3-(methylthio)-5,6-di p-tolyl-1,2,4-triazine | 63031-38-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(methylthio)-5,6-di p-tolyl-1,2,4-triazine
• 英文别名: 3-methylmercapto-5,6-bis(4-methylphenyl)-1,2,4-triazine；5,6-Bis(p-tolyl)-3-(methylthio)-as-triazine；5,6-bis(4-methylphenyl)-3-methylsulfanyl-1,2,4-triazine
• CAS: 63031-38-9
• 化学式: C₁₈H₁₇N₃S
• 分子量: 307.419
• InChiKey: YYOHQNLEWWGIMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  172-174 °C
• 沸点：
  478.3±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  3-(methylthio)-5,6-di p-tolyl-1,2,4-triazine 以 乙醇 为溶剂， 以95.1%的产率得到1-[5,6-bis(4-methylphenyl)-1,2,4-triazin-3-yl]-4-piperidinol
  参考文献：
  名称：

  Diaryl-pyrazine derivatives affecting GABA binding

  摘要：

  本发明涉及一些氨基-5,6-二芳基吡嗪，可用作GABA和苯二氮平结合的激活剂。

  公开号：

  US04513135A1
• 作为产物：
  描述：

  4,4'-二甲基联苯甲酰 在 盐酸 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 2.17h， 生成 3-(methylthio)-5,6-di p-tolyl-1,2,4-triazine
  参考文献：
  名称：

  Microwave-assisted synthesis and anticonvulsant activity of 5,6-bisaryl-1,2,4-triazine-3-thiol derivatives

  摘要：

  A series of 5,6-bisaryl-1,2,4-triazine-3-thiol derivatives were synthesized through microwave-promoted chemistry by condensation of the aromatic 1,2-diketones and thiosemicarbazide in a mixed green solvent. Subsequently, S-alkylation of 1,2,4-triazine-3-thiols afforded S-substituted derivatives. The anticonvulsant activity of the synthesized compounds was evaluated in vivo by electroshock and pentylenetetrazole (PTZ)-induced seizures tests. Among them, compound 4a bearing 4-pyridylmethylthio moiety on the triazine ring showed the highest protection in both electroshock and PTZ-induced seizures tests. Compound 4a showed no sign of neurotoxicity at the dose of 100 mg/kg in both rotarod and chimney tests.

  DOI：

  10.1007/s00044-013-0843-6

文献信息

• Room-Temperature Ionic Liquid–DMSO Promoted and Improved One-Pot Synthesis of 5,6-Diaryl-1,2,4-triazines
  作者：Riyaj S. Tamboli、Rajani Giridhar、Hemant M. Mande、Shailesh R. Shah、Mange Ram Yadav

  DOI：10.1080/00397911.2014.891040

  日期：2014.8.3

  improved and rapid one-pot synthesis of 5,6-diarylsubstituted-1,2,4-triazines in a mixture of room-temperature ionic liquid 1,3-dibutylimidazolium bromide [Bbim]+Br− and dimethylsulfoxide (DMSO) is described without the need for any added catalyst. Different polar aprotic solvents were screened along with ionic liquids and a synergistic effect with DMSO has been found. The predominance of one regioisomer

  摘要 在室温离子液体溴化 1,3-二丁基咪唑鎓 [Bbim]+Br− 和二甲亚砜 (DMSO) 的混合物中改进和快速一锅法合成 5,6-二芳基取代的-1,2,4-三嗪是无需任何添加的催化剂进行描述。与离子液体一起筛选了不同的极性非质子溶剂，并发现了与 DMSO 的协同效应。还研究了在不同反应温度下一种区域异构体优于另一种区域异构体的情况。通过简单的后处理程序实现了在短时间内获得出色分离产量的一锅法。离子液体被有效回收并重复使用3次而没有失去催化作用。所有化合物均通过红外、核磁共振、质谱和元素分析进行​​表征。图形概要
• 5,6-Diaryl-1,2,4-triazines as topically-active anti-inflammatory agents
  申请人：Eli Lilly and Company

  公开号：US04018923A1

  公开（公告）日：1977-04-19

  A method of treating inflammation which utilizes topically-active 5,6-diaryl-1,2,4-triazines having the formula, ##STR1## wherein R is hydrogen or --(X).sub.n R.sub.1, in which X is either O or S, n is an integer which is either 0 or 1, and R.sub.1 is C.sub.1 -C.sub.8 alkyl, C.sub.7 -C.sub.8 aralkyl, C.sub.3 -C.sub.8 cycloalkyl, or C.sub.4 -C.sub.8 (cycloalkyl)alkyl; and R.sub.2 and R.sub.3 independently are halo, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, or di(C.sub.1 -C.sub.3 alkyl)amino, with the proviso that at least one of R.sub.2 and R.sub.3 is halo or C.sub.1 -C.sub.3 alkyl; and the pharmaceutically-acceptable acid addition salts of basic members thereof.

