3-methylthio-5-phenyl-2H-[1,2,4]triazole | 7747-19-5

• 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-methylthio-5-phenyl-2H-[1,2,4]triazole
• 英文别名: 3-methylthio-5-phenyl-2H-1,2,4-triazole；5-methylthio-3-phenyl-1,2,4-triazole；5-phenyl-3-methylthio-1,2,4-triazole；5-methylsulfanyl-3-phenyl-1H-[1,2,4]triazole；5-Methylthio-3-phenyl-1,2,4-triazol；3-methylsulfanyl-5-phenyl-1H-1,2,4-triazole
• CAS: 7747-19-5
• 化学式: C₉H₉N₃S
• mdl: MFCD01422958
• 分子量: 191.257
• InChiKey: HKFUGORCXQUEIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 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-methylthio-5-phenyl-2H-[1,2,4]triazole 在 potassium permanganate 、 溶剂黄146 作用下， 反应 1.0h， 以90%的产率得到3-methylsulfonyl-5-phenyl-1H-1,2,4-triazole
  参考文献：
  名称：

  Toyooka, Kouhei; Kubota, Seiju, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 1, p. 96 - 106

  摘要：

  DOI：
• 作为产物：
  描述：

  dimethyl N-benzoyldithiocarbonimidate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以85%的产率得到3-methylthio-5-phenyl-2H-[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

• Development of phenyltriazole thiol-based derivatives as highly potent inhibitors of DCN1-UBC12 interaction
  作者：Wenjuan Zhou、Chenhao Xu、Guanjun Dong、Hui Qiao、Jing Yang、Hongmin Liu、Lina Ding、Kai Sun、Wen Zhao

  DOI：10.1016/j.ejmech.2021.113326

  日期：2021.5

  Defective in cullin neddylation 1(DCN1) is a co-E3 ligase that is important for cullin neddylation. Dysregulation of DCN1 highly correlates with the development of various cancers. Herein, from the initial high-throughput screening, a novel hit compound 5a containing a phenyltriazole thiol core (IC50 value of 0.95 μM for DCN1-UBC12 interaction) was discovered. Further structure-based optimization leads

  cullin neddylation 1（DCN1）中的缺陷是co-E3连接酶，对cullin neddylation很重要。DCN1的失调与各种癌症的发生高度相关。在此，从最初的高通量筛选中，发现了含有苯基三唑硫醇核（对于DCN1-UBC12相互作用的IC 50值为0.95μM）的新型命中化合物5a。进一步的基于结构的优化导致了SK-464的发展（IC 50值为26 nM）。我们发现SK-464不仅在体外直接与DCN1结合，但也参与细胞DCN1，抑制cullin3的二联化，并阻碍了两个DCN1过表达的鳞状癌细胞系（KYSE70和H2170）的迁移和侵袭。这些发现表明，SK-464可能是靶向DCN1-UBC12相互作用的新型先导化合物。
• Sulfur-Carbon Bond Formation through Ring-Opening of Triazolothiadiazole with Organometallics
  作者：Raja Ben Othman、Stéphane Massip、Mathieu Marchivie、Christian Jarry、Johnny Vercouillie、Sylvie Chalon、Gérald Guillaumet、Franck Suzenet、Sylvain Routier

  DOI：10.1002/ejoc.201400151

  日期：2014.5

  An efficient and convenient method was developed for the formation of S-substituted thiotriazoles through an unprecedented organometallic addition and subsequent ring-opening sequence of 3-substituted [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole. The method is applicable to a wide range of substrates containing different functional groups and furnishes excellent yields of the corresponding N-unsubstituted

  通过前所未有的有机金属加成和随后的 3-取代 [1,2,4] 三唑并 [3,4-b][1,3, 4]噻二唑。该方法适用于各种含有不同官能团的底物，并提供相应的 N-未取代的 3-或 5-烷基、芳基、炔基和烯基硫烷基-1,2,4-三唑产物的优异产率。
• 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。
• Regioselectivity in Reactions of Bis-Hydrazonoyl Halides with Some Bifunctional Heterocycles
  作者：Ahmad S. Shawali、Magda A. Abdallah、Mohie E. M. Zayed

  DOI：10.1002/jccs.200200148

  日期：2002.12

  chloride 1 reacts regioselectively with 3-mercapto-1,2,4-triazole 2a, 2,3-dihydro-3-thioxo-1,2,4-triazin-5(4H)-one 2b and 2-mercaptobenzimidazole 2c to give the hitherto unknown annelated 2,3-bis-(phenylhydrazono)thiazoles 6a-c, respectively. Reactions of 1 with the methylthio derivatives of such heterocycles afforded the annelated 3,3′-bis-(1,2,4-triazoles) 11a-c, respectively. Similar reaction of 1 with

  双腙酰氯 1 与 3-mercapto-1,2,4-triazole 2a、2,3-dihydro-3-thioxo-1,2,4-triazin-5(4H)-one 2b 和 2-mercaptobenzimidazole 发生区域选择性反应2c分别给出迄今未知的退火2,3-双-(苯肼基)噻唑6a-c。1 与此类杂环的甲硫基衍生物的反应分别得到退火的 3,3'-双-(1,2,4-三唑) 11a-c。1 与 2-苯基氨基-4(3H)-嘧啶酮 4 的类似反应得到 2,3-双(苯肼基)咪唑并[1,2-a]嘧啶-5(1H)-酮 16。6c 的氧化产生相应的双(苯偶氮) 衍生物 15. 讨论了所研究反应的区域化学。
• 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。