5,6-bis(4-chlorophenyl)-1,2,4-triazine-3-thiol | 88300-12-3

• 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: 5,6-bis(4-chlorophenyl)-1,2,4-triazine-3-thiol
• 英文别名: 5,6-Bis(4-chlorophenyl)-1,2,4-triazine-3(2H)-thione；5,6-bis(4-chlorophenyl)-2H-1,2,4-triazine-3-thione
• CAS: 88300-12-3
• 化学式: C₁₅H₉Cl₂N₃S
• 分子量: 334.229
• InChiKey: LKNWZOVLHNNXIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,6-bis(4-chlorophenyl)-1,2,4-triazine-3-thiol 在 sodium hydroxide 、 乙醇 作用下， 生成 1-[5,6-bis(4-chlorophenyl)-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：

  1,2-双(4-氯苯基)-2-羟基乙酮 在 硝酸铵 、 copper diacetate 、 溶剂黄146 作用下， 生成 5,6-bis(4-chlorophenyl)-1,2,4-triazine-3-thiol
  参考文献：
  名称：

  一些 5,6-二芳基-1,2,4-三嗪衍生物的合成及其环氧合酶 (COX) 抑制活性的研究

  摘要：

  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。...

  DOI：

  10.1080/10426507.2022.2062756

文献信息

• CO₂-assisted synthesis of non-symmetric α-diketones directly from aldehydes<i>via</i>C–C bond formation
  作者：Pradipbhai Hirapara、Daniel Riemer、Nabanita Hazra、Jignesh Gajera、Markus Finger、Shoubhik Das

  DOI：10.1039/c7gc02425h

  日期：——

  CO2-assisted various symmetric and non-symmetric α-diketones have been synthesized directly from the corresponding aldehydes using transition metal-free catalysts. This method can even be applied to synthesize pharmaceuticals directly from aldehydes. The crucial role of CO2 has been investigated in detail and the mechanism is proposed on the basis of experiments and DFT calculations.

  已使用无过渡金属的催化剂直接从相应的醛中合成了CO 2辅助的各种对称和非对称α-二酮。该方法甚至可以直接用于从醛合成药物。详细研究了CO 2的关键作用，并在实验和DFT计算的基础上提出了机理。
• 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。
• 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.
• Synthesis and in vitro evaluation of novel 1,2,4-triazine derivatives as neuroprotective agents
  作者：Hamid Irannejad、Mohsen Amini、Fariba Khodagholi、Niloufar Ansari、Solaleh Khoramian Tusi、Mohammad Sharifzadeh、Abbas Shafiee

  DOI：10.1016/j.bmc.2010.04.097

  日期：2010.6.15

  The role of novel triazine derivatives against oxidative stress exerted by hydrogen peroxide on differentiated rat pheochromocytoma (PC12) cell line was examined and a consistent protection from H2O2-induced cell death, associated with a marked reduction in caspase-3 activation, was observed. Moreover, activation of NF-kappa B, a known regulator of a host of genes that involves in specific stress and inflammatory responses by H2O2, was greatly impaired by triazine pretreatment in differentiated PC12 cells. Neuroprotective effect of such compounds may represent a promising approach for treatment of neurodegenerative diseases. (C) 2010 Elsevier Ltd. All rights reserved.