7-chloro-2-ethylthio-6-formyl-1,5-dihydro-5-oxo-1-phenyl-1,2,4-triazolo[1,5-a]pyridine-8-carbonitrile | 1200112-15-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 7-chloro-2-ethylthio-6-formyl-1,5-dihydro-5-oxo-1-phenyl-1,2,4-triazolo[1,5-a]pyridine-8-carbonitrile
• 英文别名: 7-Chloro-2-ethylsulfanyl-6-formyl-5-oxo-1-phenyl-[1,2,4]triazolo[1,5-a]pyridine-8-carbonitrile；7-chloro-2-ethylsulfanyl-6-formyl-5-oxo-1-phenyl-[1,2,4]triazolo[1,5-a]pyridine-8-carbonitrile
• CAS: 1200112-15-7
• 化学式: C₁₆H₁₁ClN₄O₂S
• 分子量: 358.808
• InChiKey: YHFXJZWDCYYMJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-chloro-2-ethylthio-6-formyl-1,5-dihydro-5-oxo-1-phenyl-1,2,4-triazolo[1,5-a]pyridine-8-carbonitrile 在 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以77%的产率得到7-chloro-2-ethylthio-6-[(hydroxyimino)methyl]-5-oxo-1-phenyl-1,5-dihydro-1,2,4-triazolo[1,5-a]pyridine-8-carbonitrile
  参考文献：
  名称：

  Novel 1,2,4-Triazolo[1,5-a]pyridines and Their Fused Ring Systems Attenuate Oxidative Stress and Prolong Lifespan of Caenorhabiditis elegans

  摘要：

  In this paper we report the synthesis of some novel 1,2,4-triazolo [1,5-a]pyridine and azolotriazolopyridine ring systems. The products were screened for various types of activity like antibacterial, antifungal, and antioxidative activity. Compound 13 was found to pose an antioxidative activity. In addition, this compound was found to extend the life span of Caenorhabiditis elegans under standard laboratory conditions and reduces both heat and chemical induced oxidative stress in C. elegans in a dose-dependent manner. Furthermore, treatment of worms with compound 13 was found to significantly attenuate the formation of advanced glycation end products and malondialdehyde in a dose-dependent manner.

  DOI：

  10.1021/jm2014315
• 作为产物：
  描述：

  2-ethylthio-1,5-dihydro-7-hydroxy-5-oxo-1-phenyl-1,2,4-triazolo[1,5-a]pyridine-8-carbonitrile 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 6.0h， 以70%的产率得到7-chloro-2-ethylthio-6-formyl-1,5-dihydro-5-oxo-1-phenyl-1,2,4-triazolo[1,5-a]pyridine-8-carbonitrile
  参考文献：
  名称：

  萘啶。第3部分：多官能取代的1,2,4-三唑并[1,5- g ] [1,6]萘啶环体系的第一个例子

  摘要：

  在溴苯中用丙二酸二乙酯处理1,2,4-三唑（1），得到1,2,4-三唑-[1,5- a ]吡啶2。使用POCl 3 / DMF（Vilsmeier试剂）氯化2导致分离7-氯-6-甲酰基-1,2,4-三唑并[1,5- a ]吡啶衍生物4，该衍生物与稳定的碘5反应 得到6-乙氧基羰基乙烯基-1，2，4-三唑并[1，5- a ]-吡啶6。叠氮化6产生相应的叠氮基化合物7，（方案2）。用Na 2 S 2 O还原74得到相应的7-氨基化合物8，其在沸腾的DMF中环化，得到新的1,2,4-三唑并[1,5- g ] [1,6]萘啶9。另一方面，使7与1当量的PPh 3（氮杂-维蒂希反应）在CH 2 Cl 2中反应，得到7-亚氨基-膦烷衍生物10，随后在沸腾的DMF中环化，得到新的1,2,4-三唑并[ 1,5- g ] [1,6]萘啶衍生物11（方案3）。然而，在回流温度下，在1,2-二氯苯中用异硫氰酸苯酯处理10，得到新的1

  DOI：

  10.1016/j.tet.2009.09.082

文献信息

• Synthesis and Characterization of New 1,2,4-Triazolo[1,5-<i>a</i>]pyridines That Extend the Life Span of<i>Caenorhabiditis elegans</i>via Their Anti-Inflammatory/Antioxidant Effects
  作者：Ramadan A. Mekheimer、Ahmed A. Radwan Sayed、Eltaib A. Ahmed、Kamal U. Sadek

