(3-苯基-1,2,4-噁二唑-5-基)乙腈 | 57459-36-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: (3-苯基-1,2,4-噁二唑-5-基)乙腈
• 英文名称: (3-phenyl-[1,2,4]oxadiazol-5-yl)acetonitrile
• 英文别名: 2-(3-phenyl-1,2,4-oxadiazol-5-yl)acetonitrile；3-Phenyl-5-cyanomethyl-1,2,4-oxadiazol；(phenyl-[1,2,4]oxadiazol-5-yl)-acetonitrile；(3-Phenyl-1,2,4-oxadiazol-5-yl)acetonitrile
• CAS: 57459-36-6
• 化学式: C₁₀H₇N₃O
• mdl: MFCD06357815
• 分子量: 185.185
• InChiKey: SDGOZZSULWVMFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  (3-苯基-1,2,4-噁二唑-5-基)乙腈 、 吡哆醛盐酸盐 在 哌啶 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 3.25h， 以72%的产率得到5-(hydroxymethyl)-8-methyl-3-(3-phenyl-[1,2,4]oxadiazol-5-yl)-2H-pyrano[2,3-c]pyridin-2-one
  参考文献：
  名称：

  5-Hydroxymethyl-8-methyl-3-(3-aryl-[1,2,4]oxadiazol-5-yl)-2H-pyrano[2,3-c]pyridin-2-ones及其酯的合成

  摘要：

  摘要 新的 5-hydroxymethyl-8-methyl-3-(3-aryl-[1,2,4]oxadiazol-5-yl)-2H-pyrano-[2,3-c]pyridin-2-ones 及其酯被合成。所得化合物的结构通过完整的 1 H NMR 分析确定。

  DOI：

  10.1080/00397910802219445
• 作为产物：
  描述：

  苯甲腈 N-氧化物 在 乙醇 作用下， 以 乙腈 、 苯 为溶剂， 生成 (3-苯基-1,2,4-噁二唑-5-基)乙腈
  参考文献：
  名称：

  Periselective addition of nitrile sulfides, nitrile oxides and diphenyldiazomethane to tetracyanoethylene

  摘要：

  DOI：

  10.1021/jo00866a008

文献信息

• Synthesis of new 1,2,3-triazolo[1,5-a]quinazolinones
  作者：Nazariy T. Pokhodylo、Vasyl S. Matiychuk

  DOI：10.1002/jhet.321

  日期：——

  Synthesis of novel 3‐substituted‐1,2,3‐triazolo[1,5‐a]quinazolinones in high yields was performed via anionic hetero‐domino reaction of appropriate substituted 2‐azidobenzoates prepared from isatines and acetonitriles activated by 1,3‐thiazole, 1,3‐benzothiazole, 1,3,4‐oxadiazole, and 1,2,4‐oxadiazole rings. It was shown that acetonitriles exhibited high reactivity and were convenient methylenic compounds

  通过适当的取代的2-叠氮基苯甲酸酯的阴离子杂多米诺反应，合成高产率的新型3-取代的1,2,3,3-三唑并[1,5-a]喹唑啉酮，所述取代基由由1,3-活化的靛红和乙腈制备的2-叠氮基苯甲酸酯噻唑，1,3-苯并噻唑，1,3,4-恶二唑和1,2,4-恶二唑环。已表明乙腈显示出高反应性并且是用于此类反应的方便的亚甲基化合物，提供了快速的结构变化。J.杂环化​​学。（2010）。
• Nitrileimines as an alternative to azides in base-mediated click [3 + 2] cycloaddition with methylene active nitriles
  作者：Mykola A. Tupychak、Olga Ya. Shyyka、Nazariy T. Pokhodylo、Mykola D. Obushak

  DOI：10.1039/d0ra01417f

  日期：——

  oxopropanenitriles for the straightforward 5-amino-1H-pyrazole synthesis via 1,3-dipolar cycloaddition. The reaction proceeds at room temperature in a short time with base catalysis and no chromatographic purification. High purity products were isolated by simple filtration. The selectivity of the reaction was observed.

