3-(4-chloro-phenyl)-5-methylsulfanyl-1H-[1,2,4]triazole | 57295-49-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-chloro-phenyl)-5-methylsulfanyl-1H-[1,2,4]triazole
• 英文别名: 3-(4-chlorophenyl)-5-methylthio-1,2,4-triazole；3-(4-chloro-phenyl)-5-methylsulfanyl-1H-[1,2,4]triazole；3-(4-Chlor-phenyl)-5-methylmercapto-1H-[1,2,4]triazol；5-(4-chlorophenyl)-3-methylsulfanyl-1H-1,2,4-triazole
• CAS: 57295-49-5
• 化学式: C₉H₈ClN₃S
• mdl: MFCD00124840
• 分子量: 225.702
• InChiKey: YXVAYMRODBYXIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  154 °C
• 沸点：
  424.9±47.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-chloro-phenyl)-5-methylsulfanyl-1H-[1,2,4]triazole 在 potassium permanganate 、 溶剂黄146 作用下， 反应 2.0h， 以94%的产率得到3-(4-chlorophenyl)-5-methylsulfonyl-1H-1,2,4-triazole
  参考文献：
  名称：

  Preparation of 5-aryl-3-alkylthio-l,2,4-triazoles and corresponding sulfones with antiinflammatory–analgesic activity

  摘要：

  In this study, a series of 5-aryl-3-alkylthio-1,2,4-triazoles and corresponding sulfones were prepared with the objective of developing better analgesic-antiinflammatory compounds with minimum ulcerogenic risk. The structures of the compounds were elucidated by spectral and elemental analysis. The compounds were assayed per os in mice for their antiinflammatory and analgesic activity as well as the ulcerogenic risk and acute toxicity. Several of these compounds showed significant activity. Alkylsulfone derivatives were found to be much more potent analgesic-antimflammatory agents than the corresponding alkylthio analogs. Compounds 9 and 11 were the most active of the series in both analgesic and antiinflammatory activity tests. In contrast to reference compound acetyl salicylic acid, these compounds did not induce gastric lesions in the stomach of experimental animals at the doses that exhibited analgesic/antiinflammatory activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.11.029
• 作为产物：
  描述：

  N-[bis(methylsulfanyl)methylidene]-4-chlorobenzamide 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以95%的产率得到3-(4-chloro-phenyl)-5-methylsulfanyl-1H-[1,2,4]triazole
  参考文献：
  名称：

  New Synthesis of DimethylN-Aroylcarbimidodithioates and 3-Aryl-5-methylthio-1H-1,2,4-triazoles

  摘要：

  DOI：

  10.1055/s-1981-29525

文献信息

• Synthesis and Evaluation of Anti-inflammatory and Analgesic Activities of New 1,2,4-triazole Derivatives
  作者：Fatemeh Ahmadi、Mohsen Ghayahbashi、Mohammad Sharifzadeh、Eskandar Alipoiur、Seyed Ostad、Mohsen Vosooghi、Hamid khademi、Mohsen Amini

  DOI：10.2174/1573406410666140613154507

  日期：2014.12.18

  In this study, the synthesis, anti-inflammatory and analgesic activities of eight new 5-thioalkyl-1,3-diaryl-1,2,4- triazole derivatives were reported. For the anti-inflammatory study, the carrageenan-induced rat paw edema model was used. The test compounds in 50 mg/kg and 100 mg/kg were injected as IP and paw edema was determined. The results showed that some of the compounds have good activity compared to the references drug, indomethacin. For analgesic activity, the test compounds were studied using the in Tail-flick test model in 50 and 100 mg/kg as IP injections. Their analgesic activities were determined after 30 min via latency time assay. Statistical analysis showed that all test compounds have antinociceptive activity in the range of 24% -47% as compared to the control with a dose of 50 mg/kg. However, all tested compounds have analgesic activity lower than the standard drug, morphine.

