5,6-二对甲苯基-[1,2,4]三嗪-3-硫醇 | 63031-39-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 中文名称: 5,6-二对甲苯基-[1,2,4]三嗪-3-硫醇
• 英文名称: 5,6-di-p-tolyl-1,2,4-triazine-3-thiol
• 英文别名: 5,6-di-p-tolyl-2H-[1,2,4]triazine-3-thione；3-mercapto-5,6-bis(4-methylphenyl)-1,2,4-triazine；5,6-bis(4-methylphenyl)-2H-1,2,4-triazine-3-thione
• CAS: 63031-39-0
• 化学式: C₁₇H₁₅N₃S
• mdl: MFCD02854670
• 分子量: 293.392
• InChiKey: ZYXMIZXTCAQENT-UHFFFAOYSA-N

物化性质

• 沸点：
  420.2±48.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.117
• 拓扑面积：
  68.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933699090

反应信息

• 作为反应物：
  描述：

  5,6-二对甲苯基-[1,2,4]三嗪-3-硫醇 在 sodium hydroxide 、 sodium methylate 、 sodium 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 3-methoxy-5,6-ditolyl-1,2,4-triazine
  参考文献：
  名称：

  5,6-DIARYL-1,2,4-TRIAZINES

  摘要：

  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。

  公开号：

  US04013654A1
• 作为产物：
  描述：

  对甲基苯甲醛 在 sodium cyanide 、 potassium dichromate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 14.0h， 生成 5,6-二对甲苯基-[1,2,4]三嗪-3-硫醇
  参考文献：
  名称：

  3-（烷硫基）-5,6-二芳基-1,2,4-三嗪作为微管蛋白聚合抑制剂的合成，抗增殖评价和分子对接研究

  摘要：

  背景：微管在细胞分裂和信号传导，细胞间运输和有丝分裂中的作用是众所周知的。因此，它们已成为几种抗癌药物的目标。 方法：制备了一系列3-（烷硫基）-5,6-二苯基-1,2,4-三嗪，并对其在体外对三种人类癌细胞系的细胞毒性进行了评估。通过MTT测定，人结肠癌细胞HT-29，人乳腺癌细胞系MCF-7，人白种人胃腺癌细胞系AGS以及成纤维细胞系NIH-3T3。进行对接模拟以将这些化合物在秋水仙碱结合位点插入微管蛋白的晶体结构中，以确定可能的结合模型。选择化合物5d作为最具活性的化合物来研究微管破裂。 结果：化合物5d显示出对所有细胞系的有效细胞毒性活性。分子建模研究表明，三嗪的某些衍生物强烈结合秋水仙碱结合位点。微管蛋白聚合测定试剂盒显示5d的细胞毒性活性可能与抑制微管蛋白聚合有关。 结论：合成化合物的细胞毒性和分子模型研究及其在微管蛋白聚合反应中的抑制活性表明，三嗪衍生物具有开发新的抗癌药的潜力。

  DOI：

  10.2174/1570180815666180727114216

文献信息

• 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。
• Synthesis of some 5,6-diaryl-1,2,4-triazine derivatives and investigation of their cyclooxygenase (COX) inhibitory activity
  作者：Merve Ertaş、Sevde Nur Biltekin、Barkın Berk、Leyla Yurttaş、Şeref Demirayak

  DOI：10.1080/10426507.2022.2062756

  日期：2022.11.2

  Within this study, 20 2-[(5,6-diaryl-1,2,4-triazin-3-yl)thio]-N-(benzo/thiazol-2-yl)acetamide derivatives (4a-4t) were synthesized and COX inhibitory activities of the compounds were investigated. ...

  在本研究中，合成了 20 个 2-[(5,6-diaryl-1,2,4-triazin-3-yl)thio]-N-(benzo/thiazol-2-yl)acetamide 衍生物 (4a-4t)研究了化合物的COX抑制活性。...
• Synthesis and neuroprotective activity of novel 1,2,4-triazine derivatives with ethyl acetate moiety against H 2 O2 and Aβ-induced neurotoxicity
  作者：Tuba Tuylu Kucukkilinc、Kamaledin Safari Yanghagh、Beyza Ayazgok、Mohammad Ali Roknipour、Farshad Homayouni Moghadam、Alireza Moradi、Saeed Emami、Mohsen Amini、Hamid Irannejad

  DOI：10.1007/s00044-017-2003-x

  日期：2017.11

  A series of 5,6-diaryl-1,2,4-triazine-3-thioacetate derivatives 3a-f, 8a-d and their regioisomer 8e were synthesized. Neuroprotective activity of compounds was assessed against H2O2 and beta-amyloid-induced toxicity in PC12 and SH-SY5Y cells respectively. Surprisingly, ethyl 2-(5-(4-chlorophenyl)-6-(4-methoxyphenyl)-3-thioxo-1,2,4-triazin-2(3H)-yl)acetate (8e) was the most potent compound in both tests with EC50 of 14 mu M in H2O2 induced apoptosis and also could increase 40% of cell viability revealed by cytometric analysis with Annexin V/PI staining. It was also shown that regioisomer 8e has more neuroprotective activity than Quercetin in beta-amyloid induced toxicity. Morphologic evaluation of cells by DAPI staining and TUNEL assay showed the effectiveness of this compound to improve neurite outgrowth in neuronal cells.
• Microwave-assisted synthesis and anticonvulsant activity of 5,6-bisaryl-1,2,4-triazine-3-thiol derivatives
  作者：Hamid Irannejad、Nima Naderi、Saeed Emami、Roja Qobadi Ghadikolaei、Alireza Foroumadi、Tina Zafari、Ali Mazar-Atabaki、Sakineh Dadashpour

  DOI：10.1007/s00044-013-0843-6

  日期：2014.5

  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.
• Über eine Aufsprengung des 1,2,4-Triazinringes zu Ketonen
  作者：Josef Klosa

  DOI：10.1002/ardp.19552881006

  日期：——