2-(1,3-diphenyl-1H-pyrazol-4-yl)-5-phenyl-1,3,4-oxadiazole | 917947-75-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(1,3-diphenyl-1H-pyrazol-4-yl)-5-phenyl-1,3,4-oxadiazole
• 英文别名: 2-(1,3-diphenylpyrazol-4-yl)-5-phenyl-1,3,4-oxadiazole
• CAS: 917947-75-2
• 化学式: C₂₃H₁₆N₄O
• 分子量: 364.406
• InChiKey: AGRQYEVBCNOVSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-diphenylpyrazole-4-carboxaldehyde benzoyl hydrazide 在 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到2-(1,3-diphenyl-1H-pyrazol-4-yl)-5-phenyl-1,3,4-oxadiazole
  参考文献：
  名称：

  高价碘（III）介导的新型不对称2,5-二取代的1,3,4-恶二唑类化合物作为抗菌剂和抗真菌剂

  摘要：

  通过在温和条件下由碘代苯二乙酸酯促进的吡唑基醛N-酰基hydr酮3的氧化环化反应，可以方便地合成一系列新颖的2,5-二取代的1,3,4-恶二唑4（11个实例，分离产率高达92％）。在体外测试了所有这11种化合物对革兰氏阳性菌，即金黄色葡萄球菌，枯草芽孢杆菌和两种革兰氏阴性菌，即大肠杆菌和铜绿假单胞菌的抗菌活性。还测试了所有合成的化合物对两种真菌的抑制作用。

  DOI：

  10.1016/j.ejmech.2010.06.023

文献信息

• 무용매 조건의 １,３,４－옥사디아졸 합성법
  申请人：University-Industry Cooperation Group of Kyung Hee University 경희대학교 산학협력단(220040073623) BRN ▼135-82-10789

  公开号：KR20160104255A

  公开（公告）日：2016-09-05

  본 발명은 1,3,4-옥사디아졸을 합성하는 방법으로서, a) 무용매 조건에서, 기계적 분쇄법으로 히드라지드 화합물과 알데하이드 화합물을 반응시켜 N-아실히드라존 화합물을 합성하는 단계; 및 b) 무용매 조건에서, N-아실히드라존 화합물에 아이오딘계 산화제를 첨가한 후 산화 고리화 반응으로 1,3,4-옥사디아졸을 합성하는 단계를 포함한다. 본 발명에 따른 무용매 반응에 의한 1,3,4-옥사디아졸 합성법은 매우 높은 선택성과 용이한 방법으로 1,3,4-옥사디아졸을 높은 수율로 합성할 수 있으며 핸들링이 쉽다는 장점이 있다. 또한, 용매 내부의 소량의 물에 의해 다른 부산물이 생성되는 것을 방지 할 수 있으며 이는 합성되는 중간물질이 물에 의해 출발물질로 돌아가는 일도 방지 할 수 있다.

  本发明提供了一种合成1,3,4-噻二唑的方法，包括：a) 在无溶剂条件下，通过机械研磨法使酰肼化合物与醛化合物反应，合成N-酰肼化合物；及b) 在无溶剂条件下，向N-酰肼化合物中加入碘酸系氧化剂后，通过氧化闭环反应合成1,3,4-噻二唑。根据本发明，通过无溶剂反应合成的1,3,4-噻二唑具有非常高的选择性，并且能够以简单的方法和高的产率合成1,3,4-噻二唑，操作也简便。此外，可以防止由于溶剂内部少量水分而产生其他副产品，这也可以防止合成中间体由于水分而逆反应。
• Synthesis and Biological Activity Test of Some New Five Membered Heterocycles
  作者：Qingchun Xia、Dongfang Xu、Qizhuang He、Xingyu Li、Dazhi Sun

  DOI：10.1002/cjoc.201190017

  日期：2010.12

  A new series of 1,3,4‐oxadiazoles, 1,2,4‐triazoles, 1,3,4‐thiadiazoles were synthesized using alkylhydrazides as the starting materials, and then 1,2,4‐triazoles were used to synthesize [1,2,4]triazolo[3,4‐b][1,3,4]thiadiazoles. All the compounds were evaluated for in vitro antibacterial activity and antitumor activity.

  以烷基酰肼为原料合成了一系列新的1,3,4-恶二唑，1,2,4-三唑，1,3,4-噻二唑，然后使用1,2,4-三唑合成了[ 1,2,4]三唑[3,4- b ] [1,3,4]噻二唑。评价所有化合物的体外抗菌活性和抗肿瘤活性。
• Hypervalent iodine(III) mediated synthesis of novel unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles as antibacterial and antifungal agents
  作者：Om Prakash、Manoj Kumar、Rajesh Kumar、Chetan Sharma、K.R. Aneja

  DOI：10.1016/j.ejmech.2010.06.023

  日期：2010.9

  A series of novel 2,5-disubstituted 1,3,4-oxadiazoles 4 have been conveniently synthesized by oxidative cyclization of pyrazolylaldehyde N-acylhydrazones 3 promoted by iodobenzene diacetate under mild conditions (11 examples, up to 92% isolated yields). All the eleven compounds were tested in vitro for their antibacterial activity against Gram-positive bacteria namely, Staphylococcus aureus, Bacillus

  通过在温和条件下由碘代苯二乙酸酯促进的吡唑基醛N-酰基hydr酮3的氧化环化反应，可以方便地合成一系列新颖的2,5-二取代的1,3,4-恶二唑4（11个实例，分离产率高达92％）。在体外测试了所有这11种化合物对革兰氏阳性菌，即金黄色葡萄球菌，枯草芽孢杆菌和两种革兰氏阴性菌，即大肠杆菌和铜绿假单胞菌的抗菌活性。还测试了所有合成的化合物对两种真菌的抑制作用。
• Design and synthesis of novel 2-phenyl-5-(1,3-diphenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazoles as selective COX-2 inhibitors with potent anti-inflammatory activity
  作者：Sumit Bansal、Manju Bala、Sharad Kumar Suthar、Shivani Choudhary、Shoumyo Bhattacharya、Varun Bhardwaj、Sumit Singla、Alex Joseph

  DOI：10.1016/j.ejmech.2014.04.045

  日期：2014.6

  A novel series of 2-phenyl-5-(1,3-diphenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazoles were designed and synthesized for selective COX-2 inhibition with potent anti-inflammatory activity. Among the compounds tested, 9g (2-(3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)-5-phenyl-1,3,4-oxadiazole) was found to be the most potent inhibitor of COX-2 with IC50 of 0.31 μM showing promising degree of anti-inflammatory activity in the carrageenan-induced rat paw edema model with ED50 of 74.3 mg/kg. The lead compound 9g further showed suppression of acetic acid-induced writhes comparable to that of aspirin and gastro-sparing profile superior to the aspirin. Molecular docking analysis displayed higher binding affinity of ligands towards COX-2 than COX-1.