  DOI：10.1002/ardp.201500069

  日期：2015.9

  In the present study, we describe the synthesis of a new set of 1,2,4‐triazolo[1,5‐a]pyridines and their fused ring systems. The products were assayed for various types of biological activities like anti‐inflammatory and antioxidative activity. Compounds 4c, 4f, 12a, 14, 16, and 19 were found to reduce carrageenan‐ and dextran‐induced inflammation in rats. In addition, compounds 4f and 12a were found

  在本研究中，我们描述了一组新的 1,2,4-三唑并 [1,5-a] 吡啶及其稠环系统的合成。对产品进行了各种类型的生物活性分析，如抗炎和抗氧化活性。发现化合物 4c、4f、12a、14、16 和 19 可减轻大鼠角叉菜胶和葡聚糖诱导的炎症。此外，发现化合物4f和12a具有抗氧化自由基清除活性。此外，这些化合物在模型系统 Caenorhabiditis elegans 中进行了测试，并且提高了耐热应激性，减少了晚期糖基化终产物的形成，最终延长了寿命。
• Naphthyridines. Part 3: First example of the polyfunctionally substituted 1,2,4-triazolo[1,5-g][1,6]naphthyridines ring system
  作者：Ramadan Ahmed Mekheimer、Yusria Rizk Ibrahim、Eltaib Ali Ahmed、Wolfgang Frey

  DOI：10.1016/j.tet.2009.09.082

  日期：2009.11

  Treatment of 1,2,4-triazoles (1) with diethylmalonate in bromobenzene gave 1,2,4-triazolo-[1,5-a]pyridines 2. Chlorination of 2 using POCl3/DMF (Vilsmeier reagent) led to the isolation of 7-chloro-6-formyl-1,2,4-triazolo[1,5-a]pyridine derivative 4, which reacted with the stabilized ylid 5 to afford 6-ethoxycarbonylvinyl-1,2,4-triazolo[1,5-a]-pyridines 6. Azidation of 6 yielded the corresponding azido

  在溴苯中用丙二酸二乙酯处理1,2,4-三唑（1），得到1,2,4-三唑-[1,5- a ]吡啶2。使用POCl 3 / DMF（Vilsmeier试剂）氯化2导致分离7-氯-6-甲酰基-1,2,4-三唑并[1,5- a ]吡啶衍生物4，该衍生物与稳定的碘5反应 得到6-乙氧基羰基乙烯基-1，2，4-三唑并[1，5- a ]-吡啶6。叠氮化6产生相应的叠氮基化合物7，（方案2）。用Na 2 S 2 O还原74得到相应的7-氨基化合物8，其在沸腾的DMF中环化，得到新的1,2,4-三唑并[1,5- g ] [1,6]萘啶9。另一方面，使7与1当量的PPh 3（氮杂-维蒂希反应）在CH 2 Cl 2中反应，得到7-亚氨基-膦烷衍生物10，随后在沸腾的DMF中环化，得到新的1,2,4-三唑并[ 1,5- g ] [1,6]萘啶衍生物11（方案3）。然而，在回流温度下，在1,2-二氯苯中用异硫氰酸苯酯处理10，得到新的1
• Novel 1,2,4-Triazolo[1,5-<i>a</i>]pyridines and Their Fused Ring Systems Attenuate Oxidative Stress and Prolong Lifespan of Caenorhabiditis elegans
  作者：Ramadan Ahmed Mekheimer、Ahmed Amir Radwan Sayed、Eltaib Ali Ahmed

  DOI：10.1021/jm2014315

  日期：2012.5.10

  In this paper we report the synthesis of some novel 1,2,4-triazolo [1,5-a]pyridine and azolotriazolopyridine ring systems. The products were screened for various types of activity like antibacterial, antifungal, and antioxidative activity. Compound 13 was found to pose an antioxidative activity. In addition, this compound was found to extend the life span of Caenorhabiditis elegans under standard laboratory conditions and reduces both heat and chemical induced oxidative stress in C. elegans in a dose-dependent manner. Furthermore, treatment of worms with compound 13 was found to significantly attenuate the formation of advanced glycation end products and malondialdehyde in a dose-dependent manner.