：Sanjay Samanta、Taian Cui、Yulin Lam

  DOI：10.1002/cmdc.201200136

  日期：2012.7

  study, a WNV NS2B–NS3 protease inhibitor with a 9,10‐dihydro‐3H,4aH‐1,3,9,10a‐tetraazaphenanthren‐4‐one scaffold was identified by screening a small library of non‐peptidic compounds. This initial hit was optimized by solution‐phase synthesis and screening of a focused library of compounds bearing this scaffold. This led to the identification of a novel, uncompetitive inhibitor (1a40, IC50=5.41±0.45 μM)

  西尼罗河病毒（WNV）是黄病毒科的成员，是一种由蚊子传播的病原体，每年引起大量人类感染。目前尚无疫苗和抗病毒疗法可用于人类。在这项研究中，通过筛选一个小的非肽库确定了一种具有9,10-dihydro-3 H，4a H -1,3,9,10a-四氮杂蒽酮-4-one骨架的WNV NS2B–NS3蛋白酶抑制剂化合物。通过固溶相合成和筛选带有该支架的化合物的重点文库，优化了最初的结果。这导致了一个新颖的鉴定，非竞争性抑制剂（1A40，IC 50 = 5.41±0.45μ中号）的WNV NS2B–NS3蛋白酶。该手性化合物与WNV蛋白酶的分子对接表明1a40的S 对映异构体似乎干扰了NS2B辅因子与NS3蛋白酶结构域之间的生产性相互作用。（S ] -1a40是抑制WNV NS3蛋白酶的首选异构体。
• Transcription factor modulating compounds and methods of use thereof
  申请人：Alekshun N. Michael

  公开号：US20060160799A1

  公开（公告）日：2006-07-20

  Substituted benzoimidazole compounds useful as anti-infectives that decrease resistance, virulence, or growth of microbes are provided. Methods of making and using substituted benzoimidazole compounds, as well as pharmaceutical preparations thereof, in, e.g., reducing antibiotic resistance and inhibiting biofilms.

  提供了作为抗感染剂有用的取代苯并咪唑化合物，可以降低微生物的抗药性、毒力或生长。提供了制备和使用取代苯并咪唑化合物的方法，以及其制药制剂，例如，用于降低抗生素抗性和抑制生物膜。
• 1,2,4-Triazine und kondensierte derivate—XII
  作者：G. Doleschall、K. Lempert

  DOI：10.1016/0040-4020(73)85008-2

  日期：1973.1

  3-Alkylthio-6-(2-aminophenyl)-1,2,4-triazin-5(2H)-ones (1) react with oxo compounds, the corresponding Schiff bases, as well as with methyl propionate to yield tricyclic products of type 8. The potential tautomeric equilibrium between compounds 8 and the corresponding Schiff bases 6 could not be demonstrated by spectroscopic means. The 1:1 adduct obtained with acetylacetone exists in solution as a

  3-烷硫基-6-（2-氨基苯基）-1,2,4-三嗪-5（2H）-1（1）与含氧化合物，相应的席夫碱以及丙酸甲酯反应生成三环产物类型8。化合物之间的潜在互变异构平衡8和相应的席夫碱6可以不通过光谱方法来证明。用乙酰丙酮获得的1：1加合物以8r和互变异构烯胺5的混合物形式存在于溶液中，而在结晶状态下仅存在纯烯胺5。1A与原酸酯反应生成更高的不饱和类似物21之8。讨论了制备化合物8和21的几种其他方法，其光谱以及它们的反应。
• Synthesis of Some Novel Fluorinated/Nonfluorinated <i>α</i>-Amino Acids, Bearing 3-Thioxo-5-oxo-1,2,4-triazin-6-yl and Steroidal Moieties, and Evaluation of Their Amylolytic Effects against Some Fungi, Part-II
  作者：Reda M. Abdel-Rahman、Wafa A. Bawazir

  DOI：10.1155/2020/9645949

  日期：2020.7.23

  4-triazin-6-yl and steroidal moieties have been obtained from condensation of the corresponding amino-triazinones with the steroid (Epiandrosterone). This was followed by the addition of HCN and, finally, acidic hydrolysis. The structure of the targets was established from their elemental analysis and spectral data. The amylolytic activity of the new products was evaluated against some fungi.

  一些带有 3-thioxo-5-oxo-1,2,4-triazin-6-yl 和甾体部分的新型氟化/非氟化 α-氨基酸是通过相应的氨基三嗪酮与类固醇（表雄酮）缩合获得的。然后加入 HCN，最后进行酸性水解。目标的结构是根据元素分析和光谱数据确定的。评估了新产品对某些真菌的淀粉分解活性。
• TRANSCRIPTION FACTOR MODULATING COMPOUNDS AND METHODS OF USE THEREOF
  申请人：LEVY Stuart B.

  公开号：US20110230523A1

  公开（公告）日：2011-09-22

  Substituted benzoimidazole compounds useful as anti-infectives that decrease resistance, virulence, or growth of microbes are provided. Methods of making and using substituted benzoimidazole compounds, as well as pharmaceutical preparations thereof, in, e.g., reducing antibiotic resistance and inhibiting biofilms.

  本发明提供了用作抗感染剂的取代苯并咪唑化合物，可以降低微生物的抗性、毒力或生长。本发明还提供了制备和使用取代苯并咪唑化合物的方法，以及制备其药物制剂，例如，在减少抗生素抗性和抑制生物膜方面的应用。