5-(3-methyl-1-phenyl-1H-thieno[2,3-c]pyrazol-5-yl)-1,3,4-oxadiazole-2(3H)-thione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(3-methyl-1-phenyl-1H-thieno[2,3-c]pyrazol-5-yl)-1,3,4-oxadiazole-2(3H)-thione
• 英文别名: 5-(3-methyl-1-phenylthieno[2,3-c]pyrazol-5-yl)-3H-1,3,4-oxadiazole-2-thione
• 化学式: C₁₄H₁₀N₄OS₂
• mdl: MFCD03722775
• 分子量: 314.392
• InChiKey: YNKDEHKXKOAEBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(3-methyl-1-phenyl-1H-thieno[2,3-c]pyrazol-5-yl)-1,3,4-oxadiazole-2(3H)-thione 、 溴乙腈 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 以63%的产率得到2-(5-(3-methyl-1-phenyl-1H-thieno[2,3-c]pyrazol-5-yl)-1,3,4-oxadiazol-2-ylthio)acetonitrile
  参考文献：
  名称：

  Synthesis, Antioxidant, Anti-Inflammatory, and Antimicrobial Screening of Newer Thiophene-Fused Arylpyrazolyl 1,3,4-Oxadiazoles

  摘要：

  A series of newer 1,3,4-oxadiazole derivatives 3a-h, 5a-h containing a thiophene fused with pyrazole moiety of pharmacological significance have been synthesized. The compounds were characterized by H-1 NMR, IR, and mass spectral techniques. The compounds were screened for their in vitro antioxidant, anti-inflammatory and antimicrobial activities. Among them, Compounds 3b (EC50-14.98) and 3f (EC50-12.21) showed significant antioxidant activity. Compound 3a (EC50-15.23) showed good anti-inflammatory activity. Compound 3d was found as the most active derivative against bacterial and fungal strains.

  DOI：

  10.1080/10426507.2015.1024784
• 作为产物：
  描述：

  ethyl 3-methyl-1-phenyl-1H-thieno[2,3-c]pyrazole-5-carboxylate 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 5-(3-methyl-1-phenyl-1H-thieno[2,3-c]pyrazol-5-yl)-1,3,4-oxadiazole-2(3H)-thione
  参考文献：
  名称：

  带有噻吩并[2,3-c]吡唑的新型不对称2,5-二取代-1,3,4-恶二唑和1,2,4-三唑[3,4-b] -1,3,4-噻二唑的合成部分

  摘要：

  （thieno [2,3 - c ] pyrazolo-5-yl）-[1,2,4] triazolo [3,4- b ] [1,3,4]噻二唑10a，10b，10c和（thieno [2,3 - c ]吡唑-5-基）-1,3,4-恶二唑-3（2H）-基）乙炔6a，6b，6c是由噻吩[2,3 - c ]吡唑-5合成的碳酰肼3按多步反应顺序进行。（5-芳基-1,3,4-恶二唑-2-基）-1H-噻吩并[2,3- c ]吡唑4a，4b，4c也由噻吩并[2,3 - c ]吡唑-5-碳酰肼3通过与各种芳族羧酸环化。噻吩[2,3 - c ]吡唑-5-羧酸酯2与水合肼反应可得到酰肼3，产率高，化合物2通过5-氯-3-3-甲基-1-苯基-苯胺反应可制得化合物2。在乙醇酸钠存在下1H-吡唑-4-甲醛1和2-乙基硫代乙醇酸收率高。

  DOI：

  10.1002/jhet.1584

文献信息

• Synthesis, Antioxidant, Anti-Inflammatory, and Antimicrobial Screening of Newer Thiophene-Fused Arylpyrazolyl 1,3,4-Oxadiazoles
  作者：Pravin Mahajan、Mukesh Nikam、Asha Chate、Urja Nimbalkar、Vrushali Patil、Anil Bobade、Abhay Chaudhari、Dattatray Deolankar、Balasaheb Javale、Charansingh Gill

  DOI：10.1080/10426507.2015.1024784

  日期：2015.11.2

  A series of newer 1,3,4-oxadiazole derivatives 3a-h, 5a-h containing a thiophene fused with pyrazole moiety of pharmacological significance have been synthesized. The compounds were characterized by H-1 NMR, IR, and mass spectral techniques. The compounds were screened for their in vitro antioxidant, anti-inflammatory and antimicrobial activities. Among them, Compounds 3b (EC50-14.98) and 3f (EC50-12.21) showed significant antioxidant activity. Compound 3a (EC50-15.23) showed good anti-inflammatory activity. Compound 3d was found as the most active derivative against bacterial and fungal strains.
• Syntheses of New Unsymmetrical 2,5-Disubstituted-1,3,4-oxadiazoles and 1,2,4-Triazolo[3,4-<i>b</i>]-1,3,4-thiadiazoles Bearing Thieno[2,3-<i>c</i>]pyrazolo Moiety
  作者：Shivaraj P. Patil、Shrikant B. Kanawade、Dinesh C. Bhavsar、Prashant S. Nikam、Sachin A. Gangurde、Raghunath B. Toche

  DOI：10.1002/jhet.1584

  日期：2014.3

  New series of (thieno[2,3‐c]pyrazolo‐5‐yl)‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazoles 10a, 10b, 10c and (thieno[2,3‐c]pyrazol‐5‐yl)‐1,3,4‐oxadiazol‐3(2H)‐yl)ethanones 6a, 6b, 6c has been synthesized from thieno[2,3‐c]pyrazole‐5‐carbohydrazide 3 by multistep reaction sequence. (5‐Aryl‐1,3,4‐oxadiazol‐2‐yl)‐1H‐thieno[2,3‐c]pyrazoles 4a, 4b, 4c were also synthesized from thieno[2,3‐c]pyrazole‐5‐carbohydrazide

  （thieno [2,3 - c ] pyrazolo-5-yl）-[1,2,4] triazolo [3,4- b ] [1,3,4]噻二唑10a，10b，10c和（thieno [2,3 - c ]吡唑-5-基）-1,3,4-恶二唑-3（2H）-基）乙炔6a，6b，6c是由噻吩[2,3 - c ]吡唑-5合成的碳酰肼3按多步反应顺序进行。（5-芳基-1,3,4-恶二唑-2-基）-1H-噻吩并[2,3- c ]吡唑4a，4b，4c也由噻吩并[2,3 - c ]吡唑-5-碳酰肼3通过与各种芳族羧酸环化。噻吩[2,3 - c ]吡唑-5-羧酸酯2与水合肼反应可得到酰肼3，产率高，化合物2通过5-氯-3-3-甲基-1-苯基-苯胺反应可制得化合物2。在乙醇酸钠存在下1H-吡唑-4-甲醛1和2-乙基硫代乙醇酸收率高。