  一种治疗炎症的方法，利用具有以下化学式的局部活性的5,6-二芳基-1,2,4-三嗪：其中R为氢或--(X).sub.n R.sub.1，其中X为O或S，n为0或1的整数，R.sub.1为C.sub.1 -C.sub.8烷基，C.sub.7 -C.sub.8芳基烷基，C.sub.3 -C.sub.8环烷基，或C.sub.4 -C.sub.8(环烷基)烷基；R.sub.2和R.sub.3独立地为卤素、C.sub.1 -C.sub.3烷基、C.sub.1 -C.sub.3烷氧基或二(C.sub.1 -C.sub.3烷基)氨基，但R.sub.2和R.sub.3中至少有一个为卤素或C.sub.1 -C.sub.3烷基；以及其药学上可接受的酸盐。
• 5,6-DIARYL-1,2,4-TRIAZINES
  申请人：Eli Lilly and Company

  公开号：US04013654A1

  公开（公告）日：1977-03-22

  5,6-Diaryl-1,2,4-triazines, topically-active anti-inflammatory agents, having the formula, ##STR1## wherein R is hydrogen or --(X).sub.n R.sub.1, in which X is either O or S, n is an integer which is either 0 or 1, and R.sub.1 is C.sub.1 -C.sub.8 alkyl, C.sub.7 -C.sub.8 aralkyl, C.sub.3 -C.sub.8 cycloalkyl, or C.sub.4 -C.sub.8 (cycloalkyl)alkyl; and R.sub.2 and R.sub.3 independently are halo, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, or di(C.sub.1 -C.sub.3 alkyl)amino, with the proviso that at least one of R.sub.2 and R.sub.3 is halo or C.sub.1 -C.sub.3 alkyl; and the pharmaceutically-acceptable acid addition salts of basic members thereof.

  5,6-二芳基-1,2,4-三嗪是一种具有局部活性的抗炎药物，其化学式为##STR1##其中R为氢或--(X).sub.n R.sub.1，其中X为氧或硫，n是0或1的整数，R.sub.1为C.sub.1-C.sub.8烷基，C.sub.7-C.sub.8芳基烷基，C.sub.3-C.sub.8环烷基或C.sub.4-C.sub.8(环烷基)烷基；R.sub.2和R.sub.3独立地为卤素，C.sub.1-C.sub.3烷基，C.sub.1-C.sub.3烷氧基或二(C.sub.1-C.sub.3烷基)氨基，但R.sub.2和R.sub.3中至少有一个为卤素或C.sub.1-C.sub.3烷基；以及其药用可接受的酸盐。
• Synthesis and Anti-Inflammatory Evaluation of 3-Methylthio-1,2,4-Triazines, 3-Alkoxy-1,2,4-Triazines, and 3-Aryloxy-1,2,4-Triazines
  作者：William P. Heilman、R.D. Heilman、James A. Scozzie、R.J. Wayner、James M. Gullo、Zaven S. Ariyan

  DOI：10.1002/jps.2600690310

  日期：1980.3

  the 25 compounds were selected for dose-response evaluation in the carrageenan assay based on their relative toxicity and anti-inflammatory activity. Neurotoxicity of the 13 triazines was estimated by determination of NTD50 values in mice. Five of the 13 compounds tested in the dose-response assay were active in terms of anti-inflammatory efficacy (ED50 values) and lack of overt neurotoxicity (NTD50 values)

  为了开发无胃肠道并发症的非酸性，非甾体类抗炎药，合成了一系列不对称三嗪，并在角叉菜胶诱导的踏板水肿试验中评估了抗炎功效。通过确定小鼠的LD50近似值来估计毒性。25种化合物的活性可与标准消炎痛相媲美。根据角叉菜胶的相对毒性和抗炎活性，从25种化合物中选择13种进行剂量反应评估。通过测定小鼠中的NTD50值来评估13种三嗪的神经毒性。与消炎痛相比，在剂量反应试验中测试的13种化合物中，有5种具有抗炎功效（ED50值）且没有明显的神经毒性（NTD50值）。为了确定这五种发展型三嗪对慢性炎症的作用，在佐剂诱导的多关节炎试验中对其进行了评估。在该试验中，在减少佐剂诱导的炎症方面，可与消炎痛相媲美。
• 1,2,4-Triazine and pyrazine derivatives
  申请人：ELI LILLY AND COMPANY

  公开号：EP0088593A2

  公开（公告）日：1983-09-14

  This invention relates to certain amino-5,6-diaryl-1,2,4--triazines and -pyrazines useful as activators of GABA and benzodiazepine binding.

  本发明涉及某些可作为 GABA 和苯并二氮杂卓结合激活剂的氨基-5,6-二基-1,2,4-三嗪和吡嗪。