  在本研究中，报道了八种新型5-硫代烷基-1,3-二芳基-1,2,4-三唑衍生物的合成、抗炎及镇痛活性。对于抗炎研究，采用了卡拉胶诱导的大鼠足跖肿胀模型。测试化合物分别以50 mg/kg和100 mg/kg的剂量通过腹腔注射后测定足跖肿胀情况。结果表明，与参考药物吲哚美辛相比，某些化合物显示出良好的活性。在镇痛活性方面，测试化合物在50 mg/kg和100 mg/kg剂量下通过腹腔注射，运用尾部甩击测试模型进行研究。它们的镇痛活性通过30分钟后的潜伏期时间测定来确定。统计分析显示，与50 mg/kg剂量的对照组相比，所有测试化合物均呈现出24%至47%的痛觉减退活性。然而，所有经测试的化合物镇痛活性均低于标准药物吗啡。
• Syntheses of 5-alkylthio-1,3-diaryl-1,2,4-triazoles
  作者：Latifeh Navidpour、Leila Karimi、Mohsen Amini、Mohssen Vosooghi、Abbas Shafiee

  DOI：10.1002/jhet.5570410209

  日期：2004.3

  Arylation of the readily available 3-alkythio-5-aryl-1,2,4-triazoles gave 5-alkylthio-1,3-diaryl-1,2,4-triazoles in moderate yield. The structures of the latter were confirmed by NOE and 13C-NMR.

  容易获得的3-烷硫基-5-芳基-1,2,4-三唑的丙烯酸化以中等收率得到5-烷硫基-1,3-二芳基-1,2,4-三唑。后者的结构通过NOE和13 C-NMR确认。
• THROMBIN FUNCTION COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS BASED ON THEM
  申请人：Sinauridze Elena Ivanovna

  公开号：US20100324058A1

  公开（公告）日：2010-12-23

  This invention relates to new chemical compounds, application of these compound as thrombin inhibitors, and pharmaceutical compositions based on them, and can be used to treat and prevent thrombin-dependent thromboembolic events, and in research.

  这项发明涉及新的化合物，这些化合物作为凝血酶抑制剂的应用，以及基于它们的药物组合物，可用于治疗和预防依赖凝血酶的血栓栓塞事件，并用于研究。
• 116. Compounds related to thiosemicarbazide. Part IV. 5-Amino-3-phenyl-1 : 2 : 4-triazoles
  作者：Eric Hoggarth

  DOI：10.1039/jr9500000612

  日期：——
• Synthesis and Structure−Activity Relationship for a Novel Class of Potent and Selective Carbamoyl-Triazole Based Inhibitors of Hormone Sensitive Lipase
  作者：Søren Ebdrup、Lotte Gottlieb Sørensen、Ole Hvilsted Olsen、Poul Jacobsen

  DOI：10.1021/jm031004s

  日期：2004.1.1

  The central role of the intracellular enzyme hormone-sensitive lipase (HSL) in regulating fatty acid metabolism makes it an interesting pharmacological target for the treatment of insulin resistant and dyslipidemic disorders where a decrease in delivery of fatty acids to the circulation is desirable, e.g., in individuals with type 2 diabetes, metabolic syndrome, or impaired glucose tolerance. On the basis of a lead structure from high throughput screening, we have identified a very potent type of carbamoyl-triazole inhibitors of HSL. As part of the lead optimization program, four new classes of carbamoyl-triazoles were synthesized and tested with respect to potency, efficacy and selectivity. Methyl-phenyl-carbamoyl-triazoles were identified as potent and efficacious HSL inhibitors. These compounds do not inhibit other hydrolases such as hepatic lipase, lipoprotein lipase, pancreatic lipase, and butyrylcholine esterase. However, the inhibitors 4b and 4g with IC50 values for HSL of 0.17 and 0.25 muM, respectively, were the only inhibitors selective against acetylcholine esterase. A reversible pseudosubstrate inhibition mechanism is proposed for this class of inhibitors.