  腈亚胺在实际点击方案中与氧代丙腈一起实现，通过1,3-偶极环加成直接合成 5-氨基-1H-吡唑。该反应在室温下在碱催化下在短时间内进行，无需色谱纯化。通过简单过滤分离出高纯度产物。观察反应的选择性。
• Discovery and Optimization of 5-Amino-1,2,3-triazole-4-carboxamide Series against <i>Trypanosoma cruzi</i>
  作者：Stephen Brand、Eun Jung Ko、Elisabet Viayna、Stephen Thompson、Daniel Spinks、Michael Thomas、Lars Sandberg、Amanda F. Francisco、Shiromani Jayawardhana、Victoria C. Smith、Chimed Jansen、Manu De Rycker、John Thomas、Lorna MacLean、Maria Osuna-Cabello、Jennifer Riley、Paul Scullion、Laste Stojanovski、Frederick R. C. Simeons、Ola Epemolu、Yoko Shishikura、Sabrinia D. Crouch、Tania S. Bakshi、Christopher J. Nixon、Iain H. Reid、Alan P. Hill、Tim Z. Underwood、Sean J. Hindley、Sharon A. Robinson、John M. Kelly、Jose M. Fiandor、Paul G. Wyatt、Maria Marco、Timothy J. Miles、Kevin D. Read、Ian H. Gilbert

  DOI：10.1021/acs.jmedchem.7b00463

  日期：2017.9.14

  Chagas' disease, caused by the protozoan parasite Trypanosoma cruzi, is the most common cause of cardiac-related deaths in endemic regions of Latin America. There is an urgent need for new safer treatments because current standard therapeutic options, benznidazole and nifurtimox, have significant side effects and are only effective in the acute phase of the infection with limited efficacy in the chronic phase. Phenotypic high content screening against the intracellular parasite in infected VERO cells was used to identify a novel hit series of 5-amino-1,2,3-triazole-4-carboxamides (ATC). Optimization of the ATC series gave improvements in potency, aqueous solubility, and metabolic stability, which combined to give significant improvements in oral exposure. Mitigation of a potential Ames and hERG liability ultimately led to two promising compounds, one of which demonstrated significant suppression of parasite burden in a mouse model of Chagas' disease.
• Small Molecule Inhibition of MicroRNA miR-21 Rescues Chemosensitivity of Renal-Cell Carcinoma to Topotecan
  作者：Yuta Naro、Nicholas Ankenbruck、Meryl Thomas、Yaniv Tivon、Colleen M. Connelly、Laura Gardner、Alexander Deiters

  DOI：10.1021/acs.jmedchem.7b01891

  日期：2018.7.26

  Chemical probes of microRNA (miRNA) function are potential tools for understanding miRNA biology that also provide new approaches for discovering therapeutics for miRNA-associated diseases. MicroRNA-21 (miR-21) is an oncogenic miRNA that is overexpressed in most cancers and has been strongly associated with driving chemoresistance in cancers such as renal cell carcinoma (RCC). Using a cell-based luciferase reporter assay to screen small molecules, we identified a novel inhibitor of miR-21 function. Following structure-activity relationship studies, an optimized lead compound demonstrated cytotoxicity in several cancer cell lines. In a chemoresistant-RCC cell line, inhibition of miR-21 via small molecule treatment rescued the expression of tumor-suppressor proteins and sensitized cells to topotecan-induced apoptosis. This resulted in a > 10-fold improvement in topotecan activity in cell viability and clonogenic assays. Overall, this work reports a novel small molecule inhibitor for perturbing miR-21 function and demonstrates an approach to enhancing the potency of chemotherapeutics specifically for cancers derived from oncomir addiction.
• Merckx, Bulletin des Societes Chimiques Belges, 1947, vol. 56, p. 339,347
  作者：Merckx

  DOI：——

  日期：——